Looking for an exciting rental with a pool in Key West? Discover a curated collection of vacation homes featuring indoor or outdoor swimming pools. Owner Direct makes it simple to cross-reference verified properties for your pool-side relaxation.
Cheap, Accommodations, Parking, Villas, Vacation homes, Cottages, Pet-friendly, Lodgings, Places to stay
Exceptional
1 reviews
AC, Barbecue, Dryer, Free Parking, Heater, Hot Tub, Internet, Laundry, Living Area
Exceptional
3 reviews
Cheap, Accommodations, Parking, Villas, Vacation homes, Cottages, Pet-friendly, Lodgings, Places to stay
Exceptional
1 reviews
AC, Barbecue, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry, Living Area
Accommodations, Parking, Villas, Vacation homes, Cottages, Pet-friendly, Lodgings, Places to stay
AC, Breakfast Included, Housekeeping, Internet, Microwave, Outdoor Space, Pool, TV
Superb
539 reviews
Cheap, Accommodations, Parking, Villas, Vacation homes, Cottages, Lodgings, Places to stay, Family
Exceptional
3 reviews
AC, Barbecue, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry, Living Area
Exceptional
241 reviews
Accommodations, Parking, Villas, Vacation homes, Cottages, Pet-friendly, Lodgings, Places to stay
AC, Dryer, Extra Bed, Free Parking, Internet, Kitchen, Laundry, Living Area, Microwave
Superb
41 reviews
Accommodations, Pools, Parking, Villas, Vacation homes, Cottages, Pet-friendly, Lodgings, Places to stay
AC, Barbecue, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry, Living Area
Superb
59 reviews
Accommodations, Parking, Villas, Vacation homes, Cottages, Pet-friendly, Lodgings, Places to stay
AC, Balcony, Dryer, Extra Bed, Internet, Kitchen, Laundry, Living Area, Microwave
Fabulous
47 reviews
Apartments, Accommodations, Parking, Pet-friendly, Lodgings, Places to stay
AC, Barbecue, Dryer, Free Parking, Internet, Kitchen, Laundry, Living Area, Microwave
Good
4 reviews
AC, Balcony, Barbecue, Dryer, Extra Bed, Free Parking, Heater, Internet, Kitchen
Exceptional
11 reviews
AC, Balcony, Barbecue, Dryer, Free Parking, Heater, Hot Tub, Internet, Kitchen
Exceptional
183 reviews
AC, Balcony, Barbecue, Dryer, Extra Bed, Free Parking, Heater, Hot Tub, Internet
Exceptional
164 reviews
AC, Balcony, Barbecue, Dryer, Free Parking, Internet, Kitchen, Laundry, Living Area
Exceptional
195 reviews
AC, Breakfast Included, Internet, No Smoking, Outdoor Space, Pool, TV
Fabulous
808 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 Vacation Rentals with Pool 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 vacation rentals with pool stand out?
Every vacation rentals with pool 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 vacation rentals with pool 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 Vacation Rentals wint Pool in Key West
You can explore 1518 verified vacation rentals with a pool in Key West. These include a wide range of private homes, villas, and condos that offer on-site swimming facilities for a more relaxing stay.
Prices for vacation rentals with a pool in Key West vary depending on the season, property size, and whether the pool is private or shared. Rates typically start from around $170 per night, with private pool homes and peak travel periods often costing more.
Many rentals in Key West offer private pools for exclusive use, while others provide access to shared or community pools. You can use filters to specifically find properties with private pools if that is your preference.
Yes, some vacation rentals with pools in Key West welcome pets. Currently, 31 listings allow pets, although policies may vary by property. It’s a good idea to review any rules related to pets around pool areas before booking.
Properties with pools are often in high demand, especially during warmer months and holidays, so booking 90 to 120 days in advance is recommended for the best selection. During off-peak seasons, you may still find availability closer to your travel dates.
Vacation rentals with pools in Key West often include additional outdoor features such as Pool, Wellness Facilities, and Internet. These amenities enhance comfort and make it easier to enjoy outdoor living during your stay.
Some vacation rentals in Key West offer heated pools, which can be especially useful during cooler months. In certain cases, pool heating may be available for an additional fee, so it’s best to check the property details before booking.