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Rentals 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.

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

Vacation Home

COCONUT COTTAGE CONDO at SUNSET MARINA RESIDENCES

Kick your shoes off and enjoy this laid back two bedrooms, two bath spacious condo. Watch glorious sunsets from your balcony overlooking the marina and Florida Bay. The perfect Key West retreat with a large community pool and hot tub that are well ....

2 Bedroom(s) 2 Bath(s) Condo - Sleeps 4
Key West, FL

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Key West house

"VILLAGE ROOSTER"~ Rustic!

"VILLAGE ROOSTER" ~ Quaint Cottage in Bahama Village Steps from the FUN!

BAHAMA VILLAGE TREASURE... This pet friendly Old Town Key West home is just steps from the award winning restaurants and charming boutiques of Petronia Street in historic Bahama Village. The Village Rooster greets you with a charming front porch and ....

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

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Key West condo

Vacation Home

Beautiful Duval St. Condo, Location, Location!!!!

Location, Location, Location!!! You can't find a better location than Duval St. One of only three unique units. This Condo is above and behind Antonia's Restaurant (best Italian food in Key West!). Just newly redecorated in an urban tropical styl ....

2 Bedroom(s) 1 Bath(s) Condo - Sleeps 4
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 condo

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

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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 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

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 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 house

Vacation Home

Key West Downtown Restored Historic Home

First floor large apartment boasts all new, high end finishes, furniture and fixtures. In the quiet and exclusive Casa Marina neighborhood. Beaches, grocery store and many fine restaurants are all within just a pleasant walk. Duval is just far enou ....

3 Bedroom(s) 1 Bath(s) Vacation Rental - Sleeps 6
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 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

Archipelago II

Archipelago ll @ the Truman Annex

This newer renovation is a gorgeous 2 bedroom, 2.5 bath townhouse. The kitchen and baths are new and living room, dining area, and back patio are all updated and beautiful. The bedrooms have a queen size bed and 2 twin beds that can be converted to a ....

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

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Key West condo

Duval Roost

The Duval Roost: 2 Bed / 1 Bath in the middle of Duval Street

Snuggled halfway up our island's famous Duval Street and perched above the crowds is this fantastic 2 Bedroom 1 Bathroom condo aptly named, The Duval Roost. Sitting pretty much at the center-point of Duval Street, your vacation will feel like a 'Cho ....

2 Bedroom(s) 1 Bath(s) Condo
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 townhome

"COCONUT PALM" ~ Hidden Gem!

"COCONUT PALM" ~ Old Town Hidden Gem Located in the Midst of the Action!

***The photos shown for this unit are of the townhome directly next door which is an identical unit HISTORIC CONDO WITH MODERN TRANSFORMATION... Enjoy Key West while staying in this historic Old Town condo.  Relax while being steps away from one of ....

2 Bedroom(s) 3 Bath(s) Townhome
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 condo

Margaritas in Paradise A411

Margaritas in Paradise A411: 2 BR, 2 BA Condominium in Key West, Sleeps 6

This is a beautifully renovated high end luxurious monthly rental at 1800 Atlantic. The moment you walk in you will appreciate the attention to detail. Enjoy the lovely views of the complex and Atlantic ocean from the private balcony. The master bedr ....

2 Bedroom(s) 2 Bath(s) Condo
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 condo

Riviera Americana

**RIVIERA AMERICANA @ THE BEACH** Ocean Views + LAST KEY SERVICES...

A stay in Key West calls for a light and airy oasis, with breathtaking water views and an easy beach location to fully enjoy the ultimate of island life in America. RIVIERA AMERICANA is located in an upscale private community within walking or biking ....

3 Bedroom(s) 2 Bath(s) Condo
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 Rental - Sleeps 4
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

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 house

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

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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

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

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Key West condo

KEY WEST FANTASY FEST

KEY WEST FANTASY FEST WEEK OCT. 16-23, 2021

Key West, FL. Available Sat. Oct.19 - Sat. 26, 2019. Located in the Southeast end of Key West at the Hyatt Windward Pointe. The unit offers a 2/2 resort style apartment for 6 guests. Located next to the Key West Airport and a few blocks from the beac ....

3 Bedroom(s) 2 Bath(s) Condo - Sleeps 6
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 yacht

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

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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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