Best Rental Prices in Key West, FL
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Cheap Hotels Key West, FL
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We have partnered with a major provider for Vacation Rentals by Owner, directly through Vacation Places To Stay. There are many home rentals to choose from, and we now have the selection and value to offer our visitors going to Key West, FL. Browse hundreds of Homes and Condos with Wi-Fi, Pool, Oceanview, Beachfront and other amenities they have to offer.
Tropical Jewel
Tropical Jewel in Historic Seaport - 2BR/2BA - Pool - Monthly Rental
WELCOME TO TROPICAL JEWEL! Imagine yourself staying in this immaculate restored home just two blocks away from the Historic Seaport. Relax on the front porch in Adirondack chairs while enjoying a cold beverage. This home has it all, from the beau ....
2 Bedroom(s)
2 Bath(s) Cottage
Key West, FL
Sago Palm
Sago Palm @ the Truman Annex
The Presidents Walk and Southard Court community is located in the Truman Annex Complex which is located 2 blocks from Duval Street and all of the Old Town Key West attractions. The properties are also located less than a half mile from one of the be ....
2 Bedroom(s)
3 Bath(s) Vacation Rental - Sleeps 4
Key West, FL
Fun In The Sun
Fun in the Sun @ the Truman Annex
This stately 2 bedroom townhouse in the President's Walk area of Porter Lane is furnished with tropical and luxury decor, and is loaded with amenities such as TV's in each bedroom. The community is located in the Truman Annex Complex which is located ....
2 Bedroom(s)
3 Bath(s) Vacation Rental - Sleeps 6
Key West, FL
Key West Condo
Quiet, elegant, Key West Condo close to the Ocean
This 2 bedroom (one King and one Queen, plus Queen size pull out couch in the living room), 2 bathroom unit offers all the convenience and comfort of your own home. It is spacious and fully equipped. Located one mile from Smathers Beach, two miles f ....
2 Bedroom(s)
2 Bath(s) Condo - Sleeps 6
Key West, FL
Southernmost Solace
**SOUTHERNMOST SOLACE @ OLD TOWN** Conch Cottage Near Duval + LAST KEY SERVICES...
At the Southernmost tip of America's Southernmost City lives an adorably renovated cottage that possesses a complimentary mix of classic comfort and a modern coastal style. SOUTHERNMOST SOLACE is a charming one-story private home that is located on E ....
2 Bedroom(s)
2 Bath(s) Vacation Rental
Key West, FL
Mermaids Cove at 1800 Key West Monthly
Great Monthly Rental available April 1st 2019
Mermaids Cove is a totally Renovated 2 bedroom 2 bath Condominium at 1800 Atlantic. This Condominium is tiled throughout and is immaculate. Both bedrooms have a king size bed. There is wireless high speed internet. Fully size fully equipped eat in ki ....
2 Bedroom(s)
2 Bath(s) Condo
Key West, FL
Sunset Reverie
**SUNSET REVERIE @ SUNSET MARINA** Condo / Pool & Spa + LAST KEY SERVICES...
SUNSET REVERIE is located in Sunset Marina, a gated community located on Stock Island right off the entrance to Key West. The location is a great balance between being secluded in a private community yet still only a short Uber ride into the best of ....
3 Bedroom(s)
2 Bath(s) Condo
Key West, FL
Casa Blanca
Casa Blanca: 3 BR, 2.5 BA House in Key West, Sleeps 6
This luxurious beautiful 3 bedroom 2 1/2 bathroom house is located in old town Key West. 1st Floor has open floor plan with hardwood floors, gourmet kitchen, dining Room , 1/2 bathroom and a 3rd bedroom. The 2nd floor has a large master bedroom with ....
3 Bedroom(s)
3 Bath(s) Vacation Rental
Key West, FL
"PINEAPPLE COTTAGE" ~ Relaxing!
"PINEAPPLE COTTAGE" ~ Adorable, Updated Cottage in Old Town with Pool!
RELAXED DOWNTOWN LIVING... Envelop yourself in true island living in this cute cottage just for the two of you. Located one block from Duval with charming porch and shared heated pool. Walk or stroll to dining, night life, galleries, shopping, and be ....
1 Bedroom(s)
1 Bath(s) Cottage
Key West, FL
Treehouse Island
Treehouse Island @ The Truman Annex
Treehouse Island is a traditional Key West eyebrow house. Inside it's spacious and up-to-date, yet as comfortable as you would expect a personal residence to be. Living areas include a large great room, a front sitting room and dining room. A well-fu ....
3 Bedroom(s)
4 Bath(s) Vacation Rental - Sleeps 8
Key West, FL
Sun, Sea, And Sky
Sun, Sea and Sky @ the Truman Annex
Sun Sea and Sky is only two blocks from bustling Duval Street, the heart of Old Town Key West, with an easy walk to restaurants, shops and many other Key West attractions. Sun, Sea & Sky, decorated with private art and lots of mirrored walls, boasts ....
1 Bedroom(s)
1 Bath(s) Vacation Rental - Sleeps 4
Key West, FL
Aquamarine Delight on the Ocean C333
Aquamarine Delight on the Ocean C333: 2 BR, 2 BA Condominium in Key West, Sleeps 4
Enjoy ocean views from this bright and airy 3rd floor unit. This newly renovated unit comes fully equipped with attention to your every need. King bed in the master and queen bed in the guest room will make your stay comfortable. This unit comes c ....
2 Bedroom(s)
2 Bath(s) Condo
Key West, FL
Viva Margarita!
**VIVA MARGARITA! @ OLD TOWN** Large Home & Pool Near Duval + LAST KEY SERVICES...
Key West is the mecca for those seeking to live life the way it is supposed to be lived: in the sunshine with a cold drink in hand. VIVA MARGARITA! was designed to house those sun-seekers. This tropically decorated three-story home has an open living ....
3 Bedroom(s)
5 Bath(s) Vacation Rental
Key West, FL
Dolphin Watch
Dolphin Watch @ the Truman Annex
RECENTLY UPDATED & VERY LUXURIOUS water front home located in the heart of downtown Key West within walking distance to all downtown attractions and the famous Fort Zachary Taylor Beach. This home has 2 master ensuites with king beds, and there is a ....
4 Bedroom(s)
3 Bath(s) Vacation Rental - Sleeps 8
Key West, FL
Vacation Home
DESIGN YOUR OWN WATER ADVENTURE
A well appointed and renovated 36' Morgan Out Island Sloop, at ANCHOR with no dock, north of KW harbor . 2 guest MAXIMUM. Water and coffee complimentary. Water taxi transport is available for checking in and out between 5-7pm and 10-12 DISCOUNTED ....
2 Bedroom(s)
1 Bath(s) Vacation Rental - Sleeps 2
Key West, FL
Awesome Waterfront in the Annex
@ Best of the Annex Waterfront with Fantastic Weekly Rates @
A beautifully appointed Gulf front Condo in the heart of Truman Annex. Mills place features a walkway flanked by Royal Palms. Mills place was the old military Hospital building. In the mid 80's it was purchased by a developer who renovated the entir ....
2 Bedroom(s)
2 Bath(s) Condo
Key West, FL
Away from it All
Away from it All @ The Truman Annex
Shipyard Condominiums are located in the prestigious gated community of Truman Annex in Key West’s old town area. The condos are located 2 blocks from Duval Street and all the Old Town Key West attractions. The properties are also ¼ mile from Fo ....
2 Bedroom(s)
1 Bath(s) Vacation Rental - Sleeps 4
Key West, FL
Starshine Key West
Starshine Key West @ the Truman Annex
Shipyard Condominiums are located in the Truman Annex Complex which is located 2 blocks from Duval Street and all of the Old Town Key West attractions. The properties are also located 1/4 mile from one of the best beaches on the island. The Shipyard ....
2 Bedroom(s)
1 Bath(s) Vacation Rental - Sleeps 4
Key West, FL
Meadows Manor
MEADOWS MANOR - Monthly vacation rental with 3BD/2BA - Lovely covered porches
WELCOME TO MEADOWS MANOR! Located in the sought after Meadows district, this lovely home in central to everything great Key West has to offer. This 3 bedroom, 2 bath beautifully decorated vacation home has all the comforts & style you’d expect f ....
3 Bedroom(s)
2 Bath(s) Vacation Rental
Key West, FL
Hearts & Palms House
Hearts & Palms House-Quaint 3BD/3Bath Monthly Home Rental - Private Pool
WELCOME TO HEARTS & PALMS HOUSE! Come and enjoy this quaint home on Elizabeth Street that boasts high ceilings and the original Dade County Pine wood walls. The main house has 2 bedrooms with each having it's own en suite bathroom. The guest cottag ....
3 Bedroom(s)
3 Bath(s) Vacation Rental
Key West, FL
Joan's Caribbean Hideaway
Joan's Caribbean Hideaway
Just a few minutes from Key West, enjoy the peace and tranquility of this 2 story home, located in the Key West Golf Club with two community pools and a spacious clubhouse perfect for a home away in the tropics. A quick ride will get to Downtown Key ....
2 Bedroom(s)
2 Bath(s) Townhome - Sleeps 2
Key West, FL
Key West Kokomo Condo Rental
Ocean Front with Ocean View. Across from Smathers beach. Sleeps 5, 2/2 baths.
"Kokomo" is what we have named our unit. It is a 2 bedroom 2 baths with queen sleeper sofa in living room . Central AC in unit, clean unit, living/dinning is open concept. Master bedroom with a king bed, with private bathroom and access to balcony. W ....
2 Bedroom(s)
2 Bath(s) Condo - Sleeps 4
Key West, FL
A Southern Conch Cottage
A Southern Conch Cottage @ the Truman Annex
A Southern Conch Cottage is tucked away at the end of quiet Porter Lane in the award-winning gated community of the Truman Annex known as President's Walk. This wonderful 2 bedroom, 2 and 1/2 bathroom getaway has recently been updated! Enjoy the love ....
2 Bedroom(s)
3 Bath(s) Vacation Rental - Sleeps 4
Key West, FL
Vacation Home
Endless dreams a boat on a mooring in Key West
A 34 foot sailboat on a mooring in the harbor of Key West the boat has 2 good size beds a bigger than usual cockpit area 6 foot two Headroom there is also a boat bathroom and shower. This is an entire boat not a shared boat everybody who goes onto th ....
1 Bedroom(s)
1 Bath(s) Vacation Rental
Key West, FL
Dolphin Bay
Dolphin Bay: 2 BR, 2 BA House in Saddlebunch Key, Sleeps 6
Ocean view home with kayak near beaches, parks, shops & restaurants! Fresh ocean air, soft sands, and bright sunshine await you at this home in the Florida Keys! You and your loved ones can take in the tropics in peace and comfort, while still being ....
2 Bedroom(s)
2 Bath(s) Vacation Rental
Key West, FL
La Grande Reunion
**LA GRANDE REUNION @ OLD TOWN** Estate & Pool + LAST KEY SERVICES...
Traveling with a large group requires a special home. To maximize comfort, large common areas are offered both indoor and outdoor. Private bedroom accommodations with en-suite bathrooms and TVs are a must for your group. And don't forget about the lo ....
5 Bedroom(s)
6 Bath(s) Vacation Rental
Key West, FL
Blu On White
Blu on White · New to the Market! 4 Bed, 3 Bath-Old town w/ Pool!
NEW ON THE RENTAL MARKET This recently renovated four bedroom, three bathroom traditional shotgun house with a twist, has a master suite which can be accessed both privately and through the main house. The home has a spacious post and beam addition ....
4 Bedroom(s)
3 Bath(s) Vacation Rental - Sleeps 8
Key West, FL
Vacation Home
Old Town Key West Cottage
This funky shotgun house is located in the heart of Old Town Key West. The house has one large bedroom, a loft, and a pull out sofa. The house is designed with an open layout with large living room and kitchen. The kitchen is equipped with large frid ....
2 Bedroom(s)
2 Bath(s) Vacation Rental
Key West, FL
Poolside Hangover
Poolside Hangover @ the Truman Annex
Shipyard Condominiums are located in the Truman Annex Complex which is located 2 blocks from Duval Street and close to all of the Old Town Key West attractions. The properties are also located 1 mile from one of the best beaches on the island. All pr ....
2 Bedroom(s)
2 Bath(s) Vacation Rental - Sleeps 4
Key West, FL
La Vie En Rose
**LA VIE EN ROSE @ BEACHSIDE** Modern Home / Large Pool + LAST KEY SERVICES...
LA VIE EN ROSE is a classic mid-century modern home set in the Beachside district of Key West, just a couple blocks from Smathers Beach on Rose Street. As the lyrics to that sweet love song go, you'll be in 'a world apart'. You'll also be close to th ....
4 Bedroom(s)
4 Bath(s) Vacation Rental
Key West, FL
Find many Hotel Options and hundreds of Beachfront Vacation Rentals in Key West.
Spend quality time with your family and friends at cheap low rates you can afford, all while near the beach, nightlife, entertainment and a wide variety of beach activities. We have historic Key West Vacation Rentals, you may even find a Vacation Rental with Boat Dock or Boat Slip. Hundreds of properties to choose from, search for availability, photos, descriptions and best price. If you visit Key West in October, make sure to book your Vacation Rental here for Fantasy Fest.