Pet-friendly holiday rentals in Stock Island

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.

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.

Tiny House | 35 min to KW + Free Parking & Pool

Discover a hidden gem in the Florida Keys with this charming Tiny House, surrounded by nature and the famous Key Deer. Located in the peaceful Breezy Pine RV Resort, it offers a cozy yet spacious layout for the whole family. Relax outdoors on the private patio with sofa and grill, perfect for enjoying the laid-back Keys lifestyle. With all the essentials for comfort and just a short drive to Key West, Bahia Honda beaches, shops and restaurants. This retreat is ideal for relaxation and fun.

Curaçao Key West 2BR Condo w/ Pool&Waterfront Dock

Time to relax! Bring your family & friends to this 1200 sqft Waterfront home - Stay spacious in Key West. Boat slips available on site with commercial ice machine, fish cleaning station and BBQ grills. Located in Downtown Key West. Walk/Bike everywhere less 1mi to Duval Street, Historic Seaport, Hemingway House, etc. On-site amenities: heated pool, tiki bar & grill, bike rentals, parking, secure keyless entry, & elevator. Large park adjacent with tennis courts. 10min from airport (EYW).

Waterfront Cozy Cottage with Boat Ramp & Dock!

Welcome to Paradise! Stay in the amazing Keys and beautiful waterfront home with 250 foot dock, ramp, and basin for your boat. It's a must-see rustic outdoor environment and fishery experience, very typical in the Keys! The property lot is almost an acre with a work section and still very spacious. 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 dock and enjoy the underwater scenery!

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***

Luxurious 40' Sailing Yacht!

Enjoy exclusive use of this 40-foot yacht all to yourselves, with the opportunity to get close to ocean life. This yacht is docked at the Perry Hotel & Marina, with free access to two stunning waterfront swimming pools, live music, three restaurants, complimentary shuttle service, & more. Come and go on the yacht anytime, day or night. Participating in an ocean excursion on this yacht is mandatory & comes at an extra charge. Inquire here about our other yachts in our fleet

Duval Corner - Pet friendly with Balcony

Welcome to Duval Corner! A beautifully updated one-bedroom condo in the heart of Downtown Key West. This second-floor retreat is perfect for travelers wanting to be steps from it all. Within walking distance to iconic attractions like the Southernmost Point, The Ernest Hemingway Home, and Mallory Square, plus dining hotspots such as Blue Heaven, 7 Fish, and Louie's Backyard; Duval Corner is the ideal base for your Key West adventure.

Tiny Fish Haus

Great location in the lower keys , 28 miles to Key West..8 miles to Bahia Honda State Park and right next to the National Key Deer Refuge! Relax on our covered patio next to a large Swimming Pool, Cook dinner on a Blackstone grill and enjoy WIFI, Games, a Flat Screen TV , we have Premium Organic Bedding on our Queen beds for comfort. Turkish Towels for bath and beach..Explore Big Pine Key with our 2 beach cruiser bicycles!

Classic 30’ Sailboat

A Unique Key West Getaway! Welcome aboard Sparhawk! This beautiful 30-foot Baba double-ender sailboat offers a cozy and unforgettable stay for 2 adults and 2 small children’s . Crafted with warm teak interiors and timeless nautical charm, Sparhawk is perfect for couples, small families, or adventurous souls looking for something off the beaten path.

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.

Island Style - the only way to vacation!

This quaint property offers resort-style accommodations at an affordable price! Nestled among a colony of freestanding Conch style cottages, amid lush tropical landscaping, sits Island Style, the sister cottage of Hidden Treasure.