Pet-friendly holiday rentals in Stock Island

Cottage 30 min from Key West, free parking, pool

Escape the everyday and unwind under the stars in this charming, nature-surrounded getaway where deer are frequent visitors. This cozy tiny house of offers 1 bedroom, 1 bathroom, and 3 beds, comfortably sleeping up to 4 guests. Enjoy peaceful surroundings, fresh air, and convenient double parking with space for a truck and boat trailer—perfect for outdoor adventures and total relaxation. Ideal for couples, families, or friends seeking quiet nights, wildlife views, and a simple, memorable stay!

Starlight Serenity - Hideaway with Stunning Views

Escape to paradise at this serene 1-bedroom, 1-bath home in beautiful Sugarloaf Key sleeping up to four guests. Enjoy breathtaking views from the expansive wrap-around balcony, perfect for sunrise coffee or sunset cocktails. The spacious outdoor area is ideal for dining, lounging, and soaking in the tropical ambiance. Whether you're relaxing indoors or savoring the outdoors, this home offers the perfect blend of comfort and tranquility. Book your next getaway for 3 nights or more!

Waterfront Dock Pool Condo Near Duval St Pet OK

Bring friends and family to this spacious 1,350 sq ft waterfront corner condo in historic downtown Key West. Enjoy a full kitchen, open living space, and a private balcony with marina and pool views. Dockage available with a fish cleaning station and commercial ice maker, perfect for boating and fishing. Located about 1 mile from Duval Street, the Historic Seaport, and Hemingway House. Amenities include a heated pool, tiki area, BBQ grills, parking, elevator, and secure entry.

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***

Near Duval: Hot Tub, Sleeps 6, Top Location

Just 30 seconds from vibrant Duval Street, this iconic conch home is your perfect Key West escape! With two bedrooms, one bathroom, a full kitchen, and private outdoor perks—like a hot tub, second-story sundeck, and outdoor shower—you’ll have everything you need to relax in paradise. Ideal for up to 6 guests, it’s a tropical haven steps from world-class dining, shopping, and beaches. Book now and soak up the island life! Don’t forget to click the ♥ to save it for later.

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.

Strictly Pleasure | Unique Yacht Stay in the Keys

Staying aboard Strictly Pleasure offers a truly unique Keys experience. Enjoy life on the water with beautiful marina views, sunsets from the bow, and the charm of staying on a classic yacht. Located at Perry Marina, guests have access to pools, waterfront restaurants, and the trolley to downtown Key West. It’s the perfect mix of relaxation, location, and a one-of-a-kind stay you won’t find in a typical hotel.

Sunset Suite-Historic 2 BR, K/Q, Sleeps 4, Spa!

Historic 1880's Cigar Maker's cottage completely renovated. 1 K and 1 Q BR’s, half bath upstairs between BR’s, 32” Smart TV's, Full kitchen with granite counter tops, new stainless steel appliances. A newly remodeled bath with tumbled marbled tile, hairdryer. Also a totally private outdoor shower located in your private patio. All bath amenities provided, plus pool towels and daily housekeeping!

Castaway Cove: Pet-friendly 2/2 condo near beach!

Welcome to the tranquil, tucked away community of Sunrise Suites in beautiful Key West, Florida. When you choose to spend your vacation with us at the pet-friendly Castaway Cove Condo, you will be just 1 mile from Smather's Beach and a quick 10 minute drive to the fun and excitement of downtown Duval Street with tons of restaurants, bars, art galleries, museums, live music and people watching.

Paradise found

Located on Stock Island this 3 bedroom home is only 8 minutes from Duval street. Walking distance to several great restaurants. Gated community with a gym and large resort style swimming pool. Queen bedroom on first floor with full bath. Second floor King room with private full bath. 3rd bedroom as two twin beds beds with private full bath.

Houseboat in Key West

Enjoy this 45-ft '71 houseboat, single stateroom with queen bed, perfect for a couple or solo adventure. No resort frills, just old-school Key West vibes, mile-wide water views, and mangroves. Full bath, full kitchen, and a spacious sun deck to enjoy stunning sunsets and stargazing at its finest. 15 mins to Duval.