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Amelia House

3 Bedrooms
2 Bathrooms
4.7460317460317
(63 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...

Captain's Quarters

2 Bedrooms
2 Bathrooms
Due to city restrictions, this beautiful rental property requires a minimum stay of 28 nights.

This completely private & secluded 2 bed 2 bath Key West home features an incredible, large outdoor area and pool that is perfect for entertaining. This Nautically themed house has the true feeling...

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...

A Key Escape

3 Bedrooms
2 Bathrooms
4.9012345679012
(81 Reviews)
A Key Escape 3 br 2.5 bath w/ private heated pool. Professionally decorated in a Coastal Living style, this elegant yet very comfortable custom built 3 bedroom, 2.5 bath, 3 story home has a living room (Q sleeper sofa) with rose hardwood floors, a gourmet kitchen with granite countertops and...

Key Lime Cottage

Studio
1 Bathroom
4.6363636363636
(33 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...

Villa Azul

3 Bedrooms
3 Bathrooms
5
(1 Review)
You will certainly enjoy this wonderful historic home with recent renovations, perfectly placed pool, and plenty of outdoor living space located at 1116 Curry Lane. This home is situated in the heart of Old Town, just 4 blocks to the Historic Seaport District or the Art Gallery District on White...

Casa Cubana @ Duval Square R14

2 Bedrooms
2 Bathrooms
4.7397260273973
(73 Reviews)
Lush and tropical gardens surround this beautiful development in the heart of historic Old Town. Private, secured parking beneath the complex and security entrances gives the feeling of exclusivity unparalleled in Key West.

The foyer of this Mediterranean Style unit with Mexican Tile downstairs...

Curry House Room 1

Studio
1 Bathroom
4.7916666666667
(48 Reviews)
Room 1 is considered by many to be one of the nicest rooms the Curry House has to offer. The recently remodeled private bathroom is spacious and includes a stunning tiled, marble shower. A semi-private veranda overlooks the pool. The veranda provides an excellent place to sit, relax & enjoy the...

Saint Thomas Suite #302

2 Bedrooms
2 Bathrooms
4.84375
(32 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...

Curry House Room 6

Studio
1 Bathroom
4.7027027027027
(37 Reviews)
Room 6 is conveniently located on the main floor. It has a door that opens onto the side deck with a secluded sitting area. The front porch sitting area is only a few steps away. People that stay in Room six often comment on how pleasant it is to wake up to the smell of breakfast cooking nearby in...

Sapodilla House

3 Bedrooms
3 Bathrooms
This charming home, built in 1928, is the the epitome of a Bahama Village living. The combination of lush eclectic flora and vivid colors transport you to your own tropical retreat. Situated in the front yard is a Sapodilla tree in which the house is named after.

Sitting only two blocks from Duval...

West Indies

Studio
1 Bathroom
4.452380952381
(42 Reviews)
With its rich wood flooring and triple windows, this selection is truly fit for a king. Wood and cane furnishings and metal sculpted palm lamps with intricate shell shades make the guest feel welcome and relaxed.

Double nightstands and a writer's desk add to the atmosphere without compromising it'...

Helen's Hideaway

2 Bedrooms
2 Bathrooms
4.8
(55 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...

Samana Cay Suite #405

2 Bedrooms
2 Bathrooms
4.6590909090909
(44 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...

Mermaid Manor

4 Bedrooms
3 Bathrooms
In one of the most desirable lanes in Old Town Key West. The perfect location for walking to Duval Street and the historic Seaport. Situated at the end of a quiet lane on a lush tropical lot. This 4 bedroom home is in one of the most sought after neighborhoods on the island. High ceilings, hardwood...

*Paradise Found*

3 Bedrooms
2 Bathrooms
Looking for the perfect piece of paradise in the Florida Keys? Well, look no further! "Paradise Found” is just 30 minutes from Key West making this home's casual luxury "close to perfect, yet far from normal”. Located on a quiet lane a couple blocks off US Hwy 1, Paradise Found is the ideal...

Havana Daydream @ Key Cove

4 Bedrooms
4 Bathrooms
Enjoy the island life in your own oasis tucked away from the bustle of Old Town in a private waterfront retreat, with your own private waterfront pool. Luxurious furnishings and spacious interiors centered around the expansive water views perfectly compliment the beautiful outdoor spaces. Slow down...

Island Oasis

2 Bedrooms
2 Bathrooms
4.7777777777778
(45 Reviews)
The beaches of the Atlantic Ocean are less than a 7 minute walk 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. Sitting in a row of 6 townhomes built by Key West's premier builder, Island...

Palm Isle

1 Bedroom
1 Bathroom
4.7209302325581
(43 Reviews)
Luxury and fine details define these units on White Street, the heart of the art district and just six blocks from Duval Street and the Historic Seaport. Stroll out your door and enjoy cafe con leche and the best Cuban Sandwiches at Sandy's Cafe, pulled pork sandwiches and homemade ice-cream at the...

Trinidad Suite #105

2 Bedrooms
2 Bathrooms
4.6829268292683
(41 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...

Hispaniola Suite #101

2 Bedrooms
2 Bathrooms
4.7037037037037
(27 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...

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