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Key West Nightly Rentals

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Ibis Suite

Studio
1 Bathroom
4.7000
(40 Reviews)
Part of Southernmost Sanctuary Suites

The Ibis Suite is located at The Sanctuary in Old Town key West, Only steps to the action, this studio suite has all the comforts of home but surrounds you in island style! Lush gardens surround the Jacuzzi and the calm atmosphere is exactly what you'll need...

Truman @ Duval - Two Bedroom

2 Bedrooms
1 Bathroom
4.4490
(49 Reviews)
Truman at Duval - if you're looking for South Beach slick-- not here!

If you're looking for Key West charm and location, look no further. Small 2 bedroom, 1 bath, apartment that just screams fun and good times! Duval, with its world class reputation, beckons you to come play. Sight-seeing, people...

The Galleria - Andy's Attic #12

Studio
1 Bathroom
4.4000
(10 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...

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...

Duval Street Retreat

4 Bedrooms
2 Bathrooms
4.7500
(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...

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...

Tropical Village - Toon Hall

3 Bedrooms
2 Bathrooms
4.7143
(35 Reviews)
Toon Hall: World-class comfort, lush tropical surroundings and unmatched privacy characterize the former winter home of Pulitzer Prize winning cartoonist, author and artist, Jeff MacNelly. Designed to accommodate a large family or group, this three bedroom home has two full baths plus the...

Sweet Caroline

2 Bedrooms
2 Bathrooms
4.7027
(37 Reviews)
Part of Banana's Foster Guest House

This spacious 2 bedroom apartment takes up the first floor of this historic Key West home located on the corner of Caroline St and Simonton Dt. From the off street parking and shared courtyard entrance off Simonton opening into the kitchen to the private front...

Sunrise Suites - Hispaniola Suite 101

2 Bedrooms
2 Bathrooms
4.7037
(27 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...

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...

Casa Cubana @ Duval Square R14

2 Bedrooms
2 Bathrooms
4.7397
(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...

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!...

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...

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...

Curry House Room 1

Studio
1 Bathroom
4.7917
(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...

Sunrise Suites - Catalina Suite 311

2 Bedrooms
2 Bathrooms
4.7021
(47 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...

Almost Southernmost Retreat

5 Bedrooms
3 Bathrooms
4.8519
(27 Reviews)
Almost Southernmost Retreat is made up of ALMOST SOUTHERNMOST and ALMOST SOUTHERNMOST TOO on the 400 block of Truman Avenue is the perfect location between Duval Street and Whitehead Streets.

This style is common throughout the islands. Located in a row of identical cigar-maker cottages, the...

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...

Tropical Village - Tropical Cottage

2 Bedrooms
2 Bathrooms
4.6364
(33 Reviews)
Tropical Village Cottage - is a two bedroom, two bath vacation cottage that overlooks a large shared seasonally heated pool, sun-deck and pool-side grilling station. With all the amenities of contemporary living set in island style and decor. Tropical Village Cottage is your ticket to a stress free...

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...

Old Town Garden Villas - Bermuda Suite

1 Bedroom
1 Bathroom
4.7551
(49 Reviews)
Nestled in extensive tropical and flowering gardens, complete with aviaries with singing cockatiels is the Bermuda Suite.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!

Downstairs is a...

Sunrise Suites - Cayo Coco Suite 208

2 Bedrooms
2 Bathrooms
5.0000
(1 Review)

(Recently updated!) *** 1 Private, covered parking spot is included when you rent this particular vacation condo 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...

Spa On Duval @ Duval Square R11

2 Bedrooms
2 Bathrooms
4.6400
(50 Reviews)
A Key West Gem!

Fine dining abounds here with great restaurants such as Square One, Origami Sushi Bar and Panini/Panini, which offers free wi-fi). In the “must have” location of historic, old town Key West, it is a second story home-away-from-home, just steps from the sights, sounds and...

Sunrise Suites - Grenada Suite 209

2 Bedrooms
2 Bathrooms
4.7419
(31 Reviews)

*** 1 Private, covered parking spot is included when you rent this particular vacation condo 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...

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