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Key West Rentals

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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 one...

The Galleria - Leo's Lodge

Studio
1 Bathroom
4.6667
(18 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...

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...

Paradise on Sunset Key

2 Bedrooms
2 Bathrooms
5.0000
(2 Reviews)
Paradise at its finest is exactly what you can expect from this immaculate and unique home. Sunset Paradise is a stunning two bedroom, two and a half bathroom house on the private island of Sunset Key, in Key West. Enjoy access to private owner’s beach on western facing side of island with...

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...

Shipyard Perch

2 Bedrooms
2 Bathrooms
4.6667
(42 Reviews)
***Due to licensing restrictions, this property requires a minimum stay of 7 nights.***

The Shipyard’s Perch is a great place to stay and play near the water and Old Town Key West!

Located in Truman Annex, a secure enclave of historic and exclusive residences, Truman Annex is the most exclusive...

Hemingway's Retreat

4 Bedrooms
3 Bathrooms

Steps away from Hemingway’s house sits his “Hideaway”. Allow the authentic feel of old Key West inspire you like the famed author. Recently renovated and with enough room to sleep 10, this luxury Conch House will allow you and your guests to experience island living at its finest. Few locations...

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...

Commodore's Cove

4 Bedrooms
4 Bathrooms
4.6000
(10 Reviews)
When you walk into Commodore's Cove, you will be greeted by beautiful exposed-Dade County Pine walls, impeccable decor and gorgeous furnishings. Not only is this property BRAND NEW but it is also STEPS from all of the hottest spots in Key West. It might even take you longer to lock the door, than...

Duval Dreamin'

2 Bedrooms
2 Bathrooms
This property is quite the hidden gem! Located on the second story of one of the most famous streets in the world, you will find Duval Dreamin'. The home over looks Duval Street and features TWO living areas, TWO bedrooms and TWO bathrooms. This is the perfect pad for couples, friends or family...

Flagler's Crossing

2 Bedrooms
2 Bathrooms
Flagler's Crossing is a stunning 3 story condo with 2 bedrooms and 2 1/2 bathrooms. This home is one of the very few in Key West with a backyard ocean view! There is off-street covered parking, boat dockage, shared pool, multiple balconies, and an outdoor living area.

The backyard haven includes a...

La Brisa - Beach View Breeze

2 Bedrooms
2 Bathrooms
4.5000
(8 Reviews)
Beachfront Breeze is located on S. Roosevelt Blvd., directly across from world famous Smathers Beach on the Atlantic Ocean. You can choose to join in activities held in the club house overlooking the pool, tennis courts and gardens or make your own at the pool, hot tub, saunas, under the tropical...

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...

Oceana Suite

1 Bedroom
1 Bathroom
4.7143
(112 Reviews)
This immaculately clean and comfortable well air conditioned suite features beautiful vaulted ceilings and pastel colored walls as well as a top of the line flat screen TV and stereo. The living room has tropical furniture and a new Queen Sleeper Sofa with gel memory foam mattress.

The efficiency...

Sunrise Suites - Panama Suite 310

2 Bedrooms
2 Bathrooms
4.4857
(70 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 - Salt Cay Suite 410

2 Bedrooms
2 Bathrooms
4.6905
(84 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...

Seagull Suite

Studio
1 Bathroom
4.6047
(86 Reviews)
Part of Southernmost Sanctuary Suites

People looking for a vacation getaway in Key West are thrilled when they find a hidden gem like The Seagull Suite - located in the gardens of a private compound called The Sanctuary. Location, charm, and island appeal - the Seagull Suite is located in the back...

Old Town Garden Villas - Bermuda Suite

1 Bedroom
1 Bathroom
4.7551
(98 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...

Mary's Trio

3 Bedrooms
2 Bathrooms
MARY'S TRIO is comprised of the two side by side apartment style homes named MARY'S BACKYARD and MARY'S BACKYARD TOO.

MARY'S BACKYARD:

This 1 bedroom, 1 bathroom unit is right downtown and features everything you will need for your Key West getaway! Located next door to other vacation rentals...

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...

Tsalta

3 Bedrooms
3 Bathrooms
5.0000
(4 Reviews)
At last, a magnificent 3-bedroom home in the middle of Old Town with room for all. This home is a BIG secret but not for long! Lushly landscaped grounds with meandering brick walkways leading to the main house, pool and guest cottage. New owners with new furnishings and linens, breathing new life...

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