Holiday Rentals in Key West, FL

Set within a quiet, upscale, gated enclave of six historic Old Key West vacation rentals, this apartment is just 300 metres from Higgs Beach and a 10-minute walk to the Ernest Hemingway Home and Museum.
This pet-friendly apartment, offering accommodation for four guests, features a private treetop balcony, a shared swimming pool, and is conveniently located near public transportation and seaside attractions, making it ideal for dog-friendly holidays.

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.

Located in the historic Casa Marina Neighbourhood, this apartment is just a short stroll from Key West's beaches and dining, offering a prime spot in a gated enclave of six historic rentals.
This pet-friendly apartment, ideal for up to four guests, boasts a granite kitchen, a private balcony with treetop views, and access to shared amenities including a swimming pool and gas grill, making it a great choice for dog-friendly holidays near the beach.

Offering stunning sunset views from a private balcony, this updated two-bedroom condo is located on the east side of Key West within the Sunrise Suites community, approximately 1.6 kilometres from Smathers Beach and a 10-minute drive to Duval Street.
This pet-friendly apartment boasts a modern coastal interior, a fully equipped kitchen, an in-unit washer/dryer, and access to a shared heated pool and hot tub, comfortably accommodating up to six guests.

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.

Located on Key West's southeast side within Sunrise Suites, this apartment is just 1.6 kilometres from Smathers Beach and a 10-minute drive to Duval Street.
This pet-friendly apartment offers 74 square meters of space with two bedrooms and two bathrooms, accommodating up to six guests with a king bed, queen bed, and queen sleeper sofa, plus access to a heated pool, hot tub, and tennis court.

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.

Bahama Village in Key West offers a pet-friendly apartment, just a few blocks from Duval Street and within walking distance of the Ernest Hemingway Home and the Southernmost Point.
This newly updated 12 square meter apartment accommodates two guests and features a kitchenette with a mini-fridge and microwave, plus access to a shared heated swimming pool and sundeck with BBQ facilities, making it an ideal choice for dog-friendly holidays.

This apartment on Key West's southeast side is located just 1.6 kilometres from Smathers Beach and a 10-minute drive from Duval Street.
This pet-friendly apartment, allowing up to two pets with a 40lb weight limit, boasts 74 square meters of floor area and comfortably accommodates six guests with two bedrooms and two bathrooms, plus access to a shared hot tub and heated pool.

This pet-friendly house in Key West is conveniently located just 400 metres from the city centre, offering an 11-minute walk to South Beach and an 18-minute walk to the Key West Aquarium.
Boasting a private balcony, free WiFi, and a spa, this 49 square metre house accommodates up to 7 guests and is ideal for active travellers looking for a dog-friendly base near Mallory Dock.

This pet-friendly apartment in Old Town Key West is ideally situated just 150 meters from the Key West Lighthouse and 150 meters from Hemingway Home, offering a prime location on the doorstep of Duval Street.
Boasting ample space for up to 16 guests across two connected cottages, this accommodation features two kitchens, two living areas, private laundry facilities, a swimming pool, and a hot tub, ensuring a comfortable and enjoyable stay for all.

Located in Key West's Cuban district, this studio is a short walk from acclaimed coffee spots and offers excellent proximity to the Southernmost Point and Ernest Hemingway Home and Museum.
This pet-friendly studio boasts 42 square meters of space, including a kitchen with a fridge, freezer, and microwave, plus complimentary bikes for exploring the island, which is near the beach.

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.

Discover this pet-friendly apartment in Key West’s Bahama Village, just a short walk from Duval Street, the Ernest Hemingway Home, and the Southernmost Point.
This updated one-bedroom apartment, ideal for two guests, offers a swimming pool, garden, and fitness centre, with pets allowed for an additional fee.

Enjoy captivating sunset views from the private balcony of this spacious two-bedroom, two-bathroom apartment, conveniently located just 1.9 kilometers from Fort East Martello Museum and 5.9 kilometers from Key West International Airport.
This pet-friendly Key West condo offers 74 square meters of living space, accommodating up to six guests with a fully equipped kitchen, access to a swimming pool, and elevator access.

This waterfront condo in Key West offers direct access to a private boat slip and is just a 1.6 kilometre walk to Rest Beach and 1.9 kilometres to Duval Street, with the Ernest Hemingway Home and Museum a mere 1.6 kilometres away, making it a truly pet-friendly base.
Boasting 112 square metres of living space, this dog-friendly accommodation accommodates up to 10 guests with two bedrooms and two bathrooms, featuring a Key West-themed swimming pool, air conditioning, a balcony, a fully equipped kitchen, and complimentary on-site private parking.

This pet-friendly apartment in Key West, situated in the private Key Cove Landings community within Northside Resort, offers a quiet waterfront escape just 500 meters from the island's largest shopping centre and a Publix grocery store.
Boasting expansive water views from floor-to-ceiling windows and private balcony access from multiple bedrooms, this luxurious four-bedroom apartment features a private heated pool, a covered lanai with outdoor dining, a Jacuzzi tub in the master suite, and is conveniently located near the Ernest Hemingway Home and Museum and Southernmost Point, with opportunities for jet skiing and snorkelling nearby.

This oceanfront resort in Key West's Northside Resort, specifically Key Cove Landings, is a pet-friendly haven offering a private waterfront retreat with a private heated pool and lush landscaping, conveniently located within walking distance to grocery stores and a major shopping centre, yet only a short drive from Old Town's attractions.
Boasting 250 square meters of luxurious living space, this resort home features four bedrooms, including three en-suites with porch access, a gourmet kitchen, and a covered outdoor dining area with a grill, ensuring a comfortable and well-equipped stay for you and your dog-friendly companions.

This architect-designed, pet-friendly apartment in Key West's Meadows district offers stunning waterfront views of Garrison Bight and is just a short distance from historic sites like the Ernest Hemingway Home and Museum and Southernmost Point.
Boasting 265 square meters of floor area, this luxurious apartment accommodates up to 8 guests with 3 bedrooms and 3 bathrooms, featuring a professional kitchen, an outdoor kitchen, a private swimming pool, and multiple balconies for enjoying the seaside environment, making it ideal for families and dog-friendly holidays.

Perfectly positioned in Old Town Key West, this apartment is just steps from Duval Street and the Southernmost Point, offering prime access to local attractions and nightlife.
This pet-friendly apartment, covering 60 square meters, features two bedrooms accommodating up to four guests, a fully equipped kitchen, and a parking space, with concierge services available for planning island activities.

Prime downtown Key West waterfront accommodation, this penthouse is situated 2.1 kilometres from the Southernmost Point and 2.4 kilometres from the Key West Aquarium, offering excellent access to key attractions and a truly seaside experience.
This pet-friendly house boasts a private patio with sea views, a garden, and on-site parking, making it ideal for travellers with pets looking for a dog-friendly stay near the beach.

Parrot Key Hotel & Villas is a resort located on Florida Bay, offering easy access to historic Old Town Key West via a complimentary shuttle, just a short drive away.
This pet-friendly resort boasts four outdoor swimming pools, kayaking opportunities directly from the property, and private terraces with scenic views, making it ideal for travellers seeking dog-friendly accommodation near the beach.

Just 400 metres from the city centre, this Key West house is a 6-minute walk from the Ernest Hemingway Home and Museum and 700 metres from Duval Street.
This pet-friendly house offers air-conditioned accommodation with a private balcony, a kitchen with a microwave, and access to a swimming pool and spa, perfect for enjoying the seaside atmosphere.

Located in downtown Key West, this apartment is a short walk to numerous attractions and 24 kilometers from the airport.
This pet-friendly apartment offers a private balcony with Simonton Street views, a shared pool, and a fully stocked kitchen, perfect for guests with pets.

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.

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.

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.

Prime downtown Key West, this studio apartment is just 100 metres from the Truman Avenue and Whitehead Street junction, placing you a short walk from the Southernmost Point and Ernest Hemingway Home.
This pet-friendly studio offers modern comforts, including WiFi and air conditioning, with pets allowed for a nightly fee, making it ideal for couples or solo travellers exploring the local restaurants and nightlife.

Just 640 meters from the Atlantic Ocean, this Key West house is located in Old Town, a short walk to Duval Street's entertainment.
This pet-friendly house offers two bedroom suites, a private pool, and concierge services, making it ideal for families and their dogs.

Located in the tranquil Sunrise Suites community, this apartment offers easy access to Smathers Beach and Higgs Beach, with Key West International Airport just 5 kilometers away.
This pet-friendly apartment welcomes pets up to 40 lbs for an additional nightly fee and features resort-style amenities including a communal heated pool, hot tub, and an on-site tennis court, making it ideal for families and dog-friendly holidays.

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 expansive 2,400 sq ft waterfront penthouse in downtown Key West offers a private boat slip and is located less than 1 kilometre from Duval Street and the Historic Seaport, making it a prime spot for boating and fishing enthusiasts.
This pet-friendly apartment welcomes dogs up to 11.3 kg for an additional fee and comfortably accommodates up to 16 guests across 4 bedrooms and a loft, with access to a heated community pool and tiki area with BBQ grills.