Key West Florida Vacation Rentals, Hotels & Resorts

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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.

Key West house

Captains Wheel

Captains Wheel @ the Truman Annex

This very popular getaway in the award-winning Truman Annex is a tropically decorated 2 bedroom, 2.5 bath town home featuring an open floor plan with a great rear deck for entertaining and relaxing. The master bedroom has it's own balcony and the gue ....

2 Bedroom(s) 3 Bath(s) Vacation Rental - Sleeps 6
Key West, FL

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Key West apartment

Suite Blu

Suite Blu - A monthly rental apartment in a great location

Location, location, location! Situated in the heart of the Cuban district, steps from arguably the best 'con leche' in Key West. This monthly rental is minutes from everything on the island. No cars are necessary, bikes and beach chairs are provided ....

1 Bedroom(s) 1 Bath(s) Apartment - Sleeps 2
Key West, FL

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Key West house

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

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Key West townhome

"CORAL CABANA" ~ Tropical Comfort!

"CORAL CABANA" ~ Lush Porch Views of the Pool & Gardens, near Golf Course!

GATED COMMUNITY, CLOSE TO BOATING AND GOLFING... Coral Cabana, in the Coral Hammock Community is a gorgeous three bedroom, three bath townhome with over 2,000 square feet of indoor/outdoor living space. A tranquil pool view can be easily appreciated ....

3 Bedroom(s) 3 Bath(s) Townhome
Key West, FL

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Key West house

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

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Key West house

Worlds End

Worlds End @ the Truman Annex

This Harbour Place condominium is in Key West's most prestigious community of Truman Annex offering breath taking water and sunset views from the large and luxurious pool area. This beautifully decorated stately Condo has wonderful views of the Pool ....

2 Bedroom(s) 3 Bath(s) Vacation Rental - Sleeps 6
Key West, FL

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Key West condo

Anglers Retreat Crystal Waters C429

@March 2020 $7750 plus fees Anglers Retreat open @@

Welcome to our paradise please enjoy our modern 1400 square foot 2 bedroom 2 bathroom totally renovated condo. This condo is one of the nicest you will find in the complex. There is music available in every room even the master bathroom. We have thou ....

2 Bedroom(s) 2 Bath(s) Condo
Key West, FL

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Key West condo

Shipyard 253

Shipyard 253 - 2 Bedroom Condo with a Shared Pool

7 night minimum stay condo upstairs unit with 2 bedrooms and 1 Bathroom upstairs spacious unit with 1 queen, 2 twins and 1 pullout sofa. . The unit comes with one assigned parking spot. There is alot to see and do in historic Key West. Enjoy touring ....

2 Bedroom(s) 1 Bath(s) Condo
Key West, FL

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Key West condo

Walking on Sunshine

**WALKING ON SUNSHINE @ THE BEACH** Oceanfront Condo w/ Community Pool + LAST KEY SERVICES…

WALKING ON SUNSHINE is a modern, tastefully decorated penthouse condo featuring a large wrap-around balcony that offers a front row seat to those famous Key West sunsets and overlooks the peaceful nature preserve and Atlantic Ocean beyond. Best of al ....

2 Bedroom(s) 2 Bath(s) Condo
Key West, FL

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Key West house

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

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Key West townhome

"THE NAUTILUS" ~ Near it All!

"THE NAUTILUS" ~ Updated 2 bed, 2.5 bath in Truman Annex w/ pool & Gas Grill

SURROUNDED BY HISTORY AND BEAUTY... Nestled in Truman Annex along President’s Walk you will find The Nautilus; a sophisticated unit with comfort and luxury plus the convenience of an Old Town location and walking distance to Fort Zachary Taylor Bea ....

2 Bedroom(s) 3 Bath(s) Townhome
Key West, FL

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Key West house

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

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Key West house

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

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Key West condo

Pelican Landing Dominica Retreat

Pelican Landing Dominica Retreat

Families are welcomed in our vacation rentals. Student groups are not permitted. Our minimum age requirement to rent is 25 years old. Everyone in your party must be 25 years old to check in unless accompanied by a parent. No Birthday Bachelor or Bach ....

2 Bedroom(s) 2 Bath(s) Condo
Key West, FL

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Key West condo

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

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Key West condo

Smooth Sailing

**SMOOTH SAILING @ THE BEACH** Ocean Condo / Pool & Tennis + LAST KEY SERVICES...

Formerly La Bonne Vie, SMOOTH SAILING has been meticulously furnished with a modern coastal feel, and the only beauty that competes with the interior is the spectacular views from your private oceanfront balcony. You'll be able to enjoy quiet afterno ....

2 Bedroom(s) 2 Bath(s) Condo
Key West, FL

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Key West house

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

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Key West house

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

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Key West townhome

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

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Key West house

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

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Key West house

Blue Pelican

Blue Pelican - Comes With 6 Passenger Gas Golf Cart

Beautiful, BRAND NEW open floor plan, custom décor, private pool, gas golf cart, and ALL the amenities! KITCHEN Modern chef’s kitchen, with large island seating overlooking the beautifully appointed dining, living area, and sparkling pool. Fu ....

4 Bedroom(s) 3 Bath(s) Vacation Rental - Sleeps 8
Key West, FL

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Key West house

Memory Lane

**MEMORY LANE @ OLD TOWN** Cottage + Pool + LAST KEY SERVICES…

Preserving the best of Old Key West with the added comforts of the latest modern luxuries, this quintessential Conch Cottage transports you back to all that we love about the magical Key West experience. Tucked at the very end of a famed Old Town la ....

2 Bedroom(s) 2 Bath(s) Vacation Rental
Key West, FL

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Key West house

Banana Breeze

Oceanview home with expansive decks and private pool in lush landscaping

"Banana Breeze" is an upscale escape by the sea, and considered by some to be a hidden gem. Tucked away in your own oasis in a private waterfront retreat, with your own heated pool. Look out at the open water views while enjoying the professionally ....

4 Bedroom(s) 3 Bath(s) Vacation Rental
Key West, FL

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Key West house

Brisa Fresca

**BRISA FRESCA @ THE ANNEX** Airy Home by Duval & Beach + LAST KEY SERVICES...

A trip to Key West is like a breath of fresh air! The sounds of rustling palm trees, the scent of fragrant flowers and the smell of salt air are the rejuvenation that only the tropics can provide. This home is a breath of Key West fresh air, or BRISA ....

3 Bedroom(s) 3 Bath(s) Vacation Rental
Key West, FL

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Key West house

Old Town Luxury Oasis

Old Town Luxury Oasis

Old Town Luxury Oasis One block off of the world famous Duval Street for the best in entertainment, night life, restaurants, shopping and more. Walking distance to the beach as well as the Sunset celebration at Mallory Square. This fully renovated ....

3 Bedroom(s) 2 Bath(s) Vacation Rental - Sleeps 6
Key West, FL

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Key West condo

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

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Key West condo

Pelican Landing Abaco Retreat

Pelican Landing Abaco Retreat

Families are welcomed in our vacation rentals. Student groups are not permitted. Our minimum age requirement to rent is 25 years old. Everyone in your party must be 25 years old to check in unless accompanied by a parent. No Birthday Bachelor or Bach ....

2 Bedroom(s) 2 Bath(s) Condo
Key West, FL

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Key West cottage

"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

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Key West house

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

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Key West house

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

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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.

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