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United House

2 Bedrooms
1 Bathroom
This house is perfect for anyone looking for the true Key West living feel. Centrally located on the island in midtown you are close enough to downtown to enjoy all of the festivities but still have a quiet, serene place to call home. Located on a large, fenced in lot, this house has a great...

Duval Street Retreat

4 Bedrooms
2 Bathrooms
4.75
(16 Reviews)
Welcome to "Duval Street Retreat" - The perfect vacation rental for large groups looking to be around all the Duval St action!

Duval St. Retreat consists of two separate two-bed, one-bath condos located at 1124 Duval St. The property is only a couple steps (or stumbles) away from fine dining, bars...

Seaport Suite

4 Bedrooms
3 Bathrooms
4.8235294117647
(34 Reviews)
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 block off Duval Street and within walking distance to every single thing you could possibly want to do. With...

Duval Delight

1 Bedroom
1 Bathroom
4.8245614035088
(57 Reviews)
Duval Delight is a breathtaking, newly-renovated 2-story condo located at the historic "Cuban Club" on the "quieter" side of world famous Duval St. This high end vacation rental features a huge 55-inch flatscreen TV in the living room and all brand new furniture including a comfy, pull-out queen...

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...

Puerto Rico Suite #103

2 Bedrooms
2 Bathrooms
4.6923076923077
(26 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...

Casa Hermosa

2 Bedrooms
2 Bathrooms
Secluded yet conveniently located near great attractions, it's perfect for a relaxing getaway to the island of Key West. Plus, it comes complete with a fully fenced-in yard and perfect patio so that you can enjoy the indoor and outdoor living spaces. And there's a Pool!

Bright and inviting open...

Southern Cross - Tropical Village

2 Bedrooms
2 Bathrooms
4.7826086956522
(23 Reviews)
Southern Cross: Lounging next to the gorgeous shared pool or sitting in the shade of your own Royal Poinciana tree, Southern Cross is the perfect place to relax in paradise. This one and a half story vacation cottage is surrounded by exotic gardens, and situated in the Tropical Village Compound...

Traveler's Palm

Studio
1 Bathroom
4.7428571428571
(35 Reviews)
Traveler's Palm (formerly Palm Isle) - a room ahead of its time - A truly "green unit". Your roommate, or in this case, "suite mate" is a giant Sapodilla tree that provides the ambiance and shade to your private hot tub and tree-top hammock. The second-story studio apartment comes complete with a...

Garden of Roses

3 Bedrooms
2 Bathrooms

Originally built in 1933, this fully renovated, three-bedroom home has a yard, a cozy front porch where you can sit back and watch the day go by, and room for up to eight guests (six comfortably). Stroll to shopping, entertainment, and beaches, all within a few blocks of this rental....

Havana Oasis

4 Bedrooms
4 Bathrooms
4.6666666666667
(12 Reviews)
Havana Oasis is comprised of two of our most popular homes!

Island Oasis

The beaches of the Atlantic Ocean are less than a 7 minute blocks away.

This ultra luxurious 2 bedroom, 2-1/2 bath, 2 story house has been totally redecorated by one of Key West’s most talented designers, Michael Pelkey...

Waterfall 4

Studio
1 Bathroom
4.4545454545455
(33 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...

Tahiti Suite #104

2 Bedrooms
2 Bathrooms
4.6
(5 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...

Royal Oasis

2 Bedrooms
2 Bathrooms
5
(3 Reviews)
Beautifully decorated with abstract art throughout, this 2 bed 2 bath monthly rental is the perfect "get away" spot for individuals looking to fully immerse themselves in Key West culture. This house is located in on Royal St. in Old Town Key West. It is located only a few blocks from Duval St and...

Pescado Penthouse On Duval

3 Bedrooms
3 Bathrooms
5
(4 Reviews)
This 3 bed 3 bath group unit is perfect for any group looking to enjoy Key West for all it has to offer. It is comprised of the 3 units Kingfish Keep, Yellowfin Ledge, and Wahoo Way. Located on upper Duval St, this property is in the perfect location and is walking distance to Southernmost Point,...

Casa Atlantic

3 Bedrooms
3 Bathrooms
This three bedroom, three bathroom home is an absolute dream! From its perfect location to the picturesque street and impeccable interior, Casa Atlantic is just what you need to enjoy an extended stay on our beautiful island.

You will enjoy strolls to the beach and to dinner at Salute and the...

Casa Havana @ Duval Square R22

2 Bedrooms
2 Bathrooms
4.6511627906977
(43 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...

Curry House Room 7

Studio
1 Bathroom
4.7142857142857
(42 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...

Cozumel Suite #112

2 Bedrooms
2 Bathrooms
4.6666666666667
(30 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...

Hibiscus Room

Studio
1 Bathroom
4.5454545454545
(22 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...

Cat Island Suite #205

2 Bedrooms
2 Bathrooms
4.5769230769231
(26 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...

Saint Lucia Suite #201

2 Bedrooms
2 Bathrooms
4.6842105263158
(19 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...

Ellen's Casa

2 Bedrooms
2 Bathrooms
5
(2 Reviews)
Welcome to a truly magnificent Key West conch home. Ellen's Casa resides on the lovely Pearl St in midtown Key West just a couple blocks away from parks, marinas and only a 5 minute drive to Duval St. The high class neighborhood is home to many local residents and is very quiet, no matter the time...

Osprey Suite

Studio
1 Bathroom
4.5135135135135
(37 Reviews)
Part of Southernmost Sanctuary Suites

The Osprey Suite - Located in the Garden at the Southernmost Studios, the Osprey Suite is the perfect island getaway. Located within walking distance to all of the charms in Old Town you'll never want to leave! The Osprey has a Queen Bed as well as a sofa for...

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