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Key West Condo Rentals
We offer Vacation Rentals: Book your Condos securely here and save!
Stay steps from the sand in a Key West Beachfront Condo designed for convenience, coastal style, and those perfect Gulf sunsets — ideal for couples, families, and anyone who wants a seamless Florida Keys getaway.
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 stay in Key West.
To book a selected property, follow the "Search Availability" button or "View Rental" for Pricing & Rates, which will take you directly on our partner website. All bookings are securely completed on our partner websites.
Your Condo by the Beach with Ocean View
The Jungle Breeze condo at LaBrisa Condominiums.
*Ocean View
*Free WiFi
* Free Covered Parking
* Final cleaning included in price
* KING size bed.
* Accommodates 2 adults
* Recently renovated this condo features all new flooring and a brand new kitchen
* Full size washer and dryer.
This is not a hotel; it is a privately owned condo facing the ocean with a view of swaying palms and turquoise waters. The Jungle Breeze condo is the perfect getaway for a romantic cou.......
Panoramic 3BR/3BA Condo - Direct Beach Ocean Front
Location, location, location. Our spacious1800 Atlantic 3 bedroom condo offers a fabulous view of the ocean from all three bedrooms, the kitchen and the living room. Birds of various types, boating activities, lush oasis gardens are just a few reasons why people keep returning to our paradise property. "Click" on 'more information' also "click" on 'More info on Brad & Dee' to learn more about island.
1800 Atlantic is located in the middle of the Island on the Atlantic side. Two miles u.......
Villa Fleur at Shipyard Condominiums
Relax at Villa Fleur in luxurious surroundings. Renovated in 2018 it has a fully equipped kitchen with bar seating and dining area. The living room features comfy furniture and a panel TV. One queen bedroom and one twin bedroom. Enjoy outdoor dining on the brick patio surrounded by a tropical landscape.
Villa Fleur 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. Jus.......
Rose Lane Villas - Villa Vista - 2 bedrooms - Downtown Key West
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
Key West Rooster
Please call or text if you’d like to book our home
702 232... 3750
When booking our home please include a brief description of who you’ll be traveling with and what brings you to the area with your reservation request. We like to know who will be staying in our home 🤗
Welcome to your front row seat of the New Truman Waterfront Park with water views and beautiful sunsets right from our porch. There are only a few homes in the Shipyard with a view like this! Most of th.......
Peaceful Setting Amongst The Active Island Life Style
Enjoy the New and Completely Renovated bathrooms to this tropical residence. This is quiet, peaceful living on the Atlantic Ocean. The spectacular view can be seen immediately upon entering the condo. The floor to ceiling glass walls provide a full sea panorama from the living room, dining room, kitchen and master bedroom. The 31 foot oceanfront balcony is accessed from both the living area and master bedroom. The master bedroom has a king size bed, walk-in closet, and en suite bath. the guest b.......
Rare Penthouse 2 bed/2bath additional King in loft
Perfect vacation rental that allows you to enjoy breakfast on your private balcony, unwind and relax in the master bath jacuzzi, have front row seats to the variegated lights of Mother Nature's Sunrises, have the convenience of a fully equipped kitchen, two sitting areas for extra comfort and flexibility and for countless hours to enjoy the views of the Gulf of Mexico and the tarpon swimming below. This can be your place in the sun, a world of quiet pleasures and glorious sunsets, you'll revel.......
Old Town 2 Bicycles, Grill, WiFi, 1st Floor, Pool! Rent 30 days get 20% discount
We are moving to a monthly rental model and passing on the savings to you. Here in Key West we believe in One Human Family where everyone is welcome and treated like family. Our condo has always received great reviews on cleanliness. There will always be disinfectant wipes, liquid hand soap, dish detergent, laundry detergent, dishwasher tablets and a multitude of other cleaning supplies available for your use during your stay. It’s not just a place on the map, it’s a frame of mind, an At.......
MAJESTIC PARADISE @ Truman Annex - Heart of Old Town, Key West
This wonderful 2 bedroom downstairs unit is owner's second home and has just been beautifully and professionally decorated. Fresh paint throughout, all new hardwood flooring, new kitchen with granite counter tops, stainless steel appliances, and brand new designer furnishings make this a home away from home. A large rear courtyard with a wood sun deck and outdoor grill is perfect for entertaining. Located in the heart of old town Key West, Truman Annex is a gated community of private homes and c.......
Henry's Penthouse on the Ocean in Key West - weekly / nightly rentals
Spectacular ocean views from this condo located on the top floor with 1350 sq ft of fabulous living space and a 45 ft private balcony accessible from the living and both bedrooms will make your vacation a memorable one and keep you coming back year after year. If the dates you need are not available check my other Key West vacation rental (Henry's Piece Of Paradise) located in the same 1800 Atlantic complex.
Both these Key West vacation rental properties were decorated and are managed (a.......
Rose Lane Villas - Villa Porta - 1 Bedroom - Downtown Key West
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 thin.......
Caroline On My Mind - Paradise, Upgraded - 2BD/2Bath - Prime Location!
This beautifully restored, remodeled second-floor 1933 Key West home on Caroline Street offers a unique and inviting experience. The location is highlighted as a key factor, emphasizing the significance of its surroundings.
As you enter "Caroline on My Mind," you'll notice a stairway adorned with wainscoting, leading you to the entry. The home boasts an open and comfortable living area, allowing ample natural light to fill the space. The living room features high-vaulted ceilings and cath.......
The Caribbean Suite - 2-K-bedroom /1 bath/ kitchenette/sleeps 6
This deluxe "Key West Charmer" is a beautifully restored Victorian home built in the 1880's that was converted into individual condominiums many years ago, located just one block from Duval Street in the Heart of Old Town Key West. Our casual atmosphere allows you to chill out and enjoy having the best of Key West within easy walking distance of all the restaurants, bars, entertainment and museums that we are most famous for.
Mingle with other guests around the tropical gardens surroundin.......
**SOUL OF DUVAL @ DUVAL** Modern/Centrally Located + LAST KEY SERVICES...
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival!
There’s no doubt you’ve heard of Duval Street; phenomenal restaurants, eclectic shops and legendary nightlife. This immaculate condo is just a half block away, giving you access to everything Duval Street has to offer while still allowing you to get a restful night’s sleep. SOUL OF DUVAL truly captures the essence of what makes Key West so special, with its playful decor, luxuri.......
Sunset Harbor - Old Town Key West Location - Beautiful Property
Welcome to the perfect location in old town Key West. Situated on the western side of the island, this resort is located near the Gulf of Mexico. Outside the property enjoy the charms of Duval Street and a nightly sunset celebration at Mallory Square. There are also many activities like diving, scuba or snorkeling, parasailing, fishing charters, boat tours, and more.
Property amenities include: onsite washer and dryers, wireless internet access, pool, hot tub, and excellent location. Take.......
Truman Annex Best Location in Town
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 nightl.......
Key West, Gated Truman Annex Condo, new Waterfront Park, and Ft. Zach Beach.
This condo has a unique location in the Gated Truman Annex. It is very quiet, but yet very close to all Key West has to offer.
The entrance road to the Ft Zachary Taylor St. Beach Park is right at the end of our block, for Lazy Days of snorkeling, swimming and sightseeing. The best sunset spot.
Duval St. is 2 blocks up, with shopping, restaurants and world class entertainment.
The 2 porches, for privacy and sun options, also separates this from other properties.
We also have a .......
Rose Lane Villas - Villa Rosa - 1 Bedroom - Downtown Key West
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.......
ATLANTIC HIDEAWAY- Key West
Atlantic Hideaway at 1800 Atlantic – Luxury 2BR Condo with Resort Amenities
Welcome to Atlantic Hideaway, your private escape in paradise. Located in the highly desirable 1800 Atlantic condo complex, this beautifully updated 2-bedroom, 2-bathroom third-floor unit offers spacious accommodations, resort-style amenities, and a prime Key West location. Just 1 mile from the Key West International Airport and 2 miles from Duval Street, you're perfectly situated to explore all that the island .......
MAI TAI TERRACE - KEY WEST
Welcome to Mai Tai Terrace – Your Tropical Getaway in Key West
Located in The Shipyard subdivision of the sought-after Truman Annex, this bright and breezy 2-bedroom, 2-bath end-unit condo offers the perfect island escape just steps from the best of Key West.
SPACIOUS, SUNNY AND PERFECTLY POSITIONED
Situated on the second floor, this open-concept condo features vaulted ceilings, large windows, and a light-filled layout that flows seamlessly from kitchen to lanai—perfect .......
A Fish Bowl at The Truman Annex in Key West
A Fish Bowl has been completely remodeled with attention to detail. A beautiful 1 bedroom, 1 bath downstairs condo located in The Shipyard section of Truman Annex. The new kitchen sparkles with brand new top-of-the-line appliances, cabinetry and every amenity needed. The gourmet kitchen opens nicely to a sunny living room with glass doors leading to a private garden area with room for outside dining and lounging.
From the private patio, the back gate opens to the refreshing waters of the .......
A Touch Of Cuba In Key West
MINIMUM STAY 29 DAYS/28 NIGHTS
About This Property
A Touch of Cuba is a privately owned, two-bedroom, one-bathroom condominium in the Shipyard section of Truman Annex — one of Key West's most sought-after residential neighborhoods. Located on Southard Street, the main entrance to the Truman Annex, the property is within walking distance of Duval Street, the Ernest Hemingway Home, the Key West Butterfly Conservatory, and the island's best restaurants, galleries, and beaches.
This.......
10.0 Star Review
2 Bedrooms
- Sleeps 4
Key West Vacation Rental
Pet Friendly 
THE WEEKEND HOUSE ~ 3 Bedroom, 2 Bath Condo Centrally Located w/ Pool!
WHERE LIFE IS PURE…
This dreamy 3 bedroom, 2 bathroom island getaway is sure to captivate the true essence of Key West charm within its tranquil setting. Peacefully located with convenience to everything, this home truly has it all making your Key West love story one never to forget!
***PRIMARY GUEST MUST BE AT LEAST 25 YEARS OF AGE
DETAILS AND AMENITIES…
Pull up to the first floor of this island beauty showcasing lush, vibrant foliage surrounding this quaint abode. Step on.......
10.0 Star Review
3 Bedrooms
- Sleeps 6
Key West Vacation Rental
Pet Friendly
Heart of Key West - 2BR Waterfront at the Galleon Resort
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 jacuzzi or sauna during your stay or workout in the onsite fitness center. Enjoy fishing off the dock, or rent bicycles and take in all that Old Town Key West has to offer.
Key West Shipwreck Museum and Mallory Square are just a 5 minute walk from this conveniently located resort. The Ernest Hemingway Home & Museum.......
2 Bedrooms
- Sleeps 6
Key West Vacation Rental
Heart of Key West - 2BR Waterfront at the Galleon Resort
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 jacuzzi or sauna during your stay or workout in the onsite fitness center. Enjoy fishing off the dock, or rent bicycles and take in all that Old Town Key West has to offer.
Key West Shipwreck Museum and Mallory Square are just a 5 minute walk from this conveniently located resort. The Ernest Hemingway Home & Museum.......
2 Bedrooms
- Sleeps 6
Key West Vacation Rental
Waterfront Property - Marina Access - Spacious - Excellent Key West Condo
Featuring direct marina access and located just 2 miles from picturesque Smathers Beach, this well appointed two bedroom, two bath condo is ideally situated in Key West. Explore all Key West has to offer, located just 3 miles from vibrant Duval Street, and 4 miles from historic and majestic Mallory Square.
This two bedroom condo features a spacious primary bedroom with a king size bed and hardwood flooring, a connecting ensuite full bathroom with shower and bathtub. The guest bedroom fea.......
Key West's Crown Jewel
Key West's Crown Jewel is a penthouse condominium at 1800 Atlantic Condominium development with two-bedroom, two-bath with approximately 1350 square feet of living space. Guests will enjoy absolutely breathtaking ocean views and the colors of the sunset from the 35-foot balcony, as well as from both bedrooms and the living room.
The Living spaces:
The wood beamed, soaring ceilings of the living room provide an extremely open feeling. Upgraded appointments include high speed (up to 100 .......
Waterfront Property - Marina Access - Spacious - Excellent Key West Condo
Located just two miles from picturesque Smathers Beach, this well appointed two bedroom, two bath condo is ideally situated in Key West. Explore all Key West has to offer, located just three miles from vibrant Duval Street, and four miles from historic and majestic Mallory Square.
The property features two pools, a hot tub, park-style grills, picnic tables, onsite bar, and much more.
This spacious two bedroom condo features a king primary suite with hardwood flooring, a connecting ensu.......
Tropical Escape at Sunrise
This luxurious recently renovated condo features a wonderful contempory interior design. It includes 2 spacious BR's: king bed/ full bath, queen bed/ full bath). Our living room sofa bed accommodates 1 guest. A fully equipped kitchen. Patio overlooks pool. WiFi, cable, 3 TV's, A/C, washer-dryer, workout center, BBQ, tennis court, elevator, parking. Accommodates no more than 5 guests only. Must be 25 and older.
The space
Our place is good for couples, business travelers and families wi.......
Rose Lane Villas - Villa Grande - 3 bedrooms - Downtown Key West
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 Villa Grande 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 Margar.......
Galleon Resort Efficiency Historic District
$25,00 Renovation completed end of 2016/beginning of 2017!! Different than ANY other Efficiency at the Galleon!! You will not be disappointed!
Location..Location...Location...this one has it all! Resort is located on the Ocean and is within steps of famous Duval Street. The Galleon Resort offers many amenities to enhance your vacation needs.
The Efficiency Unit features a King Size Bed, Mini Kitchenette, Walk-in Closet and French Doors that lead to a small private balcony with a reso.......
Sunset views at the Galleon
You will be back year after year! Unit features full kitchen with Master King Bedroom, Guest Bedroom with Twin Beds, and Pull out Sleeper Sofa in Living Room. 2 Bdrm, 2 Bath, Pull out sofa. Sleeps 6. Jacuzzi Tub in Master. Property features Pool, Sauna, Private Beach, Tiki Bar, Rooftop viewing deck, Grills and daily activities. Premium location for easy walks to Duval Street, Mallory Square, Key West Aquarium, Shipwreckers Museum, Mel Fisher Museum and much, much more........
Location, Location, Location!!! Downtown Key West - Truman Annex!!!
All the amenities of a fantastic resort suite and free assigned parking in the middle of everything in Key West...2/1 that is 1 min away from the beach and 2 blocks off Duval surrounded by amazing entertainment Green Parrot is across the street) and some of the best and most famous Key West Restaurants and Landmarks...you will love it!!!
Southermost Point and Mallory Square are within walking distance and so is The Grand Cafe (my fav) restaurant...Enjoy and hope to hear from you soon!!!
Henry's Piece of Paradise on the Ocean in Key West - Weekly / Nightly
Thirteen-hundred-fifty square feet of fabulous living space located on the second floor with garden and partial ocean views from a 38-foot private balcony accessible from the living and both bedrooms will make your vacation a memorable one and keep you coming back year after year.
Click on the calendar icon to check dated that are available. If the dates you need are not available check my other Key West vacation rental (Henry's Penthouse) located in the same (1800 Atlantic) complex.
.......
Summer is here! Don't wait- book your dream stay now.
City of Key West Business License # 28224
We hope you will enjoy this home where Ernest Hemingway and Jimmy Buffet memorabilia welcome you into the abode our first guest affectionately called “The Writer's Retreat'.
This two bedroom, one bath condo with bleached grey hardwood flooring throughout is highlighted by a massive 65 inch Plasma TV loaded with thousands of movies at your fingertips. Relax on the designer furniture while enjoying the full collection of Hemingway's books or l.......
Spacious Ocean Front Resort - 3 Bedroom Condo
This 2,000-square ft-condo is unique in that it has two large master bedroom suites with changing areas and private baths plus a third bedroom w/bath. A pull out sofa bed allows for total accommodations for 8 people. With the master suites on opposite ends of the condo, it is a great set-up for 2 or 3 couples as well as for friends or families who want additional space with luxury surroundings. There is a well equipped kitchen if you wish to dine in, free high speed internet, washer/dryer, iron .......