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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!

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Sunrise Suites - Panama Suite 310

2 Bedrooms
2 Bathrooms
4.0000
(2 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 Village Utopia

2 Bedrooms
1 Bathroom
4.6667
(30 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...

Hemingway's View

3 Bedrooms
2 Bathrooms
4.6667
(63 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...

Poolside Suite

2 Bedrooms
1 Bathroom
4.6364
(22 Reviews)
One-half block off world famous Duval Street sits the beautifully renovated home on the 500 block of Olivia Street. A semi-private pool with waterfall (shared with Poolside Retreat) and Private Off-Street Parking makes this the ideal Old town location.

Enjoy nearby bars, shops, and fine dining...

Southern Comfort @ Key Cove #8

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 - Antigua Suite 312

2 Bedrooms
2 Bathrooms
4.4706
(17 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...

Audubon House

1 Bedroom
2 Bathrooms
4.8039
(51 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...

Old Town Garden Villas - Bermuda Suite

1 Bedroom
1 Bathroom
4.7551
(49 Reviews)
Nestled in extensive tropical and flowering gardens, complete with aviaries with singing cockatiels is the Bermuda Suite.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!

Downstairs is a...

Kingfish Keep On Duval

1 Bedroom
1 Bathroom
4.8889
(9 Reviews)
This large and luxurious apartment is second to none when it comes to properties on Duval St. Walking distance to Southernmost Point, Mallory Square, beaches, restaurants, and bars, you cant beat the location. No detail was overlooked in the design of this property. There are vaulted ceilings,...

Sunrise Suites - Grand Cayman Suite 309

2 Bedrooms
2 Bathrooms
4.5556
(45 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 Key West @ Duval Square R32

3 Bedrooms
2 Bathrooms
4.6500
(60 Reviews)
**Recently Renovated!!

Located in Duval Square (between Duval St and Simonton St) where fine and varied dining abounds (Square One, Origami Sushi Restaurant and New York Garden Cafe),

The foyer opens to the expansive living room with vaulted ceilings, dining room with seating for six and kitchen...

Osprey Suite

Studio
1 Bathroom
4.5135
(37 Reviews)
Part of Southernmost Sanctuary Suites

The Osprey Suite - Located in the Garden at the Southernmost Studios, the Osprey Suite is the perfect island getaway. Located within walking distance to all of the charms in Old Town you'll never want to leave! The Osprey has a Queen Bed as well as a sofa for...

Truman @ Duval - Two Bedroom

2 Bedrooms
1 Bathroom
4.4490
(49 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...

Helen's Hideaway

2 Bedrooms
2 Bathrooms
4.8000
(55 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...

Sweet Caroline

2 Bedrooms
2 Bathrooms
4.7027
(37 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...

Egret Suite

Studio
1 Bathroom
4.5208
(48 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...

Tropical Village

12 Bedrooms
9 Bathrooms
5.0000
(12 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:...

Royal Palm

Studio
1 Bathroom
4.7143
(28 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 - Barbados Suite 204

2 Bedrooms
2 Bathrooms
4.5455
(33 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 Split

1 Bedroom
1 Bathroom
4.4737
(19 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...

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...

Heron Hideaway

1 Bedroom
1 Bathroom
4.5581
(43 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...

Sunrise Suites - Saint Thomas Suite 302

2 Bedrooms
2 Bathrooms
4.8438
(32 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...

Spa On Duval @ Duval Square R11

2 Bedrooms
2 Bathrooms
4.6400
(50 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...

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