Pet-friendly vacation rentals in Key Haven

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.

4.91 out of 5 average rating, 229 reviews

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.

Condo in Key West

"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***

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!

4.92 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.

Apartment 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.

4.92 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 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.

4.93 out of 5 average rating, 165 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 homes 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.

4.92 out of 5 average rating, 64 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!

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, 117 reviews

Paradise found

Located on Stock Island this 3 bedroom home is 8 minutes from Duval street. Walking distance to several great restaurants. Gated community with a gym and large swimming pool.

Popular amenities for Key Haven 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

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

4.91 out of 5 average rating, 11 reviews

Yellowfin Ledge | Inviting Getaway On Duval! Balco

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, 69 reviews

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

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 private pool area is surrounded by tropical landscaping, featuring lush greenery. Several lounge chairs with blue and white stripes are positioned around the pool, inviting relaxation. Bright sunshine casts light across the tranquil water, enhancing the peaceful outdoor setting.

5 out of 5 average rating, 9 reviews

Casablanca ~ Fabulous Home w/ Private Pool/Parking

A private pool area is surrounded by lush tropical vegetation, featuring a serene blue-tiled pool. Brightly colored pool lounges are positioned on the patio, with light terracotta tiles leading to the water's edge. Sunlight filters through the greenery, creating a peaceful outdoor environment.

4.96 out of 5 average rating, 26 reviews

Villa Paradiso: A unique mid-town paradise

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

5 out of 5 average rating, 13 reviews

A spacious concrete dock extends into clear blue waters, featuring thatched-roof palapas for shade. Palm trees sway gently, while colorful buoys line the water. The sky is mostly sunny with a few clouds, enhancing the serene waterfront setting.

Campsite in Cudjoe Key

Little Palm By The Sea- RV Site, Cudjoe Key Fl.

4.67 out of 5 average rating, 3 reviews

43' Classic Yacht Views, Pools, Duval Shuttle

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)

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 !

Camper/RV in Big Pine Key

The exterior of the RV is set against a backdrop of lush palm trees and tropical foliage. Decorative elements, including colorful painted shells and a seahorse, adorn wooden fences. Potted plants add greenery, complementing the sandy ground.

4.7 out of 5 average rating, 20 reviews

Island Girl Big Pine Key

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

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, 80 reviews

The Island Gypsy

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 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

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.

Camper/RV in Big Pine Key

4.66 out of 5 average rating, 35 reviews

Tiny home in RV park with pool

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

4.95 out of 5 average rating, 337 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!

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

4.97 out of 5 average rating, 275 reviews

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

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.