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Key West Nightly Rentals

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The Galleria - Coral Cove

Studio
1 Bathroom
4.6111
(72 Reviews)
This wonderful unit that has been completely remodeled in July 2013 has a private entrance in to the quaint efficiency on the back side of the complex.

Featuring hardwood floors, Dade County Pine walls and a high-end, fully stocked kitchenette, this secluded hideaway offers the finest of...

The Galleria - Andy's Attic

Studio
1 Bathroom
4.4000
(20 Reviews)
Affordable studio w/ private bathroom and kitchenette located in The Galleria condominium complex in the heart of "Old Town" Key West. Walking distance to Ft Zachary Taylor State Park & Beach, Blue Heaven, The Earnest Hemingway House, and much more! Free WiFi, cable TV, & daily housekeeping...

Sunrise Suites - Trinidad Suite 105

2 Bedrooms
2 Bathrooms
4.6829
(82 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...

Coconut Palm

3 Bedrooms
2 Bathrooms
4.7368
(76 Reviews)
COCONUT PALM (formerly Island Oasis). Take a lot of history and a lot of charm - mix it with a great location and you have the perfect Key West hideaway. A vacation rental home built and operated in the late 1800's as the city's hack concession and stables, has been transformed with bits and...

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...

Windward Isle

2 Bedrooms
1 Bathroom
4.6000
(70 Reviews)
One half of the group unit Tradewinds and opposite Leeward Isle The style is common throughout the islands. Our shotgun offers original Dade County pine floors and sandblasted walls that reflect the antiquity of design.

The Webster Dictionary dates windward back to 1549; defined as, the side or...

Almost Southernmost Too

3 Bedrooms
2 Bathrooms
4.5517
(58 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...

Poolside Suite

2 Bedrooms
1 Bathroom
4.6364
(44 Reviews)
One-half block off world famous Duval Street sits the beautifully renovated home on the 500 block of Olivia Street. A semi-private pool with waterfall (shared with Poolside Retreat) and Private Off-Street Parking makes this the ideal Old town location.

Enjoy nearby bars, shops, and fine dining...

Curry House Bed & Breakfast

9 Bedrooms
9 Bathrooms
5.0000
(2 Reviews)
The Curry House is an historic piece of Old Key West. Pearl Curry originally opened her home as "Curry's Rooms" in the mid-1900's. Now the inn offers nine beautiful guestrooms and the commercial kitchen serves breakfast each morning by the pool. Eight of the rooms have doors onto verandas, four...

Curry House Room 6

Studio
1 Bathroom
4.7027
(74 Reviews)
Room 6 is conveniently located on the main floor. It has a door that opens onto the side deck with a secluded sitting area. The front porch sitting area is only a few steps away. People that stay in Room six often comment on how pleasant it is to wake up to the smell of breakfast cooking nearby in...

Sunrise Suites - Jamaica Suite 102

2 Bedrooms
2 Bathrooms
4.5870
(92 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

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...

Almost Southernmost

2 Bedrooms
1 Bathroom
4.6316
(76 Reviews)
This Truman Avenue home is the perfect location, located between Duval Street and Whitehead St.

The style is common throughout the islands. Our shotgun was renovated in March, 2008. Located in among a row of identical cigar-maker cottages, this gem features a King pillow top bed upstairs, another...

Traveler's Palm

Studio
1 Bathroom
4.7429
(70 Reviews)
Traveler's Palm (formerly Palm Isle) - a room ahead of its time - A truly "green unit". Your roommate, or in this case, "suite mate" is a giant Sapodilla tree that provides the ambiance and shade to your private hot tub and tree-top hammock. The second-story studio apartment comes complete with a...

Sunrise Suites - Catalina Suite 311

2 Bedrooms
2 Bathrooms
4.7021
(94 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...

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...

Duval Corner

1 Bedroom
1 Bathroom
4.6444
(90 Reviews)
With world class nightlife, shopping and restaurants all within walking distance, you are in the center of the best that Key West has to offer.

Located on the second floor of a lovely Victorian-styled complex, this 1 bedroom/1 bathroom condominium features a full kitchen, high ceilings and a...

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...

Sunrise Suites - Great Exuma Suite 406

2 Bedrooms
2 Bathrooms
4.7879
(66 Reviews)

***Recently updated 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...

Egret Suite

Studio
1 Bathroom
4.5208
(96 Reviews)
Part of Southernmost Sanctuary Suites

Located on Historic Simonton Street, these suites are the perfect cozy escape you've been looking for! An adorable front porch to watch the people biking, walking or scooting along. Start your mornings on the porch with your Cuban coffee and a good book before...

Casa Caribe @ Duval Square

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...

Casa Bonita @ Duval Square R1

2 Bedrooms
2 Bathrooms
4.8000
(140 Reviews)
Short walk to Fort Zachary State Park and South Beach!

This spacious unit is only steps from a large pool and covered gazebo. On the ground floor is a secured garage for parking your vehicle.

Lush and tropical gardens surround this beautiful development in the heart of historic Old Town. Private...

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...

Tropical Retreat

3 Bedrooms
3 Bathrooms
4.8714
(140 Reviews)
Tropical Retreat, at 519 Catherine Street, is on a quiet lane half a block off the upscale Upper end of Duval St. where there are many sophisticated restaurants, high-end art galleries and shops. Downtown Duval St. is within easy walking distance from Tropical Retreat to enjoy the exciting...

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