Enjoy an upgraded stay with total privacy in Osterville. 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, Resorts, Parking, 3-star, Lodgings, Jacuzzis, Places to stay, Family
Very Good
131 reviews
AC, Barbecue, Dryer, Fireplace, Free Parking, Heater, Internet, Kitchen, Laundry
Exceptional
14 reviews
Accommodations, Pools, Resorts, Parking, Spa, Pet-friendly, 3-star, Lodgings, Hot tubs
Very Good
127 reviews
AC, Barbecue, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry, Microwave
Exceptional
4 reviews
Pool, Air Conditioner, Child Friendly, Parking, Barbecue/Outdoor Cooking, Private Pool, Sports/Activities
Fabulous
66 reviews
AC, Arcade, Barbecue, Dryer, Fireplace, Free Parking, Heater, Internet, Kitchen
Exceptional
45 reviews
Apartments, Cheap, Accommodations, Pools, Parking, Serviced apartments, Lodgings, Vacation rentals, Places to stay
Good
87 reviews
AC, Barbecue, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry, Living Area
Cheap, Accommodations, Pools, Resorts, Parking, Golf, Ramada, 3-star, Lodgings
Very Good
114 reviews
AC, Barbecue, Dryer, Fireplace, Free Parking, Heater, Internet, Kitchen, Laundry
Exceptional
31 reviews
AC, Barbecue, Dryer, Fireplace, Free Parking, Heater, Internet, Kitchen, Laundry
Exceptional
11 reviews
AC, Arcade, Balcony, Barbecue, Dryer, Elevator, Free Parking, Hot Tub, Internet
AC, Barbecue, Crib, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry
Superb
9 reviews
AC, Arcade, Balcony, Barbecue, Dryer, Fireplace, Free Parking, Heater, Hot Tub
Exceptional
2 reviews
AC, Barbecue, Dryer, Free Parking, Hot Tub, Internet, Kitchen, Laundry, Living Area
Exceptional
1 reviews
AC, Barbecue, Dryer, Fireplace, Free Parking, Heater, Hot Tub, Internet, Kitchen
AC, Hot Tub, Internet, No Smoking, Pool, TV
Exceptional
3 reviews
AC, Arcade, Balcony, Barbecue, Dryer, Fireplace, Free Parking, Heater, Internet
Very Good
5 reviews
AC, Barbecue, Dryer, Free Parking, Heater, Hot Tub, Internet, Kitchen, Laundry
Superb
3 reviews
AC, Balcony, Barbecue, Dryer, Fireplace, Free Parking, Heater, Hot Tub, Internet
AC, Arcade, Balcony, Barbecue, Dryer, Fireplace, Fitness Equipment, Free Parking, Heater
Exceptional
35 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 Osterville.
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 Osterville are:
There are a lot of options in Osterville. If you plan on staying in the Osterville 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 Osterville
You can explore 72 verified vacation rentals with a private pool in Osterville. These include standalone villas and private homes where the pool is reserved exclusively for your group.
Prices for rentals with a private pool in Osterville vary depending on the property size, location, and travel season. Rates typically start from around $359 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 Osterville also welcome pets. Currently, 25 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 Osterville often include additional features such as Private Pool, Pool, and Laundry. These amenities enhance comfort and create a more relaxing, self-contained stay.
Some family-friendly vacation rentals in Osterville 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.