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Key West Rentals

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Waterfall 4

Studio
1 Bathroom
4.4545
(66 Reviews)
As the name suggests, the Garden House's "Waterfall" rooms are tucked behind the tropical lagoon's waterfall... Just steps away from the breakfast and sitting area. Considering the location and price, you will not find a better deal in all of Key West

This cozy bedroom shares a bathroom with...

Helen's Hideaway

2 Bedrooms
2 Bathrooms
4.8000
(110 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...

Amelia House

3 Bedrooms
2 Bathrooms
4.7460
(126 Reviews)
Amelia House is surrounded by fine restaurants, art galleries, and fine shopping.

The living room incorporates a sofa and chairs, in a colorful Caribbean print, which compliments the soft peach wall color. Included are rattan tables to complete the comfortable ambiance of the great room which...

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...

Orchid Suite

1 Bedroom
1 Bathroom
4.6250
(128 Reviews)
Part of the Nightly group unit 4 Flowers

You won't find a better private off-street parking is just outside your door. Turn down 'Free School House Lane' (1/2 block from the Marquesa Hotel & Restaurant) and you are home!

Featuring a queen pillow-top bed with light weight down comforter, the...

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...

Tropical Village Hideaway

2 Bedrooms
1 Bathroom
4.6875
(96 Reviews)
Tropical Hideaway - Lush gardens surround this lovingly renovated vacation home. This one-story, 2 bedroom 1 bathroom condo features a living room with queen sized pull out sleeper sofa, cable TV, DVD, stereo with CD player, and FREE wireless internet. Each bedroom has a queen sized bed and flat...

Casa Diamante

3 Bedrooms
2 Bathrooms
Casa Diamante is a beautiful three bedroom, two and a half bathroom home in the perfect location of downtown Key West. This newly renovated home is sure to impress and is the perfect island getaway! When you walk through the frosted glass door, you will be welcomed by an expansive living area with...

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...

Almost Southernmost Retreat

5 Bedrooms
3 Bathrooms
4.8519
(54 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...

Curry House Room 7

Studio
1 Bathroom
4.7143
(84 Reviews)
Room Seven is a magnificent room on the third floor with unique and fun architecture. It is painted in a tropical green tone that is soothing and a lovely contrast to the tropical greens of Key West. The private bath will make this room an exceptionally comfortable home away from home. This room...

Sunrise Suites - Saint Croix Suite 212

2 Bedrooms
2 Bathrooms
4.5714
(56 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 - Grand Bahama Suite 106

2 Bedrooms
2 Bathrooms
4.6538
(52 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...

Truman @ Duval - Two Bedroom

2 Bedrooms
1 Bathroom
4.4490
(98 Reviews)
Truman at Duval - if you're looking for South Beach slick-- not here!

If you're looking for Key West charm and location, look no further. Small 2 bedroom, 1 bath, apartment that just screams fun and good times! Duval, with its world class reputation, beckons you to come play. Sight-seeing, people...

Gecko Grotto

Studio
1 Bathroom
4.3333
(66 Reviews)
Decorated in a cozy island style, the Gecko Grotto is located adjacent to our heated lagoon-style pool, and just steps away from breakfast!

Throw your suitcase on the luggage rack and start to relax! The theme is truly Key West and little island touches are sprinkled throughout the decor.

Island...

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...

Sugar Pie Suite

Studio
1 Bathroom
4.7083
(48 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...

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 3

Studio
1 Bathroom
4.6750
(80 Reviews)
An excellent value, Room 3 is delightful and comfortable. This room is unique in the Curry House in that it is the only room with French doors that open up onto the second-floor porch. Room 3 shares a bathroom with Room 4. The bathroom is exclusive to these two rooms and has an island charm all it'...

Tropical Village - Poolside Paradise

Studio
1 Bathroom
4.7778
(108 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,...

Casa Havana @ Duval Square R22

2 Bedrooms
2 Bathrooms
4.6512
(86 Reviews)
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, secured parking beneath the complex and security...

Sunrise Suites - Grenada Suite 209

2 Bedrooms
2 Bathrooms
4.7419
(62 Reviews)

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

Old Town Garden Villas - Andros Suite

1 Bedroom
1 Bathroom
4.8293
(82 Reviews)
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!

Andros Suite is a bi-level suite with a very spacious bedroom upstairs with Caribbean colors and wood floors.

Key West Vacation Rentals...

Paradise Palms

2 Bedrooms
2 Bathrooms
5.0000
(2 Reviews)
Paradise Palms is located in a cute, quiet neighborhood on the edge of Old Town Key West. The exterior features of this home include one off street parking spot, a small courtyard with seating, a side deck which includes an outdoor shower and gas grill!

The master bedroom features a king-size bed...

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