Pet-friendly holiday rentals in Sunset Key

Romantic Retreat - 2 person K Suite, Pvt deck/Spa!

Romantic Retreat is an Historic, free standing cottage which, in the 1800's, was the cistern for the Cigar Maker cottages here. It is decorated in a light Caribbean motif, efficiency kitchen (frig, microwave, hot plate) and a very airy bathroom with tub/shower. King memory foam bed and sleeps 2 persons only. 32” Smart TV (bring your Netflix, Amazon UN/PW's). Bose Bluetooth speaker, Amazon Alexa provided. A private adjacent deck with a 2 person Solana spa/seating. Also handicapped accessible.

Duval Vibes • Pool • 10 Guests

Located only 30 seconds from Duval Street, this house will be your Key West headquarters for bachelor parties, family reunions, or any celebration that bring you to town. This 3 bedroom/ 2.5 bathroom home has a full kitchen, spacious outdoor living space, outdoor shower, private second story sundeck, and a pool. Your group of up to 10 will love being steps away from all KW has to offer- be Hemingway's neighbor! Add this listing to your wishlist by clicking the ♥ in the upper right hand corner.

The Writer's Block- Key West

Discover tranquility aboard this unique floating haven. It's a sleek modern retreat for those who crave space to read, write or find inspiration far from the stresses of the modern world --yet it's steps away from upscale restaurants, two fabulous pools, a gym and so much more. From a king bed to a full-sized shower and kitchenette, you'll enjoy the comforts of home while living directly on the water. Features a large private deck with panoramic views of the marina and its glorious sunsets.

Downtown Key West 2BR/2BA•Pool, Dock, Pet "Aruba"

Enjoy true space in Key West! This 1,200 sq ft waterfront condo offers a full kitchen, dining area, living room, 2 bedrooms, and a private balcony—so much more than a hotel. Bring your boat—dockage is included with water, power, and a fish cleaning station. Relax by the heated pool or grill out at the tiki area. Walk or bike to Duval Street, the Seaport, Hemingway House, and more—less than 1 mile away. Pet-friendly, free on-site parking, and just 10 minutes from EYW airport.

Spanish Queen @Venture Out

Experience the beautiful Florida Keys and stay at the popular Venture Out Private Community at Cudjoe Key. Newly furnished two-bedroom, 2 bath stilt home checks all the boxes for the ultimate Florida Keys Vacation. Sun- filled open floor plan allows family to spend the their precious time together cooking and entertaining. Two-2 person kayaks and 4 bikes included *** Please note that guests must pay a resort entry fee of $125 directly to security upon entry into the park***

1 Bedroom Aqualodge # 6 Tarpon

This memorable place is anything but ordinary. This beautiful Aqualodge is located at The Florida Keys Resort and Marina (Old Wooden Bridge) in quiet Big Pine Key, FL. It overlooks the Bogie Channel. Sit on the front porch and see the gorgeous sunrise. You are able to enjoy the amenities of the resort during your stay. There is NO Swimming in the Marina Boat Basin. There is a beautiful salt water pool. This is a marina with houseboats and rental boats in slips.

Waterfront Haven House with Boat Basin & Ramp!

Welcome to Paradise! Stay in the amazing Keys and beautiful waterfront home with boat basin and ramp for your boat. The property lot is almost an acre with another rental home and still very spacious (search for Anchor House to reserve both homes if available). Stunning panoramic water views, sunrise and sunset. Steps away from ocean water. Bring or rent fishing and snorkel gear nearby to fish right off the point and enjoy the underwater scenery!

The Dancing Rooster - 1 Block to Duval!

Located just 2 short blocks from Duval and in the center of downtown, the Southernmost Retreat is a recently renovated and decorated 3 bedroom, 2 bath house. The Southernmost Retreat is part of the Simonton Historic Cottage enclave and is surrounded by fine restaurants, art galleries, shopping and proximate to all attractions in the Old Town District. No car is needed as you can walk to the beaches and all of the famous attractions.

Oceanfront Condo in Key West

Key West Beach Club is a serene waterfront oasis located in an upscale gated community within walking or biking distance to the local’s finest spots, including restaurants, beaches, shopping centers, bars and the infamous Duval Street. This complex prides itself for being one of the very few on the island that sits directly on the water.

Gone Coastal

Relax with the whole family at this peaceful place to stay. Completely renovated 3 bedroom 2.5 bath townhome in Coral hammock. Enjoy the pool and excellent location on Stock island. Walking distance to Roostica and Hogfish grill. Dogs are welcome but not over 25lbs. Pitsbulls are not allowed by hoa.

Casa Capri 3 bed 3 bath sleeps 8 tropical decorate

Bring the whole family to this great place with lots of room for fun. Sleeps 8. Three bedroom house each with its own bathroom. Two king bedrooms upstairs, downstairs bedroom can have two twins or convert into a king upon request.

Beach Club Ocean Front 2BR Condo

Come fall in love with Key West in our luxurious ocean front condo. The Key West Beach Club is located directly on the Atlantic in a quiet residential secured building. It is a 2BR, 2 1/2 Bath located in Mid-Town.