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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 153 results matching your search criteria
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Egret Suite

Studio
1 Bathroom
4.5208
(96 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...

Sweet Caroline

2 Bedrooms
2 Bathrooms
4.7027
(74 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...

Southern Cross - Tropical Village

2 Bedrooms
2 Bathrooms
4.7826
(46 Reviews)
Southern Cross: Lounging next to the gorgeous shared pool or sitting in the shade of your own Royal Poinciana tree, Southern Cross is the perfect place to relax in paradise. This one and a half story vacation cottage is surrounded by exotic gardens, and situated in the Tropical Village Compound...

Southern Comfort @ Key Cove

4 Bedrooms
3 Bathrooms
Luxurious furnishings and spacious interiors centered around the expansive water views perfectly compliment the beautiful outdoor spaces. Slow down, relax and prepare for life the way it should be at Southern Comfort. This home is located in the private community of Key Cove Landings, on an...

Sunrise Suites - Dominican Suite 110

2 Bedrooms
2 Bathrooms
4.4583
(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...

Sunrise Suites - Big Kahuna Suite 202

2 Bedrooms
2 Bathrooms
4.7429
(70 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...

Tropical Cottage

2 Bedrooms
2 Bathrooms
4.6364
(66 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...

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...

Tropical Retreat

3 Bedrooms
3 Bathrooms
4.8714
(140 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...

Sunrise Suites - Antigua Suite 312

2 Bedrooms
2 Bathrooms
4.4706
(34 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 Too

3 Bedrooms
2 Bathrooms
4.5517
(58 Reviews)
Almost Southernmost Too in the 400 block of Truman Avenue is the perfect location, located between Duval Street and Whitehead St. Just around the corner from Hemingway's House and the Historic Lighthouse Museum, Almost Southernmost Too is a perfect example of shotgun architecture with a front...

Coconut Palm

3 Bedrooms
2 Bathrooms
4.7368
(76 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...

Tsalta

3 Bedrooms
3 Bathrooms
5.0000
(4 Reviews)
At last, a magnificent 3-bedroom home in the middle of Old Town with room for all. This home is a BIG secret but not for long! Lushly landscaped grounds with meandering brick walkways leading to the main house, pool and guest cottage. New owners with new furnishings and linens, breathing new life...

Old Town Garden Villas - Caribbean Suite

1 Bedroom
1 Bathroom
4.8833
(120 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...

Key West Nest

3 Bedrooms
2 Bathrooms
This could be your home away from home… All the comforts you’re used to right here in Key West.

The 3 bedrooms and 2 baths comfortably accommodate up to 6 persons (3 couples, etc). There is a king bed in the master bedroom and queen beds in the other two bedrooms. The kitchen is well stocked with...

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...

Ibis Suite

Studio
1 Bathroom
4.7000
(80 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...

Havana Daydream @ 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 waterfront pool. Luxurious furnishings and spacious interiors centered around the expansive water views perfectly compliment the beautiful outdoor spaces. Slow down...

Club Clark

3 Bedrooms
3 Bathrooms
4.7500
(8 Reviews)
The main dwelling includes a beautiful, newly-renovated kitchen, a master bedroom with en-suite, a second bedroom with twin beds (which can be made into a king upon request), a full guest bathroom including a tub and full vanity, and an open, spacious living room with beautiful furnishings...

Conch Casa

2 Bedrooms
1 Bathroom
4.7069
(116 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,...

Key Lime Calypso

2 Bedrooms
1 Bathroom
4.4000
(20 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...

Sunrise Suites - Trinidad Suite 105

2 Bedrooms
2 Bathrooms
4.6829
(82 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...

Sunset Marina View

2 Bedrooms
2 Bathrooms
Gorgeous monthly rental next to the golf course on stock island in Key West! This spacious condo is located next to the best dining and water activities the island has to offer!

When you walk into the condo, you will be fall in love with the island feel of the home. The breeze hits the palm trees...

Traveler's Palm

Studio
1 Bathroom
4.7429
(70 Reviews)
Traveler's Palm (formerly Palm Isle) - a room ahead of its time - A truly "green unit". Your roommate, or in this case, "suite mate" is a giant Sapodilla tree that provides the ambiance and shade to your private hot tub and tree-top hammock. The second-story studio apartment comes complete with a...

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