You are here

Key West Nightly Rentals

Displaying 73 - 96 of 147 results matching your search criteria
Grid ViewMap View
List View

Old Town Garden Villas - Caribbean Suite

1 Bedroom
1 Bathroom
4.8833
(120 Reviews)
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!

The bedroom is decorated in rich tropical colors. A writing desk and chair completes the bedroom. The upstairs bath features an iridescent...

Spa On Duval @ Duval Square R11

2 Bedrooms
2 Bathrooms
4.6400
(100 Reviews)
A Key West Gem!

Fine dining abounds here with great restaurants such as Square One, Origami Sushi Bar and Panini/Panini, which offers free wi-fi). In the “must have” location of historic, old town Key West, it is a second story home-away-from-home, just steps from the sights, sounds and...

Truman Suite

Studio
1 Bathroom
4.7073
(82 Reviews)
The Truman 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...

Curry House Room 4

Studio
1 Bathroom
4.6000
(80 Reviews)
Perhaps the best value in the Curry House, Room four is simply stunning. The walls have remained unpainted, revealing the solid construction of native, Dade County pine which is naturally resistant to the adverse effects of the local environment. Room Four shares a bathroom with Room 3. The...

Casa Caribe @ Duval Square R9

2 Bedrooms
2 Bathrooms
4.7895
(114 Reviews)
Located in Duval Square (between Duval Street and Simonton Street), where fine dining abounds (Square One and Origami Sushi Bar), Casa Caribe is a second story paradise just steps from the sights, sounds and excitement of world-famous Duval Street.

Lush and tropical gardens surround this beautiful...

Pescado Penthouse On Duval

3 Bedrooms
3 Bathrooms
5.0000
(8 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,...

Old Town Garden Villas

5 Bedrooms
6 Bathrooms
4.9231
(26 Reviews)
The location is set on Center Street, which is located ½ block off Duval Street. These Villas are a favorite of our guests who like to relax in the quiet, beautiful garden area. Your party can book 1 to 5 of these Villas for a relaxing vacation.

Old Town Garden Villas is comprised of the following...

Sunrise Suites - Grand Cayman Suite 309

2 Bedrooms
2 Bathrooms
4.5556
(90 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...

Casa Key West @ Duval Square R32

3 Bedrooms
2 Bathrooms
4.6500
(120 Reviews)
**Recently Renovated!!

Located in Duval Square (between Duval St and Simonton St) where fine and varied dining abounds (Square One, Origami Sushi Restaurant and New York Garden Cafe),

The foyer opens to the expansive living room with vaulted ceilings, dining room with seating for six and kitchen...

Pelican Suite

Studio
1 Bathroom
4.6842
(76 Reviews)
Part of Southernmost Suites

The Pelican Suite is located in The Southernmost Suites on historic Simonton Street. Tucked back within the garden the Pelican Suite offers a serene escape from the hustle and bustle. The Pelican Suite has 2 Queen Beds and a kitchenette for you to enjoy meals in before...

Papa's Hideaway - Garden of Eden

2 Bedrooms
2 Bathrooms
4.8462
(156 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...

Truman @ Duval - Two Bedroom

2 Bedrooms
1 Bathroom
4.4490
(98 Reviews)
Truman at Duval - if you're looking for South Beach slick-- not here!

If you're looking for Key West charm and location, look no further. Small 2 bedroom, 1 bath, apartment that just screams fun and good times! Duval, with its world class reputation, beckons you to come play. Sight-seeing, people...

Sunrise Suites - Cozumel Suite 112

2 Bedrooms
2 Bathrooms
4.6667
(60 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 - Cat Island Suite 205

2 Bedrooms
2 Bathrooms
4.5769
(52 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 - Andros Suite

1 Bedroom
1 Bathroom
4.8293
(82 Reviews)
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!

Andros Suite is a bi-level suite with a very spacious bedroom upstairs with Caribbean colors and wood floors.

Key West Vacation Rentals...

Sunrise Suites - Barbados Suite 204

2 Bedrooms
2 Bathrooms
4.5455
(66 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 - Tierra Bomba Suite 403

2 Bedrooms
2 Bathrooms
4.3043
(46 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...

Banana Split

1 Bedroom
1 Bathroom
4.4737
(38 Reviews)
Part of
Banana's Foster Guest House

This one bedroom apartment is on the 2nd floor of this historic property and accessed through the shared gated courtyard, right beside the shared off street parking on Simonton. Once through the gates, walk around the shared plunge pool and BBQ grill, going...

Sunrise Suites - Saint Kitts 412

2 Bedrooms
2 Bathrooms
4.5294
(34 Reviews)

 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 many amenities, the specials we offer, and...

Sunrise Suites - Saint Thomas Suite 302

2 Bedrooms
2 Bathrooms
4.8438
(64 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...

Palm Isle

1 Bedroom
1 Bathroom
4.7209
(86 Reviews)
Luxury and fine details define these units on White Street, the heart of the art district and just six blocks from Duval Street and the Historic Seaport. Stroll out your door and enjoy cafe con leche and the best Cuban Sandwiches at Sandy's Cafe, pulled pork sandwiches and homemade ice-cream at the...

Tropical Village -Southern Cross

2 Bedrooms
2 Bathrooms
4.7826
(46 Reviews)
Southern Cross: Lounging next to the gorgeous shared pool or sitting in the shade of your own Royal Poinciana tree, Southern Cross is the perfect place to relax in paradise. This one and a half story vacation cottage is surrounded by exotic gardens, and situated in the Tropical Village Compound...

Kate's Krawl Off Duval

1 Bedroom
1 Bathroom
4.7857
(28 Reviews)
This 1 bed 1 bath home is the perfect home for you to enjoy Key West and all it has to offer. Located just steps from the World-Famous Duval St. you will find yourself in one of the most desired locations in Key West. Downstairs in this home you will find a full kitchen and comfortable living...

Leeward Isle

2 Bedrooms
1 Bathroom
4.7600
(50 Reviews)
One half of the group unit Tradewinds, opposite Windward Isle, the Leeward Isle sits at 529 Olivia Street, right in the center of Old Town Key West, just 1/2 block from Duval Street. This superb example of shotgun style architecture is complimented with original Dade County pine floors and walls,...

Pages