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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 73 - 96 of 135 results matching your search criteria
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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...

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...

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...

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...

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...

Sugar Pie Suite

Studio
1 Bathroom
4.7083
(24 Reviews)
This cute and colorful studio is perfect for anyone who is excited to explore Key West. You are just around the corner from all Duval Street has to offer. Restaurants, bars, shops, live music.. it's all just steps away. Be sure to catch the sunset at Mallory Square and a bite to eat on the harbor...

Casa Key West @ Duval Square R32

3 Bedrooms
2 Bathrooms
4.6500
(60 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...

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 - Grand Cayman Suite 309

2 Bedrooms
2 Bathrooms
4.5556
(45 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...

Monroe Suite

Studio
1 Bathroom
4.5000
(40 Reviews)
The Monroe Suite is nestled at the rear of the Simonton Court complex. The efficiency studio features a fully-equipped kitchen, flatscreen TV with cable, free wireless internet, and private patio furniture to relax on. The bathroom has a custom tiled shower with glass door and vanity.

Take...

Wahoo Way On Duval

1 Bedroom
1 Bathroom
5.0000
(7 Reviews)
This Studio has everything you want and a location that can not be beat. Located on upper Duval St, you are walking distance to Southernmost Point, Mallory Square, shops, restaurants, beaches and bars. The tile floors and Dade Pine walls give this Studio a real Key West feel. Outfitted with a...

Helen's Hideaway

2 Bedrooms
2 Bathrooms
4.8000
(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...

Sea Breeze

2 Bedrooms
1 Bathroom
4.7273
(55 Reviews)
Sea Breeze features all the amenities of then some! A full kitchen with glass top stove, dishwasher, icemaker, blender, toaster, coffee maker and radio/CD player to play your favorite Jimmy Buffet CD while enjoying a fresh cup of isn't a better way to start your day in paradise!

A covered porch/...

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...

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...

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...

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...

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...

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...

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...

Conch Casa

2 Bedrooms
1 Bathroom
4.7069
(58 Reviews)
The kitchen is fully equipped with a glass top stove, refrigerator with ice-maker, microwave and everything needed for cooking a gourmet meal or just heating leftovers! French doors open from the kitchen and breakfast bar onto a private deck with a large 4 person private hot tub, table and chairs,...

Island Oasis

2 Bedrooms
2 Bathrooms
4.7778
(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...

Banana Split

1 Bedroom
1 Bathroom
4.4737
(19 Reviews)
Part of
Banana's Foster Guest House

This one bedroom apartment is on the 2nd floor of this historic property and accessed through the shared gated courtyard, right beside the shared off street parking on Simonton. Once through the gates, walk around the shared plunge pool and BBQ grill, going...

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