Looking for an exciting rental with a pool in Southold? 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.
Accommodations, Pools, Parking, Villas, Vacation homes, Cottages, Pet-friendly, Lodgings, Places to stay
AC, Barbecue, Crib, Dryer, Fireplace, Free Parking, Heater, Hot Tub, Internet
Exceptional
6 reviews
Accommodations, Pools, Parking, Villas, Vacation homes, Cottages, Lodgings, Places to stay
AC, Barbecue, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry, Living Area
Apartments, Cheap, Accommodations, Pools, Parking, 3-star, Lodgings, Vacation rentals, Beach
Fabulous
233 reviews
AC, Barbecue, Crib, Dryer, Fireplace, Free Parking, Heater, Kitchen, Microwave
Accommodations, Pools, Villas, Vacation homes, Cottages, Lodgings, Vacation rentals, Places to stay
AC, Dryer, Heater, Internet, Kitchen, Laundry, Living Area, No Smoking, Outdoor Space
Luxury, Accommodations, Pools, Parking, Villas, Vacation homes, Cottages, Lodgings, Vacation rentals
AC, Arcade, Barbecue, Dryer, Fireplace, Free Parking, Heater, Internet, Kitchen
Exceptional
29 reviews
Accommodations, Pools, Parking, Villas, Vacation homes, Cottages, Pet-friendly, Lodgings, Places to stay
AC, Arcade, Balcony, Barbecue, Dryer, Fireplace, Fitness Equipment, Free Parking, Heater
Exceptional
18 reviews
Accommodations, Pools, Parking, Villas, Vacation homes, Cottages, Pet-friendly, Lodgings, Vacation rentals
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, Crib, Dryer, Heater, Internet, Kitchen, Laundry, Living Area
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
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 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 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 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 Pool in Southold
You can explore 146 verified vacation rentals with a pool in Southold. 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 Southold vary depending on the season, property size, and whether the pool is private or shared. Rates typically start from around $304 per night, with private pool homes and peak travel periods often costing more.
Many rentals in Southold 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 Southold welcome pets. Currently, 23 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 Southold often include additional outdoor features such as Pool, Fireplace/Heating, and View. These amenities enhance comfort and make it easier to enjoy outdoor living during your stay.
Some vacation rentals in Southold 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.