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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 121 - 144 of 153 results matching your search criteria
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Tradewinds

4 Bedrooms
2 Bathrooms
4.7353
(68 Reviews)
Tradewinds is comprised of the Leeward Isle and Windward Isle

Two Cigar Maker’s Cottages, side-by-side, located ½ block off Duval Street. These two cottages are a favorite of our guests who like to relax in the private, quiet, beautiful garden areas with large spas that are behind each house. Your...

Poolside Retreat

1 Bedroom
1 Bathroom
4.6957
(46 Reviews)
One-half block off world famous Duval Street sits the beautifully renovated home in the 500 block of Olivia Street. The updated kitchen features granite counter tops and beautiful wooden floors. Your bathroom offers a large walk-in tiled shower. A semi-private pool with waterfall feature(shared...

Poolside Paradise - Tropical Village

Studio
1 Bathroom
4.7778
(108 Reviews)
Where else can you find resort style accommodations at motel pricing? Poolside Paradise @ Tropical Village, features all the amenities needed for a quick weekend getaway vacation at an affordable nightly rate. Once the winter vacation suite of Pulitzer Prize winning cartoonist Jeff MacNelly,...

Sunrise Suites - Grenada Suite 209

2 Bedrooms
2 Bathrooms
4.7419
(62 Reviews)

*** 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 lush tropical foliage...

Casa Cubana @ Duval Square R14

2 Bedrooms
2 Bathrooms
4.7397
(146 Reviews)
Lush and tropical gardens surround this beautiful development in the heart of historic Old Town. Private, secured parking beneath the complex and security entrances gives the feeling of exclusivity unparalleled in Key West.

The foyer of this Mediterranean Style unit with Mexican Tile downstairs...

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...

Sunrise Suites - Puerto Rico Suite 103

2 Bedrooms
2 Bathrooms
4.6923
(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 - Tortuga Suite 301

2 Bedrooms
2 Bathrooms
4.6250
(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...

Casa Bonita @ Duval Square R1

2 Bedrooms
2 Bathrooms
4.8000
(140 Reviews)
Short walk to Fort Zachary State Park and South Beach!

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 tropical gardens surround this beautiful development in the heart of historic Old Town. Private...

Hemingway's View

3 Bedrooms
2 Bathrooms
4.6667
(126 Reviews)
One block from Center St, Hemingway's View is a 3 bedroom, 2 bath charming turn-of-the-century Conch cottage.

Each of the 3 bedrooms are air-conditioned. Both bathrooms have marble floors, large closets, hairdryers, and tubs with showers. The rear bath has a marble topped vanity with double sinks...

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...

Commodore's Compound

8 Bedrooms
7 Bathrooms
Commodore's Compound is comprised of 2 separate units - Seaport Suite and Commodore's Cove:

SEAPORT SUITE:

Seaport Suite is available for daily vacation rentals and located on the second floor of an historic Key West home in Old Town.. The location is as close to perfect as you can get, being one...

Leeward Isle

2 Bedrooms
1 Bathroom
4.7600
(50 Reviews)
One half of the group unit Tradewinds, opposite Windward Isle, the Leeward Isle sits at 529 Olivia Street, right in the center of Old Town Key West, just 1/2 block from Duval Street. This superb example of shotgun style architecture is complimented with original Dade County pine floors and walls,...

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...

Spa On Duval @ Duval Square R11

2 Bedrooms
2 Bathrooms
4.6400
(100 Reviews)
A Key West Gem!

Fine dining abounds here with great restaurants such as Square One, Origami Sushi Bar and Panini/Panini, which offers free wi-fi). In the “must have” location of historic, old town Key West, it is a second story home-away-from-home, just steps from the sights, sounds and...

Truman @ Duval - Two Bedroom

2 Bedrooms
1 Bathroom
4.4490
(98 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...

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...

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...

Duval Delight

1 Bedroom
1 Bathroom
4.8246
(114 Reviews)
Duval Delight is a breathtaking, newly-renovated 2-story condo located at the historic "Cuban Club" on the "quieter" side of world famous Duval St. This high end vacation rental features a huge 55-inch flatscreen TV in the living room and all brand new furniture including a comfy, pull-out queen...

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...

Bay Harbor View

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

a passport tucked away off of mile marker 15.

While relaxing in the 20x12 free form lagoon pool, the surrounding scenery makes you feel like you are on your own deserted island.

Around the back of the...

Sugar Pie Suite

Studio
1 Bathroom
4.7083
(48 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...

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