Holiday Rentals in Key West, FL

Located in Key West's New Town, this apartment offers waterfront access and is a short 1.6-kilometre bike ride to Duval Street and the White Street District.
This pet-friendly apartment boasts a HEATED private outdoor pool, a fenced yard for pets, and includes 2 beach bikes, an outdoor grill, and off-street parking for up to 6 guests.

This pet-friendly apartment in historic Downtown Key West offers harbour and pool views, situated less than 1 kilometre from Duval Street, the Historic Seaport, and the Hemingway House, perfect for exploring on foot or by bike.
Boasting 125 square meters of space, this two-bedroom, two-bathroom apartment accommodates up to eight guests and features a fully equipped kitchen, a private balcony, and access to a shared heated swimming pool, with one dog up to 11 kilograms welcomed.

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 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.

This newly renovated, dog-friendly Conch-style cottage is situated in Key West's city centre, a mere 300 meters from the renowned Duval Street and in close proximity to the Ernest Hemingway Home and Museum and Southernmost Point.
Boasting a 49 square meter floor area, this cottage accommodates up to four guests with one bedroom and one bathroom, and features a full kitchen, air conditioning, a swimming pool, a garden, a spa, and parking, making it an ideal pet-friendly retreat.

Amelia House is situated in the Downtown Key West district, just 500 meters from the city centre and a mere 4-minute walk from South Beach, offering a prime location near attractions like the Key West Aquarium and Mallory Dock.
This pet-friendly vacation home boasts 3 bedrooms, 2 bathrooms, air conditioning, a kitchen with a fridge and microwave, and access to on-site spa facilities and a hot tub, making it ideal for families and groups looking for dog-friendly accommodation.

Perfectly situated in the Lower Duval district of Key West, this apartment is just a short walk to Southernmost Point, the Ernest Hemingway Home, and Mallory Square, offering a prime location at the corner of Duval Street and Amelia Street.
This pet-friendly apartment, allowing up to two pets with a 40lb maximum each for an additional cleaning fee, features one bedroom with a queen bed and an en suite bathroom, plus a queen-sized pull-out sofa in the living room to accommodate up to four guests, and includes a newly renovated kitchen and shared balcony access.

Offering a complimentary shuttle service to historic Old Town Key West and Duval Street, this pet-friendly resort is conveniently located just a 3.2-kilometre drive from Key West International Airport.
This resort boasts a sparkling swimming pool with a poolside tiki bar, a fitness centre, and on-site dining at the Palm Haven Restaurant, ensuring a comfortable stay for you and your dog-friendly companion.

This historic 1920s resort in Key West is situated on a private beach, offering an oceanside experience just 7 minutes by car from Duval Street.
Casa Marina Key West, a pet-friendly resort, provides a fantastic amenity for guests with pets, alongside two oceanfront pools and a spa, with convenient access to water sports.

Located in Key West, this apartment offers a Florida Keys beach escape, just a short distance from the Southernmost Point and the Ernest Hemingway Home and Museum.
This pet-friendly accommodation boasts 74 square meters of space, two bedrooms, two bathrooms, and can host up to six guests, featuring a private balcony with views of the Salt Ponds Preserve and access to a shared swimming pool and hot tub.

Parrot Key Hotel & Villas is a resort located on Florida Bay, offering easy access to historic Old Town Key West via a complimentary shuttle, just a short drive away.
This pet-friendly resort boasts four outdoor swimming pools, kayaking opportunities directly from the property, and private terraces with scenic views, making it ideal for travellers seeking dog-friendly accommodation near the beach.

Located in the heart of Old Town Key West, this apartment is just a few blocks from Duval Street and the Historic Seaport, offering easy access to shops and restaurants.
This pet-friendly apartment boasts a private saltwater pool, a fully equipped kitchen with a wet bar, and off-street parking for scooters and bicycles, making it ideal for groups and dog-friendly holidays.

Anchored offshore Key West Island, this unique vintage yacht offers a secluded tropical paradise just a short 1.6 kilometre pontoon boat ride from downtown Key West's Ernest Hemingway Home and Museum and Southernmost Point.
This pet-friendly apartment, accommodating up to 8 guests, boasts 3 bedrooms, 2 bathrooms, a full kitchen, and a 20-foot pontoon boat for exploring nearby beaches and sandbars.

Located in Old Town Key West, this apartment is just 500 meters from Duval Street and approximately 500 meters from the Southernmost Point and Southernmost Beach.
This pet-friendly apartment boasts a stylish interior with high ceilings and a granite kitchen, offering accommodation for up to four guests and featuring a shared wraparound balcony with porch seating.

Located in Key West's historic district, this conch home offers convenient walking access to Duval Street, Fort Zachary Taylor Beach, and Mallory Square, all within 1.9 kilometres.
This pet-friendly apartment boasts 130 square meters of living space, featuring four bedrooms and two bathrooms, an open-plan kitchen and dining area, and a patio with fruit trees, perfect for accommodating up to seven guests.

Located in Old Town Key West, this loft-style apartment is a short walk from Duval Street and the Historic Seaport, offering a prime position within the Southard Square community.
This pet-friendly apartment boasts 111 square meters of space for up to five guests, featuring a fully-equipped kitchen, a private balcony, and access to a community swimming pool, with concierge services and off-street parking included.

Located in the Key West Historic District, this apartment is just 160 meters from Duval Street and a short stroll to the Historic Seaport, with Fort Zachary Taylor State Park's beach less than 1.6 kilometers away.
This pet-friendly apartment complex offers two private, heated swimming pools with waterfalls and features six en-suite bedrooms, two fully-equipped kitchens, and two living areas, along with Five-Star Guest Services and a Full-Time Concierge.

Located in the heart of Old Town Key West, this apartment is just a short walk from iconic sites such as the Southernmost Point and the Ernest Hemingway Home and Museum.
This pet-friendly apartment offers 65 square meters of living space with two bedrooms and two bathrooms, accommodating up to four guests, and features a community swimming pool and a private covered porch.

Just one block from Duval Street in Old Town Key West, this apartment offers a prime location near the Ernest Hemingway Home and Museum.
This pet-friendly apartment, boasting 68 square meters and accommodating up to four guests, features a King bed, an updated ensuite bathroom, a recently refurbished kitchen with stainless steel appliances, air conditioning, and access to a community cocktail pool, making it ideal for travellers with dogs.

Ideally situated in Old Town Key West, this apartment is merely blocks from Duval Street and within walking distance of the Ernest Hemingway Home and Museum and Southernmost Point.
This pet-friendly apartment offers 146 square meters of space for 8 guests, featuring 3 bedrooms, 2 bathrooms, air conditioning, a swimming pool, a terrace, and parking, with concierge services available for booking island activities.

Located in Old Town Key West, Casa Victoria is a historic Conch House, a mere 320 meters from Duval Street and close to the Ernest Hemingway Home and Museum and Southernmost Point.
This pet-friendly apartment offers 246 square meters of space for up to 12 guests, featuring five bedrooms, five bathrooms, a private pool, a heated spa, and off-street parking, making it ideal for group holidays.

Positioned in the Key West Historic District, this apartment is just 100 metres from Duval Street and within easy walking distance of the Historic Seaport and Mallory Square.
This pet-friendly apartment, allowing up to two pets with a 40lb maximum each for a nightly fee, offers exclusive access to the historic Curry Mansion pool and features private balconies, air conditioning, and Wi-Fi.

Located on the eastern side of Key West, this apartment offers a pet-friendly stay near Smathers Beach and within 8 kilometers of Southernmost Point and the Ernest Hemingway Home and Museum.
This 72 square meter apartment boasts two bedrooms, two bathrooms, and accommodates up to six guests, featuring a shared swimming pool, hot tub, and on-site tennis courts for your enjoyment.

Located in a sought-after district, this classic Old Key West house offers historic charm with Dade County pine and is just 1.2 kilometers from the beach, making it a perfect pet-friendly base.
This 99 square meter house boasts two bedrooms and two bathrooms, sleeping up to eight guests with a fully stocked kitchen, air conditioning, a swimming pool, and a private garden ideal for enjoying the Keys' atmosphere with your dog.

Directly on Stock Island Marina, this resort offers luxurious rooms with waterfront views and is conveniently located just over 3 kilometres from Key West International Airport.
This resort is a fantastic pet-friendly option, providing a complimentary shuttle to Old Town Key West and welcoming dogs with spacious balconies and artisanal bath products.

Offering direct access to a private dock and boasting sea views, this downtown Key West house is situated waterfront, just 2.1 kilometres from Southernmost Point and 2.4 kilometres from the Key West Aquarium.
This pet-friendly, 111 square metre house comfortably accommodates up to 14 guests in 2 bedrooms and 2 bathrooms, featuring a fully equipped kitchen, air conditioning, a swimming pool, garden, and complimentary on-site parking.

This pet-friendly resort is located in the Key West Historic District, just 1.6 kilometres from Mallory Square and the Florida Keys National Marine Sanctuary, with the Southernmost Point a mere 2 kilometres away.
Enjoy the resort's three outdoor swimming pools, on-site restaurant and bar, and fitness centre, with pets actively welcomed.

This pet-friendly apartment in Key West's Meadows district is conveniently located less than 1 kilometre from Duval Street and Bayview Park, and within 2 kilometres of Southernmost Point and Mallory Square.
Enjoy a refreshing dip in the swimming pool or make use of the on-site fitness centre and tennis court at this dog-friendly accommodation, which also offers complimentary self-parking and a picnic area for guests.

Located in a convenient Key West district, this apartment offers easy access to the island's attractions via walking, biking, or scooter rentals, and is a pet-friendly choice for your holiday.
This spacious two-bedroom, two-bathroom apartment boasts a private balcony from each bedroom, a fully equipped galley kitchen, and a tropical backyard oasis with a shared swimming pool and grill, making it ideal for families and guests travelling with their pets.

Located in the heart of downtown Key West, this apartment is just 500 meters from the historic Mallory Square and offers easy foot access to numerous attractions.
This pet-friendly apartment boasts a shared heated swimming pool and a garden, accommodating up to six guests with a king bed, queen bed, and a queen sofa bed, perfect for a dog-friendly holiday.

Located in the prime downtown district of Key West, this studio apartment offers exceptional walkability to numerous attractions, just 600 meters from Duval Street.
This pet-friendly studio welcomes pets up to 18kg for a nightly fee and features a private back deck, a shared swimming pool, and a fully-equipped kitchen, making it ideal for travellers with pets.