Rentals in Key West, FL
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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.
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
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
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
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
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
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
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
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
Sun, Sea, And Sky
Sun, Sea and Sky @ the Truman Annex
Sun Sea and Sky is only two blocks from bustling Duval Street, the heart of Old Town Key West, with an easy walk to restaurants, shops and many other Key West attractions. Sun, Sea & Sky, decorated with private art and lots of mirrored walls, boasts ....
1 Bedroom(s)
1 Bath(s) Vacation Rental - Sleeps 4
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
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
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
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
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
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
"COCONUT PALM" ~ Hidden Gem!
"COCONUT PALM" ~ Old Town Hidden Gem Located in the Midst of the Action!
***The photos shown for this unit are of the townhome directly next door which is an identical unit HISTORIC CONDO WITH MODERN TRANSFORMATION... Enjoy Key West while staying in this historic Old Town condo. Â Relax while being steps away from one of ....
2 Bedroom(s)
3 Bath(s) Townhome
Key West, FL
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
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
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
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 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
"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
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
Viva Margarita!
**VIVA MARGARITA! @ OLD TOWN** Large Home & Pool Near Duval + LAST KEY SERVICES...
Key West is the mecca for those seeking to live life the way it is supposed to be lived: in the sunshine with a cold drink in hand. VIVA MARGARITA! was designed to house those sun-seekers. This tropically decorated three-story home has an open living ....
3 Bedroom(s)
5 Bath(s) Vacation Rental
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
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
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
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
"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
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
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.