Pet-friendly holiday rentals in Stock Island

4.91 out of 5 average rating, 297 reviews

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.

Townhouse in Key West

Comfortable, clean, beautiful home Nov. Specials

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

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.

4.87 out of 5 average rating, 69 reviews

Key West Paradise

Bring the whole family or a great group of friends to this fantastic house w/lots of room for fun. 3 Bed (1 on main level, 2 up), 3 Full Baths (1 on main level, 2 up), sleeper sofa in living room and air mattress in closet, Steps to Community Pool, Sleeps up to 8. Nice Kitchen for your use. High speed internet. TV in the living room and in every bedroom. Enjoy the breeze from your nice size front porch, rear deck off living room, and balcony off upstairs bedroom. 8 minutes to Duval Street.

A charming entrance is framed by lush tropical landscaping and vibrant foliage. A brick walkway leads through a white arched gate, guiding guests between two pastel-colored cottages. Lush palm trees and colorful plants create a welcoming atmosphere, enhancing the overall serenity of the space.

5 out of 5 average rating, 8 reviews

Robinson Crusoe Cottage~ Delight In Island Vibes

Welcome to your Key West holiday! This newly acquired and improved one-bedroom cottage has all you need to relax and unwind. Whether walking to Duval Street, Mallory Square, or nearby restaurants, you will enjoy a comfortable stay in an ideal location. THE PROPERTY: Enjoy your stay with us at Robinson Crusoe Cottage, part of the quaint Conch Cottages property, which includes 3 separate rentable units: Robinson Crusoe Cottage at the rear, Royal Poinciana Cottage on the right, and Margarita ...

Top guest favourite

A serene waterfront scene is captured at sunset, featuring palm trees, boat docks, and a gently reflecting harbor. A large boat is tied up alongside the dock, with colorful lights and silhouettes of the surrounding structures visible in the background.

4.91 out of 5 average rating, 229 reviews

"Abaco" Key West • 2/2 End Unit Waterfront+Dockage

Time to fish & relax! Bring your family & friends to this 1350 sqft waterfront corner condo home. Boat slip available on-site with commercial ice machine and fish cleaning station. Located in historic Downtown Key West. Walk/Bike everywhere less 1mi to Duval Street, Seaport, Hemingway House, etc. On-site amenities: heated pool, boat slip, tiki bar & grills, parking, secure keyless entry, & building elevator. Large Park adjacent with tennis courts. 10min from airport (EYW).

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.

4.87 out of 5 average rating, 106 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***

4.91 out of 5 average rating, 102 reviews

Aerial view of a waterfront property featuring a semi-circle dock leading to a small island. Brightly colored chairs in green and turquoise sit on sandy areas, surrounded by clear blue water and lush tropical vegetation. Nearby, additional properties can be seen amidst palm trees.

Home in Summerland Key

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!

4.92 out of 5 average rating, 296 reviews

A private courtyard is displayed, featuring a hot tub, two chairs, and a small table. The entrance to the suite is visible with elegant French doors that open to the interior. Lush greenery enhances the tranquil ambiance, with a striped awning offering partial shade.

Flat in Key West

Starr's Suite - 2 person K Suite w/Private Spa!

Starr's Suite features a King Pillow-Top Memory Foam mattress. Renovated in 2010, it features a tumbled marble shower, granite counter-tops in kitchen with dishwasher and vanity. Tommy Bahama bath amenities are provided, as well as coffee, creamer and sugar. 56” Smart TV (bring UN/PW for Netflix, Amazon, etc. to watch your favorite shows). Private Solana spa in your private courtyard. Daily housekeeping is provided. Use of 2 heated pools.

4.89 out of 5 average rating, 123 reviews

A cozy living space features a navy blue sofa adorned with nautical-themed throw pillows. A dining area with a glass table and chairs is visible in the background, alongside a decorative display of framed art and a potted plant. Natural light filters through the windows.

Houseboat in Marathon

Houseboat Getaway In Marathon

Get ready to indulge in a relaxing and unforgettable experience at the first overwater houseboat getaway in Marathon, Florida! 🌴🌊 What awaits you is - fun filled days living and exploring out on the fabulous florida keys waters in your own private aqualodge, breathtaking sunsets, and a private sanctuary perched above the sea. 😍 Don't miss out on this one-of-a-kind experience! Book your stay now and create memories that will last a lifetime.

4.92 out of 5 average rating, 145 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.

A serene pool area is surrounded by lush tropical palm trees and vibrant landscaping. Sunlight reflects off the clear water, creating a calming ambiance. Nearby, a white lounge chair is positioned for relaxation, with a life preserver visible on the side.

4.89 out of 5 average rating, 114 reviews

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.

Top guest favourite

A light green two-story house is surrounded by lush tropical plants. The front porch features white railings and is accessed by a set of stairs. Nearby parking is available, and sunlight brightens the exterior under a clear blue sky.

4.95 out of 5 average rating, 38 reviews

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.

A serene pool area is visible in the foreground, bordered by lush greenery and ocean views. Tall palm trees sway gently along the shoreline, where the calm water reflects the sky. A distant pier can be seen, enhancing the coastal atmosphere.

4.93 out of 5 average rating, 165 reviews

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.

Popular amenities for Stock Island pet-friendly home rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Pet-friendly house rentals

5 out of 5 average rating, 9 reviews

Ibis Suite | Bright Hideaway, Hot Tubs, Steps from

A serene waterway is shown, flanked by palm trees and waterfront homes. A boat is seen navigating the calm waters, with clear skies enhancing the tranquil scene. The reflection of the surroundings is visible on the surface, creating a peaceful atmosphere.

4.64 out of 5 average rating, 173 reviews

Ocean Front Home in Great Location

Top guest favourite

A private pool is framed by a smooth deck with lounge chairs for sunbathing. Surrounding palm trees provide a tropical backdrop, while clear skies and gentle clouds reflect a serene atmosphere. The pool’s water is inviting and crystal clear, perfect for relaxation.

4.96 out of 5 average rating, 27 reviews

Sombrero Sunset-Marathon 7BR 6BA Waterfront Pool

A vibrant green house is presented with large windows adorned with yellow shutters. A spacious front porch is bordered by tropical plants, while a gravel pathway leads to the entrance. Nearby, a blue trash bin is visible, along with a parked vehicle.

4.76 out of 5 average rating, 21 reviews

Tropical Island Getaway

An aerial view captures the scenic beauty of the area, showcasing the azure waters and the iconic 7 Mile Bridge extending across the horizon. Surrounding residences and palm trees contribute to the coastal character, highlighting the inviting atmosphere of the Florida Keys.

4.67 out of 5 average rating, 6 reviews

Sea Glass Cottage~ Pet Friendly Tropical Home!

Aerial view of the Venture Out community showcases a large swimming pool adjacent to the sandy beach. Palm trees surround the area, with calm turquoise waters extending into the distance. Amenities include a tiki structure and a spacious lounging area, ideal for relaxation and outdoor activities.

4.78 out of 5 average rating, 46 reviews

Waterfront FL Keys Cottage @ Venture Out

A sandy beach is lined with lounge chairs under tall palms, leading towards a turquoise sea. A palapa provides shade, while colorful chairs offer additional seating. In the distance, boats are docked at a private dock, with calm waters reflecting a clear blue sky.

4.82 out of 5 average rating, 60 reviews

(#1)Beautiful 4 Bed 3 Bath Pool Home w Free Dock

4.57 out of 5 average rating, 115 reviews

A gravel pathway winds through lush tropical landscaping, flanked by vibrant palm trees and decorative stone borders. The sunlight filters through the foliage, creating a serene ambiance in the inviting outdoor space.

Home in Big Pine Key

The Hideaway - Private Paradise at its Best!

Pet-friendly home rentals with a pool

4.82 out of 5 average rating, 292 reviews

La Dolce Vita, Old Town Steps to Duval! 3 blks bch

4.67 out of 5 average rating, 3 reviews

43' Classic Yacht Views, Pools, Duval Shuttle

A bright living area features a comfortable blue sofa and armchair arranged around a glass coffee table. Natural light enters through the windows and reflects off the light-colored walls. A wooden console holds a television, while decorative art pieces enhance the homey atmosphere.

4.77 out of 5 average rating, 151 reviews

Dog Friendly 1BR | Pool | Easy Beach Access

Campervan/Motorhome in Big Pine Key

A well-maintained 28-ft Grey Wolf RV is parked on a gravel lot, surrounded by tropical greenery. Two lounge chairs are positioned on a green patch of grass, creating a relaxing outdoor seating area. Sunshine filters through the clouds, adding a bright ambiance to the scene.

4.79 out of 5 average rating, 19 reviews

RV In The Keys | Tropical Retreat

A private balcony offers a view of the pool surrounded by lush palm trees and tropical landscaping. A glass-top table and two chairs are set up for outdoor seating, allowing for enjoying the pleasant surroundings and fresh air.

4.82 out of 5 average rating, 172 reviews

Newly Renovated Condo - St. Martin Suite

4.74 out of 5 average rating, 124 reviews

An empty gravel lot is showcased, surrounded by lush greenery and palm trees. A picnic table is positioned to one side, providing a space for outdoor dining. The open area suggests ample room for a camper and additional parking.

Campsite in Big Pine Key

Bring Your Own RV! Our Lot Your RV B6 No Tents

Tiny home in Big Pine Key

4.94 out of 5 average rating, 82 reviews

Tiny Fish Haus

A spacious bed is situated against a wall adorned with a unique, colorful design. Large glass doors provide a view of the marina, revealing boats and the waterfront outside, with natural light filtering into the room.

4.73 out of 5 average rating, 26 reviews

Glamorous Houseboat Stay @ The Perry

Private, pet-friendly home rentals

A community pool is surrounded by tropical landscaping and white lounge chairs. The water is clear and inviting, with blue tile accents lining the pool's edge. Sunlight reflects off the surface, creating a refreshing atmosphere for relaxation.

Campervan/Motorhome in Big Pine Key

4.66 out of 5 average rating, 35 reviews

Tiny home in RV park with pool

Apartment in Summerland Key

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.

5 out of 5 average rating, 7 reviews

Family Suite at Sugarloaf Key Hotel (Pet Friendly)

The hotel lobby features a spacious design with high ceilings and large windows allowing natural light. A modern reception area is accented by artwork and wooden elements. Comfortable seating arrangements are provided in the lounge area, fostering a welcoming environment for guests.

4.67 out of 5 average rating, 9 reviews

Romantic Captain's Quarters

4.85 out of 5 average rating, 20 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.

Flat in Key West

Duval Corner - Pet friendly with Balcony

5 out of 5 average rating, 6 reviews

Houseboat in Key West

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.

Houseboat in Key West

4.78 out of 5 average rating, 338 reviews

Key West Houseboat Paradise

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.

Houseboat in Key West

4.72 out of 5 average rating, 255 reviews

Deluxe Bungalow

The image captures a coastal neighborhood featuring several homes with blue roofs. A view of the Atlantic Ocean is seen in the background, along with a dock and palm trees. Pathways and greenery surround the properties, illustrating a serene environment.