Pet-friendly Vacation Rentals in Key West, FL

This waterfront apartment in Key West's Meadows district is less than 1 mile from Duval Street, the Historic Seaport, and the Hemingway House, offering a prime location for exploring the city.
Enjoy a pet-friendly stay with a private balcony, harbor views, a heated swimming pool, and a full-size washer and dryer in this spacious 1190 sq ft condo that comfortably sleeps up to 6 guests.

Located just half a block from Duval Street, this historic 1874 home offers a tranquil escape on a quiet lane, providing convenient access to Key West's attractions and amenities.
This pet-friendly apartment features four bedrooms, a Queen sleeper sofa, a gourmet kitchen, and access to two shared swimming pools, making it ideal for families and groups traveling with their dogs.

Just 500 feet from historic Duval Street and the Southernmost Point, this pet-friendly apartment in Old Town Key West offers easy access to shopping, dining, and South Beach, just three blocks away.
This one-bedroom apartment features a kitchenette with a fridge and microwave, air conditioning, complimentary WiFi, and shared hot tubs, perfect for enjoying the island vibe with your small dog, weighing 30 lbs or less, for a nightly fee.

Located in the Meadows district, this waterfront penthouse is approximately 1 mile from Duval Street and the Historic Seaport, offering direct access to Garrison Bight Marina for boating and fishing.
This spacious 2,000 sq ft apartment boasts 4 bedrooms and accommodates up to 16 guests, featuring dual balconies with marina views, a private dock, and is a pet-friendly option welcoming one dog up to 25 lbs for an additional fee.

Just 400 yards from downtown Key West, this pet-friendly house offers easy access to attractions like South Beach (an 11-minute walk), the Key West Aquarium, and Mallory Dock.
This 530 square feet vacation home welcomes up to 7 guests and features a full kitchen, a private balcony, a swimming pool, and a spa, with cycling opportunities nearby.

Located in historic Bahama Village, this apartment is just a short walk to Duval Street, Hemingway's House, and Fort Zachary Taylor State Park.
This pet-friendly apartment offers a hot tub and is ideal for exploring Key West by bike, with parking available.

Perfectly situated in Old Town Key West, this pet-friendly apartment is just blocks from Duval Street and the Historic Seaport's shops and restaurants.
This spacious apartment accommodates up to 8 adults and features a private saltwater pool, a modern kitchen with a wet bar, and off-street parking for scooters and bicycles, making it ideal for travelers with pets.

Located in the tranquil Sunrise Suites community on Key West's southeast side, this pet-friendly apartment is just one mile from the beach and a 10-minute drive from Duval Street.
This newly updated 800 square foot condo offers 2 bedrooms and 2 bathrooms, accommodating up to 6 guests with a king master, queen second bedroom, and queen sleeper sofa, plus a private balcony and access to a communal heated pool and hot tub.

Just 300 feet from Fort Zachary Taylor State Park Beach, this pet-friendly house offers a prime location in Key West, also placing you a short walk from the Ernest Hemingway Home and Museum and Southernmost Point.
This 120-square-foot vacation home accommodates up to 3 guests with 1 bedroom and 1 bathroom, featuring air conditioning, a kitchenette with a microwave and fridge, and massage services available.

This Key West apartment is perfectly situated by the sea, offering easy walking access to Southernmost Point and the Ernest Hemingway Home and Museum.
Enjoy this pet-friendly Key West condo, featuring 2 bedrooms, 2 bathrooms, and 780 square feet of living space, complete with a shared swimming pool, hot tub, and private balcony.

Located in Bahama Village, this pet-friendly apartment is just steps from Duval Street, the Ernest Hemingway Home, and the Southernmost Point.
This 120 sq ft studio apartment allows pets with a nightly fee and features a kitchenette, air conditioning, and access to a shared swimming pool, making it ideal for two guests seeking a convenient Key West getaway.

Located in Old Town Key West, this apartment is just half a block from Duval Street and a short distance from the Southernmost Point and the Ernest Hemingway Home and Museum.
This dog-friendly apartment features 1450 square feet of living space with 3 bedrooms and 3 bathrooms, accommodating up to 8 guests, and includes a private heated pool and concierge services for booking local activities.

Experience a unique 'Old Key West' vintage yacht anchored offshore, offering a secluded tropical paradise with open water views, just a short pontoon boat ride from downtown Key West and its famous landmarks like the Ernest Hemingway Home and Museum and Southernmost Point.
This pet-friendly 3-bedroom, 2-bathroom Hatteras Motoryacht accommodates up to 8 guests with a full kitchen, Wi-Fi, and complimentary snorkeling gear, perfect for unforgettable honeymoons and celebrations.

This pet-friendly apartment in Key West, located in the Sunrise Suites community, is just 500 feet from Smathers Beach and Higgs Beach, with Duval Street minutes away.
This apartment offers 800 square feet of space with 2 bedrooms and 2 bathrooms, accommodating up to 6 guests, and features resort-style amenities including a communal heated pool, hot tub, on-site tennis court, and a private balcony perfect for enjoying the island scenery.

This resort offers a pet-friendly escape along Florida Bay, just a short drive from the historic Old Town Key West.
Enjoy direct access to kayaking and four outdoor pools, with a complimentary shuttle to the city center, all within a completely smoke-free property that welcomes your furry companions.

Located in Old Town Key West, this apartment is just a short walk from the Ernest Hemingway Home and Museum and Southernmost Point, and less than 1 mile from Fort Zachary Taylor Historic State Park and Florida Keys Beaches.
This pet-friendly apartment offers 1360 square feet of living space, accommodating up to 6 guests with two master suites, a private plunge pool with a waterfall, an outdoor dining area with a grill, and a fully fenced yard.

This Key West apartment is located on the island's eastern edge, providing convenient access to Key West International Airport and is just a few miles from downtown attractions.
Enjoy spectacular west-facing sunset views from your private balcony at this dog-friendly apartment, which offers 780 square feet of living space for up to 4 guests, complete with a fully equipped kitchen, a community pool, and on-site parking.

Just 0.6 miles from Key West International Airport, this pet-friendly house is located in Key West, approximately 4 miles from Southernmost Point and Ernest Hemingway Home and Museum.
This dog-friendly house offers a fully equipped kitchen, air conditioning, a swimming pool, and a hot tub, with complimentary on-site parking and free Wi-Fi for guests and their pets.

Enjoy an exclusive waterfront apartment in Key West's Northside Resort neighborhood, located in the private Key Cove Landings community, offering serene water views and just a short walk to Publix and the island's largest shopping center.
This spacious 2360 sq ft, four-bedroom apartment is pet-friendly and features floor-to-ceiling windows, a luxurious master suite with a Jacuzzi tub, a private heated pool, a gourmet kitchen, and ample parking, all within a 10-15 minute drive of the Ernest Hemingway Home and Museum and Fort Zachary Taylor Historic State Park.

Located in the private Key Cove Landings community on the waterfront in Northside Resort, this pet-friendly apartment is within walking distance to Publix and the island's largest shopping center, and just over 1 mile from Ernest Hemingway Home and Museum and Fort Zachary Taylor Historic State Park.
This spacious 2690 sq ft apartment features a private heated pool, a chef's kitchen, and four bedrooms, offering expansive water views and direct balcony access, making it ideal for travelers with pets.

This dog-friendly apartment is located by the sea in Key West, offering proximity to Southernmost Point and the Ernest Hemingway Home and Museum.
Enjoy 780 square feet of living space in this pet-friendly apartment, featuring 2 bedrooms, 2 bathrooms, a fully equipped kitchen, and access to a shared swimming pool and hot tub, perfect for accommodating up to 6 guests.

Enjoy a pet-friendly house rental in Key West, located just 1.2 miles from Key West International Airport and a short drive to the Ernest Hemingway Home and Museum (2.3 miles) and Duval Street (2.4 miles).
This spacious four-bedroom, four-bathroom house accommodates up to 15 guests and features a private swimming pool, hot tub, and a well-equipped kitchen, offering a perfect seaside escape with free WiFi and parking.

Located just 2297 feet from Mallory Square and 2625 feet from the Key West Aquarium, Hyatt Vacation Club At Sunset Harbor is a 4-star hotel in Key West offering a prime location for exploring the city.
This hotel welcomes pets and features a swimming pool, fitness center, and on-site spa, with some units including a balcony and kitchen for a comfortable stay.

Oceanfront on Key West's eastern side, this pet-friendly apartment is located in the Sunrise Suites resort community, just 500 feet from Smathers Beach and minutes from attractions like the Southernmost Point and Ernest Hemingway Home and Museum.
This recently repainted and refurnished 780 sq ft apartment accommodates up to 6 guests with 2 bedrooms and 2 bathrooms, featuring a fully equipped kitchen, a private balcony with tennis court views, and access to a shared swimming pool and hot tub.

Experience expansive water views from this waterfront apartment in Key West's Northside Resort, located on an exclusive waterfront lane just 0.3 miles from Publix grocery store and the island's largest shopping center.
This pet-friendly apartment offers a luxurious master suite with a Jacuzzi tub, a private heated pool overlooking open water, and a fully equipped chef's kitchen perfect for entertaining up to 10 guests, ensuring a comfortable and memorable stay for you and your dog-friendly companions.

Located on Key West's eastern shore, this dog-friendly condo is just 0.3 miles from Smathers Beach and Southernmost Point, offering easy access to the Ernest Hemingway Home and Museum and Harry S. Truman's home.
This 800 sq ft, 2-bedroom, 2-bathroom apartment at Sunrise Suites Resort accommodates up to 6 guests and features a private balcony with pool views, a community pool, hot tub, tennis courts, and included parking, making it a perfect pet-friendly getaway.

Located directly on Duval Street in historic Old Town Key West, this resort is steps from dining, nightlife, and shops.
This pet-friendly resort offers a swimming pool, spa, and fitness center, ensuring a comfortable stay for you and your furry companions.

Experience waterfront living in Key West's Meadows neighborhood, this corner condo is just 1 mile from Duval Street, the Historic Seaport, and the Hemingway House, offering unobstructed harbor and pool views.
This dog-friendly apartment boasts 1300 square feet of living space, accommodating up to 8 guests with a fully equipped kitchen, private balcony with direct pool access, and a shared heated pool, tiki bar, and BBQ grills, making it ideal for travelers with pets.

Casita de Catherine, a single-level house, is located less than one block off Duval Street in Key West, a few blocks from The Southernmost Point and La Te Da.
This pet-friendly accommodation offers a private outdoor space with a hot tub and accommodates up to three guests, embodying Key West's eclectic ambiance with rustic wooden cabinets and a king-sized canopy bed.

Located on the southeast side of Key West within the Sunrise Suites community, this apartment is just one mile from the beach and a 10-minute drive to Duval Street.
This pet-friendly apartment offers two bedrooms, two bathrooms, and accommodates up to six guests with a queen-sized sleeper sofa, a communal heated pool, and on-site parking, making it ideal for travelers with pets.

Located in Key West's Art District, this one-bedroom condo is just eight blocks from Duval Street and the Historic Seaport, and within biking distance to Higgs Beach.
This pet-friendly property offers 450 square feet of living space with a king bed and a queen sleeper sofa, accommodating up to four guests, and features a shared dipping pool for relaxed outdoor enjoyment.

Located in downtown Key West, this pet-friendly house is just steps from the Ernest Hemingway Home and Museum and a 7-minute walk to South Beach.
This 900 sq ft house offers 2 bedrooms, 1 bathroom, and accommodates up to 11 guests with a full kitchen, private parking, and a relaxing hot tub, making it perfect for a dog-friendly getaway near the seaside.

Located in Key West's quiet Meadows neighborhood, this pet-friendly apartment is just 500 feet from Bayview Park and Fausto's grocery store, offering easy access to the Ernest Hemingway Home and Museum and Southernmost Point.
This spacious 3610 sq ft apartment boasts 5 bedrooms, accommodating up to 12 guests, and features a private pool, a tropically furnished yard with outdoor dining, and a private 43-foot boat slip, making it ideal for families and groups traveling with their dogs.

Just 500 feet from Key West's attractions, this secluded cottage offers a private tropical escape with a pond and lush landscaping, perfect for a pet-friendly getaway.
This cottage features a full kitchen, central air conditioning, a large private deck, and accommodates up to 6 guests, making it an ideal choice for families or groups seeking a dog-friendly vacation.