Holiday Rentals in Key West, FL

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.

Boasting a private swimming pool and a terrace with sea views, this pet-friendly house in Key West is just a 19-minute walk from Rest Beach and 1.4 kilometres from Duval Street.
This dog-friendly accommodation offers four bedrooms, three bathrooms, and concierge services, ensuring a convenient and enjoyable stay for up to 19 guests.

Just two blocks from Duval Street in historic Old Town Key West, this one-bedroom apartment offers a prime location for exploring the area's attractions, shops, and restaurants, and is a pet-friendly haven.
This apartment boasts a private covered porch with a treetop view, an open-concept living area with air conditioning, and shared backyard amenities including a gas grill and laundry facilities, perfect for guests and their pets.

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.

Perfectly situated in Old Town Key West, this apartment is just a short stroll from Duval Street and one block from the Southernmost Point.
This pet-friendly apartment, offering space for up to four guests, features a kitchenette and is part of the Southernmost Sanctuary property with shared hot tubs and an outdoor patio.

Offering exclusive 137-yard private beachfront access in Old Town Key West, this resort is a mere 15-minute walk to Duval Street and 10 minutes from the Earnest Hemingway Museum.
This pet-friendly resort provides rooms and suites with private balconies, refrigerators, and access to an outdoor pool and a full-service spa, ideal for guests travelling with their dogs.

Located 6.4 kilometres south of the Southernmost Point, this apartment is a short 1 kilometre from Key West International Airport and 7.4 kilometres from the Ernest Hemingway Home and Museum and Duval Street.
This fully equipped, pet-friendly, two-bedroom apartment offers 72 square metres of living space with a private terrace, outdoor swimming pool, and access to a fitness centre and hot tub, ensuring a comfortable stay for you and your dog.

This pet-friendly apartment is located in Key West's city centre, just 80 metres from Duval Street and within walking distance of the Ernest Hemingway Home and Museum and Southernmost Point.
Boasting a bi-level design with two sleeping areas upstairs, this 1-bedroom, 1-bathroom apartment accommodates up to 4 guests and features a gourmet kitchen, air conditioning, a swimming pool, and is also dog-friendly.

This pet-friendly house in Key West is conveniently located between 1.7 and 2.2 kilometres from popular attractions such as the Southernmost Point, Key West Aquarium, Mallory Dock, and Mallory Square.
Enjoy direct sea and pool views from this air-conditioned accommodation, which features a fully equipped kitchen, complimentary Wi-Fi, and an outdoor swimming pool, making it ideal for a seaside escape with your dog-friendly family.

Just a 3-minute walk from South Beach, this pet-friendly house in Key West is conveniently located within 600 meters of the city centre, placing you a short stroll from the San Carlos Institute Casa Cuba and Jackson Square.
This 37 square meter house offers one bedroom and a living room, accommodating up to 5 guests with a kitchenette featuring a fridge and microwave, and air conditioning for a comfortable stay.

Sunrise Suites Panama Suite #310 is a pet-friendly house located in Key West, 0.6 miles from Key West International Airport and within 7 kilometres of Southernmost Point and Ernest Hemingway Home and Museum.
This accommodation offers a swimming pool, hot tub, and a balcony, ensuring a comfortable stay for you and your pets.

This pet-friendly house is located just 0.8 kilometres from the city centre, offering easy access to iconic Key West landmarks such as the Southernmost Point and the Ernest Hemingway Home and Museum, and is a mere 7-minute walk to South Beach.
Boasting a generous capacity for 19 guests across 3 bedrooms and 2 living rooms, this accommodation features a well-equipped kitchen with a dishwasher and microwave, air conditioning, a swimming pool, a garden, a spa, a fitness centre, a tennis court, and on-site parking, making it an ideal choice for a dog-friendly seaside getaway.

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 cottage in Key West's city centre is just 300 meters from the Ernest Hemingway Home and Museum and Southernmost Point.
Offering 48 square meters of space for up to 4 guests, this cottage features a full gourmet kitchen, a private deck with outdoor dining, and is steps from a shared heated pool, making it ideal for a dog-friendly getaway.

Centrally located in Key West, this apartment offers unparalleled access, being just 300 metres from the city centre and a mere 4-minute walk from the Ernest Hemingway Home and Museum.
This pet-friendly apartment boasts a private balcony, a fully equipped kitchen with a dishwasher, and a spa, ensuring a comfortable stay for up to 7 guests, with 'pets allowed' and 'dog-friendly' options readily available.

Ideally located on a quiet lane just off Duval Street, this pet-friendly apartment is a mere 500 metres from the Southernmost Point and 800 metres from the Key West Butterfly and Nature Conservatory, with Fort Zachary Taylor Beach also within easy reach.
This apartment boasts a chic, reverse floor plan with a vaulted ceiling in the open living room and a comfortable, furnished veranda on the second floor, offering two king ensuite bedrooms and allowing one dog up to 11 kg for an additional fee.

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.

Just 600 metres from the city centre, this Key West house offers a prime location, a mere 3-minute walk from South Beach and close to the Southernmost Point and Ernest Hemingway Home and Museum.
This pet-friendly house, boasting a generous 146 square metres of floor area, features air conditioning, a private swimming pool, and a fully equipped kitchen, making it ideal for accommodating up to 23 guests with pets allowed.

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.

Located in Key West's historic Casa Marina Neighbourhood, this apartment is just 2 blocks from Higgs Beach and a short walk to attractions such as the KW Butterfly and Nature Museum and Southernmost Point.
This pet-friendly one-bedroom apartment offers a cosy kitchenette, private patio dining, and access to shared amenities including a swimming pool and gas grill, making it ideal for travellers with pets.

This pet-friendly apartment is located in the Key West Historic District, just 80 meters from Duval Street and within easy walking distance of Mallory Square and the Historic Seaport.
Offering a shared heated swimming pool and wrap-around porches, this 1-bedroom, 1-bathroom apartment accommodates up to 2 guests and welcomes pets with a 40lb maximum for a nightly fee.

Conveniently located in Key West, this pet-friendly apartment is just a 2-minute walk from Simonton Street Beach and 0.8 miles from the Ernest Hemingway Home and Museum.
Offering air-conditioned comfort and stunning sea views, this 74-square-meter apartment boasts two bedrooms, two bathrooms, complimentary WiFi, and a fully equipped kitchen, making it ideal for a family of up to 11 guests who want to bring their pets along.

Boasting a prime location in Historic Old Town, this pet-friendly apartment is just 1.2 kilometres north of Truman Avenue, offering a 15-minute walk or 5-minute cycle to Duval Street, Higgs Beach, and the Southernmost Point.
This dog-friendly apartment provides 114 square metres of space, featuring a private 6.1m x 3m pool, a gas grill, and is ideal for larger groups with the option to rent adjacent units.

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.

This pet-friendly cottage in Key West's Old Town offers a private, secluded garden and dip pool, just 160 meters from the vibrant Duval Street and within walking distance of Southernmost Point and Fort Zachary Taylor State Park.
Boasting 112 square meters of living space, this 3-bedroom apartment comfortably accommodates up to 6 guests and features off-street parking, a valuable amenity in Key West, along with excellent user, location, and cleanliness ratings.

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.

Centrally located in Old Town Key West, this apartment is a short walk from the Hemingway House, Butterfly Conservatory and Duval Street, offering a prime spot for exploring the area on foot.
This pet-friendly studio apartment, measuring 28 square meters and accommodating two guests, features a full kitchen and a private patio, with Southernmost Beach just under 1 kilometer away and dog-friendly Fort Zachary Taylor State Park also accessible.

This pet-friendly apartment in Key West's Meadows district offers excellent access, situated less than 1 kilometre from Duval Street, the Historic Seaport, and the Hemingway House.
Enjoy a spacious 111 square metre apartment with a private balcony boasting harbour and pool views, featuring two bedrooms, two bathrooms, and on-site amenities including a swimming pool and parking, with a private boat slip also available.

Centrally located in Old Town Key West, this apartment is just 240 meters from Duval Street, placing you within easy reach of its attractions and dining.
This dog-friendly apartment boasts a private, heated pool in lush gardens for ultimate privacy, offers 151 square meters of living space for up to six guests, and includes a fully equipped kitchen and high-speed internet.

Located in Key West's Art District, this ground-level one-bedroom condo is 1.3 kilometres from Duval Street and the Historic Seaport, with Higgs Beach also within biking distance.
This pet-friendly house offers a king-size bed, a queen-size sleeper sofa, a romantic walk-in shower for two, and a shared tropical garden with an intimate dipping pool, accommodating up to four 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.

This pet-friendly apartment is located in Old Town Key West, just 800 metres from the beach and a 15-minute walk to Duval Street.
Offering 108 square metres of living space with two bedrooms and two bathrooms, this apartment boasts a shared swimming pool and a garden, perfect for families and guests with pets.

Perfectly situated in Key West, this apartment is just a 2-minute walk from Mallory Dock and 300 metres from Mallory Square, offering excellent access to the Key West Aquarium and Duval Street.
This pet-friendly apartment boasts four bathrooms, a well-equipped kitchen, and on-site parking, making it an ideal choice for families and guests travelling with their dogs.

Located in the historic Old Town of Key West, this house is just 640 meters from the Atlantic Ocean and 1 block from Duval Street's entertainment.
This pet-friendly house, offering 127 square meters of space for up to 6 guests, features a private swimming pool and a covered porch with a grill, perfect for enjoying the tropical atmosphere with your dog-friendly family.

Offering direct water access via a private 43-foot boat slip, this spacious 335 square meter apartment in Key West's quiet Meadows neighbourhood is a pet-friendly haven, just a short walk from Bayview Park and Fausto's grocery.
This five-bedroom, four-bathroom apartment comfortably accommodates up to 12 guests with a private pool, tropically furnished yard, large deck, outdoor dining, and a fully equipped chef's kitchen, ensuring a superb seaside escape for families and pets alike.

Perfectly situated in historic Old Town Key West, this ground-level apartment is a short walk to Duval Street, the Ernest Hemingway Home and Museum, and Southernmost Point, offering a prime location for exploring the city on foot.
This pet-friendly apartment, covering 42 square meters, comfortably accommodates up to four guests with a king bed and a queen sleeper sofa, featuring an open-plan living area, a fully equipped kitchen, and access to a swimming pool.