Enjoy an upgraded stay with total privacy in Southold. Browse exclusive villas and vacation homes equipped with individual, private swimming facilities. Compare verified options on Owner Direct for a peaceful, secluded getaway.
Luxury, Accommodations, Pools, Parking, Villas, Vacation homes, Cottages, Lodgings, Vacation rentals
AC, Barbecue, Crib, Dryer, Fireplace, Free Parking, Heater, Hot Tub, Internet
Exceptional
6 reviews
AC, Barbecue, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry, Living Area
AC, Barbecue, Crib, Dryer, Fireplace, Free Parking, Heater, Kitchen, Microwave
AC, Dryer, Heater, Internet, Kitchen, Laundry, Living Area, No Smoking, Outdoor Space
AC, Arcade, Barbecue, Dryer, Fireplace, Free Parking, Heater, Internet, Kitchen
Exceptional
29 reviews
AC, Arcade, Balcony, Barbecue, Dryer, Fireplace, Fitness Equipment, Free Parking, Heater
Exceptional
18 reviews
AC, Barbecue, Dryer, Fireplace, Free Parking, Heater, Hot Tub, Internet, Kitchen
Exceptional
7 reviews
AC, Barbecue, Dryer, Fireplace, Free Parking, Heater, Internet, Kitchen, Laundry
AC, Barbecue, Dryer, Free Parking, Heater, Kitchen, Microwave, No Smoking, Patio
Exceptional
2 reviews
AC, Balcony, Barbecue, Dryer, Fireplace, Fitness Equipment, Free Parking, Heater, Hot Tub
Exceptional
12 reviews
AC, Barbecue, Dryer, Fitness Equipment, Heater, Internet, Kitchen, Laundry, Microwave
Exceptional
10 reviews
AC, Barbecue, Dryer, Extra Bed, Fireplace, Fitness Equipment, Free Parking, Heater, Internet
Exceptional
24 reviews
AC, Balcony, Barbecue, Crib, Dryer, Fireplace, Free Parking, Heater, Internet
Exceptional
11 reviews
AC, Balcony, Barbecue, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry
Exceptional
6 reviews
AC, Balcony, Barbecue, Dryer, Fireplace, Fitness Equipment, Free Parking, Heater, Internet
Fabulous
2 reviews
AC, Balcony, Barbecue, Dryer, Free Parking, Heater, Kitchen, Laundry, Microwave
AC, Barbecue, Dryer, Heater, Internet, Kitchen, Microwave, No Smoking, Pool
AC, Balcony, Barbecue, Dryer, Fireplace, Free Parking, Heater, Internet, Kitchen
Exceptional
11 reviews
AC, Barbecue, Dryer, Fireplace, Free Parking, Heater, Internet, Kitchen, Laundry
Exceptional
2 reviews
AC, Balcony, Barbecue, Dryer, Fireplace, Free Parking, Heater, Hot Tub, Internet
Exceptional
3 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 Private Pool in Southold.
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 private pool stand out?
Every vacation rentals with private 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 private pool in Southold are:
There are a lot of options in Southold. If you plan on staying in the Southold area, consider making a reservation for a few nights at one of these properties as these have been rated the top Vacation Rentals wint Private Pool in Southold
You can explore 109 verified vacation rentals with a private pool in Southold. These include standalone villas and private homes where the pool is reserved exclusively for your group.
Prices for rentals with a private pool in Southold vary depending on the property size, location, and travel season. Rates typically start from around $500 per night, with higher prices for larger homes, prime locations, or peak travel periods.
Yes, properties listed with private pools are intended for the exclusive use of guests staying at that home. You can review listing photos and descriptions to better understand the layout and level of privacy offered.
Yes, some vacation rentals with private pools in Southold also welcome pets. Currently, 24 listings allow pets, although policies may vary. It’s a good idea to review any rules related to pets and outdoor areas before booking.
Private pool properties are often in high demand, especially during holidays and warmer months, so booking 90 to 120 days in advance is recommended. During quieter periods, you may still find availability closer to your travel dates.
Vacation rentals with private pools in Southold often include additional features such as Pool, Private Pool, and Fireplace/Heating. These amenities enhance comfort and create a more relaxing, self-contained stay.
Some family-friendly vacation rentals in Southold include safety features such as pool fences, covers, or screened enclosures. It’s recommended to check the property details to confirm whether a specific rental meets your safety preferences.