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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 49 - 72 of 148 results matching your search criteria
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Banana Split

1 Bedroom
1 Bathroom
4.4737
(38 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...

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,...

Sunrise Suites - Saint Martin Suite 207

2 Bedrooms
2 Bathrooms
4.8542
(96 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
(64 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...

The Galleria - Coral Cove

Studio
1 Bathroom
4.6111
(72 Reviews)
This wonderful unit that has been completely remodeled in July 2013 has a private entrance in to the quaint efficiency on the back side of the complex.

Featuring hardwood floors, Dade County Pine walls and a high-end, fully stocked kitchenette, this secluded hideaway offers the finest of...

Sunrise Suites - Grand Turk Suite 404

2 Bedrooms
2 Bathrooms
4.6500
(80 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...

Poolside Paradise

3 Bedrooms
2 Bathrooms
4.7179
(78 Reviews)
POOLSIDE PARADISE is made up of POOLSIDE RETREAT and POOLSIDE SUITE

With 3 bedrooms (K, 2 Q, plus 2 Q sleeper), 2 full baths and 2 full kitchens, this historic home is perfect for up to 10 persons. The front portion features a King bedroom, a Queen bedroom and a Queen sleeper sofa in the living...

Golf Club Getaway

2 Bedrooms
1 Bathroom
Cute 2 bed 1.5 bath house located in the Key West Golf Club with fenced in yard.

New Furnishings and Appliances. Great location, steps to golf clubhouse and visitor parking, 2 miles from airport, very close to shopping, and 4 miles from Duval. Private setting with no neighbors to back, fenced yard...

Sunrise Suites - Grand Cayman Suite 309

2 Bedrooms
2 Bathrooms
4.5556
(90 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
(26 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,...

Duval Square Penthouse R19

2 Bedrooms
2 Bathrooms
4.5714
(112 Reviews)
Located in Duval Square (between Duval Street and Simonton Street), where fine dining abounds (Square One, Origami Sushi Bar and NY Pasta Garden),
This spacious unit is only steps from a large pool and covered gazebo. On the ground floor is a secured garage for parking your vehicle.

Lush and...

Pelican Suite

Studio
1 Bathroom
4.6842
(76 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...

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...

Banana's Foster Guesthouse

7 Bedrooms
8 Bathrooms
4.7273
(44 Reviews)
All together this home has 7 separate bedrooms, each with it’s own bathroom and a ½ bath downstairs in the main house, 2 full kitchens, a BBQ grill and shared courtyard with a plunge pool. The historic downtown property also has 4 off street parking spaces right outside the gated courtyard on...

Pescado Penthouse On Duval

3 Bedrooms
3 Bathrooms
5.0000
(8 Reviews)
This 3 bed 3 bath group unit is perfect for any group looking to enjoy Key West for all it has to offer. It is comprised of the 3 units Kingfish Keep, Yellowfin Ledge, and Wahoo Way. Located on upper Duval St, this property is in the perfect location and is walking distance to Southernmost Point,...

Sea Breeze

2 Bedrooms
1 Bathroom
4.7273
(110 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/...

Royal Palm

Studio
1 Bathroom
4.7143
(56 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...

Sunrise Suites - Grand Bahama Suite 106

2 Bedrooms
2 Bathrooms
4.6538
(52 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 - Bonaire Suite 210

2 Bedrooms
2 Bathrooms
4.6333
(60 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...

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...

A Key Escape

3 Bedrooms
2 Bathrooms
4.9012
(162 Reviews)

A Key Escape 3 br 2.5 bath w/ private heated pool. Professionally decorated in a Coastal Living style, this elegant yet very comfortable custom built 3 bedroom, 2.5 bath, 3 story home has a living room (Q sleeper sofa) with rose hardwood floors, a gourmet kitchen with granite countertops and...

Sunrise Suites - Tierra Bomba Suite 403

2 Bedrooms
2 Bathrooms
4.3043
(46 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...

Truman Suite

Studio
1 Bathroom
4.7073
(82 Reviews)
The Truman 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...

Kate's Krawl Off Duval

1 Bedroom
1 Bathroom
4.7857
(28 Reviews)
This 1 bed 1 bath home is the perfect home for you to enjoy Key West and all it has to offer. Located just steps from the World-Famous Duval St. you will find yourself in one of the most desired locations in Key West. Downstairs in this home you will find a full kitchen and comfortable living...

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