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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 - Saint Barts Suite 303

2 Bedrooms
2 Bathrooms
4.5581
(86 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 Havana @ Duval Square R22

2 Bedrooms
2 Bathrooms
4.6512
(86 Reviews)
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, secured parking beneath the complex and security...

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...

Sunrise Suites - Rum Cay Suite 304

2 Bedrooms
2 Bathrooms
4.6735
(98 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...

Commodore's Cove

4 Bedrooms
4 Bathrooms
4.6000
(10 Reviews)
When you walk into Commodore's Cove, you will be greeted by beautiful exposed-Dade County Pine walls, impeccable decor and gorgeous furnishings. Not only is this property BRAND NEW but it is also STEPS from all of the hottest spots in Key West. It might even take you longer to lock the door, than...

Kate's Krawl By Duval

1 Bedroom
1 Bathroom
4.7857
(28 Reviews)
This 1 bed 1 bath home is the perfect home for you to enjoy Key West and all it has to offer. Located just steps from the World-Famous Duval St. you will find yourself in one of the most desired locations in Key West. Downstairs in this home you will find a full kitchen and comfortable living...

Hemingway's Retreat

4 Bedrooms
3 Bathrooms

Steps away from Hemingway’s house sits his “Hideaway”. Allow the authentic feel of old Key West inspire you like the famed author. Recently renovated and with enough room to sleep 10, this luxury Conch House will allow you and your guests to experience island living at its finest. Few locations...

Old Town Garden Villas

4 Bedrooms
6 Bathrooms
4.9231
(26 Reviews)
The location is set on Center Street, which is located ½ block off Duval Street. These Villas are a favorite of our guests who like to relax in the quiet, beautiful garden area. Your party can book 1 to 5 of these Villas for a relaxing vacation.

Old Town Garden Villas is comprised of the following...

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...

Tropical Village Retreat

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...

The Galleria - Carey's Corner

Studio
1 Bathroom
4.4167
(24 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 - Tahiti Suite 104

2 Bedrooms
2 Bathrooms
4.6000
(10 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 - 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...

Southernmost Retreat

2 Bedrooms
1 Bathroom
4.6591
(88 Reviews)
Southernmost Retreat 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. The perfect place to listen to your favorite music while...

Sunrise Suites - Panama Suite 310

2 Bedrooms
2 Bathrooms
4.4857
(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...

The Headquarters

2 Bedrooms
1 Bathroom
Walk into to The Headquarters and experience purer paradise! The living area has gorgeous, light wooden, vaulted ceilings and a plush couch that offers ultimate comfort.

Just off the kitchen, you will find a state of the art kitchen with stainless steel appliances and granite countertops. The...

Papa's Hideaway

6 Bedrooms
6 Bathrooms
5.0000
(28 Reviews)
Papa's Hideaway is a Guesthouse property comprised of Garden of Eden, Torrents of Spring , Sun Also Rises , For Whom the Bell Tolls, and Islands in the Stream. This private compound had a large outdoor gathering area around your private pool equipped with Grill, Sundeck, and Bar. Located on a...

A Key Escape

3 Bedrooms
2 Bathrooms
4.9012
(162 Reviews)

A Key Escape 3 br 2.5 bath w/ private heated pool. Professionally decorated in a Coastal Living style, this elegant yet very comfortable custom built 3 bedroom, 2.5 bath, 3 story home has a living room (Q sleeper sofa) with rose hardwood floors, a gourmet kitchen with granite countertops and...

Carriage Courtyard

3 Bedrooms
3 Bathrooms
Carriage courtyard prior to becoming the beautiful modern wonder that it is today was used to store a horse drawn carriage. Newly remodeled, you can now retreat to you very own courtyard paradise.

Located in Historic Bahama Village and only one block away from the World famous Duval St, places...

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...

Seaport Suite

4 Bedrooms
3 Bathrooms
4.8235
(68 Reviews)
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 block off Duval Street and within walking distance to every single thing you could possibly want to do. With...

Creme Brulee Getaway

Studio
1 Bathroom
4.6875
(64 Reviews)
Part of Banana's Foster Guest House

This comfortable 2nd floor studio right on the corner of Caroline and Simonton, just a block off Duval, is a great spot for 2 guests wanting to be in the thick of things! After entering the compound from the shared off street parking into the courtyard with...

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...

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