Key West Vacation Rentals in the Florida Keys
Book Places to Stay and Vacation Home Rentals in Key West, Florida Keys Directly Online Here and Save!
We have many choices for Key West, Florida Keys Vacation Rentals, Homes and Condos with Wi-Fi, Pool, Oceanview, Beachfront and other amenities they have to offer for your visit to Florida.
Your Condo by the Beach with Ocean View
Key West Condo 
10.0
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 Bedroom(s)
1 Bath(s) Sleeps 2
BEACH HOUSE ~ Stunning 4B/4Ba Home with Private Pool in Truman Annex!
Key West Private vacation home 10.0
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 Bedroom(s)
4 Bath(s) Sleeps 8
BOTTOMS UP BUNGALOW - PERFECT 2 Bed/2 Bath PRIVATE POOL
Key West Private vacation home 10.0
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 Bedroom(s)
2 Bath(s) Sleeps 6
Panoramic 3BR/3BA Condo - Direct Beach Ocean Front
key west Condo 10.0
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 Bedroom(s)
3 Bath(s) Sleeps 8
Villa Fleur at Shipyard Condominiums
Key West Condo 9.8
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 Bedroom(s)
1 Bath(s) Sleeps 4
Rose Lane Villas - Villa Vista - 2 bedrooms - Downtown Key West
Key West Condo 9.8
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 Bedroom(s)
2 Bath(s) Sleeps 4
Simonton Studio, an Old Town get-away for 2
Key West Apartment 9.8
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
1 Bath(s) Sleeps 2
Key West Rooster
Key West Condo 10.0
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 Bedroom(s)
1 Bath(s) Sleeps 4
~DREAMING ON DUVAL~ Grand 5 bedroom, 4.5 bath home with private pool/parking
Key West Private vacation home 10.0
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 Bedroom(s)
5 Bath(s) Sleeps 10
Peaceful Setting Amongst The Active Island Life Style
Key West Condo 9.8
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 Bedroom(s)
2 Bath(s) Sleeps 4
Rare Penthouse 2 bed/2bath additional King in loft
Key West Condo 9.4
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 Bedroom(s)
2 Bath(s) Sleeps 8
Old Town 2 Bicycles, Grill, WiFi, 1st Floor, Pool! Rent 30 days get 20% discount
Key West Condo 10.0
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 you.......read more
2 Bedroom(s)
1 Bath(s) Sleeps 4
MAJESTIC PARADISE @ Truman Annex - Heart of Old Town, Key West
Key West Condo 10.0
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 Bedroom(s)
1 Bath(s) Sleeps 5
Henry's Penthouse on the Ocean in Key West - weekly / nightly rentals
Key West Condo 9.6
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 Bedroom(s)
2 Bath(s) Sleeps 5
Key West Suites Hotel - Adam Scott Rote Suite
Key West Apartment 9.6
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 Bedroom(s)
1 Bath(s) Sleeps 6
Location, location, location in the heart of Old Town!
Key West Private vacation home 10.0
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 Bedroom(s)
3 Bath(s) Sleeps 6
Beach Paradise in the Keys! Location! Location! 2 Blocks to Duval St
Key West Private vacation home 9.4
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 Bedroom(s)
3 Bath(s) Sleeps 8
Shady Palms - Stay In Comfort- May - Aug 10% OFF - 2BD/2.5Bath - Private Pool
Key West Private vacation home 10.0
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 Bedroom(s)
3 Bath(s) Sleeps 6
Superb Location, Affordably Priced
Key West Apartment 9.8
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 Bedroom(s)
1 Bath(s) Sleeps 2
Rose Lane Villas - Villa Porta - 1 Bedroom - Downtown Key West
Key West Condo 9.6
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 Bedroom(s)
1 Bath(s) Sleeps 4
A Touch of Bermuda in Key West
Key West Cottage 9.8
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 Bedroom(s)
2 Bath(s) Sleeps 6
The Gumbo Limbo Cottage - Your Happy Place - 2BD/2.5 Bath
Key West Private vacation home 10.0
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 Bedroom(s)
3 Bath(s) Sleeps 4
Caroline On My Mind - Paradise, Upgraded - 2BD/2Bath - Prime Location!
Key West Condo 10.0
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 Bedroom(s)
2 Bath(s) Sleeps 4
Your own Private Resort! 50ft Dock on Canal w/ Pool, Tiki and RV Hookup!
Key West Private vacation home 10.0
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 Bedroom(s)
2 Bath(s) Sleeps 8
The Caribbean Suite - 2-K-bedroom /1 bath/ kitchenette/sleeps 6
Key West Condo 9.8
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 Bedroom(s)
1 Bath(s) Sleeps 4
BRIGHT SUNSHINY DAY ~ Renovated 3 BR, 4 Ba Home w/ Pool, Spa & Exercise Room!
Key West Private vacation home 10.0
OLD TOWN CLASSIC...
This beautifully redesigned Conch house is in the heart of Key West. Located in the outstanding location of Southard and Ashe Streets, this upscale abode is just minutes from Duval's many restaurants and bars. You are within walking and biking distance to museums, shopping, and Fort Zachary Taylor beach. Come inside this bri.......read more
3 Bedroom(s)
4 Bath(s) Sleeps 6
SEA FOREVER ~ Downtown Ocean View Home w/ 3 BR, 3.5 Ba w/ Pool!
Key West Private vacation home 9.6
MODERN TROPICAL JEWEL WITH STUNNING OCEAN VIEWS…
This contemporary and spacious custom-built gated home will beguile your senses, luring you inside with the finest of amenities and stunning design. Just a stone's throw away from the infamous Whitehead Southernmost Buoy, you are truly seated in the heart of paradise in this small gated communit.......read more
3 Bedroom(s)
4 Bath(s) Sleeps 6
TROPICAL PROPERTIES VACATION RENTAL - KEY WEST
Key West Private vacation home 10.0
****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 f.......read more
3 Bedroom(s)
2 Bath(s) Sleeps 8
Duval Square Retreat w/ Private Hot Tub, Pool, Parking & Walkable Location!
Key West Private vacation home 9.4
"Welcome to Duval Square" a secluded and gated community located on
upper Duval St; these properties are some of the most prestigious
on the island, which offer lush tropical landscaping, swimming pool
and private jacuzzi. This location is perfect for either complete
seclusion or if you prefer to view the many sights from above. Y.......read more
2 Bedroom(s)
3 Bath(s) Sleeps 6
Key West dream townhouse -Sleeps 6 Like new! Old Town - Perfect location
Key West Private vacation home 10.0
This property is a rare find! Sleeping 6 and located over 2 floors, its located in the beautiful resort of Santa Maria. The condo itself is overlooking the pool, enjoys 2 stunning balconies with its own outdoor furniture. Fully equipped kitchen, 2 1/2 bathrooms, TVs and wifi throughout. The property is located in one of the best destinations within.......read more
2 Bedroom(s)
3 Bath(s) Sleeps 6
Hyatt Windward Pointe 2 Bedroom
Key West Apartment
★Excellent Key West Location - Oceanside Property - 2-Bedroom - 2-Bathroom - Sleeps 6.
★Very Clean - Very Nice Property.
Guests can enjoy the beautiful ocean breeze right next to the property. Guests may also enjoy the relaxing pool and the fully-equipped health and fitness center.
LOCATION:
Enjoy the white sands of the .......read more
2 Bedroom(s)
2 Bath(s) Sleeps 6
Hyatt Windward Pointe 2 Bedroom
Key West Apartment 10.0
★Excellent Key West Location - Oceanside Property - 2-Bedroom - 2-Bathroom - Sleeps 6.
★Very Clean - Very Nice Property.
Guests can enjoy the beautiful ocean breeze right next to the property. Guests may also enjoy the relaxing pool and the fully-equipped health and fitness center.
LOCATION:
Enjoy the white sands of the .......read more
2 Bedroom(s)
2 Bath(s) Sleeps 6
Tranquil Beauty-Private Pool - Outside Lanai-Beaches Nearby
Key West Private vacation home 10.0
A gorgeous 3 bedroom / 2 bathroom vacation rental home with high vaulted ceilings and French doors. Three private bedrooms with all "smart" flat screen tv's and high speed internet. The backyard features a large covered patio and an in-ground heated swimming pool for the winter months and a chiller for the summer months perfect for relaxing anytim.......read more
3 Bedroom(s)
2 Bath(s) Sleeps 8
Quiet Lane in the Heart of Old Town, Sleeps 4, Dog Friendly
Key West Private vacation home 10.0
Recently renovated home located on a quiet lane just 1 block from the iconic Green Parrot Bar and 2 blocks from world famous Duval Street. Blue Heaven, Hemingway House and Willie T’s are all just a few hundred feet from the front door, and you’d never know it because the house is on a private and quiet one-block lane.
The house itself ha.......read more
2 Bedroom(s)
3 Bath(s) Sleeps 2
**SOUL OF DUVAL @ DUVAL** Modern/Centrally Located + LAST KEY SERVICES...
Key West Condo 10.0
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 all.......read more
2 Bedroom(s)
1 Bath(s) Sleeps 4
Sunset Harbor - Old Town Key West Location - Beautiful Property
Key West Condo 8.0
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, bo.......read more
1 Bedroom(s)
1 Bath(s) Sleeps 4
Old Town Key West Compound with Pool, Parking and Privacy One Block Off Duval!
Key West Cottage 10.0
Down a hidden lane in the heart of Old Town Key West you will find Loco Court. The compound is located one block off Duval St but is completely private and serene.
The compound consists of THREE STAND ALONE COTTAGES alongside a tranquil PRIVATE POOL and connected to each other by a spacious deck.
The first cottage (unit 1) and second .......read more
4 Bedroom(s)
4 Bath(s) Sleeps 12
Truman Annex Best Location in Town
Key West Condo 9.8
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 wo.......read more
2 Bedroom(s)
1 Bath(s) Sleeps 5
**JASMINE JEWEL @ THE ANNEX** Lush Private Home & Pool + LAST KEY SERVICES…
Key West Private vacation home 9.8
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival!
Hidden amongst the thick of Old Town Key West, within Truman Annex, Key West's most exclusive gated community, lives a 'gem' of a home that will surely capture your heart's desire from the moment you lay eyes on it. JASMINE JEWEL is a tw.......read more
2 Bedroom(s)
3 Bath(s) Sleeps 6
Key West, Gated Truman Annex Condo, new Waterfront Park, and Ft. Zach Beach.
Key West Condo 9.6
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, res.......read more
2 Bedroom(s)
1 Bath(s) Sleeps 4
Amelia`s Hideaway - Hidden Key West Courtyard - Steps off Duval w Private Pool
Key West Villa 8.8
"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 i.......read more
4 Bedroom(s)
4 Bath(s) Sleeps 10
Rose Lane Villas - Villa Rosa - 1 Bedroom - Downtown Key West
Key West Condo 9.6
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.......read more
1 Bedroom(s)
1 Bath(s) Sleeps 4
Freshly Renovated Cottage Old Town MONTHLY
Key West Private vacation home 9.0
This 1200 sq ft luxury apartment in the the heart of Old Key West is located only 2 blocks off Duval St and is a short walk or bike to all the fun of Key West ! Very quiet street with no through traffic. The property is completely private and safe, surrounded by a 6 foot gated fence and tropical landscaping.
Due to local zoning laws we can only.......read more
1 Bedroom(s)
1 Bath(s) Sleeps 4
ATLANTIC HIDEAWAY- Key West
Key West Condo 9.6
NEWLY REMODELED in the Summer of 2022 this 2 bedrooms, 2-bathroom condo checks all the boxes for your vacation needs!
Located in the 1800 Atlantic condo complex with two large communal swimming pools, spa, tennis courts, fitness facilities, private beach, walking paths, BBQ area and recreation room/ library. The opportunities for entertainme.......read more
2 Bedroom(s)
2 Bath(s) Sleeps 6
MAI TAI TERRACE - KEY WEST
Key West Condo 9.6
Welcome to Mai Tai Terrace located in The Shipyard subdivision of Truman Annex in beautiful Key West.
This 2-bedroom, 2-bathroom end unit condo is spacious and comfortable for guests of all types.
An open concept living, dining and kitchen allows this second story condo to flow freely. With vaulted ceilings and large windows this tr.......read more
2 Bedroom(s)
2 Bath(s) Sleeps 6
A Fish Bowl at The Truman Annex in Key West
Key West Condo 10.0
A beautiful 2 bedroom, 1 bath downstairs condo located in The Shipyard section of Truman Annex. This pristine residential community is one of the most requested locations in the heart of Old Town Key West. A wonderful mix of a private community yet easy walking distance to the Duval Street attractions, Mallory Square, and Fort Zachary Taylor State .......read more
2 Bedroom(s)
1 Bath(s) Sleeps 4
A Touch Of Cuba In Key West
Key West Condo 10.0
HALF PRICE! A GREAT WEEK THIS NOVEMBER 25-DEC 2 Welcome to Conch Republic and the Shipyard section of the Truman Annex. You have many choices of accommodations and since I am not a real estate salesman or property manager, allow me let the photos and description speak for themselves. My oversized two bedroom, one bathroom condominium or casita .......read more
2 Bedroom(s)
1 Bath(s) Sleeps 4
THE WEEKEND HOUSE ~ 3 Bedroom, 2 Bath Condo Centrally Located w/ Pool!
Key West Condo 10.0
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
3 Bedroom(s)
2 Bath(s) Sleeps 6