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Key West Nightly Rentals

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Southernmost Retreat

2 Bedrooms
1 Bathroom
4.6591
(44 Reviews)
Southernmost Retreat features all the comforts of home, and then some! A full kitchen with everything needed to prepare a gourmet meal including washer/dryer, glass top stove, dishwasher, blender, toaster, coffee maker and radio/CD player. The perfect place to listen to your favorite music while...

Tropical Village - Poolside Paradise

Studio
1 Bathroom
4.7778
(54 Reviews)
Where else can you find resort style accommodations at motel pricing? Poolside Paradise @ Tropical Village, features all the amenities needed for a quick weekend getaway vacation at an affordable nightly rate. Once the winter vacation suite of Pulitzer Prize winning cartoonist Jeff MacNelly,...

Key Lime Cottage

Studio
1 Bathroom
Brand New to the Rental Market!


Part of
Banana's Foster Guest House

This cozy 2nd floor studio is perfect for a couple looking to be in the middle of the Duval action! After entering the compound from the shared off street parking into the courtyard with shared plunge pool and BBQ grill, go...

Sunrise Suites - Samana Cay Suite 405

2 Bedrooms
2 Bathrooms
4.6591
(44 Reviews)

Sunrise Suites Resort is an island paradise.  Spend sun-filled days pampered by our warm and friendly staff. Pull up a lounge chair and bask by our lagoon-shaped pool surrounded by lush tropical foliage where you can let your cares melt away. Please take a moment to look through our site at our...

Sunrise Suites - Saint Barts Suite 303

2 Bedrooms
2 Bathrooms
4.5581
(43 Reviews)

Sunrise Suites Resort is an island paradise.  Spend sun-filled days pampered by our warm and friendly staff. Pull up a lounge chair and bask by our lagoon-shaped pool surrounded by lush tropical foliage where you can let your cares melt away. Please take a moment to look through our site at our...

Almost Southernmost Too

3 Bedrooms
2 Bathrooms
4.5517
(29 Reviews)
Almost Southernmost Too in the 400 block of Truman Avenue is the perfect location, located between Duval Street and Whitehead St. Just around the corner from Hemingway's House and the Historic Lighthouse Museum, Almost Southernmost Too is a perfect example of shotgun architecture with a front...

Pescado Penthouse On Duval

3 Bedrooms
3 Bathrooms
5.0000
(4 Reviews)
This 3 bed 3 bath group unit is perfect for any group looking to enjoy Key West for all it has to offer. It is comprised of the 3 units Kingfish Keep, Yellowfin Ledge, and Wahoo Way. Located on upper Duval St, this property is in the perfect location and is walking distance to Southernmost Point,...

Tradewinds

4 Bedrooms
2 Bathrooms
4.7353
(34 Reviews)
Tradewinds is comprised of the Leeward Isle and Windward Isle

Two Cigar Maker’s Cottages, side-by-side, located ½ block off Duval Street. These two cottages are a favorite of our guests who like to relax in the private, quiet, beautiful garden areas with large spas that are behind each house. Your...

Hibiscus Hideaway

Studio
1 Bathroom
4.7797
(59 Reviews)

Hibiscus Hideaway is part of the group unit "4 Flowers"- located on the corner of Simonton St and Freeschool Ln, just one block from world famous Duval St. Welcome to the perfectly located and affordable apt Hibiscus Hideaway. You will not find a better spot to spend your sunny days and exciting...

Tropical Village - Toon Hall

3 Bedrooms
2 Bathrooms
4.7143
(35 Reviews)
Toon Hall: World-class comfort, lush tropical surroundings and unmatched privacy characterize the former winter home of Pulitzer Prize winning cartoonist, author and artist, Jeff MacNelly. Designed to accommodate a large family or group, this three bedroom home has two full baths plus the...

Island Oasis

2 Bedrooms
2 Bathrooms
4.7778
(45 Reviews)
The beaches of the Atlantic Ocean are less than a 7 minute walk away.

This ultra luxurious 2 bedroom, 2-1/2 bath, 2 story house has been totally redecorated by one of Key West’s most talented designers, Michael Pelkey. Sitting in a row of 6 townhomes built by Key West's premier builder, Island...

Sunrise Suites - Barbados Suite 204

2 Bedrooms
2 Bathrooms
4.5455
(33 Reviews)

Sunrise Suites Resort is an island paradise.  Spend sun-filled days pampered by our warm and friendly staff. Pull up a lounge chair and bask by our lagoon-shaped pool surrounded by lush tropical foliage where you can let your cares melt away. Please take a moment to look through our site at our...

Sunrise Suites - Cristobal Suite 411

2 Bedrooms
2 Bathrooms
4.6591
(44 Reviews)

Sunrise Suites Resort is an island paradise.  Spend sun-filled days pampered by our warm and friendly staff. Pull up a lounge chair and bask by our lagoon-shaped pool surrounded by lush tropical foliage where you can let your cares melt away. Please take a moment to look through our site at our...

Old Town Garden Villas - Bermuda Suite

1 Bedroom
1 Bathroom
4.7551
(49 Reviews)
Nestled in extensive tropical and flowering gardens, complete with aviaries with singing cockatiels is the Bermuda Suite.Enjoy a margarita while listening to songbirds in the courtyard, or work on your tan at the pool in the lushly landscaped courtyard right outside your door!

Downstairs is a...

Jasmine Suite

1 Bedroom
1 Bathroom
4.6545
(55 Reviews)

Part of the Nightly group unit 4 Flowers You won't find a better private off-street parking is just outside your door. Turn down 'Free School House Lane'  and you are home! Featuring a queen pillow-top bed with light weight down comforter, the Jasmine Suite includes TV and VCR, stereo with CD...

Sunrise Suites - Saint Thomas Suite 302

2 Bedrooms
2 Bathrooms
4.8438
(32 Reviews)

Sunrise Suites Resort is an island paradise.  Spend sun-filled days pampered by our warm and friendly staff. Pull up a lounge chair and bask by our lagoon-shaped pool surrounded by lush tropical foliage where you can let your cares melt away. Please take a moment to look through our site at our...

Hemingway's View

3 Bedrooms
2 Bathrooms
4.6667
(63 Reviews)
One block from Center St, Hemingway's View is a 3 bedroom, 2 bath charming turn-of-the-century Conch cottage.

Each of the 3 bedrooms are air-conditioned. Both bathrooms have marble floors, large closets, hairdryers, and tubs with showers. The rear bath has a marble topped vanity with double sinks...

Curry House Room 9

Studio
1 Bathroom
4.6500
(40 Reviews)
It is a pleasure to present the recently renovated Room Nine! It used to be a good room, now it's a great room! Comfortable and very peaceful, this room was originally opened up to make use of a portion of the attic space. Note that the ceiling is sloped in two directions and some taller guests...

Papa's Hideaway - Garden of Eden

2 Bedrooms
2 Bathrooms
4.8462
(78 Reviews)
Located at Papa's Hideaway, the serene grounds strike you immediately upon entering the beautifully landscaped, gated property. Located just one block off World Famous Duval Street, Garden of Eden is the perfect combination of quiet Key West living and optimum access to all of the islands best...

Monroe Suite

Studio
1 Bathroom
4.5000
(40 Reviews)
The Monroe Suite is nestled at the rear of the Simonton Court complex. The efficiency studio features a fully-equipped kitchen, flatscreen TV with cable, free wireless internet, and private patio furniture to relax on. The bathroom has a custom tiled shower with glass door and vanity.

Take...

Sunrise Suites - Cat Island Suite 205

2 Bedrooms
2 Bathrooms
4.5769
(26 Reviews)

Sunrise Suites Resort is an island paradise.  Spend sun-filled days pampered by our warm and friendly staff. Pull up a lounge chair and bask by our lagoon-shaped pool surrounded by lush tropical foliage where you can let your cares melt away. Please take a moment to look through our site at our...

Papa's Hideaway #4 - Islands in the Stream

Studio
1 Bathroom
4.5682
(44 Reviews)
Located at Papa's Hideaway an historic Key West Inn with all the charm of Hemingway's day and the convenience of being just one block off Duval Street. The perfect mix of location, atmosphere and value.

Feel your tensions release as you soak up the warm tropical sun. Listen to the trade winds...

Poolside Paradise

3 Bedrooms
2 Bathrooms
4.7179
(39 Reviews)
POOLSIDE PARADISE is made up of POOLSIDE RETREAT and POOLSIDE SUITE

With 3 bedrooms (K, 2 Q, plus 2 Q sleeper), 2 full baths and 2 full kitchens, this historic home is perfect for up to 10 persons. The front portion features a King bedroom, a Queen bedroom and a Queen sleeper sofa in the living...

Kingfish Keep On Duval

1 Bedroom
1 Bathroom
4.8889
(9 Reviews)
This large and luxurious apartment is second to none when it comes to properties on Duval St. Walking distance to Southernmost Point, Mallory Square, beaches, restaurants, and bars, you cant beat the location. No detail was overlooked in the design of this property. There are vaulted ceilings,...

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