Best Rental Prices 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.
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
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
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
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
"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
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
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
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
Blu On White
Blu on White · New to the Market! 4 Bed, 3 Bath-Old town w/ Pool!
NEW ON THE RENTAL MARKET This recently renovated four bedroom, three bathroom traditional shotgun house with a twist, has a master suite which can be accessed both privately and through the main house. The home has a spacious post and beam addition ....
4 Bedroom(s)
3 Bath(s) Vacation Rental - Sleeps 8
Key West, FL
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
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
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
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
"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
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
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
"CORAL CABANA" ~ Tropical Comfort!
"CORAL CABANA" ~ Lush Porch Views of the Pool & Gardens, near Golf Course!
GATED COMMUNITY, CLOSE TO BOATING AND GOLFING... Coral Cabana, in the Coral Hammock Community is a gorgeous three bedroom, three bath townhome with over 2,000 square feet of indoor/outdoor living space. A tranquil pool view can be easily appreciated ....
3 Bedroom(s)
3 Bath(s) Townhome
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
Awesome Waterfront in the Annex
@ Best of the Annex Waterfront with Fantastic Weekly Rates @
A beautifully appointed Gulf front Condo in the heart of Truman Annex. Mills place features a walkway flanked by Royal Palms. Mills place was the old military Hospital building. In the mid 80's it was purchased by a developer who renovated the entir ....
2 Bedroom(s)
2 Bath(s) Condo
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
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
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
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
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
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
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
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
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
"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
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.