Discover Luxury Vacation Rentals in Key West, FL

Just 0.6 miles from Key West International Airport, this luxury apartment offers convenient access to Fort East Martello Museum.
This welcoming two-bedroom, two-bathroom apartment boasts 800 square feet and a fully equipped kitchen, perfect for guests seeking upscale comfort.

Located 1.9 miles from Key West International Airport, Hyatt Vacation Club At Beach House offers a luxury resort experience in Key West.
Enjoy spacious suites featuring full kitchens and private screened balconies, with on-site amenities including an outdoor pool, hot tub, and bike hire for exploring the island.

Perfectly situated on the western edge of Key West, Ocean Key Resort & Spa offers direct Gulf of Mexico access and is steps from Mallory Square's sunset celebrations and historic Old Town.
Experience luxury with a private terrace, spa, and fitness center, complemented by complimentary Wi-Fi and car hire for effortless exploration.

Directly on Duval Street, this historic apartment offers an exclusive Key West experience with unparalleled proximity to iconic landmarks.
Enjoy premium comfort with a private balcony, full kitchen, and air conditioning in this luxury Key West accommodation, perfect for two guests.

Offering incredible sunset views over salt marshes, this serene fourth-floor condo in Key West's Sunrise Suites community is a mile from the beach and a 10-minute drive to Duval Street.
This luxury apartment accommodates up to six guests with a king bed, queen bed, and queen pullout sofa, plus access to a heated pool, hot tub, and tennis court.

Offering magnificent Gulf of Mexico views, this luxury apartment is located in Key West's prime Old Town, just minutes from iconic attractions.
This welcoming 1-bedroom, 1-bathroom apartment accommodates up to 4 guests and features a full kitchen, air conditioning, a swimming pool, jacuzzi, garden, sauna, and fitness center.

Steps from Mallory Square and the Key West Historic Seaport, the Bayview House ground-floor suite offers a luxury island escape within the historic 1928 Bayview House.
This upscale 500 sq ft apartment accommodates four guests with a queen bed and sleeper sofa, featuring a well-equipped kitchen and shared swimming pool access.

Ideally situated in Key West's desirable Pelican Landing, this waterfront condo is approximately 1 mile from Duval Street and the Seaport, offering convenient access to downtown attractions.
Experience luxury living in this spacious 1,190 sq ft apartment, featuring a private balcony with pool access, a private boat slip, and a welcoming pet-friendly environment for one dog up to 25 lbs.

Steps from the Curry Mansion Museum and a 5-minute walk to Simonton Street Beach, this luxury studio in Key West offers an exclusive escape.
This premium accommodation boasts a fully equipped kitchen, air conditioning, and free WiFi for a comfortable and convenient stay.

Prime beachfront in Key West's Old Town, Southernmost Beach Resort And Guesthouses is steps from South Beach and Southernmost Point, with Fort Zachary Taylor Historic State Park 2.1 km away.
Enjoy three outdoor pools, a spa, and a fitness center at this luxury resort, offering a premium coastal experience.

Centrally located in Key West city center, this luxury holiday home is less than 3,168 feet from the Southernmost Point and Ernest Hemingway Home and Museum, and an 8-minute walk to South Beach.
Enjoy a welcoming stay with premium amenities including a full kitchen with a barbecue, air-conditioning, free WiFi, and a private balcony, offering accommodation for 4 guests.

Directly on Duval Street in Old Town Key West, this unique Speakeasy Inn is mere blocks from the beach and the Southernmost Point, offering an exclusive 19th-century rum-running theme.
Experience luxury with a stocked kitchenette, outdoor seating, and ADA-compliant features in this 260 sq ft apartment accommodating up to 4 guests.

Just a 4-minute walk from Smathers Beach, this luxury Key West house offers an exclusive escape near water sports.
This premium 1360 sq ft accommodation features a private entrance, on-site tennis, a swimming pool, and complimentary WiFi for an unforgettable stay.

A 17-minute walk from Rest Beach places this luxury Key West house near the Ernest Hemingway Home and Museum and Duval Street, offering premium convenience.
This exclusive 1300 sq ft accommodation welcomes up to 10 guests with a private pool, garden, and fully equipped kitchen for an upscale stay.

Located in Midtown Key West, this luxury apartment is a short bike ride to Duval Street, the Southernmost Point, and Mallory Square.
This 1740 sq ft, 3-bedroom, 2-bathroom accommodation for six boasts a private fenced tropical backyard with a heated pool, outdoor dining, and grill, all complemented by AvantStay's 5-star concierge service.

Just 600 feet from Duval Street and 1200 feet from the southernmost beach, this luxury studio offers an exclusive Old Town Key West location.
This welcoming 400 sq ft studio, accommodating up to 4 guests, features a well-equipped kitchenette and access to a shared heated swimming pool.

Located in Key West's tranquil New Town, Captain's Cove offers direct canal frontage with quick ocean access, a short drive from Southernmost Point and the Ernest Hemingway Home and Museum.
This luxury 2390 sq ft apartment boasts a chef's kitchen, heated saltwater pool, and a 24,000 lb boat lift, accommodating up to 8 guests with 4 bedrooms and 4 bathrooms.

Offering panoramic sea views, this luxury four-bedroom vacation home is just 0.9 miles from Duval Street and 1.1 miles from the Ernest Hemingway Home and Museum in Key West.
With 2830 square feet and a 19-guest capacity, this pet-friendly accommodation boasts a swimming pool, Jacuzzi, fitness center, and tennis court, providing an exclusive Key West experience.

Just a 2-minute walk from Smathers Beach, this luxury apartment in Key West offers a prime location, 1.2 miles from the airport and 1.7 miles from the Southernmost Point.
Experience upscale comfort in this spacious 1360 sq ft, 2-bedroom, 2-bathroom apartment with a heated pool, complimentary parking, and water sports nearby for an exclusive getaway.

Vacation house to rent. You will be in Key West.
Facilities and services include a kitchen, a fitness center and a barbecue. Take advantage of the Free Parking with this accommodation in Key West!

Offering stunning, unobstructed Atlantic ocean views from a private 3rd-floor balcony, this luxury Key West apartment provides an exclusive oceanfront escape just moments from the city's attractions.
Experience premium comfort with a custom kitchen, top-tier appliances, a dedicated workspace, and a shared swimming pool, jacuzzi, and fitness center for an unforgettable stay.

Just one mile from Smathers Beach, this luxury Key West apartment offers convenient access to Southernmost Point and the Ernest Hemingway Home and Museum.
This upscale 780 sq ft accommodation features 2 bedrooms, 2 bathrooms, a shared pool, hot tub, and welcomes up to two dogs.

Steps from Duval Street, this luxury apartment in Key West's southernmost district offers an exclusive oasis for discerning travelers.
This premium accommodation boasts 6 bedrooms, accommodates 24 guests, and features three private hot tubs for ultimate relaxation.

Oceanfront penthouse condo in Key West's Beachside neighborhood offers vaulted ceilings and a large balcony with ocean views, just a short walk to Smathers Beach, the Southernmost Point, and the Ernest Hemingway Home and Museum.
Experience resort-style amenities including a community pool, jacuzzi, fitness center, and Key West's only clay tennis courts, alongside a newly renovated interior with a queen sleeper sofa, accommodating up to 6 guests with 2 bedrooms and 2 bathrooms.

Vacation house rental. Your accommodation will be based in Key West.
Services and facilities include an iron, a barbecue and a fitness center. The big plus of this house in Key West is the jacuzzi!

Half a block from Duval Street, the 1869 Curry Mansion apartment offers an exclusive Key West Historic District luxury experience.
This 280 sq ft, 1-bedroom apartment accommodates 2 guests and features a shared heated pool, wrap-around porches, and is pet-friendly.

Prime location in the Key West Historic District, this luxury apartment is just 2,640 feet from Duval Street and 0.4 miles from the Curry Mansion.
This upscale 8-bedroom, 8-bathroom apartment accommodates 16 guests with a private swimming pool, patio, and on-site parking.

Prime waterfront on Garrison Bight Marina, this Key West condo offers direct boating access and is just 1 mile from Duval Street and the Historic Seaport.
This 1190 sq ft, 2-bedroom, 2-bath luxury apartment boasts a private balcony, a heated community pool, and welcomes one dog up to 25 lbs.

Just 4 minutes on foot from Smathers Beach, this luxury Key West holiday home offers ocean views and massage services.
Experience premium comfort with a private entrance, a fully equipped kitchen, and a swimming pool, all within 1.2 miles of Key West International Airport.

Just 1.1 miles from the Ernest Hemingway Home and Museum, this luxury waterfront penthouse in Key West offers exclusive sea views from its private pool deck.
Enjoy spacious accommodations for up to 16 guests, featuring a private pool, garden, and boat dock, all within easy reach of Duval Street and water sports.

Just 1312 feet from the historic Ernest Hemingway Home and Museum, this luxury apartment offers prime city center access in Key West.
Enjoy exclusive access to a spa, fitness center, and tennis court, with a balcony providing city views for up to 7 guests.

Just 656 feet from the Ernest Hemingway Home and Museum, this luxury Key West house offers a prime city center location with private on-site parking.
Enjoy a welcoming 900 sq ft retreat with a private hot tub and fully equipped kitchen, perfect for up to 11 guests.