Rentals in Key West, FL
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Cheap Hotels Key West, FL
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Latitude Adjustment
Latitude Adjustment @ the Truman Annex
This Foundry townhouse is a Bostonian style 3 level home located in Old Town Key West. This home has been recently renovated to accommodate an individual couple, family, or vacationing couples that each desires the privacy of their own bedroom suite ....
2 Bedroom(s)
3 Bath(s) Vacation Rental - Sleeps 6
Key West, FL
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
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
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
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
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
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
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
Old Town Luxury Oasis
Old Town Luxury Oasis
Old Town Luxury Oasis One block off of the world famous Duval Street for the best in entertainment, night life, restaurants, shopping and more. Walking distance to the beach as well as the Sunset celebration at Mallory Square. This fully renovated ....
3 Bedroom(s)
2 Bath(s) Vacation Rental - Sleeps 6
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
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
"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
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
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
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
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
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
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
"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
Awake to the Morning Reflections C437
@ Reserve Morning Reflections for Monthly rent May - September 2020@
Beautifully renovated 2 bedroom 2 bath penthouse overlooking the Atlantic Ocean and Smathers Beach. Fabulous kitchen with stainless appliances and granite counter tops. Enjoy the amazing sunrise from the balcony of Awaken to Morning reflections. Rece ....
2 Bedroom(s)
2 Bath(s) Condo
Key West, FL
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
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
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
"LOST SHAKER OF SALT" ~ Relax!
"LOST SHAKER OF SALT" ~ 3 Bed, 2 Bath Pet Friendly Home with 40' Private Pool
THE HEART OF OLD TOWN... Charming Old Town home in the heart of Key West.  Located on Southard Street just steps from Duval's many restaurants and bars.  You are in walking distance to museums, shopping, and Fort Zachary Taylor beach.  Relax on ....
3 Bedroom(s)
2 Bath(s) Vacation Rental
Key West, FL
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
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
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
Worlds End
Worlds End @ the Truman Annex
This Harbour Place condominium is in Key West's most prestigious community of Truman Annex offering breath taking water and sunset views from the large and luxurious pool area. This beautifully decorated stately Condo has wonderful views of the Pool ....
2 Bedroom(s)
3 Bath(s) Vacation Rental - Sleeps 6
Key West, FL
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
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
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.