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Pet Friendly Key West Rentals

Over 140 of our nearly 200 Key West vacation rentals allow pets! Please make sure to check our vacation rental policies page for information on breeds that are not allowed, as well as rules to follow when bringing your pet to Key West. There is a $20 per night/per pet fee for nightly and weekly rentals, and a $200 per month/per pet fee for monthly rentals. Key West is a very dog-friendly town, so please feel free to bring your furry friend along, if your rental allows it!

Displaying 25 - 48 of 127 results matching your search criteria
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Duval Delight

1 Bedroom
1 Bathroom
4.8246
(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...

Key Lime Calypso

2 Bedrooms
1 Bathroom
4.4000
(10 Reviews)
The best of Key West, in the middle of Historic Old Town and a half block from Duval Street and the gates to Bahama Village, a perfect location for visitors to our island. Guests can stroll to Mallory Square, Fort Zachary Beach or the sunset piers which are all within easy walking distance of this...

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...

Audubon House

1 Bedroom
2 Bathrooms
4.8039
(51 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...

Old Town Garden Villas - Little Havana Suite

1 Bedroom
1 Bathroom
4.7761
(67 Reviews)
Little Havana suite is a bi-level suite with a very spacious bedroom upstairs with king bed, down pillows, tv/dvd player, writing desk and chair, in-room safe, iron & ironing board complete with Bahama ceiling fan, and a/c.. The upstairs large tiled walk-in shower with hair-dryer makes this...

Creme Brulee Getaway

Studio
1 Bathroom
4.6875
(32 Reviews)
Part of Banana's Foster Guest House

This comfortable 2nd floor studio right on the corner of Caroline and Simonton, just a block off Duval, is a great spot for 2 guests wanting to be in the thick of things! After entering the compound from the shared off street parking into the courtyard with...

Paradise Suite

1 Bedroom
1 Bathroom
4.2000
(5 Reviews)
Nestled in extensive tropical and flowering gardens, complete with aviaries with singing cockatiels lays the Paradise Suite.

Paradise Suite is a bi-level suite with one bedroom upstairs. The bedroom features a king bed and is decorated in rich tropical colors with local Key West hand colored...

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...

Pelican Suite

Studio
1 Bathroom
4.6842
(38 Reviews)
Part of Southernmost Suites

The Pelican Suite is located in The Southernmost Suites on historic Simonton Street. Tucked back within the garden the Pelican Suite offers a serene escape from the hustle and bustle. The Pelican Suite has 2 Queen Beds and a kitchenette for you to enjoy meals in before...

Sunrise Suites - Saint Martin Suite 207

2 Bedrooms
2 Bathrooms
4.8542
(48 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 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...

Egret Suite

Studio
1 Bathroom
4.5208
(48 Reviews)
Part of Southernmost Sanctuary Suites

Located on Historic Simonton Street, these suites are the perfect cozy escape you've been looking for! An adorable front porch to watch the people biking, walking or scooting along. Start your mornings on the porch with your Cuban coffee and a good book before...

The Frontier Flat

1 Bedroom
1 Bathroom
4.7500
(12 Reviews)
***Nearby construction in building thru 6/30/2017***

Nestled atop the most happening spots in Key West, is The Frontier Flat. The location of this newly renovated one-bedroom, one-bathroom unit simply cannot be beat! It sits right next to Rum Barrel so you can not get any closer to the action!...

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...

Sunrise Suites - Bonaire Suite 210

2 Bedrooms
2 Bathrooms
4.6333
(30 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...

Sunrise Suites - Dominican Suite 110

2 Bedrooms
2 Bathrooms
4.4583
(24 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...

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...

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...

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...

Coconut Palm

3 Bedrooms
2 Bathrooms
4.7368
(38 Reviews)
COCONUT PALM (formerly Island Oasis). Take a lot of history and a lot of charm - mix it with a great location and you have the perfect Key West hideaway. A vacation rental home built and operated in the late 1800's as the city's hack concession and stables, has been transformed with bits and...

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...

Sunrise Suites - Barbados Suite 204

2 Bedrooms
2 Bathrooms
4.5455
(33 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...

Bahama Dreaming

3 Bedrooms
2 Bathrooms
4.8462
(13 Reviews)
BAHAMA DREAMING: A beautifully renovated Conch cottage in Key West, conveniently located in the center of Old Town, one block behind celebrated Duval Street, quiet and private. Only a short walk to the many attractions, Key West activities, world-renowned Key West restaurants and nightclubs,...

Sunrise Suites - Saint Croix Suite 212

2 Bedrooms
2 Bathrooms
4.5714
(28 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...

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