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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 boat

The Unforgettable

Stay aboard this luxurious mega yacht!

This unique, one of a kind yacht is the perfect alternative to a hotel room. Docked in a premium slip at Stock Island Marina Village, one of the nicest marinas in Key West. The marina offers a huge salt water swimming pool, upscale hotel, and po ....

3 Bedroom(s) 4 Bath(s) Vacation Rental
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

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

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

Island Escape in Truman Annex

Quaint Island Escape Condo w/Spacious Balcony Deck in Beautiful Truman Annex

This lovely Island Escape Condo is a upper level condo located in the Truman Annex Shipyard a luxury gated community. Not just another rental property! Location is everything.!!! Our favorite room is the spacious covered deck that opens up from livin ....

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

Royal Poinciena

Royal Poinciana @ 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 ¼ mile from one of the best beaches on the island. The Shipyard u ....

1 Bedroom(s) 1 Bath(s) Vacation Rental - Sleeps 2
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

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

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 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

Island Dreaming

Extraordinary Beach Cottage... Spectacular Ocean Views..10 minutes from Key West

Enjoy the best open ocean views in all of the Florida Keys, with water on 3 sides of the property and no adjacent neighbors. This 1920 sq. ft. beach home was built in 2004 and has an open floor plan with high ceilings. It has all new appliances. Fish ....

3 Bedroom(s) 2 Bath(s) Vacation Rental - Sleeps 8
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 Rental - Sleeps 8
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 Rental - Sleeps 4
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 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 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 condo

Gulfside Vistas

**GULFSIDE VISTAS @ THE ANNEX** Ocean Penthouse & Pool + LAST KEY SERVICE...

GULFSIDE VISTAS is a beautiful penthouse condo and is the perfect place to spend your stay in Key West, with panoramic views of the Gulf and cruise ships as they dock nearby. You'll have ocean views on three sides of GULFSIDE VISTAS, and two spacious ....

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

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Key West studio

Vacation Home

Galleon Resort Efficiency in Old Town

This efficiency is located on the 5th floor of the Galleon Resort. One of only two efficiencies with both a king size bed and a balcony (resort view). This unit has a brand new kitchenette featuring new wood cabinets, granite countertop and new sta ....

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

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Key West boat

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

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Key West house

Southernmost Bliss

**SOUTHERNMOST BLISS @ OLD TOWN** Lavish Home & Pool + LAST KEY SERVICES...

Nestled at the end of a narrow, private lane just two short blocks from Duval Street and the Historic Seaport is a truly exceptional Key West home that redefines upscale charm in the heart of Old Town. This home was designed to combine the best of cl ....

3 Bedroom(s) 3 Bath(s) Vacation Rental
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

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 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 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

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

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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

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

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

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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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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