Villas and Vaction Homes in Key West, FL

Harbor House Penthouse- B offers an exclusive Key West villa experience, located a 4-minute walk from Simonton Street Beach and a 10-minute walk from Duval Street, placing you 0.8 miles from the Ernest Hemingway Home and Museum.
This spacious holiday home boasts 2500 square feet with 4 bedrooms and 4 bathrooms, accommodating up to 14 guests with a fully equipped kitchen, air conditioning, and complimentary Wi-Fi for a comfortable stay.

Waterfront, this apartment in Key West's Coconut Mallory Resort & Marina offers proximity to Smathers Beach, just 2 miles away, and convenient access to Southernmost Point and the Ernest Hemingway Home and Museum.
This 700 sq ft villa features 2 bedrooms and 2 bathrooms, accommodating up to 6 guests with a sofa bed, and boasts a recently renovated modern interior with stainless steel appliances, two community pools, an oversized jacuzzi, and on-site BBQ grills, making it an ideal holiday home.

Located in the exclusive gated community of Coral Hammock, this villa offers secure and private accommodations just a few miles from the renowned attractions of Key West.
This welcoming holiday home features 2 bedrooms and 2.5 bathrooms, accommodating up to 7 guests with a well-equipped kitchen, air conditioning, a swimming pool, and a fitness center available for use.

Located in downtown Key West, this villa offers walkable access to numerous attractions, placing you at the center of the action.
Enjoy exclusive use of a private heated pool and a gas grill on the patio, with accommodations for up to 8 guests, and a 40lb pet limit for your furry companions.

Located in Old Town Key West, this renovated apartment is situated on a quiet lane just two blocks from Duval Street, offering convenient walking access to attractions, shopping, and dining.
This welcoming villa boasts 840 square feet with two bedrooms and two bathrooms, accommodating up to four guests, and features a private wrap-around deck with a hot tub and outdoor shower for ultimate relaxation.

Located in the Meadows neighborhood of Key West, this expansive 3090 sq ft apartment is just 0.3 miles from Bayview Park and a short walk to Fausto's grocery store, offering a prime Old Town experience with convenient ocean access.
This luxurious 5-bedroom, 4-bathroom villa comfortably sleeps up to 12 guests and features a private tropically furnished yard with a pool, a 43' boat slip, gourmet chef's kitchen, and in-suite laundry, making it an ideal holiday home for large groups.

Magical Ocean Penthouse, a luxury villa in Key West, is conveniently located 1.6 miles from Southernmost Point and a 4-minute walk from Smathers Beach, offering easy access to Key West International Airport, just 1.2 miles away.
This 1360 square foot holiday home accommodates up to 11 guests with 2 bedrooms and 2 bathrooms, featuring a well-equipped kitchen, air conditioning, a jacuzzi, sauna, spa, fitness center, tennis court, and private parking, ensuring a comfortable and enjoyable stay.

Prime waterfront property in downtown Key West offers a private dock and is located just 1.3 miles from the iconic Southernmost Point and 1.5 miles from the Key West Aquarium, presenting an excellent holiday home opportunity.
This welcoming villa boasts a 2400 square foot layout with 4 bedrooms and 4 bathrooms, accommodating up to 25 guests, and features an air-conditioned interior, a full kitchen, a swimming pool, and complimentary on-site parking, making it an ideal beach house for your Key West getaway.

Located in Old Town Key West, this cottage offers convenient walking or biking access to Duval Street, Mallory Square, and El Siboney Cuban restaurant, placing you within a short distance of the Southernmost Point and the Ernest Hemingway Home and Museum.
This welcoming one-bedroom, one-bathroom cottage accommodates two guests and features a full kitchen, air conditioning, a private front porch, an outdoor dining area with a grill, and access to a seasonally heated shared pool, making it an ideal holiday home for exploring Key West.

Just a 4-minute walk from Southernmost Point and a 3-minute walk to South Beach, this Key West penthouse offers a prime location near Mallory Dock, making it an ideal holiday home for exploring the city center.
This welcoming villa provides 1290 square feet of accommodation with 3 bedrooms and 3 bathrooms, featuring air conditioning and a fully equipped kitchen to comfortably host up to 17 guests.

Just a 4-minute walk from Smathers Beach, this Key West villa offers a prime location, situated 1.6 miles from the Southernmost Point and 2 miles from the Ernest Hemingway Home and Museum.
This welcoming holiday home provides 1400 square feet of living space with 2 bedrooms, 2 bathrooms, a fully equipped kitchen, and capacity for 11 guests, complemented by a swimming pool with a view, a garden, and on-site services including free WiFi and private parking.

Located in Historic Old Town Key West, this newly built modern coastal villa is only a 6-minute bike ride to Duval Street and conveniently close to Smathers Beach and Higgs Beach.
This 2030 sq ft holiday home features 3 bedrooms, 3 bathrooms, and accommodates up to 8 guests with a gourmet kitchen, a private tropical outdoor oasis with a new pool and waterfall, and includes two bicycles for exploring.

Puerta Coralina is located in Key West, a short walk to the city center and South Beach, with the Key West Aquarium and Mallory Dock 1.2 miles away.
This 1360 square foot villa offers accommodation for 11 guests with a private pool, air conditioning, and a fully equipped kitchen, making it a perfect holiday home.

Located 1.2 miles from Key West International Airport, this welcoming villa is situated 2.4 miles from the Ernest Hemingway Home and Museum and Duval Street, and 2.6 miles from Southernmost Point.
This 4-bedroom, 3-bathroom holiday home comfortably accommodates 15 guests and features an exclusive private swimming pool, hot tub, full kitchen with a dishwasher, free WiFi, and private parking, offering sea views and a private entrance.

Located in Key West, this exceptional villa is just a 3-minute walk from Duval Street and half a mile from the historic Ernest Hemingway Home and Museum, with Simonton Street Beach a 9-minute walk away.
This expansive holiday home offers 3340 square feet of living space with 7 bedrooms and 7 bathrooms, accommodating up to 27 guests, and features a private swimming pool, spa, fitness center, and tennis court.

Located in Key West, this exclusive villa offers oceanfront living with a balcony providing sea views, just a 4-minute walk from Smathers Beach and conveniently situated 1.6 miles from Southernmost Point and 2 miles from the Ernest Hemingway Home and Museum.
This luxurious holiday home boasts 2100 square feet of living space with 3 bedrooms and 3 bathrooms, accommodating up to 15 guests with amenities like a swimming pool, jacuzzi, sauna, and fitness center, all while being 1.2 miles from Key West International Airport.

Located just 1.2 miles from Key West International Airport and 2.3 miles from the Ernest Hemingway Home and Museum and Duval Street, this vacation home offers sea views for a classic Key West experience.
This exclusive 4-bedroom villa, accommodating up to 15 guests, features a private pool, hot tub, complimentary WiFi, and concierge service, making it an ideal holiday home for exploring Key West.

Coral Hammock in Stock Island, Florida, offers a serene tropical setting with convenient access to Key West's attractions.
This welcoming 3-bedroom villa sleeps 8 and features air conditioning, a swimming pool, a garden, a fitness center, and a fully equipped kitchen, making it an ideal holiday home for families.

This oceanfront mini-resort in Key West, once the filming location for MTV's 'Real World Key West,' offers 500 feet of private oceanfront access and is located a 10-minute drive from Duval Street and Old Town.
This expansive villa, accommodating up to 22 guests in 8 to 10 bedrooms, features a tennis court, basketball hoop, two boat docks, a racket ball court in the optional guest house, and includes 4 kayaks and 4 paddle boards.

Located in Key West's city center, this Conch-style cottage is just two blocks from Duval Street and within walking distance of the Ernest Hemingway Home and Museum and Southern Point.
This 530 sq ft cottage offers a private bedroom with a king bed and a living room with a queen sleeper sofa, sleeping up to 4 guests, and features a full kitchen, in-unit laundry, and shared access to a heated pool, making it an ideal holiday home.