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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

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 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

"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

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 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

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 Rental - Sleeps 4
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 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 house

Dolphin Watch

Dolphin Watch @ the Truman Annex

RECENTLY UPDATED & VERY LUXURIOUS water front home located in the heart of downtown Key West within walking distance to all downtown attractions and the famous Fort Zachary Taylor Beach. This home has 2 master ensuites with king beds, and there is a ....

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

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 Rental
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

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 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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Key West condo

Shipyard 199

Paradise Found 2 Bedroom Condo with a Shared Pool Completely Renovated

Completely renovated, 7 night minimum rental. This condo has everything you want and more. Paradise is definitely found in this Non-Smoking, first floor end unit condo only two short blocks off of "happening" Duval Street in Old Town Key West. Locate ....

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

Key West Condo

Quiet, elegant, Key West Condo close to the Ocean

This 2 bedroom (one King and one Queen, plus Queen size pull out couch in the living room), 2 bathroom unit offers all the convenience and comfort of your own home. It is spacious and fully equipped. Located one mile from Smathers Beach, two miles f ....

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

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

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 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

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 Rental
Key West, FL

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Key West condo

Spinnaker

Spinnaker-Waterfront Monthly Vacation Rental 2 bedroom, 2 bath-Shared Pool

Harbour Place Condominiums: View passing ships and sunsets from your own deck or balcony in the Truman Annex's most prestigious building, the former U.S. Naval Headquarters in Key West. Take in the sunshine from the lap pool overlooking the ever chan ....

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 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 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 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

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 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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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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