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Key West Rentals

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Almost Southernmost Too

3 Bedrooms
2 Bathrooms
4.551724137931
(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...

Dominican Suite #110

2 Bedrooms
2 Bathrooms
4.4583333333333
(24 Reviews)
Sunrise Suites Resort is an island paradise. Complimentary hourly shuttle service from 9:15 AM - 5:30 PM daily between the Resort, beaches, airport, ferry terminal, & downtown make this resort's location ideal. Spend sun-filled days pampered by our warm and friendly staff. Pull up a lounge...

Heron Suite

Studio
1 Bathroom
4.5833333333333
(24 Reviews)
Part of Southernmost Sanctuary Suites

The Heron Suite is located street side with it's own porch for people watching. Get one of Ana's Cuban mixes - it just doesn't get any better! Conveniently located to the beach, Duval Street, great restaurants, Ana's for great Cuban fare and morning coffee -...

Claude Monet Suite

Studio
1 Bathroom
4.74
(50 Reviews)
This wonderful unit is set apart from the others with cathedral ceilings and a skylight in each room; light and airy and yet very cozy and comfortable. This efficiency condo is perfect for 2 and can even accommodate the occasional guest with the living room sleeper sofa.

The bedroom has a queen...

Four Flowers Guesthouse

4 Bedrooms
4 Bathrooms
4.8
(15 Reviews)
Four Flowers is the perfect island getaway spot for friends and family that want to be close together while maintaining privacy. Four Flowers is a combination of 4 condos located on Simonton St - Orchid Escape, Jasmine Suite, Hibiscus Hideaway, & Gardenia Getaway

Hibiscus Suite is a queen...

Poolside Retreat

1 Bedroom
1 Bathroom
4.695652173913
(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...

Casa Caribe @ Duval Square

2 Bedrooms
2 Bathrooms
4.7894736842105
(57 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...

Sugar Pie Suite

Studio
1 Bathroom
4.7083333333333
(24 Reviews)
This cute and colorful studio is perfect for anyone who is excited to explore Key West. You are just around the corner from all Duval Street has to offer. Restaurants, bars, shops, live music.. it's all just steps away. Be sure to catch the sunset at Mallory Square and a bite to eat on the harbor...

Mary's Backyard

1 Bedroom
1 Bathroom
4.9117647058824
(34 Reviews)
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 such as Mary's Backyard Too and Banana's Foster Guesthouse and across the street from Seaport Suite.

The location itself could not be...

Eliza's Escape

4 Bedrooms
3 Bathrooms
Unwind on the wrap around patio, cool off in the pool, explore the wonders of your next vacation. Let Eliza's Escape become your favorite vacation spot!

Surprisingly elegant tropical oasis. Unassuming and hidden by lush mature foliage, in a quite Key West neighborhood. Be swept away by warm...

Great Exuma Suite #406

2 Bedrooms
2 Bathrooms
4.7878787878788
(33 Reviews)
***Recently updated

Sunrise Suites Resort is an island paradise. Complimentary hourly shuttle service from 9:15 AM - 5:30 PM daily between the Resort, beaches, airport, ferry terminal, & downtown make this resort's location ideal. Spend sun-filled days pampered by our warm and friendly staff...

Hemingway's Shadow

1 Bedroom
1 Bathroom
4.6666666666667
(3 Reviews)
Hemingway's Shadow is a well-appointed, 1 bedroom home located on Thomas Street, directly behind the Key West Lighthouse Museum.

The living room, dining area and kitchen form an L-shape open area. The kitchen also has a counter with seating for those times you don't care to use the dining table...

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...

Duval Heaven

1 Bedroom
1 Bathroom
4.8846153846154
(26 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-style complex, this 1 bedroom/1 bathroom condominium features a full kitchen, high ceilings and a...

Toon Hall - Tropical Village

3 Bedrooms
2 Bathrooms
4.7142857142857
(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...

Poolside Paradise

3 Bedrooms
2 Bathrooms
4.7179487179487
(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...

Abaco Suite

1 Bedroom
1 Bathroom
4.7843137254902
(51 Reviews)
With 1 bedroom 1 bath this Townhouse with shared heated pool will be your favorite. 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!

Abaco Suite, is a bi-level suite with a very spacious...

Tobago Grande

3 Bedrooms
3 Bathrooms
4.75
(4 Reviews)
***Due to licensing restrictions, this property requires a minimum stay of 28 nights.***

Tobago House is just steps from restaurants, night life, Hemingway's House, and the 'Southernmost Point' of the United States. This home offers an open, airy floor plan with old style pine walls and floors,...

Tropical Cottage

2 Bedrooms
2 Bathrooms
4.6363636363636
(33 Reviews)
Tropical Village Cottage - is a two bedroom, two bath vacation cottage that overlooks a large shared seasonally heated pool, sun-deck and pool-side grilling station. With all the amenities of contemporary living set in island style and decor. Tropical Village Cottage is your ticket to a stress free...

Cayo Coco Suite #208

2 Bedrooms
2 Bathrooms
4.7435897435897
(39 Reviews)
(Recently updated!)

*** 1 Private, covered parking spot is included when you rent this particular vacation condo

Sunrise Suites Resort is an island paradise. Complimentary hourly shuttle service from 9:15 AM - 5:30 PM daily between the Resort, beaches, airport, ferry terminal, & downtown make...

Shipyard Perch

2 Bedrooms
2 Bathrooms
4.6666666666667
(21 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...

Lazy Lane

2 Bedrooms
1 Bathroom
4.5833333333333
(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...

Wahoo Way On Duval

1 Bedroom
1 Bathroom
5
(7 Reviews)
This Studio has everything you want and a location that can not be beat. Located on upper Duval St, you are walking distance to Southernmost Point, Mallory Square, shops, restaurants, beaches and bars. The tile floors and Dade Pine walls give this Studio a real Key West feel. Outfitted with a...

Casa Key West @ Duval Square

3 Bedrooms
2 Bathrooms
4.65
(60 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...

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