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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

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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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 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 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 condo

"JUST OFF DUVAL" ~ Heart of Key West!

"JUST OFF DUVAL" ~ Charming Condo in Center of Duval St. with Parking Space!

STEPS TO DUVAL ST… Take advantage of this premier opportunity to indulge in all your desired Key West bucket list items at this crisp condo centered in the heartbeat of Duval St. Located in the upbeat and lively district of Key West, this home is j ....

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

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Key West condo

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

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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 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 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 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 condo

"VILLA AZUL" ~ Perfect Location!

"VILLA AZUL" ~ Beautiful Unit Located in Truman Annex - Walk to all the Fun!

COMFORT AND VALUE IN OLD TOWN…. This second floor two bedroom condo is located in The Shipyard, a Truman Annex neighborhood.  You will enjoy being in the heart of Old Town Key West with food and fun just a short walk or bike ride away.   FURNISH ....

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 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

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 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 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 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 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 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

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 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

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

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

Starrs Atlantic Oasis C138

Starrs Atlantic Oasis C138: 2 BR, 2 BA Condominium in Key West, Sleeps 6

Beautiful 2 bedroom 2 bath unit, with a lovely view of the Atlantic Ocean. This unit is an extra large floor plan with a slighly large balcony. Access the Balcony from both bedrooms and the living room. There is a full size fully equipped eat in Kitc ....

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

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Key West boat

Key West Sailing Adventure

42 ft Sailboat Currently Out Of Service-Check Back With Us

Vacation Sailing Time Charter on your own private sailing vessel for a specific period of time with a customized sailing itinerary. Sunset sailing for two nights and 4 hour snorkeling 3-5 or more nights. Bird watching during migration month of Nove ....

2 Bedroom(s) 2 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 house

A Golf Club Oasis

A Golf Club Oasis in the Sanctuary @ the Key West Golf Club.

You will love this beautiful monthly rental spa home in the exclusive Sanctuary at the Key West Golf Club. Wonderfully renovated and maintained with 2 bedrooms and 2 1/2 baths with plenty of indoor and outdoor space to spread out. This lovely single ....

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