Pet-friendly holiday rentals in Stock Island

A shared pool area is depicted, featuring clear blue water and a thatched roof gazebo. Surrounding palm trees and lush greenery create a serene atmosphere. Lounge chairs are placed along the pool deck, complemented by the light-colored brick pathway paving the area.

4.92 out of 5 average rating, 332 reviews

Comfortable, clean, beautiful home in Key West

Introducing a brand new property hosted by AirBnb Superhost Roy Svenningsen. This home was fully renovated in January 2019. It features all new furnishings, stainless steel appliances, new flooring, marble countertops, and top quality mattresses. I look forward to hosting you in this beautiful family oriented gated community situated across from the Key West Golf Course and only 3 miles from Duval St. The home comes with parking for 2 cars. I am always available to answer any questions. Roy

PetsWalkabilityCheckout

Tiny home in Big Pine Key

A serene beach scene captures soft sands meeting clear waters under a bright blue sky. Lush palm trees frame the view, while visitors are seen enjoying the tranquil coastline and gentle waves. Green foliage and distant beach cabanas are also visible, enhancing the natural beauty.

4.88 out of 5 average rating, 129 reviews

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!

Outdoor spacesPetsKitchen

4.97 out of 5 average rating, 319 reviews

Harrison's Hideaway-Sleeps up to 4, K & F Sl Sofa!

Historic Harrison's Hideaway is in an 1880's Cigar Maker's cottage renovated in 2010. It features a K size Pottery Barn memory foam bed, custom made full sleeper sofa, renovated kitchen with granite counter tops, 2 burner stove, under counter fridge/freezer, dishwasher, microwave, air fryer/oven tumbled marble 2 person shower, private front deck with seating for 4, 2 person Solana spa. Perfect for a couple or a family with children. Freshly painted a Caribbean blue with plantation shutters.

Outdoor spacesPetsAir conditioning

4.89 out of 5 average rating, 150 reviews

A spacious balcony overlooks the harbor, featuring a dining table and wooden chairs. Lush palm trees are visible nearby, with the serene water reflecting the blue sky. The scene is perfect for outdoor relaxation and enjoying the coastal ambiance.

Condo in Key West

Waterfront Condo Dock Pool Near Duval St

Relax above it all in this spacious top-floor waterfront condo in downtown Key West, offering added privacy and sweeping marina views. Perfect for families and groups, enjoy a full kitchen, open living space, and private balcony. Dockage available with a fish cleaning station and ice maker, ideal for boating and fishing. Located about 1 mile from Duval Street, restaurants, and nightlife, and 10 minutes from EYW airport, with a heated pool, tiki area, BBQ grills, parking, and secure entry.

WalkabilityOutdoor spacesParking

Cottage in Little Torch Key

A waterfront property is surrounded by lush palm trees, with a gravel area leading to a private dock. The home is painted in soft blue tones, reflecting a comfortable coastal vibe. The expansive water views offer shimmering reflections under the clear sky.

4.89 out of 5 average rating, 183 reviews

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!

WalkabilityPetsSleep quality

4.97 out of 5 average rating, 34 reviews

Home in Summerland Key

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!

WalkabilityOutdoor spacesHospitality

An aerial view captures a vibrant community of stilt homes nestled along the coastline, with clear blue waters stretching in the background. Lush palm trees dot the landscape, while a distinctive red marker indicates a specific location within this scenic setting.

4.84 out of 5 average rating, 127 reviews

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***

PetsWalkabilityComfort

A private outdoor area features a hot tub surrounded by tropical foliage. A dining table with chairs is situated nearby on a wooden deck, offering shade from the overhead structure and a relaxing atmosphere for outdoor meals.

4.88 out of 5 average rating, 121 reviews

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.

Outdoor spacesPetsValue

4.91 out of 5 average rating, 170 reviews

A charming yellow cottage is framed by a white picket fence, with blue awnings above the windows and door. The entrance is marked by a simple white door. Lush greenery surrounds the property, enhancing the inviting appearance of the home.

Cottage in Key West

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.

Outdoor spacesWalkabilityCheck-in

5.0 out of 5 average rating, 19 reviews

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.

WalkabilityNearbyAccuracy

4.89 out of 5 average rating, 116 reviews

A bright living area features light-colored furniture, including a comfortable sofa and armchair. A wooden coffee table is centrally placed. Art displays adorn the walls, enhancing the inviting ambiance. Nearby seating accommodates dining for four, with large windows allowing natural light to flow in.

Apartment in Key West

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.

PetsWalkabilityTV

The outdoor swimming pool features a circular design surrounded by tropical palm trees and lounge chairs. Bright blue umbrellas provide shade for guests, while the clear blue sky enhances the vibrant atmosphere of the gated community.

4.94 out of 5 average rating, 155 reviews

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.

WalkabilityOutdoor spacesFamily

Popular amenities for Stock Island pet-friendly home rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Pet-friendly house rentals

A well-maintained community pool is surrounded by lush tropical landscaping, featuring lounge chairs with blue umbrellas. The clear water reflects the bright blue sky and palm trees, creating a relaxing atmosphere for guests to enjoy.

4.89 out of 5 average rating, 99 reviews

Key West Paradise

PetsOutdoor spacesParking

A well-maintained two-story house features light-colored siding and contrasting blue shutters. A spacious, welcoming front porch is framed by tropical plants and neatly arranged landscaping. Steps lead up to the front door, providing easy access to the entrance.

5.0 out of 5 average rating, 39 reviews

Casa Calypso 3bed3bath sleeps 8 beautiful decorate

PetsWalkabilityQuiet

4.77 out of 5 average rating, 13 reviews

KW CanalFront 3BR: Htd Pool, Boat Tie-Up, Pet OK

PetsWalkabilityAir conditioning

4.93 out of 5 average rating, 96 reviews

Oceanfront w/ Dock, Swimming pool, Hot Tub, Kayaks

Outdoor spacesPetsDecor

4.94 out of 5 average rating, 17 reviews

Oceanfront 2BR in Venture Out - 35’ Dock + Pool

WalkabilityNearbyGetting around

A wooden sign displaying the word 'paradise' is mounted above a window. The letters are painted in a mix of colors, with a weathered finish. Soft sunlight filters through the white blinds, casting gentle shadows on the wall.

4.96 out of 5 average rating, 26 reviews

Island Paradise

WalkabilityOutdoor spacesQuiet

5.0 out of 5 average rating, 4 reviews

Flagler House in Key West

Outdoor spacesTVKitchen

A shared pool is surrounded by lush tropical foliage and palm trees, providing a serene atmosphere. Two lounge chairs are visible beside the pool, inviting relaxation while the nearby fence adds a touch of privacy.

4.78 out of 5 average rating, 40 reviews

Paradise Place by AvantStay | Condo w/ Shared Pool

WalkabilityOutdoor spacesSleep quality

Pet-friendly home rentals with a pool

4.64 out of 5 average rating, 28 reviews

43' Classic Yacht Views, Pools, Duval Shuttle

Outdoor spacesWalkabilityAmenities

Tiny home in Summerland Key

4.94 out of 5 average rating, 79 reviews

Cottage

Outdoor spacesPetsDecor

4.97 out of 5 average rating, 36 reviews

An aerial view showcases the resort's central pool surrounded by palm trees and landscaped gardens. The inviting pool area is complemented by a spacious pavilion with a metal roof, providing a gathering space. The background features the resort's accommodations and the lush natural environment.

Condo in Summerland Key

Family Suite at Sugarloaf Key Hotel (Pet Friendly)

PetsOutdoor spacesAccuracy

Casa particular in Summerland Key

5.0 out of 5 average rating, 9 reviews

La casita del Retiro

Outdoor spacesFamilyComfort

5.0 out of 5 average rating, 4 reviews

Key West • The Harbor House • Luxury Sea Charters

NearbyAmenitiesHospitality

A wooden bridge leads through a lush garden, framed by greenery and festive decorations. A stone wall is visible at the end of the path, flanked by potted plants. Light filters softly through the nearby trees, creating a serene and inviting entryway.

4.75 out of 5 average rating, 28 reviews

Hemingway First Floor Townhouse @ Suite Dreams Inn

Outdoor spacesWalkabilityIndoor spaces

4.88 out of 5 average rating, 32 reviews

A bright living area features a plush blue sofa adorned with colorful throw pillows. A coffee table sits in front of the sofa, surrounded by light wood accents. Large glass doors lead to a private balcony, inviting natural light and views of greenery.

Condo in Key West

The Butterfly Nest | Newly Updated w/ Shared Pool

CheckoutParkingLaundry

A bright and inviting exterior view captures the charming two-story townhome nestled among tropical foliage. A white picket fence surrounds the property, and the entrance features double doors flanked by decorative plants. Sunlight bathes the scene, enhancing the serene outdoor environment.

4.81 out of 5 average rating, 118 reviews

Location Location Beach Paradise in the Keys Duval

PetsWalkabilityBackyard

Private, pet-friendly home rentals

4.89 out of 5 average rating, 18 reviews

Love Shack: 2BR Houseboat w/ Decks & Views

Outdoor spacesFamilyAccuracy

A private conch cottage floats on calm waters, featuring a light green exterior with white trim. Spacious decks are present at the front and back, while paddle boards and kayaks are visible nearby, highlighting the connection to the surrounding nature.

4.95 out of 5 average rating, 83 reviews

Key West Outpost: eco-vacation

PetsOutdoor spacesBreakfast

4.86 out of 5 average rating, 56 reviews

A light and airy living area features a modern blue sofa adorned with patterned throw pillows. A wooden coffee table sits in front, complemented by a tall indoor plant. A full-length mirror reflects the space, while natural light brightens the room through the patio door.

Apartment in Key West

Duval Corner - Pet friendly with Balcony

PetsWalkabilityQuiet

A 40-foot catamaran is anchored in clear turquoise waters. Two individuals are enjoying the ocean; one is swimming while another relaxes on the deck. The yacht features a modern design with a spacious deck for sunbathing and enjoying the surrounding scenery.

4.96 out of 5 average rating, 25 reviews

Luxurious 40' Sailing Yacht!

Check-inSleep qualityCondition

A tranquil marina scene is captured at sunset, with colorful clouds reflecting on calm water. A row of Aqualodges is visible along the water's edge, alongside several parked boats and a tiki hut, creating a serene atmosphere.

4.69 out of 5 average rating, 423 reviews

Deluxe Bungalow

WalkabilityOutdoor spacesLong stay

A spacious living room features two sofas, one of which is a fold-out bed, and a coffee table centered on a patterned area rug. Large windows with wooden blinds allow light to fill the room, highlighting the full kitchen area and breakfast bar in the background.

4.77 out of 5 average rating, 366 reviews

Key West Houseboat Paradise

PetsOutdoor spacesParks

A shared heated pool is surrounded by lush tropical landscaping, featuring palm trees and vibrant greenery. Sun loungers are positioned around the pool area, inviting relaxation under the clear blue sky. The tranquil atmosphere is enhanced by the gentle curves of the pool's edge.

4.82 out of 5 average rating, 34 reviews

Coral Oasis: 3BR Retreat, Pool, Dogs OK, Parking

Outdoor spacesWalkabilityComfort

The master bedroom features a four-poster bed dressed in light bedding, accompanied by soft decorative elements. Natural light floods the space through a large window, which opens to an outdoor balcony adorned with greenery. A side table and ceiling fan add to the room's ambiance.