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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 1 - 24 of 145 results matching your search criteria
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Paradise Suite

1 Bedroom
1 Bathroom
4.2000
(10 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 - Salt Cay Suite 410

2 Bedrooms
2 Bathrooms
4.6905
(84 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...

Coastal Comfort @ Key Cove

4 Bedrooms
3 Bathrooms
This home is located in the private community of Key Cove Landings, on an exclusive lane of waterfront residential homes. The perks of this little-known location are many: walking distance to the essentials such a Publix grocery store and the largest shopping center on the island, while still being...

Tropical Village - 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...

The Galleria - Andy's Attic

Studio
1 Bathroom
4.4000
(20 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...

Sunrise Suites - Cayo Cruz Suite 308

2 Bedrooms
2 Bathrooms
4.7632
(76 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...

Shark Key Chateau

5 Bedrooms
4 Bathrooms
4.7500
(8 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...

Palm Isle

1 Bedroom
1 Bathroom
4.7209
(86 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...

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...

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...

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...

Sunrise Suites - Margarita Suite 305

2 Bedrooms
2 Bathrooms
4.7188
(64 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 - 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...

Seagull Suite

Studio
1 Bathroom
4.6047
(86 Reviews)
Part of Southernmost Sanctuary Suites

People looking for a vacation getaway in Key West are thrilled when they find a hidden gem like The Seagull Suite - located in the gardens of a private compound called The Sanctuary. Location, charm, and island appeal - the Seagull Suite is located in the back...

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,...

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,...

Heron Hideaway

1 Bedroom
1 Bathroom
4.5581
(86 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.

Historic homes dating to the late 1880s, the tropical paradise has just undergone a complete restoration with exceptional attention to details...

Duval Hideaway

2 Bedrooms
1 Bathroom
4.6970
(66 Reviews)
Duval Hideaway features all the comforts of home, and then some! A full kitchen with everything needed to prepare a gourmet meal including washer/dryer, glass top stove, dishwasher, blender, toaster, coffee maker and radio/CD player.

Each of the queen bedrooms has a 24' LCD TV, spacious closets...

Tropical Village

12 Bedrooms
9 Bathrooms
5.0000
(24 Reviews)
Tropical Village is comprised of 6 separate vacation rentals properties that can also be rented separately.
Located at 706 and 708 South St - near The Southernmost Point - this nightly group unit is the perfect getaway spot for large groups of friends and family.

COTTAGE @ TROPICAL VILLAGE:...

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 - 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...

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...

The Galleria - Salvador's Suite

Studio
1 Bathroom
4.5714
(42 Reviews)
Welcome to the Salvador Dali Suite, located in Old Town Key West just a few blocks from Duval St! Efficiency and affordability at its finest! The Salvador Dali Suite has everything you need to fulfill your Key West Vacation needs - a super comfy, full-sized bed, a kitchenette complete with a...

Tobago House

2 Bedrooms
2 Bathrooms
4.7500
(8 Reviews)
***Due to licensing restrictions, this property requires a minimum stay of 28 nights.***

Tobago House is just steps from restaurants, night life, Hemingway's House, and the 'Southernmost Point' of the United States. This home offers an open, airy floor plan with old style pine walls and floors,...

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