Key West Vacation Rental Homes
Large selection of Vacation Homes, book your Key West Vacation Rental here and save!
Many properties to choose from, including private Homes, Cottages or Condos with Wi-Fi, Pool, Oceanview, Beachfront and other amenities that will make your Florida visit the perfect getaway.
Your Condo by the Beach with Ocean View
Key West Condo 
4.9 Star Review
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 privat.......read more
1 Bedrooms
- Sleeps 2
Condo in Key West
BEACH HOUSE ~ Stunning 4B/4Ba Home with Private Pool in Truman Annex!
Key West Vacation Rental 5.0 Star Review
PRESTIGIOUS TROPICAL RETREAT...
Indulge in this spectacular two-story home situated in the premier gated community of historic Truman Annex. Escape to a sun-kissed dream as soon you enter this picturesque community, surrounded by swaying palm trees inviting you to enter your island vacation home which is tucked away on a quiet lane. Totaling 4 b.......read more
4 Bedrooms
- Sleeps 8
Vacation Rental Home in Key West
BOTTOMS UP BUNGALOW - 2 Bedroom / 2 Bathroom With PRIVATE POOL
Key West Vacation Rental 5.0 Star Review
Welcome to Bottom’s Up Bungalow located The Meadows subdivision in Old Town Key West.
This pristine Florida Bungalow is 2 bedrooms, 2 bathroom single family home and offers all the amenities you need to make this your perfect vacation. Including off-street parking, swimming pool, quaint gazebo equipped with wet bar and custom seating. Th.......read more
2 Bedrooms
- Sleeps 6
Vacation Rental Home in Key West
Panoramic 3BR/3BA Condo - Direct Beach Ocean Front
key west Condo 4.9 Star Review
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" o.......read more
3 Bedrooms
- Sleeps 8
Condo in key west
Villa Fleur at Shipyard Condominiums
Key West Condo 4.9 Star Review
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 Co.......read more
2 Bedrooms
- Sleeps 4
Condo in Key West
Rose Lane Villas - Villa Vista - 2 bedrooms - Downtown Key West
Key West Condo 4.9 Star Review
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 .......read more
2 Bedrooms
- Sleeps 4
Condo in Key West
Simonton Studio, an Old Town get-away for 2
Key West Apartment 4.9 Star Review
The Simonton Studio is neat, sweet and complete. This pet friendly accommodation is the perfect location for exploring Key West. So, get out there and live it up in Key West and come home to a king size bed and everthing you need to fix your own cocktails and prepare some shrimp on the shared propane grill in the Courtyard.
Located in a .......read more
Studio
- Sleeps 2
Apartment in Key West
Key West Rooster
Key West Condo 4.9 Star Review
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 Waterfron.......read more
2 Bedrooms
- Sleeps 4
Condo in Key West
~DREAMING ON DUVAL~ Grand 5 bedroom, 4.5 bath home with private pool/parking
Key West Vacation Rental 4.8 Star Review
THE PROPERTY: Dreams do come true in Key West! As you enter the front gate of this luxury property, you arrive in a private wonderland on the quieter end of Duval Street. Enjoy morning coffee or people watching on the elevated, partially covered front porch. The home’s backyard oasis includes a covered rear patio, a pool with waterfall feature an.......read more
5 Bedrooms
- Sleeps 10
Vacation Rental Home in Key West
Peaceful Setting Amongst The Active Island Life Style
Key West Condo 4.8 Star Review
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 ba.......read more
2 Bedrooms
- Sleeps 4
Condo in Key West
Rare Penthouse 2 bed/2bath additional King in loft
Key West Condo 4.7 Star Review
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.......read more
2 Bedrooms
- Sleeps 8
Condo in Key West
MAJESTIC PARADISE @ Truman Annex - Heart of Old Town, Key West
Key West Condo 5.0 Star Review
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 d.......read more
2 Bedrooms
- Sleeps 5
Condo in Key West
Henry's Penthouse on the Ocean in Key West (weekly / nightly rentals)
Key West Condo 4.8 Star Review
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.......read more
2 Bedrooms
- Sleeps 5
Condo in Key West
Key West Suites Hotel - Adam Scott Rote Suite
Key West Apartment 4.8 Star Review
Welcome to your charming private studio apartment right on Duval street! Built in 1919, it used to be called the Central Hotel because it’s located at the most central location on Duval bordering Southard Street and is just steps up on the second floor overlooking both Duval and Southard Streets.
The building once housed the Chrysler/Deso.......read more
1 Bedrooms
- Sleeps 6
Apartment in Key West
Location, location, location in the heart of Old Town!
Key West Vacation Rental
Tricksy's Place located in the heart of Old Town, Key West is a perfect retreat to relax, and the perfect starting point to explore all that our beautiful tropical island has to offer. Only one block from Duval St., a short walk to the Southernmost Point, Hemingway House, Key West Lighthouse, and more. Stay in and cook an elegant meal in our modern.......read more
3 Bedrooms
- Sleeps 6
Vacation Rental Home in Key West
Old Town Key West Condo - MONTHLY RENTALS ONLY
Key West Condo 4.9 Star Review
Our condo is located is in the heart of Key West's Old Town. This neighborhood is filled with historic homes dating from the period when Key West was the wealthiest city in the United States. The condo is in a historic home with three other condo units. The location is ideal to explore Key West by foot or bike. Great restaurants are within a fi.......read more
2 Bedrooms
- Sleeps 4
Condo in Key West
Lush retreat minutes away from both Mallory Square & Duval Street.
Key West Condo
f bedrooms, full kitchen, screened in patio with a relaxing pool, and dock area perfect for sunset over the Gulf of Mexico. Free covered parking. A great place to rest from your frolicking fun times!.......read more
2 Bedrooms
- Sleeps 6
Condo in Key West
The Maria Luz, a Key West Monthly Rental
Key West Apartment
The Maria Luz a is located in a Historic Conch house from the early 1900’s updated and decorated by its owner.
Features original hardwood floors, updated bathroom. The galley-style kitchen is fully stocked with all the necessary essentials. Other features include also features WIFI, cold A/C, private washer and dryer in the unit.
You c.......read more
1 Bedrooms
- Sleeps 2
Apartment in Key West
The Cordelia, a Key West Monthly Rental
Key West Vacation Rental
The Cordelia is located in a Historic Conch house from the early 1900’s updated and decorated by its owner. Features original hardwood floors, new bathroom and chic decor items. The galley-style kitchen is equipped with white quartz countertops, a black retro tile backsplash, and stainless-steel appliances; fully stocked with all the necessary e.......read more
1 Bedrooms
- Sleeps 2
Vacation Rental Home in Key West
The Gisela, a Key West Monthly Rental
Key West Vacation Rental
The Gisela is located in the rear of an adorable Conch Cottage. Finished with a soft and neutral color scheme that will take your breath away. Enter through your private entrance into the living room with features high ceilings and a spectacular light filled living space. 45-inch flat-screen TV with cable and streaming services. Between the kitch.......read more
1 Bedrooms
- Sleeps 1
Vacation Rental Home in Key West
The Rex, a Key West Monthly Rental
Key West Vacation Rental 5.0 Star Review
Enjoy a stylish experience at this centrally-located apartment. Just a short walk from some of Key West best restaurants and shopping. This 1 bedroom, 1 bath has been beautifully furnished, features stainless steel appliances, private washer and dryer in unit, private porch with a view of a lush courtyard........read more
1 Bedrooms
- Sleeps 2
Vacation Rental Home in Key West
Hyatt Residence Club Sunset Harbor-Old Town- Heart of Key West, Sleeps 4!
Key West Apart-hotel
Tropical Key West welcomes you to a classic Florida condominium, offering a one bedroom unit with plush queen bed, fully equipped kitchen, dining area, living room with sleeper sofa, TV, stereo and DVD player, and private balcony with pool or harbor views. Walk to Duval St. and Mallory Square! You will be in the middle of it all while you enjoy the.......read more
1 Bedrooms
- Sleeps 4
Apart-hotel in Key West
Beach Paradise in the Keys! Location! Location! 2 Blocks to Duval St
Key West Vacation Rental 4.6 Star Review
You will love our newly renovated 2 bed/ 2 1/2 bath private townhome in a secure community. Perfect location. This property doubles as our second home when we are in town. Renovations include new wood flooring, fresh paint, new kitchen with stainless appliances and granite tops. All furnishings and accessories are new. Private courtyard with sundec.......read more
2 Bedrooms
- Sleeps 8
Vacation Rental Home in Key West
Stunning tropical home in Old Town Key West with private pool and hot tub
Key West Vacation Rental
Spacious home with open floor plan. Completely renovated in 2018. Large heated pool and hot tub in a quiet tropical oasis. Located 2 blocks from the famous Duval with restaurants, shopping & live music........read more
7 Bedrooms
- Sleeps 8
Vacation Rental Home in Key West
Welcome to the Shady Palms - Private Pool - RealKeyWest
Key West Vacation Rental 5.0 Star Review
Step into this beautifully restored and redecorated 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 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.......read more
2 Bedrooms
- Sleeps 6
Vacation Rental Home in Key West
Superb Location, Affordably Priced
Key West Apartment 4.8 Star Review
This Studio is a lovely charmer nestled in a 6 unit compound in a residential neighborhood in the center of Old Town Key West. This pet friendly accommodation is the perfect location for exploring Key West. You can walk to the Hemmingway House, the Butterfly Conservatory and stroll Duval St with it's many restaurants, shops, galleries and museums. .......read more
1 Bedrooms
- Sleeps 2
Apartment in Key West
Villa Nomade at Shipyard Condominiums
Key West Condo 4.9 Star Review
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.......read more
2 Bedrooms
- Sleeps 4
Condo in Key West
Little Casita: Key West Monthly rental Close to Duval - RealKeyWest
Key West Apartment 4.3 Star Review
WELCOME TO LITTLE CASITA!
If looking for the perfect couple’s retreat, look no further!
This one bedroom, one bath historic apartment is located just blocks from Key West’s famous Duval Street & Historic Seaport where you’ll find restaurants, shops, and bars. The residential neighborhood will make you feel like a local!
.......read more
1 Bedrooms
- Sleeps 2
Apartment in Key West
Rose Lane Villas - Villa Porta - 1 Bedroom - Downtown Key West
Key West Condo 4.8 Star Review
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 av.......read more
1 Bedrooms
- Sleeps 4
Condo in Key West
Hidden Treasure- 2 bedroom 2 bath with shared pool
Key West Cabin 4.7 Star Review
Hidden from sight, among a colony of freestanding conch cottages, surrounded by lush tropical landscaping, you will find Hidden Treasure. Truly a treasure, it is the sister cottage of Island Style, owned by two sisters who share a passion for Key West. It features every high-end amenity that you could possibly desire. Two master bedrooms, two full .......read more
2 Bedrooms
- Sleeps 6
Cabin in Key West
A Touch of Bermuda at Truman Annex
Key West Cottage 4.8 Star Review
50% OFF I JUST HAD A CANCELLATION FOR THE WEEK OF DECEMBER 2-9. Envision yourself relaxing in a beautiful wood framed conch cottage with overhead fans lazily turning below the sloping tin roof in the heart of Old Town in Key West. This is the best value in Key West as it is no cookie cutter small rental condo but a private townhome (one of only .......read more
2 Bedrooms
- Sleeps 6
Cottage in Key West
Escape to The Gumbo Limbo Cottage, a charming 2BR, 2.5BA vacation rental
Key West Vacation Rental 5.0 Star Review
Escape to the laid-back charm of Key West with The Gumbo Limbo Cottage, a beautiful and beachy vacation rental. Nestled in the heart of the island, this charming 1933 shotgun house has been impeccably restored and uniquely decorated, creating a tranquil and inviting atmosphere for your month-long getaway.
As soon as you step inside, you'll b.......read more
2 Bedrooms
- Sleeps 4
Vacation Rental Home in Key West
Mulligan's Place - New Listing - Beautiful 3/2 Golf Course Home
Key West Vacation Rental 5.0 Star Review
Welcome to this Key West Tropical charmer located only 15 minutes away from Downtown Duval Street. This townhome is located in a gated community called the Key West Golf Club.
This pleasant, bright and spacious townhome comes with a large backyard space for entertaining or just lounging around and is located on a quiet cul de sac. This townhome .......read more
3 Bedrooms
- Sleeps 6
Vacation Rental Home in Key West
Caroline On My Mind-New Listing-Light, Bright and Airy!
Key West Condo
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 ho.......read more
2 Bedrooms
- Sleeps 4
Condo in Key West
Your own Private Resort! 50ft Dock on Canal w/ Pool and RV Hookup!
Key West Vacation Rental 5.0 Star Review
Discover your private paradise in the Keys! This exquisite waterfront home offers a unique opportunity to experience the beauty of the area with your own private beach, resort-style tiki hut, pool, and a 50ft dock. Just 15 minutes away from Duval Street, this is your ultimate getaway.
Highlights of your stay:
*A 1/3-acre property wit.......read more
3 Bedrooms
- Sleeps 8
Vacation Rental Home in Key West
The Caribbean Suite - 2-K-bedroom /1 bath/ kitchenette/sleeps 6
Key West Condo 4.9 Star Review
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 al.......read more
2 Bedrooms
- Sleeps 4
Condo in Key West
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.
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, Florida 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.