Holiday Rentals in Key West, FL

Perfectly situated on the eastern edge of Key West, this dog-friendly apartment is just a few kilometres from downtown attractions and Key West International Airport, offering easy access to Smathers Beach and Florida Keys Beaches.
This 72 square metre apartment, accommodating up to 4 guests, boasts 2 bedrooms and 2 bathrooms, a fully equipped kitchen, a private deck, and access to a shared swimming pool and exercise room, making it ideal for pet-friendly holidays near the Key West Tropical Forest and Botanical Garden.

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.

This pet-friendly apartment is perfectly situated in Key West's Old Town, just a short 500-meter walk from White Street Pier and the beach, offering convenient access to ocean activities and scenic views.
Enjoy a comfortable stay in this 1-bedroom, 1-bathroom apartment that accommodates up to two guests, complete with essential amenities like air conditioning, internet, a kitchen, and dedicated parking, making it an ideal base for experiencing Key West's laid-back lifestyle.

Prime Old Town Key West, this apartment is just 100 metres from the iconic Southernmost Point and a few steps from Duval Street's attractions.
This pet-friendly apartment offers 37 square metres of space with a kitchenette, air conditioning, and access to shared hot tubs, making it ideal for travellers with pets.

In the Meadows district of Key West, this waterfront apartment offers marina views and is less than 1.6 kilometres from Duval Street, the Historic Seaport, and the Hemingway House, providing convenient access to island attractions.
This spacious, pet-friendly apartment boasts 111 square meters of living space, featuring two bedrooms and two bathrooms, with direct access to a shared heated swimming pool and a private balcony perfect for enjoying the seaside location.

Located in Old Town Key West, this studio is a short walk from the Hemingway House and Duval Street, offering a pet-friendly base for exploring the historic district.
This dog-friendly studio for two features a king-size bed, a kitchenette with a microwave and fridge, air conditioning, and a balcony, with parking available on-site.

Located in Key West, this apartment is 2.4 kilometres from Smathers Beach, 5.6 kilometres from Old Town, and 5.6 kilometres from the Southernmost Point.
This dog-friendly apartment, offering 72 square metres of space for up to six guests, boasts a private deck and access to resort amenities including a swimming pool and hot tub.

Conveniently located just 0.6 miles from Key West International Airport, this apartment offers easy access to Southernmost Point, 6.4 kilometres away, and the Ernest Hemingway Home and Museum, 6.9 kilometres away.
This pet-friendly apartment provides 74 square metres of living space, featuring two bedrooms and two bathrooms, along with a fully equipped kitchen and air conditioning, ensuring a comfortable stay with your dog-friendly companions.

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.

Prime Old Town Key West apartment, situated just 80 metres from Duval Street, offers a pet-friendly retreat with a gated entrance for added privacy.
This dog-friendly accommodation boasts a king-sized bed in an upstairs loft with a skylight, a full kitchen with modern appliances, and access to a shared swimming pool approximately 320 metres away.

Boasting stunning sunset views, this apartment is located on the east side of Key West, approximately 1.6 kilometers from Smathers Beach and a 10-minute drive from Duval Street.
This pet-friendly apartment offers two bedrooms and two bathrooms, accommodating up to six guests with a fully equipped kitchen and on-site amenities including a swimming pool and hot tub.

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 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.

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.

This pet-friendly apartment is located in the prestigious Casa Marina residential district, on the southern side of Key West, offering a tranquil island setting surrounded by luxurious homes and tropical gardens, perfect for leisurely strolls.
Enjoy a peaceful escape with your pets in this 2-bedroom apartment, featuring air conditioning, a swimming pool, garden, and parking, all within easy reach of the Casa Marina district and offering a sense of seclusion ideal for those seeking a residential feel away from the busiest tourist hubs.

Perfectly situated for exploring Key West, this apartment is just 300 meters from the sea and offers convenient access to the Salt Ponds Preserve, Southernmost Point, and the Ernest Hemingway Home and Museum.
This dog-friendly, 72 square meter apartment provides accommodation for up to six guests, featuring two bedrooms, two bathrooms, a fully equipped kitchen, and a private balcony, with shared access to a swimming pool and hot tub.

Just 320 metres from the beach at Fort Zachary Taylor State Park and moments from Duval Street's shops and eateries, this apartment offers a prime Key West location.
This pet-friendly apartment boasts a private patio with a grill, a shared hot tub, and in-unit laundry, perfect for a comfortable stay with your dog.

Directly opposite Smathers Beach, Key West's largest, this ocean-view apartment at La Brisa resort offers direct access to 1.6 kilometres of sand and sea.
This pet-friendly apartment boasts two bedrooms and two bathrooms, accommodating up to four guests with resort amenities including a swimming pool, hot tub, and sauna, ensuring a comfortable stay with your dog-friendly family.

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 house in Key West offers a prime location, just 500 metres from the city centre and a 5-minute walk to South Beach.
Enjoy a 127 square metre home with air conditioning, a private swimming pool, and a garden, perfect for a dog-friendly getaway near the Ernest Hemingway Home and Museum.

Boasting sea views, this spacious house is conveniently situated just 2.3 kilometres from the Ernest Hemingway Home and Museum, 2.4 kilometres from Duval Street, and a mere 1.2 kilometres from Key West International Airport, making it an ideal pet-friendly base for exploring the island.
This dog-friendly accommodation features four bedrooms, four bathrooms, a private outdoor swimming pool, and a hot tub, with a fully equipped kitchen and air conditioning ensuring a comfortable stay for up to 15 guests, all within easy reach of water sports.

Boasting a prime waterfront position within Key West's gated Key Cove community, this apartment offers a secluded yet convenient base, just a short drive from Old Town and within walking distance of shops.
This spacious 223 square meter apartment, ideal for up to 8 guests, is a pet-friendly haven featuring a heated swimming pool, a gourmet kitchen, and a covered lanai with a grill, perfect for enjoying the seaside views.

Prime Old Town Key West location places this resort within 2 kilometres of the Southernmost Point and the Ernest Hemingway Home and Museum, offering a pet-friendly base near Florida Keys Beaches and Duval Street.
Enjoy a garden and complimentary self-parking at this resort, perfect for outdoor dining with barbecue grills, and a smoke-free environment for a comfortable stay.

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 waterfront apartment in Key West's Northside Resort neighbourhood offers quiet seclusion, just a short walk from major shopping and dining, and is a pet-friendly option for your holiday.
Boasting a generous 219 square meters of living space, this apartment features four bedrooms, a private heated swimming pool, a fully equipped chef's kitchen, and ample off-street parking, ensuring a comfortable stay for you and your pets near the seaside.

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 Meadows, Key West, this waterfront corner apartment is just 1.6 kilometres from Duval Street, the Historic Seaport and the Hemingway House, offering unobstructed harbour and pool views.
This pet-friendly apartment boasts a spacious 121 square metre layout with two bedrooms and two bathrooms, comfortably sleeping up to six guests and featuring a private balcony with direct stair access to the shared heated pool and tiki bar.

Located in Key West's Historic Old Town, this apartment is just 320 meters from Duval Street, offering easy access to shops and attractions.
This dog-friendly apartment features a shared garden with a gas grill and outdoor dining, and permits one dog up to 11 kilograms for an additional fee.

Boasting unobstructed marina and pool views from a second-floor corner unit in Key West's Pelican Landing community, this apartment is situated just 1.6 kilometres from Duval Street and its nightlife.
This pet-friendly apartment welcomes dogs up to 11 kg for a fee, offering a private balcony with direct stair access to the pool and docks, a private boat slip with water, and convenient proximity to Charter Row for excursions, making it an ideal seaside escape.

Located on the east side of Key West within the Sunrise Suites community, this apartment is approximately 1.6 kilometres from the beach and a 10-minute drive from Duval Street and the Key West airport.
This pet-friendly apartment offers a shared heated pool and hot tub, a fully equipped kitchen, and is ideal for families with a capacity for six guests, with one dog up to 40lbs allowed for a nightly fee.

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.

Located in Old Town Key West, this ground-floor studio is just 320 meters from Duval Street and offers a quiet setting with easy walking access to the Ernest Hemingway Home and Museum and Southernmost Point.
This pet-friendly studio, measuring 45 square meters, accommodates up to four guests and features a kitchenette, air conditioning, and French doors opening to a deck near a shared swimming pool and spa, making it an ideal choice for dog-friendly holidays near Florida Keys Beaches and Fort Zachary Taylor Historic State Park.

Prime waterfront penthouse accommodation in downtown Key West offers spectacular marina and sunset views from dual balconies, situated just 1.6 kilometres from Duval Street and the Historic Seaport.
This pet-friendly apartment boasts a spacious 185 square metre, two-storey layout with a loft, comfortably sleeping 16 guests and featuring a private boat slip, community heated pool, and BBQ area.

Located in downtown Key West, this studio is just a short walk from the historic Curry Mansion and numerous attractions.
This pet-friendly studio offers a queen bed, a sleeper sofa for up to three guests, a kitchenette, and access to shared outdoor spaces including a swimming pool, making it ideal for travellers with pets.

Centrally located in Old Town Key West, this Conch-style apartment is a 10-minute walk to the beach and a 15-minute stroll to Duval Street, offering a prime spot for exploring the area.
This two-bedroom, two-bathroom apartment welcomes pets with a 40lb maximum per pet and nightly fee, featuring a shared tropical backyard oasis with a swimming pool and grill, perfect for families and dog-friendly holidays.

Located in the heart of downtown Key West, this pet-friendly house offers easy walking access to numerous attractions, including Mallory Square and Duval Street, all within 1 kilometer.
This spacious accommodation, spread across three units, welcomes up to 16 guests and their pets (up to two, 40lb max each) and features a hot tub, BBQ grill, and a balcony with a hammock, making it ideal for a memorable getaway.