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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 164 results matching your search criteria
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Captain's Quarters

2 Bedrooms
2 Bathrooms
Due to city restrictions, this beautiful rental property requires a minimum stay of 28 nights.

This completely private & secluded 2 bed 2 bath Key West home features an incredible, large outdoor area and pool that is perfect for entertaining. This Nautically themed house has the true feeling...

Poolside Paradise - Tropical Village

Studio
1 Bathroom
4.7778
(@ct 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,...

Sunset Marina View

2 Bedrooms
2 Bathrooms
Gorgeous monthly rental next to the golf course on stock island in Key West! This spacious condo is located next to the best dining and water activities the island has to offer!

When you walk into the condo, you will be fall in love with the island feel of the home. The breeze hits the palm trees...

Eliza's Escape

4 Bedrooms
3 Bathrooms
Unwind on the wrap around patio, cool off in the pool, explore the wonders of your next vacation. Let Eliza's Escape become your favorite vacation spot!

Surprisingly elegant tropical oasis. Unassuming and hidden by lush mature foliage, in a quite Key West neighborhood. Be swept away by warm...

Southern Cross - Tropical Village

2 Bedrooms
2 Bathrooms
4.7826
(@ct Reviews)
Southern Cross: Lounging next to the gorgeous shared pool or sitting in the shade of your own Royal Poinciana tree, Southern Cross is the perfect place to relax in paradise. This one and a half story vacation cottage is surrounded by exotic gardens, and situated in the Tropical Village Compound...

Saint Lucia Suite #201

2 Bedrooms
2 Bathrooms
4.6842
(@ct Reviews)
Sunrise Suites Resort is an island paradise. Complimentary hourly shuttle service from 9:15 AM - 5:30 PM daily between the Resort, beaches, airport, ferry terminal, & downtown make this resort's location ideal. Spend sun-filled days pampered by our warm and friendly staff. Pull up a lounge...

Great Exuma Suite #406

2 Bedrooms
2 Bathrooms
4.7879
(@ct Reviews)
***Recently updated

Sunrise Suites Resort is an island paradise. Complimentary hourly shuttle service from 9:15 AM - 5:30 PM daily between the Resort, beaches, airport, ferry terminal, & downtown make this resort's location ideal. Spend sun-filled days pampered by our warm and friendly staff...

Saint Barts Suite #303

2 Bedrooms
2 Bathrooms
4.5581
(@ct Reviews)
Sunrise Suites Resort is an island paradise. Complimentary shuttle service from 9:15 AM - 5:30 PM daily between the Resort, beaches, airport, ferry terminal, & downtown make this resort's location ideal. Spend sun-filled days pampered by our warm and friendly staff. Pull up a lounge chair and...

Duval Hideaway

2 Bedrooms
1 Bathroom
4.6970
(@ct 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...

Big Kahuna Suite #202

2 Bedrooms
2 Bathrooms
4.7429
(@ct Reviews)
Sunrise Suites Resort is an island paradise. Complimentary hourly shuttle service from 9:15 AM - 5:30 PM daily between the Resort, beaches, airport, ferry terminal, & downtown make this resort's location ideal. Spend sun-filled days pampered by our warm and friendly staff. Pull up a lounge...

Commodore's Cove

4 Bedrooms
4 Bathrooms
4.6000
(@ct 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...

Almost Southernmost Retreat

5 Bedrooms
3 Bathrooms
4.8519
(@ct Reviews)
Almost Southernmost Retreat is made up of ALMOST SOUTHERNMOST and ALMOST SOUTHERNMOST TOO on the 400 block of Truman Avenue is the perfect location between Duval Street and Whitehead Streets.

This style is common throughout the islands. Located in a row of identical cigar-maker cottages, the...

Tahiti Suite #104

2 Bedrooms
2 Bathrooms
4.6000
(@ct Reviews)
Sunrise Suites Resort is an island paradise. Complimentary hourly shuttle service from 9am - 6pm daily between the Resort, beaches, airport, ferry terminal, & downtown make this resort's location ideal. Spend sun-filled days pampered by our warm and friendly staff. Pull up a lounge chair and...

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...

Hemingway's View

3 Bedrooms
2 Bathrooms
4.6667
(@ct 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...

Sugar Pie Suite

Studio
1 Bathroom
4.7083
(@ct 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...

Puerto Rico Suite #103

2 Bedrooms
2 Bathrooms
4.6923
(@ct Reviews)
Sunrise Suites Resort is an island paradise. Complimentary hourly shuttle service from 9:15 AM - 5:30 PM daily between the Resort, beaches, airport, ferry terminal, & downtown make this resort's location ideal. Spend sun-filled days pampered by our warm and friendly staff. Pull up a lounge...

Grenada Suite #209

2 Bedrooms
2 Bathrooms
4.7419
(@ct Reviews)
*** 1 Private, covered parking spot is included when you rent this particular vacation condo

Sunrise Suites Resort is an island paradise. Complimentary hourly shuttle service from 9:15 AM - 5:30 PM daily between the Resort, beaches, airport, ferry terminal, & downtown make this resort's...

Cabana Retreat

3 Bedrooms
3 Bathrooms
Welcome to Cabana Retreat, a newly constructed monthly rental located in the brand new Southernmost Cabana Town Home Complex.

Cabana Retreat is nothing short of pure perfection. A complete turnkey, fully accommodating monthly vacation rental is hard to come by. Located in the heart of 'Old Town...

Banana Breeze @ Key Cove

4 Bedrooms
3 Bathrooms
Newly Decorated And Fully Appointed With Water View *30 NIGHT MIN STAY REQUIRED*

Look out at the open water views while enjoying the professionally decorated interior and spacious outdoor patio. Imagine relaxing at "Banana Breeze" with friends, family or both while listening to island music and...

Heron Suite

Studio
1 Bathroom
4.5833
(@ct 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 -...

Sea Breeze

2 Bedrooms
1 Bathroom
4.7273
(@ct 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/...

Nautical Wheeler

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 Nautical Wheeler. This home is located in the private community of Key Cove Landings, on an...

Saint Thomas Suite #302

2 Bedrooms
2 Bathrooms
4.8438
(@ct Reviews)
Sunrise Suites Resort is an island paradise. Complimentary hourly shuttle service from 9:15 AM - 5:30 PM daily between the Resort, beaches, airport, ferry terminal, & downtown make this resort's location ideal. Spend sun-filled days pampered by our warm and friendly staff. Pull up a lounge...

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