Holiday Rentals in Key West, FL

Located in Old Town Key West, this apartment is just steps from Duval Street, 160 meters from the Southernmost Point, and 480 meters from South Beach.
This pet-friendly apartment, accommodating up to four guests, features a kitchenette, air conditioning, and access to shared hot tubs and a communal patio.

Authentically experience a historic Conch home in a local Key West neighbourhood, just 800 meters from nearby beaches, parks, and cafes, offering a truly dog-friendly stay.
This renovated apartment boasts a private porch with seating and a grill, a full suite of stainless steel appliances, and provides access to a pool at a sister property, accommodating up to four guests and one pet.

Just a few steps from South Beach, this pet-friendly house is located 0.8 kilometres from Key West's city centre, offering immediate coastal access and proximity to Mallory Dock and Mallory Square.
This air-conditioned house, featuring a kitchen with a fridge and microwave, welcomes pets and provides towels and bed linen for up to 7 guests across 37 square metres with 1 bedroom.

Ideally located in the Duval Street district, this apartment is just steps from the street itself, 160 meters from the Southernmost Point, and 480 meters from South Beach.
This pet-friendly apartment allows one small dog for an extra fee and offers a kitchenette, air conditioning, and access to shared hot tubs and laundry facilities, sleeping up to four guests.

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.

Located in Old Town Key West's Bahama Village, this studio is a short 800-metre stroll from Duval Street and within walking distance of the Southernmost Point and Ernest Hemingway Home.
This pet-friendly studio offers a well-appointed kitchenette, air conditioning, and access to a heated swimming pool, perfect for guests travelling with their dog.

Located in Conch Key, this house is an 8-minute walk to Rest Beach and 1.2 kilometres from Southernmost Point, with Key West International Airport also 1.2 kilometres away.
This pet-friendly house offers 2 bedrooms, 2 bathrooms, air conditioning, a private swimming pool, and a fully equipped kitchen, perfect for accommodating up to 7 guests.

This pet-friendly apartment in Key West's Historic Seaport district is just 200 meters from the waterfront and Mallory Square's sunset celebrations, offering immediate proximity to dining and nightlife.
With two bedrooms and a guest capacity of six, this accommodation provides Tempur-Pedic mattresses, free Wi-Fi, a mini fridge, microwave, Keurig coffee maker, and access to a shared dipping pool with a waterfall feature.

Centrally located in Old Town Key West, this apartment is a short walk to Duval Street and a local grocery store, with a fishing pier nearby.
This pet-friendly apartment boasts an outdoor fenced area and air conditioning, perfect for two guests seeking a 28-night minimum stay in Key West.

Situated in the Key West Historic District, this apartment is just 100 meters from Duval Street and within easy walking distance of the Historic Seaport and Mallory Square.
This pet-friendly apartment offers a shared heated swimming pool, a terrace and air conditioning, perfect for a couple visiting Key West.

Just 300 metres from Key West city centre, this apartment is ideally situated for exploring the area, being a mere 7-minute walk to South Beach and 0.9 miles from Mallory Dock.
This pet-friendly apartment offers accommodation for up to 3 guests, featuring air conditioning, a separate bedroom, a bathroom, and a kitchenette with a microwave and fridge, making it a convenient choice for travellers with pets.

Located 5 kilometres from Key West city centre, Blue Flamingo Resort Key West offers a pet-friendly escape near the Key West Tropical Forest and Botanical Garden.
This resort boasts multiple swimming options, on-site dining with live music, a fitness centre, and tour assistance, ensuring a comfortable stay for guests and their dogs.

Perfectly situated, Opal Key Resort & Marina in Key West is a mere 500 metres from Mallory Square and a 3-minute walk to Duval Street, offering a prime location for exploring the city and is also 0.5 kilometres from Florida Keys Beaches and 0.7 kilometres from the Ernest Hemingway Home and Museum.
This pet-friendly resort boasts an outdoor pool and a 24-hour fitness centre, with rooms featuring flat-screen TVs and rainfall showerheads, ensuring a comfortable stay for you and your dog-friendly companions.

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.

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.

Located in Bahama Village, this studio is just a few blocks from Duval Street and within walking distance of the Southernmost Point and Hemingway House.
This pet-friendly studio, measuring 24 square meters, offers a Queen bed, a full-size sleeper sofa, and a kitchenette, with a heated swimming pool and sundeck available for 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.

Ideally situated in Old Town Key West, this apartment is just steps from Duval Street's attractions and a mere 320 meters from Fort Zachary Taylor State Park beach.
This pet-friendly apartment offers a private patio with a grill, shared hot tub, and off-street parking, sleeping up to six guests across three bedrooms with a fully equipped kitchen and washer/dryer.

Situated in Key West's White St. Gallery district, this pet-friendly apartment offers easy access to Duval Street, the Southernmost Point, Ernest Hemingway Home, and Fort Zachary Taylor Historic State Park, with off-street and covered parking a significant advantage.
Boasting a private pool and an entertainment-ready patio with a covered outdoor bar, this renovated 152 square meter apartment features 2 bedrooms and 2 bathrooms, comfortably accommodating up to 4 guests with its coastal-modern aesthetic and fully equipped kitchen.

Located in Key West's prime Old Town, this apartment is just one block from Duval Street and within easy walking distance of the Ernest Hemingway Home & Museum and the Key West Lighthouse.
This pet-friendly apartment offers a two-level, 70-square-meter space for up to four guests, featuring a fully equipped kitchen, a dedicated workspace, and a semi-private balcony, with your well-behaved dog up to 22.5 kg welcome.

Boasting a private waterfront pool and located in the exclusive gated Key Cove community on an quiet lane, this Key West apartment offers a secluded yet convenient base, just a short drive from Old Town and within walking distance of grocery stores and the island's largest shopping centre.
This spacious 223 square meter, four-bedroom apartment is perfectly pet-friendly, featuring two luxurious en-suite master bedrooms with King beds and direct balcony access, a gourmet kitchen, and an expansive open-plan living area with stunning water views, ideal for families and groups seeking a dog-friendly seaside escape with ample off-street parking.

Located in the Key West Historic District, this pet-friendly apartment is just 160 meters from Duval Street and within easy reach of the Historic Seaport and Mallory Square.
This 26 square meter apartment offers a private room with an en-suite bathroom and balcony, accommodating up to 4 guests with a daybed and twin trundle in the adjoining sitting room, and guests enjoy complimentary access to a swimming pool and the historic Curry Mansion.

Ocean Key Resort & Spa, a luxury resort in Key West, boasts a prime waterfront position directly on the Gulf of Mexico, just a 1-minute walk from Mallory Square and the entertainment of Duval Street.
This pet-friendly resort offers guests a relaxing stay with amenities including a swimming pool, spa, and on-site dining, whilst being conveniently located near the beach.

Located in historic Old Town Key West, this pet-friendly house is just a few blocks from Duval Street, offering easy walking access to shops and restaurants.
This dog-friendly one-bedroom house, ideal for two guests, features a kitchenette, a king-size bed, air conditioning, and access to a shared swimming pool within a secure gated community.

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.

This pet-friendly apartment is situated in the Key West Historic District, just 80 metres from Duval Street and within walking distance of the Historic Seaport and Mallory Square.
Offering a historic mansion experience with a shared heated pool and wrap-around porches, this apartment allows up to 4 guests and is ideal for travellers seeking a dog-friendly getaway near the seaside.

Just 0.97 kilometres from the city centre, this Key West cottage is a 17-minute walk from Mallory Square and one kilometre from the Ernest Hemingway Home and Museum.
This pet-friendly house welcomes up to 11 guests and offers a private terrace, complimentary parking, and is a 14-minute walk to Simonton Street Beach, making it ideal for travellers with pets.

This pet-friendly apartment in Key West's Meadows neighbourhood is less than 1.6 kilometres from Duval Street, the Historic Seaport, and the Hemingway House.
Enjoy direct waterfront views from your private balcony, with access to a shared heated pool, tiki bar, and boat slip, all within easy reach of Key West International Airport.

Just 80 metres from Duval Street, this two-bedroom apartment offers a prime location in Key West, ideal for exploring the area's attractions with your dog-friendly holiday.
This pet-friendly accommodation boasts a private heated pool and a fully equipped kitchen, providing a comfortable and convenient stay for up to six guests, including your pets.

Just 500 meters from Duval Street and a 2-minute walk to the Ernest Hemingway Home and Museum, this apartment offers a prime Old Town Key West location with easy access to dining and shopping.
This two-bedroom, two-bathroom apartment is pet-friendly, featuring a full kitchen, laundry facilities, and a swim spa in a shared outdoor space, ideal for families or couples seeking an extended stay in Key West.

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.

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 Key West townhouse offers a serene waterfront retreat, boasting a prime location on two sides within the Key Cove community, just a short distance from the vibrant shopping, dining, and Duval Street.
This dog-friendly accommodation features a private outdoor patio, a shared community pool, and an open-concept first floor with a chef's kitchen, perfect for families and guests with pets, sleeping up to six people.

This houseboat offers a unique waterfront experience on Stock Island, a mere 10-minute drive from Key West's Duval Street and the Key West Tropical Forest and Botanical Garden, and is situated within 7.4 kilometres of Smathers Beach and Mallory Square.
Enjoy on-site activities like paddleboarding and kayaking, with this pet-friendly accommodation also featuring a full kitchen, separate sitting area, and complimentary Wi-Fi, making it ideal for travellers seeking dog-friendly stays near the seaside.

Centrally located in Key West's prime Old Town district, this fully renovated classic duplex offers peaceful island living just 500 meters from parks, the beach, and renowned restaurants.
This pet-friendly apartment boasts modern amenities including air conditioning and a full kitchen, making it ideal for families, couples, and business travellers seeking a convenient and dog-friendly seaside escape.

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.