Pet-friendly holiday rentals in Stock Island

A charming cottage features a covered deck with a dining table and chairs, positioned beside a pool. Lush palm trees and tropical plants surround the area, adding greenery. The pool water is clear and inviting, with a depth marking visible at the edge.

4.95 out of 5 average rating, 363 reviews

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.

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

Houseboat in Stock Island

A spacious sleeping area features a king bed dressed in soft linens and adorned with decorative pillows. Natural light enters through sliding glass doors that open to views of the marina. Warm wood flooring complements the modern design.

4.95 out of 5 average rating, 38 reviews

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.

4.87 out of 5 average rating, 106 reviews

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.

Home in Cudjoe Key

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***

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.

4.91 out of 5 average rating, 11 reviews

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

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!

4.89 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 scenic view of the waterfront reveals a calm harbor lined with boat slips. The vibrant blue water reflects the sky, while a tiki hut and chaise lounge chairs surround a heated pool in the foreground, enhancing the coastal ambiance.

4.88 out of 5 average rating, 226 reviews

Florida | Waterfront 2BR/2BA w/ Pool + Dock Access

Bring friends and family to this updated 1,350 sqft waterfront corner condo in historic downtown Key West! Just 1 mile to Duval St, the Seaport, and Hemingway House. Enjoy on-site boat slips, heated pool, tiki bar, BBQ grills, parking, elevator, and secure keyless entry. Fish cleaning station and commercial ice machine available. Large park with tennis courts next door. Walk or bike everywhere—only 10 minutes from EYW airport!

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.

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

The outdoor living area features a private pool surrounded by tropical greenery. Chaise lounges and an umbrella provide shaded seating options, while a porch with colorful cushions offers additional relaxation space. A glimpse of the home's porch and vibrant landscaping enhances the tranquil setting.

4.98 out of 5 average rating, 44 reviews

Casa Serendipity at Old Town

4.64 out of 5 average rating, 173 reviews

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.

Home in Cudjoe Key

Ocean Front Home in Great Location

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

Home in Upper Sugarloaf Key

A sandy beach area is framed by swaying palm trees, leading to a two-story bungalow elevated on stilts. Lounge chairs are arranged on the shore, providing a relaxing spot, while kayaks are visible in the background, enhancing the inviting beach setting.

4.74 out of 5 average rating, 97 reviews

Palm - Beach Houses Key West

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!

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!

5 out of 5 average rating, 3 reviews

A serene waterfront view captures the calm canal lined with palm trees. A concrete patio area is visible, accompanied by a fishing dock featuring rod holders. Nearby, a cozy seating area invites relaxation while enjoying the gentle breeze and scenic surroundings.

Home in Cudjoe Key

Canal Front Home in Gated Community. Salt Life

Pet-friendly home rentals with a pool

4.81 out of 5 average rating, 291 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

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

A spacious houseboat is moored at the marina, featuring multiple deck levels and seating areas for relaxation. The surrounding water reflects a clear blue sky, while neighboring yachts are visible in the background. This inviting setting showcases the boat's modern design.

Houseboat in Key West

4.84 out of 5 average rating, 260 reviews

Key West Luxury Houseboat at Yacht Club Resort

4.74 out of 5 average rating, 123 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

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

An interior view of the boat reveals a comfortable sleeping area with a spacious bed, adorned with a colorful throw pillow. A well-equipped kitchenette is visible, featuring modern appliances and storage. Soft natural light filters through a skylight above, enhancing the cozy ambiance.

Houseboat in Key West

5 out of 5 average rating, 4 reviews

"Losin It", super cute super cozy boat

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

A 22-foot sailboat is docked at a marina, showcasing a yellow hull that contrasts with the water's surface. The boat features a blue canopy and is equipped with multiple lines and sails. Palm trees are visible in the background, framing a serene evening sky.

4.6 out of 5 average rating, 5 reviews

Sailboats Docked @ Key West&ALL Hotel Amenities !

5 out of 5 average rating, 6 reviews

Houseboat in Key West

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.