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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 148 results matching your search criteria
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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...

Sunrise Suites - Martinique Suite 108

2 Bedrooms
2 Bathrooms
4.7105
(76 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...

Southern Palms

5 Bedrooms
4 Bathrooms
4.8000
(30 Reviews)
Located at 729 Whitehead St, "Southern Palms" is the group property consisting of the following homes Coconut Palm, Traveler's Palm, and Royal Palm which can all be booked individually.

All together, these three units have 5 separate bedrooms, 3 separate hot tubs, and share an incredibly luscious...

Key Lime Cottage

Studio
1 Bathroom
4.6364
(66 Reviews)
Brand New to the Rental Market!


Part of
Banana's Foster Guest House

This cozy 2nd floor studio is perfect for a couple looking to be in the middle of the Duval action! After entering the compound from the shared off street parking into the courtyard with shared plunge pool and BBQ grill, go...

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...

Audubon House

1 Bedroom
2 Bathrooms
4.8039
(102 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...

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...

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...

Salty Air Retreat

2 Bedrooms
1 Bathroom
3.5000
(4 Reviews)
***Due to licensing restrictions, this property requires a minimum stay of 7 nights.***

****Exterior of property being painted 10/9-10/20****

This gorgeous two bedroom, one bathroom property is located in one of the most desirable areas of downtown Key West. With it's lavish walkways, on-site...

Sunrise Suites - Cayo Coco Suite 208

2 Bedrooms
2 Bathrooms
4.7436
(78 Reviews)

(Recently updated!) *** 1 Private, covered parking spot is included when you rent this particular vacation condo 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...

Casa Caribe @ Duval Square

2 Bedrooms
2 Bathrooms
4.7895
(114 Reviews)
Located in Duval Square (between Duval Street and Simonton Street), where fine dining abounds (Square One and Origami Sushi Bar), Casa Caribe is a second story paradise just steps from the sights, sounds and excitement of world-famous Duval Street.

Lush and tropical gardens surround this beautiful...

Amelia House

3 Bedrooms
2 Bathrooms
4.7460
(126 Reviews)
Amelia House is surrounded by fine restaurants, art galleries, and fine shopping.

The living room incorporates a sofa and chairs, in a colorful Caribbean print, which compliments the soft peach wall color. Included are rattan tables to complete the comfortable ambiance of the great room which...

Tropical Village Utopia

2 Bedrooms
1 Bathroom
4.6667
(60 Reviews)
Tropical Village Retreat - Lush gardens surround this lovingly restored two-story vacation house.

This upstairs suite has two bedrooms each featuring a queen bed. The fully equipped kitchen is perfect for the serious cook or enjoy your meals on the gas BBQ grill in a tropical setting. The living...

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...

Villa Azul

3 Bedrooms
3 Bathrooms
5.0000
(2 Reviews)
You will certainly enjoy this wonderful historic home with recent renovations, perfectly placed pool, and plenty of outdoor living space located at 1116 Curry Lane. This home is situated in the heart of Old Town, just 4 blocks to the Historic Seaport District or the Art Gallery District on White...

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...

Helen's Hideaway

2 Bedrooms
2 Bathrooms
4.8000
(110 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...

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...

Heron Suite

Studio
1 Bathroom
4.5833
(48 Reviews)
Part of Southernmost Sanctuary Suites

The Heron Suite is located street side with it's own porch for people watching. Get one of Ana's Cuban mixes - it just doesn't get any better! Conveniently located to the beach, Duval Street, great restaurants, Ana's for great Cuban fare and morning coffee -...

The Galleria - Claude Monet Suite

Studio
1 Bathroom
4.7400
(100 Reviews)
This wonderful unit is set apart from the others with cathedral ceilings and a skylight in each room; light and airy and yet very cozy and comfortable. This efficiency condo is perfect for 2 and can even accommodate the occasional guest with the living room sleeper sofa.

The bedroom has a queen...

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,...

Duval Dreamin'

2 Bedrooms
2 Bathrooms
This property is quite the hidden gem! Located on the second story of one of the most famous streets in the world, you will find Duval Dreamin'. The home over looks Duval Street and features TWO living areas, TWO bedrooms and TWO bathrooms. This is the perfect pad for couples, friends or family...

Bahama House

3 Bedrooms
3 Bathrooms
4.8182
(88 Reviews)
The BAHAMA HOUSE located at 508 Amelia Street is a historic Bahamian-style Conch Cottage. It is a perfect example of turn-of-the-century island architecture. This adorable 3 bedroom home includes 2 bedrooms in the main house and an additional mother-in-law suite by the pool. Each bedroom features...

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...

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