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Key West Rentals

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Tropical Retreat

3 Bedrooms
3 Bathrooms
4.8714285714286
(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...

Curry House Room 2

Studio
1 Bathroom
4.8048780487805
(41 Reviews)
Room 2's pale shade of colors will continually remind you that you're staying in a tropical paradise. Step out onto the semi-private veranda overlooking the pool. Sit and relax, surrounded by the tropical vegetation that abounds on this magnificent island. An oversized shower in the private...

Bimini Suite #211

2 Bedrooms
2 Bathrooms
4.3636363636364
(22 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 many...

Salt Pond Hideaway

2 Bedrooms
2 Bathrooms
4
(2 Reviews)
Salt Pond Hideaway is located right off of South Roosevelt Blvd. in the oceanfront Salt Ponds Condominium Complex.

It offers a neighborly and relaxing atmosphere with the ocean breezes of the Atlantic right across the street. Taking a walk or bike ride down the oceanfront stretch right outside of...

Curry House Room 5

Studio
1 Bathroom
4.7692307692308
(39 Reviews)
Room 5 is on the ground floor with a King-sized bed, private bathroom & has access to a wraparound porch.

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...

Carey's Corner

Studio
1 Bathroom
4.4166666666667
(12 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...

Southern Comfort @ Key Cove

4 Bedrooms
3 Bathrooms
Luxurious furnishings and spacious interiors centered around the expansive water views perfectly compliment the beautiful outdoor spaces. Slow down, relax and prepare for life the way it should be at Southern Comfort. This home is located in the private community of Key Cove Landings, on an...

Banana's Foster Guesthouse

7 Bedrooms
7 Bathrooms
4.7272727272727
(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...

Sweet Caroline

2 Bedrooms
2 Bathrooms
4.7027027027027
(37 Reviews)
Part of Banana's Foster Guest House

This spacious 2 bedroom apartment takes up the first floor of this historic Key West home located on the corner of Caroline St and Simonton Dt. From the off street parking and shared courtyard entrance off Simonton opening into the kitchen to the private front...

Kingfish Keep On Duval

1 Bedroom
1 Bathroom
4.8888888888889
(9 Reviews)
This large and luxurious apartment is second to none when it comes to properties on Duval St. Walking distance to Southernmost Point, Mallory Square, beaches, restaurants, and bars, you cant beat the location. No detail was overlooked in the design of this property. There are vaulted ceilings,...

Beach House

3 Bedrooms
3 Bathrooms
The Beach House is your perfect Key West retreat. This 3 bedroom 3 bath classic conch house defines Key West's unique housing style.

Relaxing and quiet, Historic Bahama Village puts you in the perfect location for delicious restaurants and fun attractions! South Beach, Fort Zachary Taylor and...

Almost Southernmost Retreat

5 Bedrooms
3 Bathrooms
4.8518518518519
(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...

Poolside Paradise - Tropical Village

Studio
1 Bathroom
4.7777777777778
(54 Reviews)
Where else can you find resort style accommodations at motel pricing? Poolside Paradise @ Tropical Village, features all the amenities needed for a quick weekend getaway vacation at an affordable nightly rate. Once the winter vacation suite of Pulitzer Prize winning cartoonist Jeff MacNelly,...

Writer's King Room

Studio
1 Bathroom
4.6190476190476
(21 Reviews)
The Writer's King is located at the end of our second floor balcony at our Key West lodging, located directly over the Lagoon where you can listen to our gentle waterfall on cool evenings.

Featuring a King size bed with Tiffany reading lamps, the Writers' King is a relaxing way to enjoy your Key...

Casa Serendipity

3 Bedrooms
2 Bathrooms
4.8780487804878
(41 Reviews)
Located on one of old town's prettiest historic streets, Frances Street. Casa Serendipity is one of the finest examples of the 'conch cottage' style architecture that Key West is famous for.

Designed to accommodate a family, this three-bedroom home has two full baths, one full bath upstairs and...

Coastal Comfort @ Key Cove

4 Bedrooms
3 Bathrooms
This home is located in the private community of Key Cove Landings, on an exclusive lane of waterfront residential homes. The perks of this little-known location are many: walking distance to the essentials such a Publix grocery store and the largest shopping center on the island, while still being...

Catalina Suite #311

2 Bedrooms
2 Bathrooms
4.7021276595745
(47 Reviews)
Sunrise Suites Resort is an island paradise. Complimentary hourly shuttle service from 9:15 AM to 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...

Atlantic Ocean View

2 Bedrooms
2 Bathrooms
*** POOL WILL BE CLOSED SEPT 5 - OCT 20****

New King-sized bed w/ pillow top mattress installed June 2015

Outside the front of the complex are the tennis courts. If you choose to stay inside the complex you can enjoy the lush landscape on the inside of the courtyard. Just a short stroll takes you...

Howe Street Hideaway

2 Bedrooms
2 Bathrooms
4.8
(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, beauty...

Paradise Palms

Studio
1 Bathroom
4.5416666666667
(24 Reviews)
Paradise Palms is decorated in a tropical motif, with a palm matelassé and herb-green pinstriped bed skirt. There are wood furnishings throughout, along with nautical prints and souvenirs.

Double doors open onto our second story landing where you are only steps away from the upper sun deck of our...

Salvador's Suite

Studio
1 Bathroom
4.5714285714286
(21 Reviews)
Welcome to the Salvador Dali Suite, located in Old Town Key West just a few blocks from Duval St! Efficiency and affordability at its finest! The Salvador Dali Suite has everything you need to fulfill your Key West Vacation needs - a super comfy, full-sized bed, a kitchenette complete with a...

Sky Loft

1 Bedroom
1 Bathroom
5
(6 Reviews)
This newly renovated, one bedroom, one bathroom unit comfortably sleeps four guests. From the moment you walk in, you will be amazed by the detail, decor and furnishings. The perfect rental home for those who wish to be just above all the action!

You and your guests will enjoy the spacious kitchen...

Mangrove Lagoon

2 Bedrooms
2 Bathrooms
4.9090909090909
(11 Reviews)
***Due to licensing restrictions, this property requires a minimum stay of 7 nights.***

In one of the most desirable locations in Key West, you will find the exquisite Mangrove Lagoon. Just walking into this pristine home will take your breath away. Featuring two bedrooms and two and a half...

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