Villas and Vaction Homes in Key West, FL

Located in the desirable Pelican Landing community, this waterfront corner condo in downtown Key West offers marina views and is approximately 1 mile from Duval Street and the Historic Seaport.
This spacious apartment, accommodating up to 8 guests, features a full kitchen, in-unit laundry, a private balcony overlooking Garrison Bight Marina and pool, and includes a private boat slip with a fish cleaning station, making it an ideal holiday home for fishing enthusiasts.

Anchored in Garrison Bight Anchorage, this unique off-grid glamping experience offers a serene escape accessible via water shuttle to Key West, with the yacht 'Just Chillin' providing stunning waterfront sunsets and wildlife viewing opportunities.
This deluxe cabin cruiser yacht, accommodating up to 4 guests, features two state rooms with queen beds, two full bathrooms, air conditioning, high-speed internet, and a full kitchen, serving as an ideal holiday home for exploring the coast.

Just one block from the Southernmost Point and three blocks from South Beach, this apartment offers a prime location in Key West, steps from Duval Street's shops, dining, and nightlife.
This pet-friendly, one-bedroom unit accommodates up to four guests with a kitchenette, air conditioning, and access to shared hot tubs and a garden, providing a welcoming holiday home experience.

Located in the upscale Riviera Americana private community, this apartment offers a tranquil retreat just a short walk from Smathers Beach, Key West's largest public beach, and convenient proximity to numerous restaurants and shops.
This modern, coastal-inspired holiday home features a private balcony with panoramic water views, accommodates up to 8 guests, and includes resort-style amenities such as a community pool, jacuzzi, and fitness center, making it an ideal beach house for exploring Key West.

Prime Old Town Key West, this 677 sq.ft. one-bedroom apartment is located at the central intersection of Duval and Southard Streets, putting you within a mile of Fort Zachary State Park beach, Mallory Square, Hemingway's House, and the Southernmost Point.
This historic 1919 building offers a welcoming interior with 10-foot ceilings, accommodating up to 4 guests with a fully equipped kitchen, 55-inch 4K smart TV, and fast Wi-Fi, making it an ideal holiday home for exploring Key West.

Conveniently located 0.6 miles from Key West International Airport, this Key West condo is approximately 2.8 miles from Safe Harbor, offering easy access to island living and attractions like the Southernmost Point and Ernest Hemingway Home and Museum, both about 4.3 miles away.
This remodeled 800 square foot villa accommodates up to 11 guests with 2 bedrooms and 2 bathrooms, featuring a fully equipped kitchen with a microwave and dishwasher, making it an ideal holiday home for exploring Key West.

Old Town Key West, known for its historic architecture, is the location of this apartment, offering easy access to free street parking and a peaceful tropical setting.
This inviting villa accommodates up to 4 guests and features a private hot jacuzzi, shared pool access, a grill for outdoor cooking, and a full bathroom with an equipped kitchen, making it an ideal holiday home for exploring the island.

Offering direct Atlantic Ocean views and a private outdoor swimming pool, this Key West villa is located just a 4-minute walk from Smathers Beach and within a couple of miles of Southernmost Point and the Ernest Hemingway Home and Museum.
This spacious 1350 square foot holiday home accommodates up to 11 guests with 2 bedrooms, 2 bathrooms, a fully equipped kitchen, and features like a sauna, jacuzzi, and elevator access, providing a luxurious beach house experience.

Located in central Key West, this vacation home offers a prime spot just a 12-minute walk to Fort Zachary Taylor State Park Beach and 700 yards from Duval Street, with Mallory Square an 11-minute walk away.
This 680 sq ft villa comfortably accommodates up to 3 guests with 1 bedroom and 1 bathroom, featuring a fully equipped kitchen with a dishwasher, air conditioning, complimentary WiFi, and a private entrance, plus access to an outdoor pool and free private parking.

Just 100 feet from a community ramp offering quick access to the Atlantic and Gulf, this private canal-front villa is a short bike ride from Key West's sandy beaches, waterfront restaurants, Old Town, and Mallory Square.
This welcoming holiday home comfortably accommodates up to 6 guests with three bedrooms, a heated private pool, outdoor seating, a grill, and a fire pit, all complemented by high-speed Wi-Fi and ample free parking, a rare luxury in Key West.

Located in Old Town Key West, this 2-bedroom, 2-bathroom suite is a half-block from Duval Street, offering direct accordion door access to a brand-new plunge pool and private front porch with Key West Lighthouse and partial Duval Street views, just 2 minutes walking to the Hemingway House Museum and 8 minutes to the Southernmost Point.
This spacious 800+ sq ft villa, renovated in 2024, accommodates up to 6 guests and features exclusive off-street parking, a rare amenity in Key West, along with shared access to two heated oasis pools with waterfalls, a fire pit pergola, and a fully equipped outdoor kitchen, making it an ideal holiday home for exploring Fort Zachary Taylor State Park & Beach, just a 12-minute walk away.

Directly on the Gulf of Mexico, this apartment in Key West's Beachside Resort offers a luxurious holiday home experience with direct access to an ocean marina and options for sandbar or sunset cruises, just steps from award-winning dining at Tavern N Town.
This expansive 1-bedroom, 1-bathroom villa accommodates up to 4 guests and features a private balcony, an open-concept living area, a fully-equipped kitchen with stainless-steel appliances, and an en-suite master bedroom with a King bed and whirlpool tub, complemented by resort amenities like a heated pool, hot tub, and a waterview fitness center.

Located in Old Town Key West, this apartment is just two blocks from Duval Street and two blocks from the beach, offering convenient access to historic landmarks and the Santa Maria resort.
This exclusive villa, spanning 1000 square feet across two levels with four balconies, accommodates up to six guests and includes a fully equipped kitchen, in-unit laundry, and access to the resort's fitness center and swimming pool, all while exempting guests from the daily resort fee.

Offering a private 8 x 24' heated pool surrounded by tropical landscaping, this 1-bedroom apartment provides a tranquil escape within Key West, granting easy access to the island's attractions.
This welcoming holiday home features complimentary WiFi, an in-unit washer and dryer, and a comfortable queen bed, accommodating up to 2 guests in an ample-size cottage with a private deck perfect for enjoying the Key West ambiance.

Located in Key West's Historic Old Town, this villa is just 0.8 miles from Higgs Beach and 0.9 miles from South Beach, offering proximity to the Ernest Hemingway Home and Museum.
This 1650 sq ft holiday home accommodates up to 10 guests across three bedrooms in the main house and a separate one-bedroom cottage, featuring a private lagoon-style pool, a fully equipped kitchen, and outdoor living space with a grill and dining area.

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.

Just 600 yards from Key West's city center, this vacation home is an 8-minute walk from the Ernest Hemingway Home and Museum and a 12-minute walk from South Beach, offering a prime location for exploring the island.
This 1540 sq ft holiday home accommodates 15 guests with 3 bedrooms and 4 bathrooms, featuring a private swimming pool, spa, tennis court, and complimentary WiFi, making it an ideal villa for a memorable Key West getaway.

Directly on the Atlantic in Key West, this oceanfront condominium offers expansive ocean views and is located on the eastern side of the island, providing convenient access to watersports and local attractions.
This 2-bedroom, 2-bathroom luxury villa, accommodating up to 6 guests, features a 40 ft private balcony, a full-sized kitchen, and access to exclusive amenities at '1800 Atlantic' including a heated Olympic-sized pool, 20-person jacuzzi, fitness center, and tennis courts, making it an ideal beach house for your holiday home needs.

Atlantic Parrot is a welcoming villa located in Key West, just a 2-minute walk from Smathers Beach and 1.7 miles from Southernmost Point, offering convenient access to Ernest Hemingway Home and Museum and Duval Street, 2.1 miles away.
This 1310 square foot holiday home accommodates up to 9 guests with 2 bedrooms, features a fully equipped kitchen with a dishwasher and oven, air conditioning, internet, and an outdoor swimming pool, all accessible via an elevator and located 1.2 miles from Key West International Airport.

Located in Key West's historic Old Town, this apartment is situated in the 'Cigar House' of the Island City House Hotel, just three blocks from Duval Street and within walking distance to all attractions.
This exclusive villa offers a private balcony overlooking the pool, a private entrance, and access to hotel amenities including on-site bike rental, making it an ideal holiday home for up to four guests.