You are here

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 73 - 96 of 144 results matching your search criteria
Map ViewGrid view
List View

Wahoo Way On Duval

1 Bedroom
1 Bathroom
5.0000
(14 Reviews)
This Studio has everything you want and a location that can not be beat. Located on upper Duval St, you are walking distance to Southernmost Point, Mallory Square, shops, restaurants, beaches and bars. The tile floors and Dade Pine walls give this Studio a real Key West feel. Outfitted with a...

Ibis Suite

Studio
1 Bathroom
4.7000
(80 Reviews)
Part of Southernmost Sanctuary Suites

The Ibis Suite is located at The Sanctuary in Old Town key West, Only steps to the action, this studio suite has all the comforts of home but surrounds you in island style! Lush gardens surround the Jacuzzi and the calm atmosphere is exactly what you'll need...

Sunrise Suites - Hispaniola Suite 101

2 Bedrooms
2 Bathrooms
4.7037
(54 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 - Cozumel Suite 112

2 Bedrooms
2 Bathrooms
4.6667
(60 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...

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...

Mermaid Manor

4 Bedrooms
3 Bathrooms
In one of the most desirable lanes in Old Town Key West. The perfect location for walking to Duval Street and the historic Seaport. Situated at the end of a quiet lane on a lush tropical lot. This 4 bedroom home is in one of the most sought after neighborhoods on the island. High ceilings, hardwood...

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...

Palm Gardens

3 Bedrooms
3 Bathrooms
4.9474
(38 Reviews)
The Condos are tied together in a lushly landscaped garden setting with a spa pool in the rear. Booking all three condos gives you a great alternative to booking a single house as you are offered privacy and closeness at the same time. Call to book your Island Paradise while there is still time!...

Sunrise Suites - Big Kahuna Suite 202

2 Bedrooms
2 Bathrooms
4.7429
(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...

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...

Southern Comfort @ Key Cove

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...

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...

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...

Old Town Garden Villas - Little Havana Suite

1 Bedroom
1 Bathroom
4.7761
(134 Reviews)
Little Havana suite is a bi-level suite with a very spacious bedroom upstairs with king bed, down pillows, tv/dvd player, writing desk and chair, in-room safe, iron & ironing board complete with Bahama ceiling fan, and a/c.. The upstairs large tiled walk-in shower with hair-dryer makes this...

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...

Tropical Village Hideaway

2 Bedrooms
1 Bathroom
4.6875
(96 Reviews)
Tropical Hideaway - Lush gardens surround this lovingly renovated vacation home. This one-story, 2 bedroom 1 bathroom condo features a living room with queen sized pull out sleeper sofa, cable TV, DVD, stereo with CD player, and FREE wireless internet. Each bedroom has a queen sized bed and flat...

Sunrise Suites - Great Exuma Suite 406

2 Bedrooms
2 Bathrooms
4.7879
(66 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...

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...

Sea Breeze

2 Bedrooms
1 Bathroom
4.7273
(110 Reviews)
Sea Breeze features all the amenities of then some! A full kitchen with glass top stove, dishwasher, icemaker, blender, toaster, coffee maker and radio/CD player to play your favorite Jimmy Buffet CD while enjoying a fresh cup of isn't a better way to start your day in paradise!

A covered porch/...

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...

Southernmost Sanctuary

6 Bedrooms
6 Bathrooms
4.8571
(14 Reviews)
Southernmost Sanctuary Suites are comprised of the following homes Egret Suite, Heron Suite, Ibis Suite, Osprey Suite, Pelican Suite, Seagull Suite which can all be booked individually.

Located on Historic Simonton Street, these suites are the perfect cozy escape you've been looking for! An...

Poolside Paradise

3 Bedrooms
2 Bathrooms
4.7179
(78 Reviews)
POOLSIDE PARADISE is made up of POOLSIDE RETREAT and POOLSIDE SUITE

With 3 bedrooms (K, 2 Q, plus 2 Q sleeper), 2 full baths and 2 full kitchens, this historic home is perfect for up to 10 persons. The front portion features a King bedroom, a Queen bedroom and a Queen sleeper sofa in the living...

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...

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...

Pages