Pet-friendly vacation rentals in Stock Island

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.

4.79 out of 5 average rating, 47 reviews

Waterfront FL Keys Cottage @ Venture Out

Welcome to the BEAUTIFUL Florida Keys! The Keys Cottage 116 is a cute 2 bed, 1 bath home ON THE WATER in the desirable and SAFE Venture Out community on Cudjoe Key just 20 minutes from Key West. Starting at $195/night with weekly & monthly discounts & NO fees for EXTRA GUESTS! The amenities are INCREDIBLE! Large pool, hot tub, kiddie pool, PICKLEBALL, tennis, Bball, marina, 24 hr security, store, boat launch ramp, etc. We can do NIGHTLY rentals & WE ALLOW PETS, all for much less than a hotel.

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

4.97 out of 5 average rating, 276 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.

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, 39 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.

4.85 out of 5 average rating, 251 reviews

Condo in Key West

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).

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.

4.88 out of 5 average rating, 171 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!

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.

4.85 out of 5 average rating, 108 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***

4.92 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.

4.89 out of 5 average rating, 19 reviews

A covered outdoor dining area features a round table surrounded by six cushioned chairs. Scenic views of the turquoise water and distant shoreline are visible through the railing, with soft, natural light illuminating the space.

Bungalow in Cudjoe Key

Oceanfront Bungalow Venture Out

Wonderful, oceanfront, two bedroom, two bath, bungalow home is just ten feet from the open water ...incredible views. 52' concrete dock/seawall complete with dock posts and fishing table. Lovely decor. Bocce ball, playground. Tennis, Hot Tub, 2 pools. Recreation center with billiards, darts, and ping pong. Post Office and a Library 24 Hour Gated Security. . 40" screened TV. WIFI Saturday to Saturday only 7 night minimum.

5 out of 5 average rating, 16 reviews

Casa Cove 3bed3bath sleeps 8 beautiful decorated

Forget your worries in this spacious and serene space. Family home in gated community Coral Hammock on Stock Island just 2 miles from Key West. Spacious three bedrooms each with their own bathrooms. Fully stocked plenty of towels, beach towels and paper products.

4.93 out of 5 average rating, 166 reviews

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.

Condo in Key West

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.

Tiny home in Big Pine Key

A coastal scene showcases palm trees swaying gently by the water. Thatched roofs provide shaded seating areas along the shoreline. Sailboats are visible on the horizon, amidst clear turquoise waters under a bright blue sky, with a few fluffy clouds drifting by.

4.93 out of 5 average rating, 67 reviews

Cottage 30 min from Key West, free parking, pool

Get away from it all when you stay under the stars in this amazing little gateaway, surrounded by nature and amazing deers . This is Tiny house with 1 bedroom, 1 bathroom and 3 beds, accommodating up to 4 people!

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, 3 reviews

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

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, 45 reviews

Casa Serendipity at Old Town

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

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

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

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, 9 reviews

Robinson Crusoe Cottage~ Delight In Island Vibes

The exterior of the vacation home is framed by vibrant palm trees, providing a tropical feel. A white staircase leads to the covered front porch, which features a round glass door. Decorative stone landscaping complements the structure, enhancing its inviting appearance.

4.94 out of 5 average rating, 70 reviews

Atlantic access w/ Ocean view, 35’ seawall, pool

A covered front porch features comfortable seating options. Lush tropical plants and vibrant flowers surround the area, enhancing the welcoming entrance. Light blue and white accents on the structure provide a cheerful contrast with the greenery.

5 out of 5 average rating, 27 reviews

Catherine House: A charming Old Town Key West

Pet-friendly home rentals with a pool

Camper/RV in Big Pine Key

4.66 out of 5 average rating, 35 reviews

Camper in RV park in the Keys- Tiki Breezy

5 out of 5 average rating, 7 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)

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.

Boat in Key West

4.67 out of 5 average rating, 9 reviews

Romantic Captain's Quarters

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.

Boat in Key West

4.6 out of 5 average rating, 5 reviews

Sailboats Docked @ Key West&ALL Hotel Amenities !

A balcony with a light blue table and matching chairs overlooks a calm ocean. Soft clouds float in a bright sky, reflecting off the water's surface. An island is visible in the distance, creating a serene focal point.

4.86 out of 5 average rating, 22 reviews

Venture Out Million Dollar Ocean View

A bright living area is featured, with a comfortable grey sofa adorned with decorative pillows. Natural light filters through large sliding doors, leading to a balcony with seating. Vibrant yellow curtains frame the view, and wooden flooring enhances the space's warm ambiance.

Condo in Key West

4.5 out of 5 average rating, 228 reviews

2BR Suite | Pool | Hot Tub | Tennis | Dog Friendly

Camper/RV in Big Pine Key

A charming 5th wheel trailer sits amid tropical landscaping, surrounded by palm trees and potted plants. The exterior is painted in a soft blue hue, and details such as bike racks and a wood fence add character to the welcoming outdoor space.

4.79 out of 5 average rating, 82 reviews

The Island Gypsy

A bright window offers views of the canal and vibrant outdoor scenery. Two stools are positioned in front of the window, inviting guests to relax and enjoy the surroundings. Colorful decorations add a charming touch to the space, enhancing the coastal atmosphere.

Cottage in Cudjoe Key

4.71 out of 5 average rating, 162 reviews

Calypso Cottage

Private, pet-friendly home rentals

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.

4.9 out of 5 average rating, 115 reviews

Gone Coastal

A refreshing pool is framed by lush tropical foliage and features a welcoming entrance to a light gray cottage. Comfortable lounge chairs are positioned nearby, inviting relaxation. The water reflects the clear blue sky, enhancing the serene atmosphere of the outdoor space.

4.92 out of 5 average rating, 307 reviews

Family House, 2 K BR's, Private Spa/Deck, 2 pools.

4.95 out of 5 average rating, 338 reviews

A decorative wooden sign is mounted on a white post, featuring the text 'Center Court Historic Inn & Cottages' in bold letters. Lush tropical greenery surrounds the area, with palm trees and vibrant plants visible, creating a welcoming entrance to the property.

Apartment in Key West

Honeymoon Hideaway, King bed, Private Deck & Spa!

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!

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.

Townhouse in Key West

4.83 out of 5 average rating, 89 reviews

Location Location Beach Paradise in the Keys Duval

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, 364 reviews

Romantic Retreat - 2 person K Suite, Pvt deck/Spa!

4.92 out of 5 average rating, 300 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.

Apartment in Key West

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

A welcoming sign for Center Court is prominently displayed, surrounded by lush tropical foliage. The structure features white wooden details, with the sign's text clearly visible in a stylish font. The bright blue sky peeks through the greenery, enhancing the serene atmosphere.