Villas and Vacation Homes in Key West, FL

Accommodation. You will be based in Key West.
Services and facilities include an iron, a terrace and a kitchen. Enjoy free parking with this accommodation in Key West!

Centrally located in Key West, this villa is just 400 yards from the city center and a 6-minute walk to South Beach, offering convenient access to the Ernest Hemingway Home and Museum, Southernmost Point, and Duval Street.
This 800 sq ft holiday home features 2 bedrooms, 1 bathroom, a fully equipped kitchen with a dishwasher and oven, complimentary on-site parking, free WiFi, and an on-site water park, with cycling opportunities nearby.

Located in Old Key West, this private, gated cottage is just two blocks from Higgs Beach, offering a tranquil escape within walking distance to dining and the KW Butterfly & Nature Museum.
This family-friendly holiday home features 2 bedrooms, 2 bathrooms, and a guest capacity of 6, boasting a swimming pool, spa, tennis court, and a fragrant garden with orchids and bromeliads, making it an ideal villa for your Key West getaway.

Prime Old Town Key West condo on Duval Street offers a 10-minute walk to the Hemingway Home and Southernmost Point, with immediate proximity to dining within Duval Square, providing a perfect holiday home base.
This 2-bedroom, 2-bathroom villa accommodates up to 4 guests and features a private deck, balcony, in-unit washer/dryer, and access to a rooftop pool, complemented by a private garage for convenience in Key West.

Book this vacation rental. Your accommodation will be based in Key West.
Services and facilities include free parking, air conditioning and a fridge. Take advantage of the pool in this house.

Centrally located in downtown Key West, this holiday home is a 5-minute walk to Simonton Street Beach and a 4-minute walk to Mallory Dock, placing you steps from the ocean and Key West's historic attractions.
This welcoming villa offers 610 sq ft of living space with 1 bedroom and 1 bathroom, accommodating up to 4 guests, and features a heated pool, spa, fitness center, and a well-equipped kitchen for a comfortable stay.

Vacation house. You will stay in Key West.
Facilities and services include a barbecue, a swimming pool and a fitness center. Take advantage of the Free Parking with this accommodation in Key West!

Perfectly situated in Key West's southernmost district, this welcoming villa is just steps from South Beach and half a mile from the city center, with Mallory Dock and Mallory Square both 1.3 miles away.
This 400 square foot holiday home offers air-conditioned comfort for up to 7 guests, featuring a kitchen with a fridge and microwave, and is conveniently located within walking distance of the Southernmost Point and Ernest Hemingway Home and Museum.

Book this vacation rental. You will stay in Key West.
Services and facilities: air conditioning, a dish washer and a kitchen. Take advantage of the terrace in this house!

Vacation rental listing. This accommodation is based in Key West.
Facilities and services: a kitchen, an access for persons with reduced mobility and a washing machine. Take advantage of the terrace in this house!

Vacation house. You will be in Key West.
Services and facilities: a swimming pool, a barbecue and a fridge. Take advantage of the gym in this house in Key West.

Vacation house. Your accommodation will be based in Key West.
Facilities and services: a barbecue, a kitchen and a terrace. Take advantage of the Free Parking with this accommodation in Key West!

Just 4 minutes on foot from South Beach, this Key West villa offers an exclusive retreat within 600 yards of the city center, placing you a stone's throw from the Southernmost Point and the Ernest Hemingway Home and Museum.
This holiday home boasts a private swimming pool, a fully equipped kitchen with a dishwasher and oven, and accommodates up to 11 guests with 1210 square feet of living space, ensuring a comfortable stay with complimentary WiFi and private parking.

Prime waterfront in Old Town Key West places this updated condo just 1.3 miles from Southernmost Point and 1.6 miles from the Key West Aquarium, offering a short distance to Rest Beach, the Ernest Hemingway Home and Museum, and Duval Street.
This welcoming holiday home provides 1300 square feet of living space with 2 bedrooms, 2 bathrooms, a fully equipped kitchen, an outdoor swimming pool, and complimentary on-site parking and WiFi, making it an ideal villa for your Key West getaway.

Just a 5-minute walk from Smathers Beach, this Key West holiday home offers an exceptional base, located 1.6 miles from Southernmost Point and 2 miles from the Ernest Hemingway Home and Museum.
This 1500 square foot villa features 2 bedrooms and 2 bathrooms, accommodating up to 11 guests with amenities including a swimming pool with a view, sauna, fitness center, tennis court, and complimentary WiFi and private parking.

Centrally located in Key West, this cottage is just a short walk to the Ernest Hemingway Home and Museum and Southernmost Point, and less than 1 mile from Fort Zachary Taylor Historic State Park.
This 690 square foot villa accommodates up to 6 guests with 2 king bedrooms and a queen sleeper sofa, featuring a shared heated oasis-style pool, a private deck with a covered dining area overlooking a pond, and high-end amenities including a full stainless steel kitchen.

Located in the upscale, gated Casa Marina Neighborhood on the south end of Duval Street, this apartment is a short stroll to Higgs Beach, dining, and attractions like the Southernmost Point.
This pet-friendly, 2-bedroom, 2-bathroom apartment accommodates up to 5 guests and offers a private deck with alfresco dining, a shared swimming pool, and outdoor showers, making it an ideal holiday home and beach house.

Offering sea views, this Key West villa is located approximately 1.2 miles from Key West International Airport, placing you 2.4 miles from the Ernest Hemingway Home and Museum and Duval Street.
This luxurious holiday home features a private swimming pool, spa, fitness center, and allows pets, with ample space for 15 guests and convenient access to attractions like Southernmost Point, just 2.6 miles away.

Located in Stock Island, this villa is situated 5.6 miles from Key West's main attractions like Duval Street and Hemingway Home, with Key West International Airport 3.1 miles away.
This welcoming four-bedroom, five-bathroom holiday home offers 2400 square feet of living space and features a private outdoor swimming pool, a fully equipped kitchen, a lush garden, and a fitness center.

Located in Key West, the Altair House is situated 1.1 miles from Sunset Watersports and 5.6 miles from both the Ernest Hemingway Home and Museum and Duval Street.
This exclusive villa offers 2900 square feet of living space with 6 bedrooms and 7 bathrooms, accommodating up to 14 guests with amenities including a private pool, garden, fitness center, and barbecue area, all complemented by free on-site parking and WiFi.

Experience a unique private island estate in Stock Island, just 8-10 minutes by car from Key West's Duval Street, offering exclusive access via a private bridge and proximity to landmarks like the Southernmost Point and Ernest Hemingway Home and Museum.
This expansive 8,000 sq ft villa, featuring Gatsby-era inspired interiors across 25 rooms, provides a luxury holiday home experience with 9 bedrooms, a private beach, a sand volleyball court, dock access, water sports equipment, and multiple WiFi networks for ultimate comfort and connectivity.

Located directly on Duval Street in Key West, this restored shotgun home offers immediate access to dining and entertainment options, with Banana Cafe Restaurant and numerous other eateries just a short walk away.
This welcoming 2-bedroom, 1-bathroom villa accommodates up to 4 guests and features a contemporary aesthetic with a semi-private deck and lounge area leading to a kidney-shaped pool with a waterfall, complemented by a loft second bedroom accessible via a spiral staircase and large kitchen windows that bi-fold to the pool deck for tropical breezes.

Located in Stock Island, this tranquil gated community offers a peaceful retreat just a short 5-mile drive from Key West's dining, shopping, and cultural attractions.
This 1400 sq ft villa accommodates up to 6 guests with 3 bedrooms and 3 bathrooms, featuring a fully equipped kitchen, a swimming pool, a fitness room, and private parking.

Located in Key West's Prime Old Town, this villa is within a gated community, just 2 blocks from Duval Street and a short walk from The Colony Suites.
This welcoming holiday home accommodates up to 4 guests with 1 bedroom and a sleeper sofa, featuring a private backyard with a BBQ grill and access to a shared swimming pool.