Rentals in Key West, FL
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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
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
DREAM MAKER at 1800 ATLANTIC
NEWLY RENOVATED ...LAST MINUTE SPECIALS...CHECK DATES
THIS IS DREAM MAKER...THE ONE YOU HAVE BEEN SEARCHING FOR Let us help make your dreams come true: Enjoy your tranquil view of the deep blue Ocean and sparkling salt water pool within our tropical garden.....There is nothing like it...anywhere. You ....
2 Bedroom(s)
2 Bath(s) Condo - Sleeps 6
Key West, FL
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
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
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
"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
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
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
"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
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
"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
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
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
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
"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
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
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
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
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
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
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
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
Blue Lagoon
Blue Lagoon @ the Truman Annex
This cheery property located on Southard Street features three bedrooms, one on the first level and two on on the second. There is a lovely kitchen, dining and living room which flows out through two sets of French doors onto the covered rear deck. T ....
3 Bedroom(s)
2 Bath(s) Vacation Rental - Sleeps 8
Key West, FL
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
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
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
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
"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
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
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.