Pet-friendly Vacation Rentals in Key West, FL

Situated on the eastern side of Key West, this apartment offers tropical comfort by the sea, just 6.4 kilometres from the Southernmost Point and Ernest Hemingway Home and Museum, and conveniently near Smathers Beach.
This pet-friendly, 72-square-meter apartment, part of the luxurious Sunrise Suites Resort, accommodates up to six guests and boasts a private washer/dryer, alongside access to a shared swimming pool, hot tub, and fitness centre.

This pet-friendly apartment is located in Key West, a mere 8-minute walk from Higgs Beach and 0.96 kilometres from the city centre, placing you close to iconic spots like the Southernmost Point and Ernest Hemingway Home and Museum.
With a generous 108 square meters of living space, this 2-bedroom apartment comfortably accommodates up to 9 guests and boasts a fully equipped kitchen, air conditioning, and a swimming pool, alongside complimentary on-site parking and free WiFi.

This pet-friendly house in Key West is centrally located, just an 11-minute walk from the Ernest Hemingway Home and Museum and Duval Street, and 0.6 miles from Mallory Dock.
Enjoy a private swimming pool and a fully equipped kitchen in this dog-friendly house, which offers 3 bedrooms, 2 bathrooms, and is conveniently situated for cycling and exploring the seaside attractions.

This waterfront corner apartment in historic Downtown Key West offers a prime location, just under 1.6 kilometres from Duval Street, the Historic Seaport, and the Hemingway House.
Boasting a generous 125 square metres of space, this pet-friendly accommodation comfortably accommodates 8 guests and features a spacious private balcony with stunning harbour and pool views, alongside access to a shared heated swimming pool and tiki bar.

This private, gated apartment within the Conch Republic Cottages offers a secluded, pet-friendly escape in Key West's city centre, just a short walk from the Ernest Hemingway Home and Museum and Southernmost Point.
Boasting a king-sized loft bedroom and a queen-sized sofa bed, this dog-friendly accommodation comfortably sleeps four and features a well-equipped kitchen, air conditioning, and a garden, with Florida Keys Beaches and Fort Zachary Taylor Historic State Park nearby for water adventures and outdoor pursuits.

Docked at the Perry Hotel in Stock Island, this houseboat offers exclusive use of a 40ft yacht with private access, just 6.4 kilometres from the Ernest Hemingway Home and Museum and Fort Zachary Taylor Historic State Park.
This pet-friendly houseboat boasts a luxurious three-stateroom interior accommodating up to 8 guests, with air conditioning, internet, and the option for flexible excursion packages including sunset sails and overnight ocean anchoring for an unparalleled stargazing experience.

This Key West apartment is perfectly situated, just 700 metres from the iconic Southernmost Point and 400 metres from South Beach, making it ideal for beach lovers and a truly pet-friendly escape.
Enjoy a 31 square metre, one-bedroom apartment offering air conditioning, a balcony, and a kitchen with an oven and microwave, all within easy reach of attractions like the Ernest Hemingway Home and Museum, and offering nearby cycling opportunities.

Located in downtown Key West, this bungalow offers direct access to Duval Street and the Historic Seaport, placing you just 500 meters from Mallory Square and a short walk to Fury Water Adventures and the Mel Fisher Maritime Museum.
This pet-friendly bungalow accommodates up to three guests, featuring a fully equipped kitchen, air conditioning, and access to shared outdoor spaces with a communal pool, ensuring a comfortable stay with your dog near the seaside.

This waterfront house in Key West offers a prime location, situated 2.1 kilometres from the Southernmost Point and 2.4 kilometres from the Key West Aquarium, with Rest Beach and the Ernest Hemingway Home and Museum nearby.
This pet-friendly house boasts a generous 223 square metres of floor area, featuring four bedrooms and four bathrooms to accommodate up to 16 guests, complete with an outdoor swimming pool and convenient on-site parking.

Perfectly positioned in Old Town Key West, this apartment is just steps from Duval Street and the Southernmost Point, offering prime access to local attractions and nightlife.
This pet-friendly apartment, covering 60 square meters, features two bedrooms accommodating up to four guests, a fully equipped kitchen, and a parking space, with concierge services available for planning island activities.

Docked at Perry Marina and Resort in Stock Island, this unique sailboat accommodation offers a truly distinctive stay, just a short shuttle ride from downtown Stock Island.
This pet-friendly sailboat provides accommodation for up to 4 guests, featuring air conditioning, a fridge, and microwave, with resort amenities including swimming pools and restaurants readily accessible, ensuring a comfortable and entertaining visit for you and your dog.

Boasting a unique, secluded location in a calm bay within New Town, Key West, this houseboat offers 360° ocean views and featured status in an Old Dominion music video, with direct access to the Gulf of Mexico for swimming and jumping off the boat.
This exceptional houseboat is pet-friendly, featuring a Sleep Number bed, air conditioning, and complimentary use of a 13-foot skiff for easy access to Key West attractions like the Southernmost Point and Ernest Hemingway Home and Museum, accommodating up to three guests.

Located in Key West, this pet-friendly holiday home is conveniently situated just 0.6 miles from Key West International Airport and approximately 6.4 kilometres from the Southernmost Point and Ernest Hemingway Home and Museum.
This 74 square metre, two-bedroom house offers air conditioning, a fully equipped kitchen with a dishwasher, and resort amenities including a heated outdoor swimming pool, hot tub, and fitness centre, ensuring a comfortable stay for you and your dog-friendly companions.

Located in the tranquil New Town district of Key West, Captain's Cove offers direct canal frontage with quick ocean access, just a short drive from Southernmost Point and the Ernest Hemingway Home and Museum.
This spacious 222 square meter, 4-bedroom, 4-bathroom apartment is pet-friendly and features a heated saltwater pool, a chef's kitchen with a waterfall island, and ample covered parking, accommodating up to 8 guests with ease.

Boasting a prime location within a gated community in the Florida Keys, Evershore House offers convenient access to public boat ramps in Key Haven and Stock Island, allowing for arrivals by car, boat, or plane.
This spacious, pet-friendly apartment in Key West welcomes up to 12 guests with four bedrooms and four bathrooms, featuring a fenced-in yard, gated dock access, and at-home gym equipment for a truly enjoyable stay with your furry companions.

Just a minute's walk from Duval Street, this adult-only hotel in Key West is also a 3-minute drive from the Key West Butterfly and Nature Conservatory.
This pet-friendly hotel offers two outdoor pools, a spa, and live jazz music in its gardens, with bicycle hire and massage services available on-site.

Enjoy a top-floor apartment in Key West offering sunrise views from a private balcony, conveniently located just 0.8 kilometres from Key West International Airport and 3.2 kilometres from Smathers Beach, providing a peaceful escape near the city's entrance.
This dog-friendly apartment boasts 74 square metres, accommodating up to six guests with three bedrooms, including two en suites, a full kitchen, central air conditioning, a swimming pool, hot tub, and on-site parking, making it perfect for a seaside getaway.

Boasting a prime location in the Key West Historic District, this apartment is just 0.8 kilometres from Duval Street and within easy walking distance to numerous shops and restaurants.
This pet-friendly apartment offers ample space for 16 guests with 7 bedrooms and 8 bathrooms, featuring a swimming pool, terrace, garden, and on-site parking for two vehicles.

Oceanfront Key West apartment with crisp sea air, located in the luxurious Sunrise Suites resort community on the eastern side, is just a short drive from Smathers Beach and popular attractions like the Southernmost Point and Ernest Hemingway Home and Museum.
This pet-friendly 2-bedroom apartment offers 72 square meters of living space, accommodating up to 6 guests with a fully equipped kitchen, private balcony with tennis court views, and access to upscale resort amenities including a shared swimming pool and hot tub.

Boasting a prime location in Key West, this brand-new Larkshine House is conveniently situated 1.8 kilometres from Sunset Watersports and 8.9 kilometres from Key West's iconic Ernest Hemingway Home and Museum, Duval Street, and the Key West Aquarium.
This spacious, pet-friendly house offers 351 square metres of living space with 8 bedrooms and 9 bathrooms, accommodating up to 19 guests, and features a private swimming pool, on-site fitness centre, and complimentary WiFi in public areas.

This private home offers a tropical island retreat feel in Old Town Key West, just off Duval Street and a short walk to the Ernest Hemingway Home and Museum and Southernmost Point.
This pet-friendly apartment, measuring 59 square metres, accommodates up to four guests and features a fully equipped kitchen with a bar area, a king bedroom with balcony access, and an outdoor living space with a grill and hammock.

Perfectly situated just off Duval Street in Key West, Florida, this house is a mere 1.1 kilometers from the Southernmost Point and a convenient 5-minute walk to the Key West Aquarium, with the Ernest Hemingway Home and Museum only 0.9 miles away.
This pet-friendly house offers a heated outdoor swimming pool and fully equipped kitchens, alongside free Wi-Fi, ensuring a comfortable stay for you and your dog-friendly companion.

Waterfront at Evershore Estate in Lunara Bay, a gated community just under 1.6 kilometres from Key West, offers a prime location for exploring local dining and kayaking tours.
This spacious, pet-friendly apartment boasts four bedrooms and four bathrooms, accommodating up to 12 guests with a private pool, dock for boats up to 15 meters, and a secure, dog-friendly yard for pets up to 18kg.

This pet-friendly apartment in historic Downtown Key West is less than 1.6 kilometers from Duval Street, the Historic Seaport, and the Hemingway House, offering easy walkability to major attractions.
Boasting 121 square meters of space, this apartment sleeps up to 8 guests with 2 bedrooms and 2 bathrooms, featuring a fully stocked kitchen, a private balcony overlooking the marina and heated pool, and on-site parking.

This pet-friendly apartment is located on Key West's southeast side, just 1.6 kilometres from the beach and a 10-minute drive from Duval Street.
With a king master bedroom, a queen bedroom, and a queen-size pullout couch, this accommodation comfortably sleeps six guests and offers a private balcony, in-unit laundry, and access to a shared heated pool and hot tub.

This ground-level, one-bedroom house in Key West's Art District is located 1.28 kilometers from Duval Street and the Historic Seaport, and within biking distance of Cuban Coffee Queen and Higgs Beach, making it a great pet-friendly base for exploring the area.
A shared dipping pool surrounded by tropical foliage and a beautifully tiled bath with a walk-in shower for two offer unique comforts, alongside a well-equipped kitchen and concierge service to ensure a relaxing stay for you and your pets.

This pet-friendly cottage in a central Key West district is a short 400 metres walk from the Ernest Hemingway Home and Museum and Southernmost Point.
Offering a private swimming pool and a patio with a gas grill, this two-bedroom, two-bathroom house accommodates up to four guests and is dog-friendly for pets up to 18kg with a nightly fee.

Just a few blocks from Key West's attractions, this former bottling plant offers a unique island getaway with historic character and modern comfort, ideal for a pet-friendly holiday.
This contemporary house boasts a heated lap pool, a gourmet kitchen, and accommodates up to 8 guests, ensuring a relaxing stay with your pets allowed.

Located in Key West's Historic Seaport District, this pet-friendly apartment is a short walk from Duval Street and near the Ernest Hemingway Home and Museum.
This 81 square meter apartment offers two bedrooms, one bathroom, and a private deck shaded by a banyan tree, perfect for guests travelling with their pets.

Conveniently located just steps from the Ernest Hemingway Home and Museum and a mere 640 meters from South Beach, this pet-friendly house offers a prime location in Key West.
This 84 square meter, 2-bedroom house accommodates up to 11 guests and features a fully equipped kitchen, air conditioning, a Jacuzzi, a terrace, and private parking, making it ideal for families and dog-friendly holidays by the seaside.

Set within a quiet, upscale, gated enclave of six historic Old Key West vacation rentals, this apartment is just 300 metres from Higgs Beach and a 10-minute walk to the Ernest Hemingway Home and Museum.
This pet-friendly apartment, offering accommodation for four guests, features a private treetop balcony, a shared swimming pool, and is conveniently located near public transportation and seaside attractions, making it ideal for dog-friendly holidays.

Nestled amongst freestanding conch cottages and lush tropical landscaping, this secluded Key West cottage offers a private deck with a pond and exotic plants, just a short walk to all the town's attractions.
This pet-friendly cottage, accommodating up to six guests, boasts a fully equipped kitchen, central air conditioning, and a swimming pool, making it ideal for families seeking a dog-friendly retreat.