Seeking an upscale villa rental in Key West? Browse our curated index of private luxury estates, complete with spacious floorplans and premium amenities. Easily compare verified listings for a truly refined holiday escape.
Accommodations, Pools, Parking, Villas, Vacation homes, Cottages, Lodgings, Vacation rentals, Jacuzzis
Exceptional
379 reviews
AC, Balcony, Barbecue, Dryer, Free Parking, Heater, Hot Tub, Internet, Kitchen
Exceptional
183 reviews
Accommodations, Pools, Parking, Villas, Vacation homes, Cottages, Pet-friendly, Lodgings, Vacation rentals
Very Good
299 reviews
Accommodations, Pools, Parking, Villas, Vacation homes, Cottages, Lodgings, Vacation rentals, Places to stay
AC, Balcony, Barbecue, Crib, Dryer, Free Parking, Heater, Internet, Kitchen
Exceptional
185 reviews
Accommodations, Pools, Parking, Villas, Vacation homes, Cottages, Lodgings, Vacation rentals, Places to stay
Good
2 reviews
AC, Balcony, Barbecue, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry
Exceptional
163 reviews
Accommodations, Pools, Parking, Villas, Vacation homes, Cottages, Pet-friendly, Lodgings, Vacation rentals
AC, Balcony, Barbecue, Dryer, Fitness Equipment, Free Parking, Heater, Internet, Kitchen
Exceptional
7 reviews
AC, Dryer, Free Parking, Hot Tub, Internet, Kitchen, Laundry, Microwave, No Smoking
Exceptional
45 reviews
AC, Dryer, Free Parking, Hot Tub, Internet, Kitchen, Laundry, Microwave, No Smoking
Exceptional
59 reviews
AC, Dryer, Free Parking, Hot Tub, Internet, Kitchen, Laundry, Microwave, No Smoking
Exceptional
24 reviews
AC, Breakfast Included, Dryer, Free Parking, Hot Tub, Internet, Kitchen, Laundry, Microwave
Exceptional
20 reviews
AC, Breakfast Included, Dryer, Free Parking, Hot Tub, Internet, Kitchen, Laundry, Living Area
Exceptional
10 reviews
AC, Breakfast Included, Dryer, Free Parking, Hot Tub, Internet, Laundry, Microwave, No Smoking
Exceptional
2 reviews
AC, Breakfast Included, Dryer, Free Parking, Hot Tub, Internet, Laundry, Microwave, No Smoking
Exceptional
1 reviews
AC, Dryer, Free Parking, Internet, Kitchen, Laundry, Living Area, Microwave, No Smoking
Exceptional
34 reviews
AC, Balcony, Dryer, Heater, Internet, Kitchen, Laundry, No Smoking, Outdoor Space
AC, Balcony, Barbecue, Dryer, Extra Bed, Free Parking, Hot Tub, Internet, Kitchen
Exceptional
3 reviews
AC, Balcony, Barbecue, Crib, Dryer, Elevator, Free Parking, Heater, Hot Tub
Exceptional
19 reviews
Pro Tip:
OwnerDirectVacationRental aggregates the best inventory from leading travel sites, including Booking.com, Agoda.com, Expedia.com, Vrbo.com, and Airbnb.com. Use our Advanced Filters to compare verified homes, villas, cabins, condos, cottages, vacation rentals, hotels, and eco-friendly stays. Our goal is to help you find the absolute best Villa Rentals in Key West.
OwnerDirectVacationRental can help you find hotels, resorts, and rentals near many of 's top attractions, neighborhoods, and points of interest.
What makes our villa rentals stand out?
Every villa rentals shown on Owner Direct comes from trusted travel sources and verified hosts, so you can browse with confidence.
Compare a range of properties and find fair, transparent pricing—no hidden fees.
From oceanfront condos and coastal cottages to luxury villas and family homes, there's a rental to fit every traveler and budget.
Some of the best villa rentals in Key West are:
There are a lot of options in Key West. If you plan on staying in the Key West area, consider making a reservation for a few nights at one of these properties as these have been rated the top Villa Rentals in Key West
You can currently explore 23 verified villa rentals in Key West. Our listings are sourced from multiple leading booking platforms, giving you a broad and up-to-date selection of luxury and private villas in one place.
Villa prices in Key West vary depending on the season, location, and amenities. Rates typically start from around $290 per night, with premium properties costing more during peak travel periods. Comparing options across different platforms can help you find the best value for your dates.
Many villas in Key West are designed for privacy and comfort, and a large number of them feature private pools. You can easily filter your search to find villas with pools, helping you choose the perfect stay for relaxation or group travel in Key West.
Yes, Key West offers a wide range of villas ideal for group stays. Many properties include 3 or more bedrooms, making them well-suited for family gatherings, events, or trips with friends. You can filter by bedroom count to quickly find options that match your group size.
For popular travel periods, it’s generally recommended to book your Key West villa around 60 to 90 days in advance to secure the best selection. However, since we compare 10+ sites, it’s still possible to find great last-minute options even 2 to 4 weeks before your trip.
Villas in Key West often include highly sought-after amenities such as Pool, Laundry, and Balcony/Terrace. These features enhance comfort and convenience, making them especially popular among travelers visiting Key West.
To discover top-rated villas in Key West, you can sort listings by guest ratings and reviews. Our platform aggregates feedback from multiple trusted sources, helping you identify highly rated properties based on real guest experiences. Use the 'Rating' filter above to start your search.