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We have partnered with a major provider of vacation rentals, 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

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 Rentals - Sleeps 8
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 Rentals - Sleeps 6
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

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 Rentals
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 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 house

The Water's Edge

Palm Trees Ocean Breeze Key West FL

Three bedroom, four bathroom private home with heated pool . Breathtaking sunsets can be seen from third floor deck overlooking the Ocean. High definition TV and surround stereo throughout the home. High Speed internet and faxing available as well. ....

4 Bedroom(s) 4 Bath(s) Vacation Rentals
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

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 Rentals - Sleeps 6
Key West, FL

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Key West house

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 Rentals - Sleeps 4
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 Rentals - Sleeps 8
Key West, FL

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Key West condo

Condominium 1

Oceanfront Oasis Summ

Summary: A beautiful oceanfront suite located at the best marina in the Keys. Located off the azure waters of the Atlantic Ocean, minutes away from downtown Key West, known for its quaint boutiques, historic landmarks, sight-seeing, suns ....

1 Bedroom(s) 3 Bath(s) Condo
Key West, FL

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Key West house

Latitude Adjustment

Latitude Adjustment @ the Truman Annex

This Foundry townhouse is a Bostonian style 3 level home located in Old Town Key West. This home has been recently renovated to accommodate an individual couple, family, or vacationing couples that each desires the privacy of their own bedroom suite ....

2 Bedroom(s) 3 Bath(s) Vacation Rentals - Sleeps 6
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 apartment

The Maloney

The Maloney // A Historic Luxury Apartment

History + Luxury. The Maloney offers a unique experience for the discerning traveler visiting our iconic island city. The perfect complement of historic architecture and modern upgrades, creates an authentic luxury experience. Woven throughout this ....

2 Bedroom(s) 2 Bath(s) Apartment - Sleeps 6
Key West, FL

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Key West house

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 Rentals
Key West, FL

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Key West house

Low Tide

Charming, first floor end unit! GREAT LOCATION!!!

Low Tide is a charming first floor end unit in the Shipyard Condominiums in the award wining gated community of the Truman Annex. This property has recently been refreshed featuring new appliances, tvs, bedding, etc.! It is is located 2 blocks from D ....

2 Bedroom(s) 1 Bath(s) Vacation Rentals - Sleeps 4
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 Rentals - Sleeps 8
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

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 Rentals
Key West, FL

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Key West condo

Smathers Retreat on the Atlantic C239

Smathers Retreat on the Atlantic C239: 2 BR, 2 BA Condominium in Key West, Sleeps 6

Spectacular 2 bedroom 2 bath ocean-view overlooking the famous Smathers Beach, Enjoy the balmy ocean breezes from your private balcony and watch the world go by. This unit features 2 bedrooms, one king and one queen. For your convenience there are ....

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 house

Queen Emma*

Queen Emma @ the Truman Annex*

This beautifully finished and decorated four bedroom, three bath home has classic Key West architecture and is located on a charming tree lined street in Truman Annex. The custom designed two story home has an open floor plan on the main level with ....

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

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Key West house

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 Rentals
Key West, FL

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Key West house

3/4 Time

Oceanfront, Resort-like luxury home with private pool & lush landscaping

If you’re looking for an upscale escape by the sea, 3/4 Time is your Key West hidden gem. Enjoy the island life in your own oasis tucked away from the bustle of Old Town in a private waterfront retreat, with your own private waterfront pool. Luxuri ....

4 Bedroom(s) 4 Bath(s) Vacation Rentals
Key West, FL

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Key West house

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 Rentals - Sleeps 4
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

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 Rentals - Sleeps 4
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 townhome

Villa Bahama

**VILLA BAHAMA @ THE ANNEX** Villa Near Duval & Beach + LAST KEY SERVICES...

VILLA BAHAMA is located at The Foundry in the Truman Annex, Key West's most exclusive gated community. You'll be just around the block from Mallory Square, Duval Street and all the attractions Key West has to offer, yet you'll benefit from the peace ....

2 Bedroom(s) 3 Bath(s) Townhome
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. If you visit Key West in October, make sure to book your Vacation Rental here for Fantasy Fest. Hundreds of properties to choose from, search for availability, photos, descriptions and best price.

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