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Key West Rentals

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Bahama Dreaming

3 Bedrooms
2 Bathrooms
4.8462
(26 Reviews)
BAHAMA DREAMING: A beautifully renovated Conch cottage in Key West, conveniently located in the center of Old Town, one block behind celebrated Duval Street, quiet and private. Only a short walk to the many attractions, Key West activities, world-renowned Key West restaurants and nightclubs,...

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...

Conch Casa

2 Bedrooms
1 Bathroom
4.7069
(116 Reviews)
The kitchen is fully equipped with a glass top stove, refrigerator with ice-maker, microwave and everything needed for cooking a gourmet meal or just heating leftovers! French doors open from the kitchen and breakfast bar onto a private deck with a large 4 person private hot tub, table and chairs,...

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...

Claude Monet Suite

Studio
1 Bathroom
4.7400
(100 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...

Duval Square Penthouse R19

2 Bedrooms
2 Bathrooms
4.5714
(112 Reviews)
Located in Duval Square (between Duval Street and Simonton Street), where fine dining abounds (Square One, Origami Sushi Bar and NY Pasta Garden),
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...

Leeward Isle

2 Bedrooms
1 Bathroom
4.7600
(50 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,...

The Headquarters

2 Bedrooms
1 Bathroom
Walk into to The Headquarters and experience purer paradise! The living area has gorgeous, light wooden, vaulted ceilings and a plush couch that offers ultimate comfort.

Just off the kitchen, you will find a state of the art kitchen with stainless steel appliances and granite countertops. The...

Secret Garden

2 Bedrooms
1 Bathroom
4.7500
(40 Reviews)
Granite counter tops are in the well outfitted kitchen. The bath has travertine on the floors and walls- its small but very attractive with a bath/ shower combination. This great location, together with interiors by one of Key West's favorite designers and its exquisite deck surrounded by palms and...

Little Havana Suite

1 Bedroom
1 Bathroom
4.7761
(134 Reviews)
Little Havana suite is a bi-level suite with a very spacious bedroom upstairs with king bed, down pillows, tv/dvd player, writing desk and chair, in-room safe, iron & ironing board complete with Bahama ceiling fan, and a/c.. The upstairs large tiled walk-in shower with hair-dryer makes this...

Garden House Bed & Breakfast

12 Bedrooms
11 Bathrooms
Located in the heart of Old Town Key West, The Garden House Bed & Breakfast is a fantastic experience for those who want to see all that Key West has to offer. Just a few blocks from the seaport and the always exciting Dante's pool bar, and only two blocks from world famous Duval St.

Please...

Margarita Suite #305

2 Bedrooms
2 Bathrooms
4.7188
(64 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...

Martinique Suite #108

2 Bedrooms
2 Bathrooms
4.7105
(76 Reviews)
Sunrise Suites Resort is an island paradise. Complimentary hourly shuttle service from 9am - 6pm 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 chair and...

Antigua Suite #312

2 Bedrooms
2 Bathrooms
4.4706
(34 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...

Curry House Room 4

Studio
1 Bathroom
4.6000
(80 Reviews)
Perhaps the best value in the Curry House, Room four is simply stunning. The walls have remained unpainted, revealing the solid construction of native, Dade County pine which is naturally resistant to the adverse effects of the local environment. Room Four shares a bathroom with Room 3. The...

Kingfish Keep On Duval

1 Bedroom
1 Bathroom
4.8889
(18 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,...

Salty Air Retreat

2 Bedrooms
1 Bathroom
3.5000
(4 Reviews)
***Due to licensing restrictions, this property requires a minimum stay of 7 nights.***

****Exterior of property being painted 10/9-10/20****

This gorgeous two bedroom, one bathroom property is located in one of the most desirable areas of downtown Key West. With it's lavish walkways, on-site...

Carey's Corner

Studio
1 Bathroom
4.4167
(24 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...

Key Lime Cottage

Studio
1 Bathroom
4.6364
(66 Reviews)
Brand New to the Rental Market!


Part of
Banana's Foster Guest House

This cozy 2nd floor studio is perfect for a couple looking to be in the middle of the Duval action! After entering the compound from the shared off street parking into the courtyard with shared plunge pool and BBQ grill, go...

Hibiscus Room

Studio
1 Bathroom
4.5455
(44 Reviews)
The Hibiscus is located just steps from our heated lagoon pool and adjacent to the Bougainvillea Room. Both Hibiscus and Bouganvillea share a large, semi-private deck, which has access to the front yard and the pool area.

This arrangement is perfect for couples traveling together: plenty of common...

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...

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...

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