Holiday Rentals in Key West, FL

Just 320 meters from Duval Street in historic Old Town Key West, this pet-friendly studio apartment offers a peaceful retreat with a gated complex ensuring security.
This dog-friendly accommodation sleeps up to four guests in a loft layout, featuring a full kitchen, private outdoor seating, an outdoor shower, and an on-site washer/dryer for ultimate convenience.

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.

Just 0.96 kilometres from Key West International Airport, Sunrise Suites Saint Lucia Suite #201 is located in Key West, approximately 6.44 kilometres from Southernmost Point and 7.40 kilometres from Ernest Hemingway Home and Museum.
This pet-friendly apartment offers 74 square metres of living space with two bedrooms and two bathrooms, including a fully equipped kitchen with a dishwasher, air conditioning, a private balcony, and access to a shared swimming pool and hot tub.

Ideally situated in a prime Key West district, this apartment is just a short stroll from Duval Street and within 500 meters of the Southernmost Point and 300 meters from South Beach, making it a superb base for exploring the area.
This pet-friendly apartment accommodates up to four guests, offering a convenient kitchenette, air conditioning, and access to shared hot tubs and a patio, with one small dog permitted for an additional fee.

Prime Old Town Key West waterfront condo offering a pet-friendly escape with complimentary on-site parking and Wi-Fi, just 2.1 kilometres from the Southernmost Point.
This updated 2-bedroom, 2-bathroom apartment boasts 121 square metres of living space, a patio with sea views, an on-site swimming pool, and is conveniently located near Duval Street and the Ernest Hemingway Home and Museum.

Just 290 metres from Southernmost Point and 190 metres from South Beach, this Key West apartment offers a fantastic pet-friendly base for exploring Ernest Hemingway Home and Museum, just 1.1 kilometres away.
This apartment features air conditioning, free WiFi, a kitchen with an oven and microwave, and access to a swimming pool, spa, and fitness centre, making it ideal for guests travelling with pets.

Located in Key West's City Centre, this luxury penthouse is just 100 meters from Mallory Square, perfect for experiencing the iconic Sunset Celebration.
This spacious 2,400 sq ft apartment boasts four en-suite bedrooms, sleeping up to 12 guests, and is fully equipped with modern amenities, including high-speed wireless internet, making it an excellent pet-friendly option.

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.

Just one block from Duval Street, this pet-friendly house is perfectly situated in Key West, a mere 800 metres from Southernmost Beach and within easy reach of the Ernest Hemingway Home & Museum and the Key West Lighthouse.
This dog-friendly accommodation offers a private heated swimming pool and off-street parking for two vehicles, with the unique layout of two separate suites making it ideal for larger groups or multi-family stays.

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.

Perfectly situated on historic Duval Street in Old Town Key West, this resort offers direct access to a wealth of dining, nightlife, and attractions, with water sports activities available within 2 kilometers.
This pet-friendly resort boasts an outdoor pool, an on-site restaurant, and a fitness centre, ensuring a comfortable stay for you and your dog-friendly companions.

Boasting unmatched sunrise and sunset views, this two-story waterfront penthouse in Downtown Key West is perched atop one of the city's tallest buildings and is located less than 1 kilometre from Duval Street, the Historic Seaport, and the Hemingway House, with public park amenities nearby.
This pet-friendly apartment offers 2,000 sq ft of space, sleeping up to 16 guests across 4 bedrooms and a loft, and features two private balconies with marina and city views, a full kitchen, and access to resort-style amenities including a shared heated pool and BBQ grills.

This ground-floor corner condo at Sunrise Suites is conveniently located in Key West, just minutes from Smathers Beach and the historic Old Town.
This pet-friendly apartment offers two bedrooms, two bathrooms, and accommodates up to six guests, featuring a heated lagoon-style community pool, on-site gym, and tennis courts for a comfortable stay with your dog.

Boasting a prime location at the prominent intersection of Caroline Street and Simonton Street, this Key West guest house is just 250 meters from the historic Old Town and offers a truly pet-friendly escape for your holiday.
This expansive property features six distinct rental units with a private pool, accommodating up to 19 guests, and is conveniently situated for exploring Key West, with ample parking and easy access to various transport options for your dog-friendly adventure.

Just 320 meters from Duval Street in Old Town Key West, this pet-friendly cottage in the Colony on Olivia Street offers convenient ground-floor studio access.
This cottage features a kitchenette, a king bed, a couch, and French doors opening to a deck beside a shared swimming pool, perfect for up to four guests with pets allowed.

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.

Waterfront corner condo in Key West's Meadows district, this apartment is located within 1.6 kilometres of Duval Street, the Historic Seaport, and the Hemingway House.
This pet-friendly apartment offers 121 square meters of space, sleeps up to 8 guests, and features a private balcony with harbour and pool views, a shared heated pool, and on-site parking.

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.

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.

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.

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.

This apartment is conveniently situated in Key West, offering proximity to Southernmost Point and Ernest Hemingway Home and Museum, with Smathers Beach and Fort Zachary Taylor Historic State Park just a short distance away.
Enjoy this pet-friendly apartment, boasting 111 square meters of space with 2 bedrooms and 2 bathrooms, accommodating up to 6 guests, and featuring a communal swimming pool, hot tub, and private covered parking.

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.

This apartment in Key West's Northside Resort neighbourhood is situated on an exclusive lane within the private Key Cove Landings community, offering an exclusive waterfront residential experience just 500 meters from a Publix grocery store and a large shopping centre.
Boasting expansive water views from floor-to-ceiling windows, this dog-friendly apartment features a gourmet kitchen, a private heated pool, and a master suite with Jacuzzi tub and direct balcony access, making it ideal for travellers seeking a pet-friendly seaside escape.

Boasting panoramic sunrise-to-sunset views, this waterfront penthouse apartment is located in the Meadows district of Key West, less than 1.6 kilometres from Duval Street, the Historic Seaport, and Hemingway House.
This pet-friendly apartment offers 186 square meters of space, sleeping up to 16 guests with dual balconies, access to a shared heated pool, BBQ grills, a tiki area, and on-site parking, with a private boat slip also available.

Centrally located in Key West's Meadows neighbourhood, this apartment is just a short distance from Garrison Bight and the historic Old Town, offering excellent views and superb pet-friendly accommodation.
This spacious apartment boasts 263 square meters of living space, accommodating up to 10 guests with four bedrooms, three bathrooms, a private boat slip, and a heated swimming pool, making it ideal for a family holiday with your dog-friendly companion.

Located in Old Town Key West, this historic Conch cottage is just a few blocks from Duval Street and the Historic Seaport, offering convenient access to shops and restaurants, and is a truly pet-friendly option for your holiday.
Boasting 173 square meters of space, this dog-friendly apartment accommodates up to six guests with three bedrooms, two bathrooms, a private pool, a garden, and off-street parking, ensuring a comfortable stay near the Ernest Hemingway Home and Museum.

This exceptional, pet-friendly apartment is located in Key West's Historic District, just a stone's throw from Mallory Square and the Ernest Hemingway Home and Museum.
Boasting 232 square meters of living space, this newly renovated penthouse offers four en-suite bedrooms, ample guest capacity for 12, and a spacious terrace, with central air conditioning and high-speed wireless internet throughout.

Directly on Duval Street in Key West's historic district, this apartment is mere steps from shops, dining, and the beach, with the Southernmost Point just a short walk away.
This dog-friendly accommodation offers a pet-friendly stay with a fee for one dog up to 30 lbs and features an upstairs balcony with Duval Street views, complimentary WiFi, and two cable TVs, perfect for a family of four.

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.

Just 50 metres from the communal swimming pool, this pet-friendly apartment in Coral Hammock, Stock Island, offers immediate access to dining and is a mere 10-minute Uber journey to Duval Street.
This spacious 3-bedroom, 2.5-bathroom apartment accommodates up to 8 guests and boasts a kitchen with a fridge, freezer, and microwave, alongside air conditioning and a garden for a comfortable stay.

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.

Located in the historic district, this Key West apartment is just steps from Duval Street, 160 meters from the Southernmost Point, and 480 meters from South Beach.
This dog-friendly accommodation offers shared hot tubs and a patio, perfect for travellers with pets, with capacity for four guests and a convenient kitchenette for light meals.

Just 1 block from Duval Street in Key West's historic district, this apartment offers immediate access to Mallory Square and numerous restaurants, with four private parking spaces available.
This pet-friendly apartment complex, comprising six separate units and accommodating up to 19 guests, features a heated private swimming pool and allows up to two pets under 40lbs for a fee, ensuring a comfortable stay for you and your dog-friendly companions.

Just 500 metres from the iconic Southernmost Point and steps from Duval Street, this Key West apartment offers a prime location in the historic district.
This pet-friendly apartment, ideal for up to four guests, features a kitchenette, air conditioning, and shared hot tubs, making it a great choice for travellers with their pets.

Centrally located in Key West, this five-bedroom apartment is just 240 meters from public parking and offers easy access to local attractions.
This dog-friendly apartment boasts a private two-storey main house with five en-suite bedrooms, accommodating up to ten guests, and features a shared outdoor area with a swimming pool and rooftop deck.