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Creme Brulee Getaway

Studio
1 Bathroom
4.6875
(32 Reviews)
Part of Banana's Foster Guest House

This comfortable 2nd floor studio right on the corner of Caroline and Simonton, just a block off Duval, is a great spot for 2 guests wanting to be in the thick of things! After entering the compound from the shared off street parking into the courtyard with...

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...

Casa Cubana @ Duval Square R14

2 Bedrooms
2 Bathrooms
4.7397
(73 Reviews)
Lush and tropical gardens surround this beautiful development in the heart of historic Old Town. Private, secured parking beneath the complex and security entrances gives the feeling of exclusivity unparalleled in Key West.

The foyer of this Mediterranean Style unit with Mexican Tile downstairs...

Sunrise Suites - Antigua Suite 312

2 Bedrooms
2 Bathrooms
4.4706
(17 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

6 Bedrooms
6 Bathrooms
5.0000
(14 Reviews)
Papa's Hideaway is a Guesthouse property comprised of Garden of Eden, Torrents of Spring , Sun Also Rises , For Whom the Bell Tolls, and Islands in the Stream. This private compound had a large outdoor gathering area around your private pool equipped with Grill, Sundeck, and Bar. Located on a...

Banana's Foster Guesthouse

7 Bedrooms
8 Bathrooms
4.7273
(22 Reviews)
All together this home has 7 separate bedrooms, each with it’s own bathroom and a ½ bath downstairs in the main house, 2 full kitchens, a BBQ grill and shared courtyard with a plunge pool. The historic downtown property also has 4 off street parking spaces right outside the gated courtyard on...

Spa On Duval @ Duval Square R11

2 Bedrooms
2 Bathrooms
4.6400
(50 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...

Helen's Hideaway

2 Bedrooms
2 Bathrooms
4.8000
(55 Reviews)
This gem is located at the end of a hidden lane, just off Simonton Street, behind The Gardens Hotel. Helen's Hideaway is a step back in time to Key West during its slumbering past. Built by David Wolkowski, who built many of Key West's premier resorts, including the Pier House, this paradise...

Almost Southernmost Retreat

5 Bedrooms
3 Bathrooms
4.8519
(27 Reviews)
Almost Southernmost Retreat is made up of ALMOST SOUTHERNMOST and ALMOST SOUTHERNMOST TOO on the 400 block of Truman Avenue is the perfect location between Duval Street and Whitehead Streets.

This style is common throughout the islands. Located in a row of identical cigar-maker cottages, 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...

Lazy Lane at Shipyard Condos

2 Bedrooms
1 Bathroom
4.5833
(24 Reviews)
***Due to licensing restrictions, this property requires a minimum stay of 7 nights.***

****Exterior of property being painted 9/4-9/15****

The spacious living room/dining room features a with large flat screen TV and DVD player. Living room French doors open up into the private deck which...

Casa Bonita @ Duval Square R1

2 Bedrooms
2 Bathrooms
4.8000
(70 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...

Poolside Retreat

1 Bedroom
1 Bathroom
4.6957
(23 Reviews)
One-half block off world famous Duval Street sits the beautifully renovated home in the 500 block of Olivia Street. The updated kitchen features granite counter tops and beautiful wooden floors. Your bathroom offers a large walk-in tiled shower. A semi-private pool with waterfall feature(shared...

A Key Escape

3 Bedrooms
2 Bathrooms
4.9012
(81 Reviews)

A Key Escape 3 br 2.5 bath w/ private heated pool. Professionally decorated in a Coastal Living style, this elegant yet very comfortable custom built 3 bedroom, 2.5 bath, 3 story home has a living room (Q sleeper sofa) with rose hardwood floors, a gourmet kitchen with granite countertops and...

Sunrise Suites - Panama Suite 310

2 Bedrooms
2 Bathrooms
4.0000
(2 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...

Howe Street Hideaway

2 Bedrooms
2 Bathrooms
4.8000
(5 Reviews)

The neighborhood is complete with conch style homes, little lanes, corner gardens and yes our famous Key West Roosters watching their chicks. Featuring a classic front porch for greeting the neighbors as they go about their day. Entering into this lovely home you are surrounded with light,...

Commodore's Compound

8 Bedrooms
7 Bathrooms

Commodore's Compound is comprised of 2 separate units - Seaport Suite and Commodore's Cove: SEAPORT SUITE: Seaport Suite is available for daily vacation rentals and located on the second floor of an historic Key West home in Old Town.. The location is as close to perfect as you can get, being...

Shark Key Chateau

5 Bedrooms
4 Bathrooms
4.7500
(4 Reviews)

Château - Merriam-Webster defines it as a "large impressive residence". This does not do the 'Shark Key Chateau' justice! Very impressive, very large, very luxurious! Set apart from any residence you have experienced. But this property does not rest on Shark Key Chateau is 'Grande' to say the...

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...

Tropical Retreat

3 Bedrooms
3 Bathrooms
4.8714
(70 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...

Leeward Isle

2 Bedrooms
1 Bathroom
4.7600
(25 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,...

Sunrise Suites - Cayo Cruz Suite 308

2 Bedrooms
2 Bathrooms
4.7632
(38 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...

Seaport Suite

4 Bedrooms
3 Bathrooms
4.8235
(34 Reviews)
Seaport Suite is available for daily vacation rentals and located on the second floor of an historic Key West home in Old Town.. The location is as close to perfect as you can get, being one block off Duval Street and within walking distance to every single thing you could possibly want to do. With...

Sunrise Suites - Big Kahuna Suite 202

2 Bedrooms
2 Bathrooms
4.7429
(35 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...

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