Enjoy an upgraded stay with total privacy in Shelter Island. Browse exclusive villas and vacation homes equipped with individual, private swimming facilities. Compare verified options on Owner Direct for a peaceful, secluded getaway.
Accommodations, Pools, Parking, Villas, Vacation homes, Cottages, Lodgings, Vacation rentals, Beach
AC, Barbecue, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry, Living Area
Exceptional
55 reviews
Luxury, Accommodations, Pools, Parking, Villas, Vacation homes, Cottages, Lodgings, Vacation rentals
AC, Balcony, Barbecue, Dryer, Fireplace, Free Parking, Heater, Internet, Kitchen
Exceptional
29 reviews
AC, Balcony, Barbecue, Dryer, Fireplace, Free Parking, Heater, Hot Tub, Internet
AC, Balcony, Barbecue, Dryer, Fireplace, Free Parking, Heater, Internet, Kitchen
Exceptional
35 reviews
AC, Barbecue, Dryer, Fireplace, Fitness Equipment, Free Parking, Heater, Internet, Kitchen
Exceptional
2 reviews
AC, Dryer, Free Parking, Heater, Kitchen, No Smoking, Patio, Pool, TV
AC, Balcony, Barbecue, Dryer, Fireplace, Free Parking, Heater, Internet, Laundry
Exceptional
40 reviews
AC, Balcony, Barbecue, Dryer, Fireplace, Free Parking, Heater, Internet, Kitchen
Exceptional
22 reviews
AC, Barbecue, Dryer, Fireplace, Free Parking, Heater, Internet, Kitchen, Laundry
AC, Balcony, Barbecue, Dryer, Fireplace, Fitness Equipment, Free Parking, Heater, Kitchen
Exceptional
1 reviews
AC, Barbecue, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry, Living Area
AC, Barbecue, Dryer, Fireplace, Free Parking, Heater, Internet, Kitchen, Laundry
Good
1 reviews
AC, Arcade, Balcony, Barbecue, Dryer, Fireplace, Free Parking, Heater, Hot Tub
Exceptional
5 reviews
AC, Arcade, Balcony, Barbecue, Dryer, Fireplace, Fitness Equipment, Free Parking, Heater
Exceptional
2 reviews
AC, Arcade, Barbecue, Dryer, Fireplace, Free Parking, Heater, Internet, Kitchen
Exceptional
30 reviews
AC, Arcade, Barbecue, Dryer, Fireplace, Free Parking, Heater, Kitchen, Laundry
AC, Arcade, Balcony, Dryer, Fireplace, Fitness Equipment, Free Parking, Heater, Internet
Exceptional
5 reviews
AC, Barbecue, Dryer, Fireplace, Free Parking, Heater, Internet, Kitchen, Laundry
Exceptional
9 reviews
AC, Arcade, Balcony, Barbecue, Dryer, Fireplace, Fitness Equipment, Free Parking, Heater
Exceptional
4 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 Shelter Island.
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 Shelter Island are:
There are a lot of options in Shelter Island. If you plan on staying in the Shelter Island 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 Shelter Island
You can explore 246 verified vacation rentals with a private pool in Shelter Island. These include standalone villas and private homes where the pool is reserved exclusively for your group.
Prices for rentals with a private pool in Shelter Island vary depending on the property size, location, and travel season. Rates typically start from around $493 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 Shelter Island also welcome pets. Currently, 27 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 Shelter Island often include additional features such as Fireplace/Heating, Private Pool, and Pool. These amenities enhance comfort and create a more relaxing, self-contained stay.
Some family-friendly vacation rentals in Shelter Island 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.