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Key West Rentals

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Paris Mango @ 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 heated pool. Luxurious furnishings and spacious interiors centered around the expansive water views perfectly compliment the beautiful outdoor spaces. Slow down,...

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...

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...

Panama Suite #310

2 Bedrooms
2 Bathrooms
4.4857
(70 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...

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...

Paradise Palms

Studio
1 Bathroom
4.5417
(48 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...

Beach View Breeze

2 Bedrooms
2 Bathrooms
4.5000
(8 Reviews)
Beachfront Breeze is located on S. Roosevelt Blvd., directly across from world famous Smathers Beach on the Atlantic Ocean. You can choose to join in activities held in the club house overlooking the pool, tennis courts and gardens or make your own at the pool, hot tub, saunas, under the tropical...

Lazy Lane

2 Bedrooms
1 Bathroom
4.5833
(48 Reviews)
***Due to licensing restrictions, this property requires a minimum stay of 7 nights.***

****Exterior of property being painted 9/4-9/15****

The spacious living room/dining room features a with large flat screen TV and DVD player. Living room French doors open up into the private deck which...

Banana Breeze @ Key Cove

4 Bedrooms
3 Bathrooms
Newly Decorated And Fully Appointed With Water View *30 NIGHT MIN STAY REQUIRED*

Look out at the open water views while enjoying the professionally decorated interior and spacious outdoor patio. Imagine relaxing at "Banana Breeze" with friends, family or both while listening to island music and...

Audubon House

1 Bedroom
2 Bathrooms
4.8039
(102 Reviews)
AUDUBON'S LIVING ROOM HAS JUST BEEN REFURBISHED WITH NEW FURNITURE INCLUDING NEW CHAIRS AND A NEW QUEEN SLEEPER SOFA!

The Audubon House is an historic free-standing one bedroom cottage featuring all the comforts of home, and more!

The spacious, beautifully furnished great room features a living...

Almost Southernmost

2 Bedrooms
1 Bathroom
4.6316
(76 Reviews)
This Truman Avenue home is the perfect location, located between Duval Street and Whitehead St.

The style is common throughout the islands. Our shotgun was renovated in March, 2008. Located in among a row of identical cigar-maker cottages, this gem features a King pillow top bed upstairs, another...

Rum Cay Suite #304

2 Bedrooms
2 Bathrooms
4.6735
(98 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...

Casa Key West @ Duval Square

3 Bedrooms
2 Bathrooms
4.6500
(120 Reviews)
**Recently Renovated!!

Located in Duval Square (between Duval St and Simonton St) where fine and varied dining abounds (Square One, Origami Sushi Restaurant and New York Garden Cafe),

The foyer opens to the expansive living room with vaulted ceilings, dining room with seating for six and kitchen...

Casa Hueso

4 Bedrooms
3 Bathrooms
**There will be construction in the surrounding developing area on and off for the next year**

Trade in your stressful workdays and chilly weather for a fresh ocean breeze and plenty of sunshine! This Newly Built Key West Home has more than enough space for all your friends and family to share...

Waterfall 3

Studio
1 Bathroom
4.3333
(54 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...

Great Egret Escape

2 Bedrooms
2 Bathrooms
As you enter the home through the beautiful stain-glass door, you will be greeted by colorful artwork, high ceilings and rich wooden floors. Just to your left is the immaculate kitchen, fit for a master chef! You will love the brand new appliances, marble counter tops and island, with bar seating...

Sweet Serenity

2 Bedrooms
3 Bathrooms
Welcome to Sweet Serenity, a newly constructed monthly rental located in the brand new Southernmost Cabana Town Home Complex.

Sweet Serenity is nothing short of pure perfection. A complete turnkey, fully accommodating monthly vacation rental is hard to come by. Located in the heart of 'Old Town...

Curry House Room 8

Studio
1 Bathroom
4.5769
(52 Reviews)
Room 8 has a king bed and private bathroom. The natural wood paneling on three walls is beautiful and timeless. This room has a lovely semi-private veranda that overlooks the pool area as well as the rooftops of Key West. The birds-eye view is spectacular and lush.

The Curry House is an historic...

Passover Cottage

2 Bedrooms
2 Bathrooms
4.8657
(134 Reviews)
This house is in a quiet residential neighborhood where loud boisterous parties are not appropriate.

This 2 bedroom, 2 bath, 2 story house has an open floor plan featuring lots of pine walls and floors throughout. Upstairs is the king bedroom and a full bath and downstairs is the second bedroom...

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...

West Indies

Studio
1 Bathroom
4.4524
(84 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'...

Fishtail Hideaway

1 Bedroom
2 Bathrooms
5.0000
(6 Reviews)
Fishtail Hideaway will make you feel like you may never want to return home with its intimate, private garden from all the fun and beauty Key West has to offer.

Your living area offers a brand new, large, comfortable couch; which also serves as a sleeper sofa. Unique art hangings and decorative...

Bahama House

3 Bedrooms
3 Bathrooms
4.8182
(88 Reviews)
The BAHAMA HOUSE located at 508 Amelia Street is a historic Bahamian-style Conch Cottage. It is a perfect example of turn-of-the-century island architecture. This adorable 3 bedroom home includes 2 bedrooms in the main house and an additional mother-in-law suite by the pool. Each bedroom features...

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