Discover Luxury Houses and Villas in Key West, FL

7 nights
2
1
  • onefinestay
  • plumguide
  • villanovo
  • booking
  • airbnb
  • marriott
  • hilton
  • hyatt
  • ihg
  • expedia
  • hotelscom
  • vrbo
Key West, FL villas

Luxury Key West, FL Vacation Houses and Villas

Contra House -Luxury Home With Pool - Key West, FL
9.6 30 reviews

Contra House -Luxury Home With Pool

house, Key West
Just a short walk from Duval Street and South Beach, this Key West luxury home offers unparalleled access to the Ernest Hemingway Home and Museum (1640 feet).
This spacious 2440 sq ft, 4-bedroom, 4-bathroom accommodation accommodates 12 guests with a private pool and free WiFi.
Poolside Cottage #412 - Key West, FL
9.8 372 reviews

Poolside Cottage #412

house, Key West
On the eastern end of Key West, this secluded waterfront oasis within Coconut Mallory Resort & Marina offers exclusive access to outdoor community pools and a hot tub, just 2.5 miles from Smathers Beach and 3.5 miles from Duval Street.
This luxury house boasts a 700 sq ft floor area, accommodates up to 6 guests, and features a fully equipped kitchen with a Keurig coffee maker, plus free parking for one motor vehicle.
The Contented Crane At Old Town - Key West, FL
9.9 362 reviews

The Contented Crane At Old Town

house, Key West
Ideally located in a Key West district, this luxury rental offers unparalleled access to the island's unique charm and attractions, with convenient off-street parking for scooters and bicycles.
Designed for group stays, this premium accommodation boasts a private pool, outdoor lounge, and spa for a comfortable and enjoyable Key West vacation experience.
Shared Pool & Near Duval - Curry House Room 9 - Key West, FL
9.0 99 reviews

Shared Pool & Near Duval - Curry House Room 9

house, Key West
Just 990 feet from Duval Street and 660 feet from the Historic Seaport, Curry House offers a luxury guesthouse experience in Key West.
Guests enjoy exclusive access to a heated swimming pool and premium amenities, including complimentary Wi-Fi and air conditioning.
Hideaway @ Speakeasy Inn Key West! - Key West, FL
No reviews

Hideaway @ Speakeasy Inn Key West!

house, Key West
House. You will be in Key West.
Facilities and services include a fridge, free parking and a kitchen. Take advantage of the air conditioning in this house!
161 M² House ∙ 3 Bedrooms ∙ 6 Guests - Key West, FL
No reviews

161 M² House ∙ 3 Bedrooms ∙ 6 Guests

house, Key West
Located in Midtown Key West, this luxury house offers easy access to beaches and local restaurants, with Old Town attractions a short drive or bike ride away.
This 1730 sq ft home accommodates up to 6 guests with 3 bedrooms, 2 bathrooms, and a private fenced tropical backyard featuring a swimming pool and outdoor dining.
Coconut Palm Studio At Travelers Palm Inn Key West - Key West, FL
No reviews

Coconut Palm Studio At Travelers Palm Inn Key West

house, Key West
Vacation house rental. You will stay in Key West.
Services and facilities: a kitchen, free parking and an iron. Take advantage of the gym in this house in Key West.
Puerta Coralina At Old Town - Key West, FL
9.8 312 reviews

Puerta Coralina At Old Town

house, Key West
In a district balancing tranquility with proximity to Key West's attractions, PUERTA CORALINA offers a peaceful retreat with its private front porch.
This luxury 2-bedroom cottage, accommodating up to 6 guests, boasts 1360 square feet and a welcoming atmosphere with a distinctive coral front door.

Luxury Villas with Private Pools in Key West, FL

Among the 1192 accommodations in Key West, FL, here are the 8 best villas and beach houses with a pool

Ocean Hideaway On The Atlantic - Key West, FL
No reviews

Ocean Hideaway On The Atlantic

house, Key West
Accommodation. You will be in Key West.
Facilities and services include a kitchen, a barbecue and air conditioning. Take advantage of the Free Parking with this accommodation in Key West!
Upper Bayview North - Key West, FL
No reviews

Upper Bayview North

house, Key West
House rental. You will be located in Key West.
Facilities and services include a kitchen, a washing machine and a dish washer. Enjoy a gym in this house in Key West!
Rose Key Cottage - Private Pool & Near Duval - Key West, FL
9.3 22 reviews

Rose Key Cottage - Private Pool & Near Duval

house, Key West
Just 600 feet from Duval Street, this historic Key West house offers a serene escape in a tranquil neighborhood.
Enjoy exclusive relaxation with a private pool and upscale amenities designed for families and groups seeking premium comfort.
Shared Pool & Parking - The Cottage At James House - Key West, FL
10 8 reviews

Shared Pool & Parking - The Cottage At James House

bungalow, Key West
Steps from Duval Street and the Historic Seaport, this downtown Key West bungalow offers a prime location for exploring Fury Water Adventures and Mallory Square.
This welcoming bungalow provides a luxury stay with a private parking spot, a communal pool, and a fully equipped kitchen for up to 3 guests.
Dream Maker On The Atlantic - Key West, FL
No reviews

Dream Maker On The Atlantic

house, Key West
House rental. You will stay in Key West.
Facilities and services include a swimming pool, free parking and an elevator. The big plus of this house in Key West is the jacuzzi!
Conch In The Treetops By Last Key Realty - Key West, FL
9.3 3 reviews

Conch In The Treetops By Last Key Realty

house, Key West
Just a 4-minute walk from Smathers Beach, this luxury Key West house offers an exclusive retreat near the Southernmost Point.
This premium accommodation boasts a heated pool, private hot tub, and spa, perfect for an upscale escape with a 1360 sq ft floor area and capacity for 11 guests.
Petes East Cottage - Key West, FL
9.3 3 reviews

Petes East Cottage

house, Key West
Just 3 minutes from South Beach, Petes East Cottage offers an exclusive Key West luxury escape near the Southernmost Point and Ernest Hemingway Home and Museum.
This premium 700 sq ft cottage accommodates up to 7 guests with a private heated pool, spa, and full kitchen.
Key West On My Mind - Key West, FL
9.4 158 reviews

Key West On My Mind

house, Key West
Just a 4-minute walk from Smathers Beach, this luxury Key West house offers an exclusive escape with sea views and premium on-site parking.
Experience ultimate relaxation with a swimming pool, hot tub, and sauna, all within 1.2 miles of Key West International Airport.

Luxury Villas with a Jacuzzi in Key West, FL

Sandpiper On The Ocean - Key West, FL
No reviews

Sandpiper On The Ocean

house, Key West
House rental listing. This accommodation is based in Key West.
Services and facilities include a barbecue, a swimming pool and a fridge. Enjoy free parking with this accommodation in Key West!
Seaside Retreat - Key West, FL
No reviews

Seaside Retreat

house, Key West
Just 1.2 miles from Key West International Airport, this luxury house offers an exclusive retreat near Ernest Hemingway Home and Museum, Duval Street, and Southernmost Point.
With 2360 sq ft, 4 bedrooms, and capacity for 15, enjoy a private pool, hot tub, and full kitchen for a premium Key West experience.
Hemingways Atlantic Retreat - Key West, FL
9.0 131 reviews

Hemingways Atlantic Retreat

house, Key West
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.
Darling Of Duval At Old Town - Key West, FL
9.7 202 reviews

Darling Of Duval At Old Town

cottage, Key West
Prime Old Town Key West, just 800 feet from Duval Street, offers 800 square feet of luxury accommodation with 2 bedrooms and 2 bathrooms.
This exclusive cottage provides 5-star in-home guest services, air conditioning, a jacuzzi, and a garden for an unforgettable stay.
The Guava Duff - Beautiful Kw Home With Space To Chill & Lots Of Free Parking!! - Key West, FL
9.8 10 reviews

The Guava Duff - Beautiful Kw Home With Space To Chill & Lots Of Free Parking!!

house, Stock Island
Located in Key West, the GUAVA DUFF is just 2297 feet from Sunset Watersports and a 19-minute walk to Safe Harbor.
This luxury four-bedroom, two-bathroom house offers a fully equipped kitchen, air conditioning, a jacuzzi, and complimentary bicycles for exploring the area.
New Grenada Suite - Parking Pool & Pets 209 - Key West, FL
No reviews

New Grenada Suite - Parking Pool & Pets 209

house, Key West
House rental listing. You will stay in Key West.
Services and facilities: free parking, a washing machine and a terrace. Enjoy a swimming pool in this house in Key West!
Bahama Gardens - Cigar House - Key West, FL
No reviews

Bahama Gardens - Cigar House

house, Key West
House. This accommodation is located in Key West.
Facilities and services: a swimming pool, a washing machine and a kitchen. Take advantage of the air conditioning in this house!
Casa Riviera Waterfront Hacienda With Pool And Boat Lift - Key West, FL
No reviews

Casa Riviera Waterfront Hacienda With Pool And Boat Lift

house, Key West
Waterfront, this luxury hacienda is situated in Key West, 2.6 miles from the Southernmost Point and 1.2 miles from Key West International Airport.
Enjoy exclusive comfort in this 2100 sq ft, 3-bedroom home with a private pool, boat elevator, and hot tub for up to 6 guests.

Nearby regions

Luxury Vacation Homes with a Balcony in Key West, FL

Pair luxury group living with breathtaking private vistas when you lock in a spectacular estate framing Key West, FL.

Atlantic Sunrise Penthouse - Key West, FL
10 1 review

Atlantic Sunrise Penthouse

house, Key West
A 4-minute walk from Smathers Beach, this luxury Key West house offers stunning sea views and is just over a mile from Key West International Airport.
This premium 2100 sq ft accommodation accommodates 15 guests with 3 bedrooms, 3 bathrooms, a private pool, jacuzzi, and on-site sauna.
Sky Loft In Key West - Key West, FL
9.5 237 reviews

Sky Loft In Key West

house, Key West
Just 984 feet from Duval Street and a 9-minute walk to the Ernest Hemingway Home and Museum, this luxury Key West house offers a private entrance and central city location.
This exclusive 680 sq ft accommodation welcomes up to 4 guests with a fully equipped kitchen, air conditioning, and access to a shared swimming pool and waterpark.
Petes Cottages - Key West, FL
No reviews

Petes Cottages

house, Key West
House to rent. You will stay in Key West.
Services and facilities: a kitchen, a dish washer and a fridge. Take advantage of the terrace in this house!
Keys Please! - Key West, FL
9.5 114 reviews

Keys Please!

house, Key West
Just a 4-minute walk to South Beach and a 7-minute stroll to the Ernest Hemingway Home and Museum, this luxury house offers an unparalleled Key West experience.
Enjoy 1230 square feet of upscale living with a private pool, complimentary WiFi, and a fully equipped kitchen, all within 2625 feet of Duval Street.
Crawl To Duval W/ Hot Tub - Key West, FL
8.6 6 reviews

Crawl To Duval W/ Hot Tub

house, Key West
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.
Toon Hall Tropical Village - Key West, FL
No reviews

Toon Hall Tropical Village

house, Key West
House listing. Your accommodation will be based in Key West.
Facilities and services: an iron, a barbecue and a fitness center.
Curacao - Large 2x2 Waterfront Condo Great View Pool & Dock - Key West, FL
9.1 13 reviews

Curacao - Large 2x2 Waterfront Condo Great View Pool & Dock

house, Key West
Offering stunning sea views from its waterfront location, this luxury house in Key West is just 1.1 miles from the Ernest Hemingway Home and Museum and Duval Street.
Enjoy 1210 square feet of living space with 2 bedrooms and 2 bathrooms, a private dock, and an outdoor swimming pool perfect for unwinding.
Sea Breeze -Great Location! - Key West, FL
No reviews

Sea Breeze -Great Location!

house, Key West
Vacation house. This accommodation is based in Key West.
Facilities and services: a dish washer, an iron and a washing machine. Enjoy free parking with this accommodation in Key West!
©2026 thechicstay.com