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Royal Palm

Studio
1 Bathroom
4.7143
(28 Reviews)
ROYAL PALM (formerly Little Palm) - What an idyllic setting! Picture the most perfect romantic getaway cottage with all the must have's for a great Key West vacation - in a setting that nature provided in the late 1800's - the hardwood canopy is stunning! The Tommy Bahama furniture is set off by...

Heron Hideaway

1 Bedroom
1 Bathroom
4.5581
(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.

Historic homes dating to the late 1880s, the tropical paradise has just undergone a complete restoration with exceptional attention to details...

Amelia House

3 Bedrooms
2 Bathrooms
4.7460
(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...

Shark Key Chateau

5 Bedrooms
4 Bathrooms
4.7500
(4 Reviews)

Château - Merriam-Webster defines it as a "large impressive residence". This does not do the 'Shark Key Chateau' justice! Very impressive, very large, very luxurious! Set apart from any residence you have experienced. But this property does not rest on Shark Key Chateau is 'Grande' to say the...

Papa's Hideaway #3 - For Whom the Bell Tolls

Studio
1 Bathroom
4.7879
(33 Reviews)
Feel your tensions release as you soak up the warm tropical sun. Listen to the trade winds rustling through the palms, blowing each of your cares away...

This Deluxe Studio is located on the ground floor and offers a private porch just off of the pool area.

The unit includes a king-size bed,...

Almost Southernmost

2 Bedrooms
1 Bathroom
4.6316
(38 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...

Old Town Garden Villas - Andros Suite

1 Bedroom
1 Bathroom
4.8293
(41 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...

Curry House Bed & Breakfast

9 Bedrooms
9 Bathrooms
5.0000
(1 Review)
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...

Leeward Isle

2 Bedrooms
1 Bathroom
4.7600
(25 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,...

Papa's Hideaway

6 Bedrooms
6 Bathrooms
5.0000
(14 Reviews)
Papa's Hideaway is a Guesthouse property comprised of Garden of Eden, Torrents of Spring , Sun Also Rises , For Whom the Bell Tolls, and Islands in the Stream. This private compound had a large outdoor gathering area around your private pool equipped with Grill, Sundeck, and Bar. Located on a...

Palm Gardens

3 Bedrooms
3 Bathrooms
4.9474
(19 Reviews)
The Condos are tied together in a lushly landscaped garden setting with a spa pool in the rear. Booking all three condos gives you a great alternative to booking a single house as you are offered privacy and closeness at the same time. Call to book your Island Paradise while there is still time!...

Papa's Hideaway #4 - Islands in the Stream

Studio
1 Bathroom
4.5682
(44 Reviews)
Located at Papa's Hideaway an historic Key West Inn with all the charm of Hemingway's day and the convenience of being just one block off Duval Street. The perfect mix of location, atmosphere and value.

Feel your tensions release as you soak up the warm tropical sun. Listen to the trade winds...

Salt Pond Hideaway

2 Bedrooms
2 Bathrooms
4.0000
(2 Reviews)
Salt Pond Hideaway is located right off of South Roosevelt Blvd. in the oceanfront Salt Ponds Condominium Complex.

It offers a neighborly and relaxing atmosphere with the ocean breezes of the Atlantic right across the street. Taking a walk or bike ride down the oceanfront stretch right outside of...

Southern Palms

5 Bedrooms
4 Bathrooms
4.8000
(15 Reviews)
Located at 729 Whitehead St, "Southern Palms" is the group property consisting of the following homes Coconut Palm, Traveler's Palm, and Royal Palm which can all be booked individually.

All together, these three units have 5 separate bedrooms, 3 separate hot tubs, and share an incredibly luscious...

Flamingo Hideaway

1 Bedroom
1 Bathroom
4.7073
(41 Reviews)
Flamingo Hideaway is on the ground floor a spacious unit.

Historic homes dating to the late 1880s, this tropical paradise has just undergone a complete restoration with exceptional attention to details.

The original Dade County pine walls have been saved to create that unique historic feel in a...

Tropical Retreat

3 Bedrooms
3 Bathrooms
4.8714
(70 Reviews)
Tropical Retreat, at 519 Catherine Street, is on a quiet lane half a block off the upscale Upper end of Duval St. where there are many sophisticated restaurants, high-end art galleries and shops. Downtown Duval St. is within easy walking distance from Tropical Retreat to enjoy the exciting...

Palm Isle

1 Bedroom
1 Bathroom
4.7209
(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...

Old Town Garden Villas - Caribbean Suite

1 Bedroom
1 Bathroom
4.8833
(60 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!

The bedroom is decorated in rich tropical colors. A writing desk and chair completes the bedroom. The upstairs bath features an iridescent...

Passover Cottage

2 Bedrooms
2 Bathrooms
4.8657
(67 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...

Papa's Hideaway #1 - Torrents of Spring

Studio
1 Bathroom
4.7059
(51 Reviews)
Papa's Hideaway was a historic Key West Inn with all the charm of Hemingway's day and the convenience of being just one block off Duval street. The perfect mix of location, atmosphere and value.

Feel your tensions release as you soak up the warm tropical sun. Listen to the trade winds rustling...

Papa's Hideaway - Garden of Eden

2 Bedrooms
2 Bathrooms
4.8462
(78 Reviews)
Located at Papa's Hideaway, the serene grounds strike you immediately upon entering the beautifully landscaped, gated property. Located just one block off World Famous Duval Street, Garden of Eden is the perfect combination of quiet Key West living and optimum access to all of the islands best...

Sunrise Suites - Great Exuma Suite 406

2 Bedrooms
2 Bathrooms
4.7879
(33 Reviews)

***Recently updated 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...

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...

Windward Isle

2 Bedrooms
1 Bathroom
4.6000
(35 Reviews)
One half of the group unit Tradewinds and opposite Leeward Isle The style is common throughout the islands. Our shotgun offers original Dade County pine floors and sandblasted walls that reflect the antiquity of design.

The Webster Dictionary dates windward back to 1549; defined as, the side or...

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