Key West Vacation Rentals by Owner

Book Your Key West Vacation Rentals Here and Save! Many to choose from, including Rental Homes or Condos with Wi-Fi, Pool, Oceanview, Beachfront and other amenities to make your Florida stay enjoyable.

Vacation Rentals by Owner in Key West Florida.

We have partnered with a major provider for Vacation Rentals by Owner directly through Florida Vacation Rental Homes. With hundreds of short term rentals to choose from, we now have the selection and value to offer our visitors searching for Places to Rent in Key West Florida.

Pilar`s Secret - An Oasis Right Of

Private vacation home
3 Bedroom(s)
2 Bath(s) Sleeps 8

Pilar’s Secret is tucked away in the heart of Key West just half a block ....more

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Luxurious Oceanfront 5BR Property

Private vacation home
5 Bedroom(s)
4 Bath(s) Sleeps 12

Tranquil island living just fifteen minutes from downtown Key West. Stay in an ....more

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$OCEANFRONT CASUAL LUXURY CONDO RENTAL 40 FT FROM THE WATER WITH BREATHTAKING & UNOBSTRUCTED VIEWS OF KEY WEST HARBOR AND THE GULF OF MEXICO. (These views are also available from the master bedroom, living area and kitchen all day, every day) 2nd FLOOR OCEANFRONT CONDO RENTAL Oceanfront privacy and luxury at The Galleon Resort in Old Town, Key West / Sleeps 6 / 1 Master King - 1 Guest Queen / 1 Queen pullout / Large private oceanfront balcony with private spiral stair to sundeck, pool & hot tub, beach, Tiki Bar and Pirates Cove Grill. EXCEPTIONAL LOCATION & CONVENIENCE The Galleon Resort is located on the ocean at the end of North Front St (literally steps from your elevator to Seaport Boardwalk happy hour bar menus, shops & multiple restaurants) / 2 blocks to Duval St + more restaurants, Mallory Square, Front Street eateries, bars and shopping—or cook steaks & seafood on newly renovated large picnic patio with Pro BBQ grills & umbrella picnic tables / 3 HD cable TVs in condo / Free wireless internet / Free private parking / Secluded but very close to all the action / Car not necessary / Rental scooters, bikes, electric golf carts, wave runners on site to explore Key West from land or water / Oceanfront Tiki Bar & Pirates Cove Marina Bar & Grill on premises RECOGNIZED & VOTED IN 2016-17-18 AS A "TOP-25 TIMESHARE RENTAL RESORT" BY TIMESHARE USERS WORLDWIDE BEAUTIFULLY LANDSCAPED OCEANFRONT SWIMMING POOL & HOT TUB, LARGE NEW OCEANFRONT COVERED TIKI BAR, NEW SUN DECKS & GAZEBOS, SMALL PRIVATE BEACH & OCEAN SWIM AREA w PLATFORM, PRIVATE FISHING PIER & NEW BBQ PATIO Full-service resort with on-premises concierge, housekeeping, maintenance and 24-hour security staffing with computerized door entry cards, security cameras, and room safes for guests. Children welcome. Suitable for seniors and handicapped with four elevators, ramps to pool, outdoor hot-tub, beach, Granite sitting ledges in Master Bathroom and open entry from walk-in shower to Jacuzzi 96-unit oceanfront property accessible by car or boat, with free parking and rented boat slips / Great for families & sailboat crews / Marina next to resort to dock your boat / Full laundry, sauna / At the entrance to the Historic Seaport boardwalk / On the ocean in the heart of Key West\'s incomparable Old Town w tin-roof conch houses, historic museums & homes, unique shops, artist galleries, and quirky Duval Street entertainment / *Don\'t miss the nightly, world-famous Mallory Square Sunset Celebration (Unique Entertainment-Food-Art-Crafts) just 2 blocks from your condo THIS CONDO has a full size, fully equipped kitchen, breakfast area, wet bar w wine storage, washer-dryer, dining area, living room with entertainment center (55” TV, DVD player, AM-FM stereo, extra wardrobe closet, drawers) in living area, master bedroom with ensuite 2-sink vanity, closet, makeup vanity with extra device outlets, shower w attachments & jet-tub Jacuzzi, guest bedroom with full bathroom FULL BALCONY has four chairs & table, and is accessible thru French doors in both the living room and master bedroom with sweeping view of Seaport Marina and boardwalk plus ocean views. EXTRA AMENITIES include 3 HD TVs with cable, DVD player, Am-FM stereo, iron & ironing board, jacuzzi tub, in-room safe and free private/secured wireless internet / Pool towels & bed linens provided / Kitchen and Master bath received complete granite & appliance renovation with new living room furniture in last 2-3 years / There is 1 free parking space for each unit Quiet and secluded, yet very close to restaurants & shopping / On-premises large oceanfront swimming pool with jetted hot tub / New oceanfront decking, lounges and umbrellas surround the resort / On-premises oceanfront TIKI BAR and Marina-side PIRATES COVE breakfast & lunch bar-grill / On-premises GIFT SHOP with unique, hand-painted & personalized souvenirs at driveway entrance / Small private beach with private fishing pier / New picnic patio with new extra large Pro BBQ grills and umbrella picnic tables / Roof-top observation deck provides amazing 360 degree views of Key West.$

SEAPORT SKYLINE At Galleon Resort

Condo
3 Bedroom(s)
2 Bath(s) Sleeps 6

OCEANFRONT CASUAL LUXURY CONDO RENTAL 40 FT FROM THE WATER WITH BREATHTAKING & ....more

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$FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! In Key West, every day is a celebration of what makes Summer such a beloved season - warm weather, no agendas, and spending quality time with family and friends. SUMMER SOLSTICE provides the perfect setting for a large group looking to enjoy exactly that. As a combination of two side-by-side private homes located in the heart of Old Town, "Summer Solstice" offers an unbeatable location and plenty of comfortable accommodations for everyone, as well as numerous luxuries, including: ** Two fully equipped kitchens ** Two spacious living areas ** Nine Private Bedrooms, each with an en-suite bathroom ** Two private pools ** Two designated off-street parking spaces SUMMER SOLSTICE can be rented exclusively through Last Key Realty and includes our Five-Star In-home Guest Services - marking a vacation that\'s sure to give you the Summer feels any time of year! THE PRIVATE POOLS... Down a tiny lane you\'d have to be looking for is a row of homes tucked just a half block from Duval Street but without the hustle and bustle of the main drag. "Summer Solstice" is the combination of the first two homes on that row and can be accessed through one of two gates opening up to the private pool areas. The pool areas are connected via an open gate that allows your crew to pass through and mingle between the homes. Fully fenced for privacy, these pools will undoubtedly be the primary gathering places for your group. The pools can be heated in the cooler months to your liking and get equal amounts of sunshine and shade throughout the day. Comfortable chaises offer the perfect lounging options for relaxing outdoors. Each home has a full outdoor dining set and a propane grill to bring the group together for happy hour or a poolside BBQ. THE LIVING AREAS... SUMMER SOLSTICE offers two spacious living areas designed to accommodate a large group. The living areas are equipped with huge SMART TVs and comfortable furnishings. In addition, the plush sofas, armchairs, and indoor dining tables provide plenty of seating options for your whole crew. Both living room sofas pull out to Queen sleepers to accommodate extra guests. Both kitchens are fully-equipped with every appliance and tool needed to prepare a meal at home, that is when you\'re not enjoying the fantastic array of Old Town restaurant options within walking distance. THE ACCOMMODATIONS... This compound of two homes will keep your whole group satisfied. Each bedroom has a flat screen TV, an overhead fan, and an en-suite bathroom. Bed Configuration Summary: House 1 = 5 Bedrooms + Sleeper Sofa ** 2 Twins OR 1 King - First Floor ** 2 Twins OR 1 King - Second Floor ** King - Second Floor ** Queen - Second Floor ** 2 Twins OR 1 King - Second Floor House 2 = 4 Bedrooms + Sleeper Sofa ** 2 Twins OR 1 King - First Floor ** 2 Twins OR 1 King - Second Floor ** Queen - Second Floor ** King - Second Floor ALL LAST KEY VACATION HOMES INCLUDE: ** Washer and Dryer ** Central Heat and A/C ** Ceiling Fans ** Flat Screen HD TVs in Living Room and All Bedrooms ** Fully-Equipped Kitchen ** Basic stock of spices ** Starter supply of paper products ** Starter set of cleaning products ** Linens and Towels provided ** Wireless high-speed Internet access and full cable is included ** Full Time Concierge Service In addition, this fully stocked home also includes, but is not limited to the amenities on this list: ** 2 Fenced and Lushly Landscaped Backyards ** 2 Private Pools with available Pool Heat ** Outdoor Shower ** 2 Propane BBQ Grills ** 2 Queen Sleeper Sofas ** 2 Off-Street Parking Spaces (with restrictions - NO LARGE VEHICLES) Other notes: ** In person welcome ** Interim housekeeping provided upon request ** Pets Allowed ** This property will accommodate 22 adults ** Last Key Realty vacation homes are rented to family groups and responsible adult groups only. Groups who expect they may cause after hours noise will not be a good fit for this home and should be aware they may incur additional penalties when in residence for violations. There will be a $500 charge for after-hours dispatch of our staff in response to calls resulting from verified noise complaints for violations by our guests in residence.$

SUMMER SOLSTICE @ OLD TOWN Uni

Private vacation home
9 Bedroom(s)
10 Bath(s) Sleeps 22

FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 ....more

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$WELCOME TO FOUR PALMS! . This lovely 2 story home is in the well-respected neighborhood of Casa Marina. The main house has 2 bedrooms, 2 1/2 bathrooms and is the ultimate in luxury. Gated parking, a private pool, and a rear guest pool cottage round out this fine home! Upon entering the main home, you\'ll walk into a large open-concept living and dining room with seating for up to 8 people, plus additional seating for 3 at the bar. Entertaining is a breeze with this high-end gourmet kitchen. With the open layout, you can be the host that you need to be all while you are still part of the party. Stainless-steel appliances and a gas range make this kitchen beautiful and practical. This house boasts beautiful Plantation shutters and tile flooring throughout. Open up the French doors and allow the island breeze to flow magically in. Perhaps the private pool is quietly asking you to jump in and splash around, while every so often taking a break to enjoy your tropical cocktail on the lanai. The outdoor table allows for seating of 4 people with a gas grill, making it simple to give everyone a taste of our endless summer. In the main house, the bedrooms are located on the second floor. The master bedroom is large and spacious with lots of storage and an en suite bathroom. The guest bedroom is spacious with a queen-size bed and access to a second-floor balcony. A separate pool cottage is on property and sleeps 4. This cottage has 1 separate bedroom with an en suite bathroom. There\'s also a sleeper sofa in the living room for overnight guests along with another full bath. Although there is no range, a small kitchenette is in the cottage with a full refrigerator and wine cooler. Monthly Rental Only. (This property must be rented for 28 or more days by city ordinance.) Small Dipping Pool Larger Pool, not heated.$

Four Palms: Casa Marina-Monthly -

Private vacation home
3 Bedroom(s)
5 Bath(s)

WELCOME TO FOUR PALMS! . This lovely 2 story hom ....more

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$Summary: Sea Breeze is the perfect location for your tropical getaway! This two bedroom is located in the heart of Old Town Key West, just steps away from the world famous Duval Street\'s shops, bars and restaurants! With off-street parking and 1-block from Duval, this property has everything you need and more! The Space: This quaint two bedroom condominium has two queen beds, and one queen sofa bed allowing for a maximum occupancy of six. With your rental you will find a a private covered porch, private off-street parking space, central A/C, and free wifi. The kitchen is fully equipped for all you may need during your stay! Guest Access: Our contactless check-in procedure makes check-in easy. Guests will receive a personalized access code prior to check-in to enter the unit. How to access: Upon check-in guests will be provided with a code for the lock box to open the gate and an access code to the front door. The Neighborhood: Located on Whitehead St which is 1 block from world famous Duval St, "Sea Breeze" is walking distance to nearly everything you will want to experience during your escape to Key West. Walk to popular spots like The Southernmost Point, Key West Lighthouse, Blue Heaven, Firefly, Green Parrot and the Earnest Hemingway Home which are all just right down the street. Want to hit the beach? Head down to Ft Zach State Park & Beach and enjoy the crystal clear waters and beautiful quiet beaches for a small admission fee. Getting Around: Parking Information: There is one off-street private parking space assigned and included in your stay. There are a variety of great ways to explore Key West including by bicycle, pedi-cab, moke, scooter, golf cart, Uber, Taxi, or by feet. As this unit is located in downtown Key West, many attractions are within walking distance. Other Things to Note: - Property includes onsite washer/dryer (located in the outside closet). - This property is 1 of 4 units in a house, however has a private entrance, and patio. - This property is not pet friendly.$

Sea Breeze- Walking Distance & Off

Condo
2 Bedroom(s)
1 Bath(s) Sleeps 6

Summary: Sea Breeze is the perfect location for your tropical getaway ....more

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$Nestled on a quiet lane in the heart of Old Town Key West, Rose Lane Villas is as close to the action as you\'ll get without sacrificing a good night\'s sleep. This two bedroom Villa Vista is generously equipped for your Key West family gathering, reunion, destination wedding, and even just a romantic Key West getaway. The number one reason why people choose the Rose Lane Villas is our fabulous location and proximity to all things worth doing in Key West. 1/2 block to Hard Rock Cafe 2 blocks to Margaritaville 2 blocks to Sloppy Joe’s 3 blocks to the Historic Seaport 4 blocks to Mallory Square 4.5 blocks to Schooner Wharf 6 blocks to Hemingway’s House Email us for availability, even if we look full. Please be aware of scams asking for wire transfers or offers from Craigslist. If you have any questions, please call our reservations desk.$

Rose Lane Villas - Villa Vista - 2

Condo
2 Bedroom(s)
2 Bath(s) Sleeps 4

Nestled on a quiet lane in the heart of Old Town Key West, Rose Lane Villas is ....more

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3 Bedroom 3 Bathroom House With A

Private vacation home
3 Bedroom(s)
3 Bath(s) Sleeps

This traditional cottage, in the heart of Old Town, was built by a shipbuilder ....more

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$****This property requires a minimum stay of 28 nights in the same calendar month**** ***Brand New Pool with waterfall, saltwater, heater, and a chiller to maximize comfort! Tropical Properties Vacation Rentals invites you to our beautiful historic home located in Historic Old Town Key West. This home is located just two blocks from Duval Street and in the center of all things Key West. This home was originally built in 1929 and has been painstakingly restored to include every modern amenity. The space LOCATION: This tropical destination is a two block walk from Duval Street where you will be dazzled with boutiques, restaurants, nightlife, gallery viewing, shopping and an abundance of other activities, yet the neighborhood is quiet and serene. The homes is located 5 blocks from South Beach, 8 blocks from the North Harbor, a comfortable walk or bike ride to everything Key West. HOUSE LAYOUT: The home is boasts a gorgeous brand new front porch and new pool, with an abundance of patio furniture an outdoors oasis. This home has hard wood floors and modern tile throughout, a spacious family room, central air, washer/dryer located inside the home, a dishwasher all rarities in Key West rentals and makes this a truly enjoyable space. BEDROOMS: This home offers 3 beautiful bedrooms with 2 full bathrooms. Every bedroom on the first floor has a TV, all have tropical décor, new linens and comforters. The first floor features 2 bedrooms. The first bedroom boasts a queen bed, dresser, two night tables and a large closet. The second bedroom also has a queen bed, two night tables and large closet. The living room included a brand new sofa queen sleeper The second floor is a loft accessed by stairs as shown in the photographs with a ceiling height of 5\'2" and has two twin beds, 2 dressers, night stands, and a clothes rack. COMMON AREAS: The kitchen contains all brand new top of the line appliances, a refrigerator with an ice-maker, microwave and dishwasher. The dining area contains a comfortable configuration. PETS: No pets are allowed in this home, this is NOT pet friendly. PARKING: There is designated parking space on property for two FULL SIZE vehicles, an absolute rarity in Key West. OUTDOOR AMENITIES: The tropical outdoor space is furnished with several seating areas both in the sunshine and shade. The back of the home offers a quiet respite from the hustle and bustle of nearby Duval Street. Security cameras are installed on the exterior of the house. Front door, side alley, and facing backyard/pool. OTHER AMENITIES: Iron & Ironing Board, 2 x Hair Dryers, Bed Linens, Towels, Beach Towels, Washing Machine, 3 x TV\'s, Washer dryer, Dryer, Garden (Private), Ceiling Fans, 2 x showers, high speed internet connection, air conditioning, 2x Fire Extinguishers Kitchen stove, Refrigerator ,Cookware & Kitchen Utensils, Dishwasher, Microwave, Toaster, Keurig, Blender and BBQ grill and utensils. ***Guests must be 25 years of age or older unless accompanied by an adult. ****This property requires a minimum stay of 28 nights in the same calendar month****$

TROPICAL PROPERTIES VACATION RENTA

Private vacation home
3 Bedroom(s)
2 Bath(s) Sleeps 8

****This property requires a minimum stay of 28 nights in the same calendar mo ....more

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$*Please note that this home only allows minimum night stays of 28 nights or longer. This is enforced by the HOA and we cannot make any exceptions. This stunning property overlooking the Gulf of Mexico boasts panoramic views from nearly every room and the private pool. Designed with hand scraped bamboo floors and a beautiful wraparound deck with several different seating options, this waterfront home is perfect for families or group getaways. Relax under the ceiling fans on the upstairs or downstairs patio, or enjoy a cup of coffee by the pool. Dogs are also welcome for a small nightly fee. What\'s nearby: This house is centrally located and within walking distance to several different shops and restaurants. Key West\'s local attractions are a short bike ride or drive away - including Duval Street, Higgs Beach, and the Hemingway House. Enjoy scuba diving, boating, fishing, paddleboarding, and more from one of the many local charter companies.Things to know: Free WiFi Full Kitchen Sofa bed in the downstairs bedroom Covered parking for one vehicle Nespresso Vertuo plus deluxe coffee machine FEATURES Heated pool Washer/dryer : Private Central AC Pool : Private KITCHEN Dishwasher Fridge Microwave Stove MEDIA Internet Cable : Xfinity Wireless router MISCELLANEOUS Snowbird-friendly OUTDOOR Gas grill : Private Balcony Deck Patio SCENIC Water view Waterfront Gulf view Gulf front Michelle B. Mar 2019 Stunning gated waterfront property, in a great location. Close and convenient to everything downtown within minutes by car or public transportation, yet quiet and peaceful privacy with your own pool. Every creature comfort you would expect at a property of this level. Our family loved it.$

NEW LISTING! Waterfront Townhouse

Private vacation home
3 Bedroom(s)
3 Bath(s) Sleeps 6

*Please note that this home only allows minimum night stays of 28 nights or lo ....more

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$WELCOME TO ISLAND PEARL This nightly rental located in sought after Old Town Key West is just steps from the famous Duval Street. The cottage is located behind the main house which makes you feel secluded from the rest of the island even though it’s within walking distance to restaurants, bars, shops, and theatres. The first floor of the unit has a twin trundle bed, full bath and seating at the bar kitchenette. For those that don’t have issues with ladders, there’s a ship ladder which leads you to a queen bed. After a day of exploring the island you can take a dip in the shared pool. Read a book or enjoy a refreshing cocktail while taking in the island breezes on the private outdoor deck. note, the option mentioned is for Covid-19 only, any other reasons to cancel would follow our normal cancellation policy and refunds would not be provided. Cozy and Complete! This nightly rental unit is also across the street from the famous Faustos grocery store. The unit\'s main sleeping area is up a ladder, which makes this unit possibly not suitable for someone who can\'t climb very well, or someone who may get nervous climbing a ladder. NOTE: ALTHOUGH THIS UNIT HAS THE POOL, KITCHEN, AND ALMOST EVERYTHING ELSE YOU COULD NEED, THE UNIT DOES NOT HAVE A DEDICATED PARKING SPACE. ONE WILL HAVE TO FIND A SPOT ON THE STREET OR PARK IN THE CITY GARAGE.$

ISLAND PEARL - Cozy Nightly Rental

Apartment
1 Bedroom(s)
1 Bath(s)

WELCOME TO ISLAND PEARL This nightly re ....more

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$THE PROPERTY: Queen Conch is a Key West hidden gem located in perhaps the best location you could ask for. Nestled in the heart of Old Town Key West - just 2 short blocks from Duval Street - you are within walking distance to anything and everything you will want to experience during your tropical vacation. Queen Conch is the perfect home with tropical pool for large groups and includes three separate vacation rentals - "Sea Conch," "Rooster Conch," and "Horse Conch." The downstairs, two bedroom unit - "Sea Conch" - offers an open and spacious floor plan throughout the living and dining area. Beautiful French doors open up to the covered porch and the lush, tropically landscaped garden and pool area. Upstairs lies two separate one-bedroom suites - "Rooster Conch" and "Horse Conch" - which can be accessed from the shaded balcony that overlooks the pool below, providing a cool spot on a hot afternoon. Each suite is decorated with its own splashes of tropical color and comfy queen beds. Each of the three units have their own fully equipped kitchens, quiet AC systems, and pull out sleeper sofas, making this the perfect home for group getaways such as family reunions, birthday celebrations, or bachelor and bachelorette parties! BED CONFIGURATION: Each of the two downstairs bedrooms includes a comfy queen bed, and ensuite bathrooms with large walk in showers and cute Key West decor. The two individual upstairs units also have an amazing queen bed. Each unit has a queen sleeper sofa as well. Please note there is NO TV in the bedroom of the Horse Conch. The shared washer/dryer is located in a shed on the left side of the home near the pool. OUTDOOR AMENITIES: The complex boasts a breathtaking tropical outdoor area with a pool that is shared by guests. The pool is heated seasonally (November through April) for an additional fee which will be assessed at the time of booking. PARKING: Off-street parking for one vehicle, which is great since parking in Key West is limited. LOCATION: A majority of the tourist attractions are located here as well as numerous restaurants, shops and galleries. The neighborhood boasts historic homes, shotgun and conch style homes. NEARBY: Grab morning coffee down the street from local favorites such at Cuban Coffee Queen, Starbucks, and 5 Brothers Coffee or go for lunch and drinks at world famous restaurants and bars like Caroline\'s, Fogarty\'s, Blue Heaven, Irish Kevin\'s and Sloppy Joe\'s - all within a 10 minute walk! PETS: This home is NOT pet friendly. (If you have pets, please browse through our many homes that are pet-friendly). SMOKING: This is a non-smoking home and property. So hurry up and come out of your "shell" - rent "Queen Conch" today! ***Guests must be 25 years of age or older unless accompanied by an adult. ***Managed by Historic Key West Vacation Rentals***$

QUEEN CONCH ~ Stunning "Old Town"

Private vacation home
4 Bedroom(s)
4 Bath(s)

THE PROPERTY: Queen Conch is a Key West hidden gem located in perhaps the bes ....more

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$5-Night Minimum Stay (Sat-Sat Check-In/Check-Out) - If you stay the full 7 nights a discount applies. This is a 4th Floor One Bedroom unit. Please see picture of room where it says "See Notes" This is the room layout. The room is the same except the cabinets are brown wood (new and recently remodeled) and the view is of the walk way outside. (I do not have a recent photo) Here is the resort with info about Efficiency accommodations. https://www.galleonresort.com/accommodations/ We look forward to welcoming you to your own waterfront sanctuary among the lush landscape of Key West. Overlooking the shimmering span of Gulf of Mexico in historic Old Town, The Galleon Resort puts you in an ideal spot to enjoy the countless charms of Key West. Mingle with friends new and old at the Tiki Bar, or relax and unwind in the swimming pool. ___ ___ ___ ___ Details About This Accommodation One-bedroom sleeps two, includes a full kitchen. Each is lovingly furnished with sandy earth tones, rattan furniture and tropical prints that perfectly set the mood for your stay in Key West. ___ ___ ___ ___ Amenities Enjoy the observation deck which guarantees a stunning view from sunrise to sunset, and even to gaze at the stars. Rent a boat for a private viewing of the Keys or take a jetski for a spin right from the resort\'s marina. Work up a sweat at the on-site exercise room and afterwards, relax your body and mind in the sauna. ___ ___ ___ ___ Neighborhood Perfectly positioned, sitting only two blocks from Duval Street - a legendary road that boasts top-notch restaurants, dazzling nightlife and non-stop soirees. Party until dawn at a carnival, swing by a cuban cigar stand or bring your camera to the exotic butterfly conservatory, all located on this versatile street that\'s earned its reputation. At the northwest end of Duval Street lies Mallory Square, a plaza which is famous for its "Sunset Celebration" - tourists gaze at the sunset while arts and crafts displays and entertainers amuse the gatherers. Key West\'s oldest attraction, the Key West Aquarium is a hit with families - everyone will enjoy scoping out the menagerie of rainbow-hued fish. ___ ___ ___ ___ Please Know: * You must provide us the Legal Name (matching Valid Photo ID) for us to put on the Guest Certificate within the first 24HRS of booking. Should you not provide this to us, we will put the name on your VRBO account. We can NOT change the name on the Guest Certificate once we have issued it after your booking and we can NOT offer a refund/cancellation as this is through our owner\'s contract. Thank you for understanding. Must be 25+ Years of Age to Check-In. We will do our best to provide the best offer for your entire stay. Non-Smoking Service animals Allowed NO Pets allowed __________________ Check in time is from 4:00 pm to 10:00 pm on your scheduled date of arrival. Check out time of your departure date is by 10:00 am. All UNIT MAXIMUMS are strictly enforced and violation could result in forfeiture of your vacation. An open security/damage deposit of $150.00 by credit card or cash will be required at check in. If you leave the room extra messy (lots of dirty dishes uncleaned or something that takes the cleaning people a large amount of time to clean they will charge a $100+ cleaning fee) No charges will applied to this credit card provided there is no damage to, extra cleaning required or items missing from your unit. There is a MANDATORY resort fee of $35.00 plus tax due at the time of check-in, for each 7 day period. Daily maid service is not provided except upon request at an additional charge. Due to limited parking, we are only able to issue ONE parking permit PER UNIT and cannot make exceptions. No RVs, campers or trailers are allowed on property. PETS ARE NOT ALLOWED. SKATEBOARDS, ROLLERBLADES AND "RAZOR" TYPE SCOOTERS ARE NOT PERMITTED to be used on our property. A limited number of high chairs and Pack-n-Plays are available upon request at check in. Roll-a-ways are available for a small fee; (restrictions apply in specific units) please ask about this at our Guest Service desk in the lobby. Lobby hours are 7:00 a.m. to 11:00 p.m. daily; please notify us if you will be arriving after 10:00 p.m. so that we may arrange for Security to meet you when you arrive. We look forward to welcoming you!$

Historic Old Town Waterfront 1-Bed

Condo
1 Bedroom(s)
1 Bath(s) Sleeps 2

5-Night Minimum Stay (Sat-Sat Check-In/Check-Out) - If you stay the full 7 nig ....more

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$In the center of Key West\'s prestigious "Millionaires Row," Conch Republic Studio is a tranquil getaway for one or a couple in the Historic District of Key West. Walk 5 blocks to world-famous Duval Street or the marina. Only 8 blocks to Ernest Hemingway\'s House and the Lighthouse. In the morning enjoy a famous Five Brothers Cuban coffee or sandwich while in the evening you may choose to dine at one of the South\'s most popular restaurants, Cafe Sole, both just 100 steps away. 1G optic internet!$

Conch Republic Studio - Key West M

Apartment
1 Bedroom(s)
1 Bath(s) Sleeps 2

In the center of Key West\'s prestigious "Millionaires Row," Co ....more

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Brand New! Luxury 3 Bedroom Condo

Condo
3 Bedroom(s)
3 Bath(s) Sleeps 6

Bayfront Suites offers incredibly spacious, meticulously designed homes for a ....more

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Old Town Key West Compound With Po

Cottage
4 Bedroom(s)
4 Bath(s) Sleeps 12

Down a hidden lane in the heart of Old Town Key West you will find “El S ....more

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$The Galleon Resort is located in the heart of Old Town Key West and the Marina is one of the most desired harbors in the United States. Within walking distance to several bars and restaurants, bars, Duval Street, Mallory Square & many other historic site About the Galleon: Overlooking the Gulf of Mexico in historic Old Town, The Galleon Resort puts you in an ideal spot to enjoy the countless charms of Key West. Mingle with friends new and old at the Tiki Bar, or relax and unwind in the swimming pool. The resort\'s observation deck guarantees a stunning view from sunrise to sunset, and even to gaze at the stars. Rent a boat for a private viewing of the Keys or take a jetski for a spin right from the resort\'s marina. Work up a sweat at the on-site exercise room and afterwards, relax your body and mind in the sauna. The resort\'s 90-slip marina accommodates boats up to 150 feet and hosts a variety of water activities. After you\'ve had your fill of fun on the water, stretch out on the private beach or outdoor pool. If you want to venture out and explore the island, there are local attractions, art galleries, shopping and restaurants within walking distance of the resort\'s doorstep. The Galleon Resort offers a multitude of accommodations, two-bedroom suites sleep up to six, and include a full kitchen, dining area and decked out living area. Each villa is furnished with sandy earth tones, rattan furniture and tropical prints that perfectly set the mood for your stay in Key West. The Galleon Resort is perfectly positioned, sitting only two blocks from Duval Street - a legendary road that boasts top-notch restaurants, dazzling nightlife and non-stop soirees. Party until dawn at a carnival, swing by a cuban cigar stand or bring your camera to the exotic butterfly conservatory, all located on this versatile street that\'s earned its reputation. At the northwest end of Duval Street lies Mallory Square, a plaza which is famous for its "Sunset Celebration" - tourists gaze at the sunset while arts and crafts displays and entertainers amuse the gatherers. Key West\'s oldest attraction, the Key West Aquarium is a hit with families - everyone will enjoy scoping out the menagerie of rainbow-hued fish. Large waterfront swimming pool Private beach Boardwalk Observation deck with a 360-degree panoramic view of Key West Dock Café Tiki Bar Sauna Diving & Snorkeling Sun Bathing Sunset Cruises Exercise Room 24 hour Security Secure Private Wireless Internet The Galleon\'s Marina offers dockage space to accommodate boats and yachts up to 140 feet. Outside of being the most highly protected harbor for your vessel, they also offer exclusive marina and resort amenities when renting a boat slip in the Marina. Wet slips are available for both seasonal and transient rentals. Fishing Charters, Sunset Cruises, Parasailing, Snorkeling, Dolphin Watching, Glass Bottom Boat Jet Ski Rental, Scooter rentals, all available onsite or nearby.$

Luxury Galleon Resort & Marina 2 B

Condo
2 Bedroom(s)
2 Bath(s) Sleeps 6

The Galleon Resort is located in the heart of Old Town Key West and the Marina ....more

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ISLAND TIME - 5 Bed/3 Bath OldTown

Private vacation home
5 Bedroom(s)
3 Bath(s) Sleeps 12

WELCOME TO ISLAND TIME! Key West Island Time is a rare find in old t ....more

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$Location, location, location! Situated in the heart of the Cuban district, steps from arguably the best \'con leche\' in Key West, this nightly rental is minutes from everything on the island. No cars are necessary, bikes and beach chairs are provided. This property will meet all of the demands a vacationer might have. Other amenities include a 1930\'s claw–foot soaking tub, free WIFI and digital HD cable. $

Location, Location, Location - Wal

Apartment
1 Bedroom(s)
1 Bath(s) Sleeps 2

Location, location, location! Situated in the heart of the ....more

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$Located in the heart of Old Town Key West. This resort overlooks the Gulf of Mexico with a private marina, private beach, pool, jacuzzi, with a restaurant and bar. Relax in the hot tub or sauna during your stay or work out in the on-site fitness center. Enjoy fishing off the dock, or rent bicycles and take in all that Old Town Key West has to offer. This spacious 2 bedroom condo sleeps 6, and features a fully equipped kitchen, including a full-sized refrigerator, microwave, toaster, coffee maker, stove and oven. The primary bedroom has a king sized bed, ensuite jacuzzi tub, as well as a full bathroom. The guest bedroom layout may vary, featuring either 2 twin beds or 1 queen bed, and has access to the full guest bathroom. Please let us know your preference before booking and we will do our best to fulfill it, though it is not a guarantee. The living room has a tv with cable, dining area for 4 and a sleeper sofa. Off the living room is a balcony to enjoy the Key West ocean breezes. Galleon Resort Marina serves breakfast. Guests can enjoy poolside drinks at Sunset Tiki Bar. Key West Shipwreck Museum and Mallory Square are just a 5 minute walk from this conveniently located resort. The Ernest Hemingway Home & Museum is 1 mile away. Please note, guest room may feature 2 twin beds or 1 queen bed. Please let us know your preference before booking. We will do our best to fulfill it, but it is not guaranteed. $75+tax resort fee per each week (7nights) due at check-in (Less than a week stays are $20 daily), along with a refundable $150 deposit, as long as no damages occur during your stay. Housekeeping changes linens and towels on Wednesday only. If daily housekeeping is desired, there is an additional charge imposed for it by the resort. Parking for 1 vehicle per unit (No oversized vehicles, RV\'s or trailers) No availability for multiple vehicles. Please note, we do not accept liability for any inconveniences beyond our control including but not limited to temporary defects or outage of utilities, closures of resort amenities, or limitation of any other service. RRI will not provide refunds, reimbursements, or compensation for inconvenience or interruption utilities, resort amenities, or any other service. This property has professional cleaners and supervisors of cleaners who follow strict guidelines and protocols. These professional cleaners utilize hospitality-grade and EPA approved cleaning solutions and sanitizers. They have increased the frequency of cleaning in public areas (including lobbies, elevators, door handles, public bathrooms, etc.).$

★Family Friendly 2BR Condo At He

Condo
2 Bedroom(s)
2 Bath(s) Sleeps 6

Located in the heart of Old Town Key West. This resort overlooks the Gulf of M ....more

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Heavenly Hideaway-Monthly 2BD 2.5B

Private vacation home
3 Bedroom(s)
2 Bath(s)

HEAVENLY HIDEAWAY! This home is tucked away on a lovely qui ....more

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$We stick to a Saturday check in during the in season months (Jan-April) Greetings from Paradise, where the temperature is 82 degrees, water temperature 80, and the wind SE at 10, just enough breeze to blow sand in my margarita. \'Margarita Villas\' are located in historic Old Town in a beautiful, very private gated compound that has won awards as the best development in Florida. (And yes it does have a blender). It’s just off Duval Street, with its bustling shops and nightlife; yet quiet and private. Fort Zachary Taylor on the south side of the property has one of our most picturesque beaches located among the tall whispering pines of the uplands; the view of the reef and the turquoise waters is magnificent. The heated pool is conveniently located nearby so you are never far from a refreshing dip or just \'conching out\' in the sun. There are two bedrooms and one baths; the master bedroom is furnished with a queen-size bed, the other, two twins. French doors in the living room open onto the garden deck for outdoor dining or to catch the tropical breezes. Outdoor porch furniture on the deck. The kitchen is completely equipped (including the mandatory BLENDER). Fully air-conditioned, all rooms have tropical ceiling fans and all linens are provided. There is off street parking for one car. Mike Wernicoff PS: Did I mention that we have a BLENDER? Keywords: Condominium$

Truman Annex Best Location In Town

Condo
2 Bedroom(s)
1 Bath(s) Sleeps 5

We stick to a Saturday check in during the in season months (Jan-April)<br ....more

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Lifetime Memories/Private Pool/WiF

Private vacation home
4 Bedroom(s)
5 Bath(s)

This elegant home has been constructed to the highest standards and is locate ....more

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$Nestled on a quiet lane in the heart of Old Town Key West, Rose Lane Villas is as close to the action as you\'ll get without sacrificing a good night\'s sleep. The one bedroom Villa Porta is generously equipped for your Key West family gathering, reunion, destination wedding, and even just a romantic Key West getaway. Please email us even if the availability calendar looks full. The number one reason why people choose the Rose Lane Villas is our fabulous location and proximity to all things worth doing in Key West. 1/2 block to Hard Rock Cafe 2 blocks to Margaritaville 2 blocks to Sloppy Joe’s 3 blocks to the Historic Seaport 4 blocks to Mallory Square 4.5 blocks to Schooner Wharf 6 blocks to Hemingway’s House Please be aware of scams asking for wire transfers or offers from Craigslist. If you have any questions, please call our reservations desk.$

Rose Lane Villas - Villa Porta - 1

Condo
1 Bedroom(s)
1 Bath(s) Sleeps 4

Nestled on a quiet lane in the heart of Old Town Key West, Rose Lane Villas is ....more

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Brand New! Waterfront 4 Bedroom Co

Condo
4 Bedroom(s)
3 Bath(s) Sleeps 8

Bayfront Suites offers incredibly spacious, meticulously designed homes for a ....more

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Our Key West Dream In Seaport.

Private vacation home
2 Bedroom(s)
3 Bath(s) Sleeps

Family home for over 20 years, we would like to share our home to those that w ....more

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Your Condo By The Beach With Ocean

Condo
1 Bedroom(s)
1 Bath(s) Sleeps 2

The Jungle Breeze condo at LaBrisa Condominiums. *Ocean View ....more

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$La Dolce Vita is located in the heart of Old Town Key West and just steps to Duval Street in the heart of the Historic District!! Southernmost Point and Southernmost Beach on the Atlantic Ocean are just 3 short blocks away! This is a totally renovated condo. Please check out my calendar for availability and the photos and video. It is on the second floor of an old, beautiful, Victorian, Key West style building. It has high 14 ft ceilings, a granite galley style kitchen, stainless steel appliances, fridge, freezer, ice maker, new 2 burner stove, new microwave, lights in the kitchen drawers & cabinets. It has cherry wood laminate floors, queen size bed w/ memory foam mattress, 50\' flat screen TV in living room, 32\' flat screen TV in bedroom, new ceiling fans, all new bathroom, crown molding throughout with recessed lighting on dimmer switches and also rope lighting on the ceiling throughout the condo for a cozy, relaxing feel. This condo has a shared porch with 2 sitting chairs on a large wrap around balcony. There is a pool at a condo complex you can use just a few blocks away. You will need to pick up a key at our property managements office. Dante\'s Pool & Raw Bar is located at 951 Caroline St, which has a large pool, full bar and grill. It is a short bike ride away. The Community Center is a block away at 300 Catherine St. which has a large pool, picnic tables, basketball courts, & playground. Just 3 short blocks away is Southernmost Beach and Southernmost Point on the Atlantic Ocean. Also, a few blocks away is Fort Zachary Taylor Beach which is a 20 minute walk. You will not need a car with this location! Walk to all the shops, restaurants, bars and beaches of Old Town, Key West! If you would like to purchase any of the artwork in the condo, please inquire. thanks! :)$

'LA DOLCE VITA' OLD TOWN, STEPS TO

Condo
1 Bedroom(s)
1 Bath(s) Sleeps 4

La Dolce Vita is located in the heart of Old Town Key West and just steps to ....more

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BOTTOMS UP BUNGALOW - 2 Bedroom /

Private vacation home
2 Bedroom(s)
2 Bath(s) Sleeps 6

Welcome to Bottom’s Up Bungalow located The Meadows subdivision in Old T ....more

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Tropical Getaway! 3 Pools, On-site

Hotel
1 Bedroom(s)
1 Bath(s) Sleeps 2

Tropical island paradise! Breathe in the ocean air from your private balcony. ....more

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$Step into this beautifully restored and redoracated 1933 Key West Home. This first floor home has Bahama shutters throughout the house to open up and let in the Key West sun. Relax in the living with with a large screen TV or sit on the front porch to read a book and relax with the breezes or if needed, the porch fan. The kitchen is perfect to cook your fresh caught fish with enough room to seat four at the counter top. The master has a queen bed with its own ensuite that has a shower with multiple heads for a very luxurious shower. The guest room has two twins(that can be converted to a king)and it\'s own ensuite bathroom. This bathroom does have a shower/bath combination. Both bedrooms have walk in closets. The backyard has its own private pool and can be heated during our Winter months if needed. There is a table for 4 to eat al dente if preferred and two lounge chairs to get your tan on. This home does come with off street parking and a driveway for a medium sized vehicle. Come, enjoy a month in this beautiful Key West Home!$

Welcome To The Shady Palms - Priva

Private vacation home
2 Bedroom(s)
3 Bath(s) Sleeps 6

Step into this beautifully restored and redoracated 1933 Key West Home. This f ....more

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The Cordelia, A Key West Monthly R

Private vacation home
1 Bedroom(s)
1 Bath(s) Sleeps 2

The Cordelia is located in a Historic Conch house from the early 1900’s ....more

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$Tortuga Hammock is located on Stock Island in the Coral Hammock private gated community. This 2 bedroom 2.5 bathroom townhouse is an end unit and renovated throughout in 2020. With granite countertops, stainless appliances, beautiful tile and bamboo floors and has a large open main floor with French doors to a private balcony. This townhouse is the perfect place to call home for your month in The Florida Keys. Positioned on up and coming Stock Island you are close enough to the downtown Key West action or just 2 blocks from marinas and boat launch ramps to enjoy your stay by both land & sea and just steps from delicious restaurants like Roostica, Hogfish Bar & Grill and Matt\'s Stock Island. Comfortably furnished and beautifully decorated with custom artwork and tropical furnishings. The home offers 2 queen beds each private en-suite bathrooms, the master bedroom is host to an additional balcony for your outdoor enjoyment. The main floor also has a powder room and sitting, dining for up to 6 guests. The unit overlooks the pool area and lush mature trees and landscaping where you can enjoy the privacy and tranquility that Coral Hammock offers within their gated community. This home is available for 30+ day rentals and offers secure and assigned parking to its guests. $

Tortuga Hammock

Private vacation home
2 Bedroom(s)
3 Bath(s) Sleeps 6

Tortuga Hammock is located on Stock Island in the Coral Hammock private gated ....more

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$The condo is quite large at over 1150 square feet and looks directly at beautiful Smathers Beach. The \'Sea Jay\' is located in La Brisa which is a gated community. It features a very large master bedroom with dressing room and a full bathroom. We look out at the beautiful Atlantic Ocean from the master bedroom, balcony and living room. Adjacent to the beach is Key West\'s longest sidewalk along the ocean for bike riding, jogging or walking. La Brisa has a heated pool, jacuzzi, sauna, clubhouse, lighted tennis court, three BBQ grills, picnic benches and covered Tiki huts. It is a quiet, family friendly location surrounded by tropical foliage. Consider us your 4 star luxury hotel suite but with the advantage of your own kitchen and a large second bedroom with another full bathroom. The condo has central A/C, cable TV in each room and a washer/dryer with all the conveniences of home in a secure setting. La Brisa is on the edge of old and new town in beautiful Key West. Key West is easy to find and you can\'t get lost! Starting at the Miami International Airport or simply driving down from the north, you only need to get on U.S. Hwy. 1 and go south. The drive is just beautiful as the keys are linked by 42 bridges including the spectacular 7 mile bridge with outstanding water views all the way. The mile markers will tell you how far you have come. Key West is located approximately 160 miles south of Miami and is about a 3 1/2 hour drive. You can also fly directly into Key West Airport and we are located only one mile away. NOTE: No RV’s or Camping Trailers.$

Key West Oceanfront Condo - 'The S

Condo
2 Bedroom(s)
2 Bath(s) Sleeps 6

The condo is quite large at over 1150 square feet and looks directly at beauti ....more

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$If you’re looking for an upscale escape by the sea, Havana Daydream is your Key West hidden gem. Enjoy the island life in your own oasis tucked away from the bustle of Old Town in a private waterfront retreat, with your own private waterfront pool. Luxurious furnishings and spacious interiors centered around the expansive water views perfectly compliment the beautiful outdoor space. Slow down, relax and prepare for life the way it should be at Havana Daydream. Key Features: 2 en\'suite bedrooms each with porch access 4 full bathrooms LOCATION: This home is located in the gated community of Key Cove, on an exclusive lane of waterfront luxury homes. The perks of this little-known location are many: walking distance to the essentials such a grocery stores and the largest shopping center on the island, while still being tucked away in your own quiet neighborhood. The excitement of downtown Old Town is just a few minutes away by car, moped, or bicycle. This home includes plenty of off-street parking in the private garages, as well as private driveways. LIVING AREA & KITCHEN: The main entrance to this home is at the top of the stairs leading from the ground level. This home’s highlight is the wall of floor-to-ceiling windows facing the water to provide the optimal view from every part of the house. The large open plan living room has a spacious seating area with plush couches around a large HD flat screen Smart TV. One of the couches also pulls out to a Queen-sized sleeper sofa for additional guests. There is a dining table with seating for up to 8 diners, with additional seating at the kitchen bar. The gourmet kitchen has state-of-the-art appliances and is fully equipped with all of the tools and utensils one could want or need. The sliding glass doors open up to a wide waterfront deck with additional space for a light meal, coffee, a glass of wine, or just taking in the view. ACCOMMODATIONS: This home has two master suites, both of which are located on the top floor. The first master bedroom has a King size bed, a large flat-screen HD TV, and a beautiful two-room en-suite bathroom complete with a glass shower, large Jacuzzi tub and separate room for the facilities. The first master bedroom also has a wall of floor-to-ceiling glass doors opening out to your waterfront balcony, with gorgeous water views. The second master suite is down the opposite hallway, with a King size bed and an en-suite bathroom. The second master suite also has a flat-screen HD TV, large walk-in closet, and a glass sliding door with access to the waterfront balcony. The third bedroom is beside the second master suite, with two twin beds that covert to 1 King upon request, flat screen TV. An additional bathroom is situated in the hall next to the stairs and across from the third bedroom. On the main floor there is a fourth bedroom with two twin beds that also convert to a King bed upon request. This bedroom also has a flat screen TV, and a full bathroom down the hall. LANAI: Out back is the covered outdoor dining area comfortably seats six and has ample room for entertaining. With visiting heron on the tropical greenery that surround the back yard, your guest will enjoy the natural splendor Havana Daydream and Key West have to offer. Enjoy the brand new, kidney shaped, heated pool. The backyard is complete with a large propane grill. Additional space under the house also offers another covered indoor/outdoor area for playing, additional storage, etc. RATES: we have 3 night (not always available) and 4 night rates available. We also have a 7 night and 21+ night discounted rate (automatically provided with dates).$

Spacious Waterfront 4 Bedroom Home

Private vacation home
4 Bedroom(s)
4 Bath(s) Sleeps 8

If you’re looking for an upscale escape by the sea, Havana Daydream is y ....more

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"VILLAGE ROOSTER" ~ Quaint Cottage

Private vacation home
2 Bedroom(s)
2 Bath(s) Sleeps 4

BAHAMA VILLAGE TREASURE... This Old Town Key West home is just steps ....more

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$THE PROPERTY: Sea Conch is a Key West hidden gem located in perhaps the best location you could ask for. Nestled in the heart of Old Town Key West - just 2 short blocks from Duval Street - you are within walking distance to anything and everything you will want to experience during your tropical vacation. Sea Conch is part of the highly touted "Queen Conch" complex which includes 3 separate rentable units - Rooster Conch, Horse Conch, and Sea Conch. Sea Conch includes a private covered back deck which looks out onto the shared pool. The pool is shared with the two upstairs 1 BR units - "Horse Conch" and "Rooster Conch." The inside of the unit offers adorable Key West decor throughout with colorful furnishings. The open concept living room includes a flat screen TV, queen sized pull out sleeper sofa, and plenty of seating for you and your guests. The dining table seats up to 8 and rests under hanging track lighting fixtures. The kitchen comes fully equipped and offers all the amenities of home such as a fridge, freezer, stove, oven, dishwasher, microwave, coffee maker and plenty of cabinet space. The shared washer/dryer is located in a shed on the left side of the home near the pool. BED CONFIGURATION: Each of the two bedrooms includes a comfy queen bed and ensuite bathroom with large walk in shower and is decorated with works from local artists. There is a pull out sleeper sofa in the living room for two. "Sea Conch" can sleep up to 6 adults. OUTDOOR AMENITIES: The complex boasts a breathtaking tropical outdoor area with a pool that is shared by guests. The pool is heated seasonally (November through April) for an additional fee which will be assessed at the time of booking. Plenty of seating and loungers as well as a grill complete the outdoor space. LOCATION: A majority of the tourist attractions are located here as well as numerous restaurants, shops and galleries. The neighborhood boasts historic homes, shotgun and conch style homes. NEARBY: Grab morning coffee down the street from local favorites such at Cuban Coffee Queen, Starbucks, and 5 Brothers Coffee or go for lunch and drinks at world famous restaurants and bars like Caroline\'s, Fogarty\'s, Blue Heaven, Irish Kevin\'s and Sloppy Joe\'s - all within a 10 minute walk! PETS: This home is NOT pet friendly. (If you have pets, please browse through our many homes that are pet-friendly). PARKING: Sea Conch is located downstairs on the first story and offers 1 designated off street parking spot for 1 vehicle. SMOKING: This is a non-smoking home and property. So hurry up and come out of your "shell" - book "Sea Conch" today! ***Guests must be 25 years of age or older unless accompanied by an adult. ***Managed by Historic Key West Vacation Rentals***$

SEA CONCH~ Gorgeous "Old Town" Hom

Apartment
2 Bedroom(s)
2 Bath(s)

THE PROPERTY: Sea Conch is a Key West hidden gem located in perhaps the best ....more

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$FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! OLD TOWN OASIS is back! After three years out of the rental program, this luxurious condo has returned, with all the same elegance enjoyed by many guests since 2004, and with many improvements. You’ll be staying right near the ocean in Old Town but with all the quiet and solitude of an exclusive gated community. The Green Parrot (oldest blues bar in America) is just two blocks away, and yet Fort Zachery Taylor Park with its beautiful beach is just a short walk from your front door. THE LIVING AREA… The moment you step into the spacious foyer, you\'ll know you have entered a special place. OLD TOWN OASIS has been elegantly decorated to reflect tropical living at its finest, featuring local art and photography. All of the rooms are over-sized, with 11-foot ceilings and overhead fans. The large sectional converts to a queen sleeper for extra guests. There’s a large Smart TV for those evenings you need a break from the excitement in Old Town. The kitchen has been equipped with everything a demanding chef might require, on those nights you are not enjoying local cuisine out on the town. THE POOL & THE BEACH… The Community Pool is right downstairs, located directly on the waterfront. There are plenty of chaises for your comfort, and a cabana with restrooms for your convenience. Best of all, you’ll have “orchestra seats” to watch the sun set on the Gulf of Mexico. Fort Zachary Taylor State Park is a half mile away, with the prettiest beach in Key West. THE ACCOMMODATIONS… ** Master Bedroom - King bed, sitting area, large TV, private balcony, a large walk-in closet and an en-suite bathroom with a spacious walk-in shower. ** Second Bedroom - Two Twins OR One King, a flat screen, large closets, and access to the hall bathroom with a walk-in shower. ALL LAST KEY VACATION HOMES INCLUDE: ** Washer and Dryer ** Central Heat and A/C ** Ceiling Fans ** Flat Screen TVs in Living Room & All Bedrooms ** Fully Equipped Kitchen ** Basic stock of spices ** Starter supply of paper products ** Starter set of cleaning products ** Linens and Towels provided ** Wireless high-speed Internet access & full cable included In addition, this fully stocked home also includes, but is not limited to the amenities on this list: ** Large Heated Community Pool ** One Garaged Off-street Parking Space Other notes: ** Interim housekeeping provided upon request ** This property will accommodate up to 6 adults ** No Pets Allowed ** Last Key Realty vacation homes are rented to family groups and responsible adult groups only. Groups who expect they may cause after hours noise will not be a good fit for this home and should be aware they may incur additional penalties when in residence for violations. There will be a $500 charge for after-hours dispatch of our staff in response to calls resulting from verified noise complaints for violations by our guests in residence.$

OLD TOWN OASIS @ THE ANNEX Oce

Condo
2 Bedroom(s)
2 Bath(s) Sleeps 6

FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 ....more

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$Flagler Station Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click \'Book Now!\' Recline next to a shimmering pool, with a banana tree and avocado tree completing your view! This pleasant home is designed for guest comfort from top to bottom, with everything from central air conditioning to a private gas grill to help with vacation cookouts. The home is all one floor, so guests who have trouble with stairs don\'t need to worry. A desk workspace in the living room is a great spot for if someone has to finish up remote work or schooling. The private washer/dryer will take care of clothes from the day while you change into your swimsuit. Of course, reclining on the hammock is always an option What\'s nearby: It\'s just a short walk or bike ride to Old Town Key West, just a mile away. Beach fans will enjoy staying less than one-and-a-half miles from the Smathers and a half-mile from Higgs Beach, White Street Pier, and Martello Tower on the Atlantic side of the island. Take in a bit of history at the Ernest Hemingway Home and Museum, just one-and-a-half miles away. But if you\'re looking for a different kind of escape, take a walk through a sanctuary of colorful birds and over 50 species of butterflies at the Key West Butterfly & Nature Conservatory - just one mile from the home! Things to know: Free high-speed and cable Full kitchen with a dishwasher Guests must stay for a minimum of 28 nights Flat path to front door On bike path and bus route Beach towels are available for guest use A futon in the living room provides an extra sleeping space Snowbird-friendly * Please note that there is an active security camera in the garage that looks into the car port This property is managed by Vacasa Florida LLC. Parking notes: There is room for two vehicles in the off-street parking area. An off-street parking space is located on the side of the home on Leon street. Additional non-designated parking is available on Flagler street. Security camera details: One in the garage looking into the car port Damage waiver: The total cost of your reservation for this Property includes a nightly damage waiver fee, plus tax if applicable (the “Damage Waiver”). (A discount may be applied for stays of 28 nights or longer, if permitted.) The Damage Waiver covers you for up to $3,000 of accidental damage to the Property or its contents (such as furniture, fixtures, and appliances) as long as you report the incident to the host prior to checking out. The Damage Waiver fee eliminates the need for a traditional security deposit. More information can be downloaded from the "Rental Agreement" on the checkout page. County permit number: 25230-114992 City/town permit number: 30962$

Comfortable Home With Private Pool

Private vacation home
3 Bedroom(s)
2 Bath(s) Sleeps 8

Flagler Station Our calendar is updated in real-time & ....more

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$FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! Nestled under the branches of a majestic Banyan tree, BANYAN ROSE is a classic mid-century modern, ranch-style home set in the Beachside district of Key West, just a couple blocks from Smathers Beach on Rose Street. BANYAN ROSE was designed for those looking to enjoy the things that make Key West such a magical place - basking in beautiful weather, spending time with your loved ones (two and four legged alike in this pet-friendly home), and visiting world famous restaurants and attractions. The entire property is surrounded by a privacy fence and boasts a lushly landscaped front and backyard, which includes a spacious outdoor living space and swimming pool. Combined with Last Key Realty’s unrivaled Guest Services and Complimentary Concierge, your month at BANYAN ROSE will surely be an unforgettable one. THE LOCATION... The Beachside neighborhood of Old Town Key West is a quiet, mostly residential neighborhood on the southern side of the island. Just a couple blocks from the west end of Smathers Beach off Atlantic Blvd, and just down the street from Higgs Beach, BANYAN ROSE is a dream for beach-lovers who prefer to pack their coolers and towels and walk the few steps down to the sand and water. Watch the sunset from Smathers beach or the White Street Pier just around the corner. Take the short stroll to Salute for a beachside meal, or bike ride down to Duval Street or the Historic Seaport for the most popular Key West attractions. There’s off-street parking available in the driveway, as well as additional on-street parking for extra vehicles, mopeds, and bicycles in front of the house. THE LIVING AREA & KITCHEN... The living area of BANYAN ROSE has an open layout, with vaulted ceilings and a set of French Doors that open to the backyard. The cozy living room has a large flat screen TV and is furnished in a style that reflects its modern architectural roots. Just next to the living room is the fully equipped kitchen with brand new appliances and all of the tools you will need to create a gourmet meal. The dining area is just across from the kitchen, with space for up to eight diners at the elegant dining table. There are two stools at the kitchen bar for extra guests or a casual bite. A full bathroom is located off the living room, which also has direct access to the pool area. THE HEATED POOL & GROUNDS... The private back yard is ideal for enjoying Key West\'s beautiful weather, year-round. The pool is perfect for cooling off in the warmer months and can be conveniently heated in the cooler months. Work on your suntan while relaxing poolside in the chaise lounges or enjoy a BBQ in the shade of the Banyan tree, using the propane grill and outdoor dining set. The back yard is fully fenced, providing plenty of privacy and there\'s even an outdoor shower for rinsing off after a swim in the pool. THE ACCOMMODATIONS... ** First Bedroom: King bed, a large flat screen TV, a closet, private workspace in the form of a desk and chair, sliding doors to the side yard, and access to the full shared bathroom located in the hall. ** Second Bedroom: Two Twins OR One King bed, a flat screen TV, and access to the full shared bathroom located in the hall. ** Third Bedroom: Queen bed, a large flat screen TV, a closet, private workspace in the form of a desk and chair, sliding doors to the backyard, and access to the full shared bathroom located in the hall. ** Pool House: Two Twins OR One King bed, a dresser, and multiple sets of French Doors that open to the pool deck. ALL LAST KEY VACATION HOMES INCLUDE: ** Washer and Dryer ** Central Heat and A/C ** Ceiling Fans ** Flat Screen TVs in Living Room and All Bedrooms ** Fully Equipped Kitchen ** Basic stock of spices ** Starter supply of paper products ** Starter set of cleaning products ** Linens and Towels provided ** Wireless high-speed Internet access In addition, this fully stocked home also includes, but is not limited to the amenities on this list: ** Fully Fenced and Lushly Landscaped Private Yard ** Private Heated Pool ** Outdoor Shower ** Off-street Parking in Driveway ** Propane BBQ Grill ** Youtube TV and HBO Max TV Services Other notes: ** All monthly rentals include a mandatory interim clean. Multi-month stays require 1 interim clean per month. ** Additional interim cleanings available ** This property will accommodate up to 8 adults ** Pets Allowed$

BANYAN ROSE @ BEACHSIDE Modern

Private vacation home
4 Bedroom(s)
2 Bath(s) Sleeps 8

FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 ....more

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TROPICAL VINEYARD In The Truman An

Condo
1 Bedroom(s)
1 Bath(s) Sleeps 4

Shipyard Condominiums are located in the prestigious gated community of Truman ....more

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$Want to “ Get Away from it all” but still in the heart of Old Town Key West with everything you need within walking distance? Then this is the property for you. Part of the Banyan Resort this bungalow was once part of a Cuban Cigar Factory and is a classic, historic “Conch House”. This resort consists of lush, tropical gardens, grills for cooking that fresh fish that you will catch or buy from the local seafood market just blocks away and 2 pols, jacuzzi and tiki bar that serves drinks and breakfast and lunch as well complimentary coffee in the morning. This cozy and historic cottage has a kitchen, living room with a fold out queen size sleeper sofa, a queen bed in the bedroom, fully equipped kitchen, and a luxurious bath with a shower and tub. There is a front door with street access to Eaton street, across from the historic Tropic movie theater, or enter your cottage through the gardens and adult pool. This refreshing adult pools is literally 6 steps from your back porch. Perfect for an early morning swim or a quick dip just before bed. There is a parking space adjacent to the Eaton street entrance that can be used for additional fee (based on availability). You will not need a car, but parking is available on sight for 20.00 a day, a bargain in K.W. Everything is within walking distance or biking, with bikes available for rental at the resort. The beach is a short 5 minute bike ride or 15 minute walk and famous Duval street is 1 block from your front door. You wouldn’t know it from how secluded and quiet this complex is. Saturday and Sunday of your week is the International Speedboat races with celebrities and power boats from all over the world. Stroll at night to listen to jazz and blues and people watch or dance to the music 3 blocks away at Hemingway’s Sloppy Joe’s or Hog’s Breath Saloon. The sampling’s of Key Lime pie are endless, as well as fabulous restaurants with a variety of cuisine for everyone along with Happy Hour specials. Visit art galleries, wine and rum , bourbon and cigar bars and much more are all right there on Duval. Spend your days by the pool, out sailing, snorkeling, kayaking among the mangroves or fishing only to sail back into port to catch the famous K.W. sunset from your boat. The staff at The Banyan will help you find just what is right for you. There is also a 24 hour security guard and cameras that monitor the grounds with locked access after sundown. We bought this property 35 years ago and always miss it when we can’t go. You are in luck. This is your year to go! Check in\'s at 4 pm, Check out\'s at 10am. $15 daily resort fee due at checkout at the resort.$

3 Blocks From Waterfront And 1 Blo

Cottage
1 Bedroom(s)
1 Bath(s) Sleeps 4

Want to “ Get Away from it all” but still in the heart of Old Town ....more

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$Nestled on a quiet lane in the heart of Old Town Key West, Rose Lane Villas is as close to the action as you\'ll get without sacrificing a good night\'s sleep. The one bedroom Villa Rosa is generously equipped for your Key West family gathering, reunion, destination wedding, and even just a romantic Key West getaway. The number one reason why people choose the Rose Lane Villas is our fabulous location and proximity to all things worth doing in Key West. 1/2 block to Hard Rock Cafe 2 blocks to Margaritaville 1 1/2 blocks to Sloppy Joe’s 3 blocks to the Historic Seaport 4 blocks to Mallory Square 4.5 blocks to Schooner Wharf 6 blocks to Hemingway’s House Email us for availability, even if we look full. Please be aware of scams asking for wire transfers or offers from Craigslist. If you have any questions, please call our reservations desk.$

Rose Lane Villas - Villa Rosa - 1

Condo
1 Bedroom(s)
1 Bath(s) Sleeps 4

Nestled on a quiet lane in the heart of Old Town Key West, Rose Lane Villas i ....more

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$Relax at Villa Nomade in luxurious surroundings. Featuring a fully equipped kitchen with bar seating and dining area. The living room is furnished with comfy furniture and a 50"TV. The bedrooms have queen beds. Enjoy outdoor dining on the deck surrounded by a tropical landscape. Villa Nomade is located in the Shipyard Condominiums at the Truman Annex. The Shipyard is in the heart of Old Town Key West on the former U.S. Navy property of Truman\'s Little White house. Just steps from Duval St. and located near the Ft. Zach beach and Hemingway\'s house, all of Old Key West\'s sites are within easy walking distance. Our private oasis can be your tropical retreat. COVID-19 UPDATE after May 1, 2020. Please note our 60 day refund policy. We will no longer offer a cash refund after the 60 day period has passed. We will offer a credit if local authorities issue travel restrictions that prevent your visit to Key West.$

Villa Nomade At Shipyard Condomini

Condo
2 Bedroom(s)
1 Bath(s) Sleeps 4

Relax at Villa Nomade in luxurious surroundings. Featuring a fully equipped ki ....more

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$"In-the-know" travelers who return to Key West to vacation love to choose the more elegant area of Upper Duval St. as their favorite area to stay... and this is exactly where you find Amelia\'s Hideaway vacation rental. This one-of-a-kind vacation villa is perfectly situated just off Upper Duval, and because it is way at the end of an unknown lane it is well hidden from public view. Unless you\'ve stayed in this villa before, there\'s no-way you\'d ever know it\'s just steps off Upper Duval Street in one of the prettiest parts of Old Town Key West. The property itself is authentic Key West and unique all-the-way. Pineapple carvings on the fence gracing this property just hint at the island-living charm you find inside. Art work by famous local Caaribbean folk artist David Wegman perched above the gates welcomes you at the entrance. Enter the large wooden blue-green gate off the little private lane and you step into the beautiful courtyard with a crystal clear swimming pool. A statue of the happy Buddha graces the pool side and further welcomes you to your home in Key West and once inside the courtyard you are treated to even more art work; this time canvas art pieces painted by the late Key West artist Sanford Birdsey are uniquely incorporated into the courtyard walls. The layout of this vacation villa was re-worked in October 2008 by local designers to maximize comfort and sleeping options that now include four full bedrooms that all open to the private courtyard. The room layout features one spacious great-room with open kitchen / living room and a flat screen HD TV. The great-room opens directly to a covered lanai that has a dining table for \'el fresco\' dining. The best way to visualize the layout of this Amelia\'s Hideaway is to consider each room as it is situated within the courtyard. The house is built as an \'L-Shaped\' villa with each room in the house opening to the courtyard, and then 3/4 of the roof of the villa is an expansive Mexican tiled roof-top deck. We begin our descriptive tour as you pass the rooms once inside the courtyard gates. Room One: Bedroom #1 (yellow room) is a large room and is set as a full suite offering 2 twin beds that can be put together to make a king size bed and a private full bath divided into two - shower room and powder room with commode and sink. There is also a table conveniently placed for your lap-top. This room also offers a full size sofa that can be made into a queen bed. Room Two: Bedroom #2 (blue room) has a king size bed. This bedroom connects to a full bathroom with bath tub. The design is decidedly unique and very tropical using tumbled marble in an unusual design. Room Three: Bedroom #3 (rose room) has a Queen bed and offers a writing desk. While this bedroom connects to the same full bathroom as bedroom #2, the door connecting this bedroom to the courtyard is just steps from the \'pool bath\' which can be used as a private bath for the \'rose room\'. Room Four: The great-room (living room / kitchen) is the fourth room down the line of the courtyard. The great-room has a beautiful retro-style blue and white kitchen that is open to the cream colored living room area on the other end of the room that provides a sofa and love seat. This combined living area has a flat screen HD TV. The sofa in this great-room is a queen sleeper sofa if you need another bed in a private sleeping area. The main dining area for this room is found in the covered lanai just out the French doors from the kitchen offering a Caribbean \'el fresco\' dining. Room Five: The \'pool bath\' is an artistically tiled full bathroom with a blue and white design created by a local Key West artist. This bathroom has entrances from the lanai as well as the \'great room.\' Room Six: The sixth room (green room) is Bedroom #4 and is considered the master suite for this villa as it is situated \'off to itself\' offering the most privacy. This bedroom offers a king size bed and a private full bathroom. The bathroom is tiled in tumbled marble tile of muted tones of golden brown. Roof Top Deck: The next living space in this unique Key West villa is outdoors and upstairs on the large Mexican tiled roof top deck which expands over 3/4 of the roof. This upper deck is reached by a stair case just outside the master suite. The upper deck offers the perfect spot for private lounging, sunning, star gazing, catching the ocean breeze, or staging a roof top cocktail party or dinner. This deck is furnished with outdoor furniture, built-in side bench seating, and outdoor lighting. Laundry: Finally, back towards the entrance gate is a separate building which serves as the laundry and utility area. The general design of this property lends itself perfectly to small gatherings of families and friends and should be considered an ideal spot for a gathering of family or friends. Bedding Summary: Bedroom #1 - 2 twin size beds (can be made as a king size bed); queen sleeper sofa. Bedroom #2 - king size bed. Bedroom #3 - queen size bed. Bedroom #4 - king size bed. See Floor Plan Here Amenities: Well hidden at the end of little known lane. Private swimming pool, large private gated courtyard, expansive private roof-top sun deck, privacy fences. Fully equipped kitchen, el fresco dining, a/c, telephone, color cable TVs, stereo. Laundry room with washer / dryer. Linens and towels are provided. Catering can be arranged. Maid service can be scheduled. Activities: Elegant Upper Duval St. - Close to the Southern Most Point of the United States. Cafe neighborhood features art galleries, wonderful eateries and internationally famous fine restaurants, coffee house, fine gift and clothing stores, Grand Vin wine tasting, home made ice cream. Here you start at the top of Duval St. near the Atlantic Ocean and can take the 20 min stroll to the Gulf of Mexico (remember it takes 3 to 4 Key West streets to equal the distance of a typical city block). Sailing, boating, diving, museums, nightlife. Area: Walk out your gate and down the lane to all you want to see in Historic Key West. Best restaurants, shops, galleries, clubs, Hemingway House Museum, Light House Museum, Custom House Museum, aquarium, Ship Wreck Museum, 4 blocks from Southern Most Point of the U.S., close to beaches. Walk everywhere from here. Restrictions: Smoke free house. Smoking permitted outside only. No pets please. We do not accept guests less than 25 years of age unless accompanied by a family group or guardian.$

Amelia's Hideaway ~ Hidden Courtya

Villa
4 Bedroom(s)
4 Bath(s) Sleeps 10

"In-the-know" travelers who return to Key West to vacation love to c ....more

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$Our "Forever Gem" is a whimsical home with modern flare in Mid-town and minutes from the airport, beaches, parks and other attractions. It features an open floorplan with an updated kitchen designed for entertaining and a separate dining area. We offer 3 bedrooms (king, 2-twins (adjusts to king) and queen) that are arranged and nicely appointed for comfort as well as 2 full bathrooms and on-demand hot water. In the backyard there is a spacious screened in porch off the dining room with 2 rocking chairs and a large private pool and deck chairs to enjoy after a long day exploring Key West! We offer an outdoor shower to rinse off before or after your pool activities. We love the backyard with the salt water outdoor pool especially after a day of bicycling around Key West. It\'s private and relaxing with lush tropical surroundings, expansive outdoor eating area, gas grill, outdoor shower and even ocean breezes! Forever Gem is centrally located in a quiet neighborhood in "mid-town" with easy access Higgs Beach and Smathers Beach as well as one of our favorite restaurants, Salute\' On The Beach! Within minutes you can enjoy all the tourist attractions that Key West has to offer from the Southern Most Point down Duval Street to Mallory Square.$

Key West Charmer W/Private Swimmin

Private vacation home
3 Bedroom(s)
2 Bath(s) Sleeps 6

Our "Forever Gem" is a whimsical home with modern flare in Mid-town ....more

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$PROFESSIONAL CLEANING PER CDC GUIDELINES BEFORE & AFTER EACH STAY Ocean views from every room with floor to ceiling windows. Feel the warm tropical breezes as the palm trees sway to the music . It\'s a magical rhythm set into motion over a century ago by pirates, artists, writers and other champions of leisure. Yes ... THERE STILL IS MAGIC IN KEY WEST. Today that same rhythm beckons you to discover the charm and grace of Key West in a new and distinctive setting.. We hope you will enjoy staying directly on the ocean with the comfort that Magic Ocean Penthouse has for you.. This is a two-bedroom, two-bath condominium with 1357 square feet of living space, Your 35-foot balcony is ideal for lounging sunning and dining.. Master bedroom has a comfortable king-size bed; second bedroom has a comfortable Queen and twin size bed. Queen-size sleeper sofa is in living room. The Kitchen has just had a major renovation, custom cabinets and beautiful granite counter tops. All new stainless appliances too. For those guests who choose to get away from the kitchen.... those options are still open to the wonderful restaurants around the island. By the way.... for our guests looking to escape the ordinary... There is a heavy duty blender in the kitchen that makes great Margaritas! The living area has a brand new 55 inch HD smart TV.... Every sleeping area has its TV and WiFi Oceanfront Key West Resort Living: The property features a Resort sized swimming pool, bubbling hot tub, sauna and gym.. Several picnic and barbecue areas surrounded by the native tropical gardens. are always available complimentary to our guests. Water sports,Snorkeling and the Coral Reef are all available foot steps away at Smathers Beach (our next door). Smathers is a popular public beach that is free to use and a welcome neighbor There Still Is Magic in Key West . ..MAGIC OCEAN PENTHOUSE WELCOMES YOU$

Penthouse Level Ocean Views From E

Condo
2 Bedroom(s)
2 Bath(s) Sleeps 6

PROFESSIONAL CLEANING PER CDC GUIDELINES BEFORE & AFTER EACH STAY ....more

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Key West Dream Townhouse * Sleeps

Private vacation home
2 Bedroom(s)
3 Bath(s) Sleeps 6

This property is a rare find! Sleeping 6 and located over 2 floors, its locate ....more

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Things to Do while on Vacation In Key West Florida

Key West is just about the perfect vacation destination in Florida. As cliché as it sounds, there truly is something for everyone. Whether you are looking to party like a rock star or seeking a relaxing vacation in nature, Key West has what you are looking for. Whether you are interested in bar hopping, beach hopping, dolphin watching, bird and wildlife watching, or some of the best people watching around; Key West is a must-visit spot in Florida.

Duval Street

You truly can’t visit Key West without experiencing Duval Street. This 1.2-mile street is the main thoroughfare and has so much to offer. Click here to see the live feeds of Duval Street from the world-famous Sloppy Joes, coined a Key West tradition. There are more than 100 bars and dozens of shops and boutiques along this stretch. If you love live music be sure to visit the Green Parrot Bar and The Hogs Breath Saloon, both locations are well-known for hosting phenomenal national act.

The Ernest Hemmingway Home and Museum

If you enjoy literature and history, you will want to plan a visit to Hemingway Home & Museum. The estate was built in 1851 and is the most popular tourist attraction in Key West. Ernest Hemingway lived there from 1931 to 1939 and wrote some of his most popular literary works on the estate.

Mallory Square – Sunset Celebration

One of Key West’s most popular activities is the Sunset Celebration at Mallory Square Dock. People visit from all over the world to catch these exquisite sunsets and experience this nightly arts festival. There are street performers, food vendors, art installations, and extraordinary shopping options.

Key West Butterfly and Nature Conservatory

If you are a nature-lover, you will want to plan a visit to The Key West Butterfly & Nature Conservatory. Click here to check out the live webcams set up at the conservatory. You can walk among hundreds of butterflies and beautiful, colorful birds inside their habitat.

Dry Tortugas National Park

You can also take a ferry ride on the Yankee Freedom to visit Fort Jefferson Dry Tortugas National park. Take a guided tour and learn about life at the fort in the 1860s. The park is 100-square-miles and, aside from the fort, is known for is gorgeous blue waters, coral reefs, and wildlife watching.

Discover the Best Deals for Key West Vacation Rentals in the Florida Keys.

We have 2,3 or 4 Bedroom beachfront Vacation Rental Homes with ocean view or a Beach House for the entire family. Book Direct Here!

Key West, FL is known for water sports, lively nightlife, beaches, historic sites and its pastel, conch-style architecture. Located at the southernmost point in the Florida Keys and the United States, visitors can enjoy the Ernest Hemingway Home and Museum, tour the Harry S. Truman Little White House, explore beautiful tropical gardens or visit Mallory Square, a waterfront plaza just west of Duval Street where its “Sunset Celebration” is one of the most popular things to see and do in Key West.

Key West Vacation Rentals by Owner

Book Your Key West Vacation Rentals Here and Save! Many to choose from, including Rental Homes or Condos with Wi-Fi, Pool, Oceanview, Beachfront and other amenities to make your Florida stay enjoyable.

Vacation Rentals by Owner in Key West Florida.

Pilar`s Secret - An Oasis Right Of

Luxurious Oceanfront 5BR Property

SEAPORT SKYLINE At Galleon Resort

**SUMMER SOLSTICE @ OLD TOWN** Uni

Four Palms: Casa Marina-Monthly -

Sea Breeze- Walking Distance & Off

Rose Lane Villas - Villa Vista - 2

3 Bedroom 3 Bathroom House With A

TROPICAL PROPERTIES VACATION RENTA

NEW LISTING! Waterfront Townhouse

ISLAND PEARL - Cozy Nightly Rental

QUEEN CONCH ~ Stunning "Old Town"

Historic Old Town Waterfront 1-Bed

Conch Republic Studio - Key West M

Brand New! Luxury 3 Bedroom Condo

Old Town Key West Compound With Po

Luxury Galleon Resort & Marina 2 B

ISLAND TIME - 5 Bed/3 Bath OldTown

Location, Location, Location - Wal

★Family Friendly 2BR Condo At He

Heavenly Hideaway-Monthly 2BD 2.5B

Truman Annex Best Location In Town

Lifetime Memories/Private Pool/WiF

Rose Lane Villas - Villa Porta - 1

Brand New! Waterfront 4 Bedroom Co

Our Key West Dream In Seaport.

Your Condo By The Beach With Ocean

'LA DOLCE VITA' OLD TOWN, STEPS TO

BOTTOMS UP BUNGALOW - 2 Bedroom /

Tropical Getaway! 3 Pools, On-site

Welcome To The Shady Palms - Priva

The Cordelia, A Key West Monthly R

Tortuga Hammock

Key West Oceanfront Condo - 'The S

Spacious Waterfront 4 Bedroom Home

"VILLAGE ROOSTER" ~ Quaint Cottage

SEA CONCH~ Gorgeous "Old Town" Hom

**OLD TOWN OASIS @ THE ANNEX** Oce

Comfortable Home With Private Pool

**BANYAN ROSE @ BEACHSIDE** Modern

TROPICAL VINEYARD In The Truman An

3 Blocks From Waterfront And 1 Blo

Rose Lane Villas - Villa Rosa - 1

Villa Nomade At Shipyard Condomini

Amelia's Hideaway ~ Hidden Courtya

Key West Charmer W/Private Swimmin

Penthouse Level Ocean Views From E

Key West Dream Townhouse * Sleeps

Things to Do while on Vacation In Key West Florida

Duval Street

The Ernest Hemmingway Home and Museum

Mallory Square – Sunset Celebration

Key West Butterfly and Nature Conservatory

Dry Tortugas National Park

Discover the Best Deals for Key West Vacation Rentals in the Florida Keys.

We have 2,3 or 4 Bedroom beachfront Vacation Rental Homes with ocean view or a Beach House for the entire family. Book Direct Here!

SUMMER SOLSTICE @ OLD TOWN Uni

OLD TOWN OASIS @ THE ANNEX Oce

BANYAN ROSE @ BEACHSIDE Modern