Vacation Rentals with Private Pool in Shelter Island Heights, NY: Compare 10+ Sites & Save

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  2. Vacation Rentals with Private Pool
  3.  USA

  4.  New York

  5.  Shelter Island Heights

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134 Best Vacation Rentals with Private Pool in Shelter Island Heights (Starting from $471)

Villa Ebrar - Luxury with pool
Villa Ebrar - Luxury with pool
Villa
Sag Harbor, NY, USA
9.3k from Shelter Island Heights center

Luxury, Accommodations, Pools, Parking, Villas, Vacation homes, Cottages, Lodgings, Vacation rentals

4 Bedrooms8 Guests
New to Booking
$500
Average price / night
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Chic Shelter Island Home, Pool and Gardens
Chic Shelter Island Home, Pool and Gardens
House
Shelter Island, NY, 11965, United States
0.7k from Shelter Island Heights center

AC, Barbecue, Dryer, Fireplace, Free Parking, Heater, Internet, Kitchen, Laundry

3 Bedrooms6 Guests
10.0

Exceptional

2 reviews

$1754
Average price / night
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Relax By The Pool, Or Walk To The Beach And Restaurants
Relax By The Pool, Or Walk To The Beach And Restaurants
House
Shelter Island Heights, NY, 11965, United States
0.8k from Shelter Island Heights center

AC, Barbecue, Dryer, Fireplace, Free Parking, Heater, Internet, Kitchen, Laundry

3 Bedrooms6 Guests
10.0

Exceptional

4 reviews

$710
Average price / night
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NEWLY RENOVATED WITH POOL, HOT TUB, AND FIREPLACE!
NEWLY RENOVATED WITH POOL, HOT TUB, AND FIREPLACE!
House
Shelter Island, NY, 11965, United States
0.9k from Shelter Island Heights center

AC, Barbecue, Dryer, Fireplace, Free Parking, Heater, Hot Tub, Internet, Kitchen

3 Bedrooms6 Guests
9.8

Exceptional

41 reviews

$504
Average price / night
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Chic Shelter Island A-Frame with Private Pool, Stylish Interiors, and...
Chic Shelter Island A-Frame with Private Pool, Stylish Interiors, and...
House
Shelter Island, NY, 11964, United States
1.0k from Shelter Island Heights center

AC, Dryer, Free Parking, Heater, Kitchen, No Smoking, Patio, Pool, TV

3 Bedrooms6 Guests
New to Booking
$997
Average price / night
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 Perfect Family Summer Vacation Home Close to beach 18x42 pool
Perfect Family Summer Vacation Home Close to beach 18x42 pool
House
Shelter Island, NY, 11964, United States
1.0k from Shelter Island Heights center

AC, Barbecue, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry, Microwave

3 Bedrooms6 Guests
9.6

Exceptional

54 reviews

$756
Average price / night
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Tranquility Base; Architect-Renovated, Modern Ranch With Heated Pool
Tranquility Base; Architect-Renovated, Modern Ranch With Heated Pool
House
Shelter Island, NY, 11964, United States
1.4k from Shelter Island Heights center

AC, Arcade, Barbecue, Dryer, Fireplace, Free Parking, Heater, Internet, Kitchen

4 Bedrooms8 Guests
10.0

Exceptional

30 reviews

$1035
Average price / night
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Farmhouse Nestled by Meadow, Pool, Near Beaches and Centrally Located!
Farmhouse Nestled by Meadow, Pool, Near Beaches and Centrally Located!
House
Shelter Island, NY, 11964, United States
1.5k from Shelter Island Heights center

AC, Balcony, Barbecue, Dryer, Fireplace, Free Parking, Heater, Internet, Laundry

4 Bedrooms8 Guests
10.0

Exceptional

39 reviews

$942
Average price / night
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Shelter Island, NY Fully Renovated Farmhouse with Pool
Shelter Island, NY Fully Renovated Farmhouse with Pool
House
Shelter Island, NY, 11964, United States
1.5k from Shelter Island Heights center

AC, Barbecue, Dryer, Fireplace, Free Parking, Heater, Internet, Kitchen, Laundry

3 Bedrooms8 Guests
8.0

Good

1 reviews

$875
Average price / night
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Newly renovated! Shelter Island Gem,  3 blocks from Sunset Beach
Newly renovated! Shelter Island Gem, 3 blocks from Sunset Beach
House
Shelter Island Heights, NY, 11968, United States
1.5k from Shelter Island Heights center

AC, Barbecue, Dryer, Fireplace, Free Parking, Heater, Internet, Kitchen, Laundry

3 Bedrooms6 Guests
9.8

Exceptional

17 reviews

$1079
Average price / night
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 Shelter Island Tranquil Modern Barn on Private Acre to Rest & Renew All Year
Shelter Island Tranquil Modern Barn on Private Acre to Rest & Renew All Year
House
Shelter Island Heights, NY, 11964, United States
1.5k from Shelter Island Heights center

AC, Barbecue, Dryer, Fireplace, Free Parking, Heater, Internet, Kitchen, Laundry

3 Bedrooms6 Guests
9.4

Superb

6 reviews

$931
Average price / night
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Spacious house next to the beach, Ferry and Eateries.
Spacious house next to the beach, Ferry and Eateries.
House
Shelter Island Heights, NY, 11965, United States
1.5k from Shelter Island Heights center

AC, Arcade, Balcony, Barbecue, Dryer, Fireplace, Free Parking, Heater, Internet

6 Bedrooms11 Guests
10.0

Exceptional

4 reviews

$2343
Average price / night
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Relax and Enjoy!
Relax and Enjoy!
House
Shelter Island, NY, 11965, United States
1.6k from Shelter Island Heights center

AC, Balcony, Barbecue, Dryer, Extra Bed, Fireplace, Fitness Equipment, Free Parking, Heater

4 Bedrooms10 Guests
10.0

Exceptional

16 reviews

$1958
Average price / night
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Shore House - A Luxury Beach Retreat
Shore House - A Luxury Beach Retreat
House
Shelter Island Heights, NY, 11965, United States
1.7k from Shelter Island Heights center

AC, Barbecue, Dryer, Fitness Equipment, Free Parking, Heater, Internet, Kitchen, Laundry

4 Bedrooms8 Guests
New to Booking
$3370
Average price / night
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Lovely home by the sea with dock and heated Gunite pool!
Lovely home by the sea with dock and heated Gunite pool!
House
Shelter Island, NY, 11964, United States
1.9k from Shelter Island Heights center

AC, Balcony, Barbecue, Dryer, Fireplace, Free Parking, Heater, Internet, Kitchen

4 Bedrooms10 Guests
10.0

Exceptional

22 reviews

$579
Average price / night
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This large Estate on Shelter Island w Heated Pool is the Perfect Summer Rental!
This large Estate on Shelter Island w Heated Pool is the Perfect Summer Rental!
House
Shelter Island, NY, 11964, United States
2.0k from Shelter Island Heights center

AC, Arcade, Balcony, Barbecue, Dryer, Fireplace, Fitness Equipment, Free Parking, Heater

7 Bedrooms16 Guests
10.0

Exceptional

4 reviews

$2868
Average price / night
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Private oasis with new baths and heated Gunite pool near Wades Beach
Private oasis with new baths and heated Gunite pool near Wades Beach
House
Shelter Island, NY, 11964, United States
2.1k from Shelter Island Heights center

AC, Balcony, Barbecue, Dryer, Fireplace, Free Parking, Heater, Internet, Kitchen

4 Bedrooms8 Guests
10.0

Exceptional

33 reviews

$961
Average price / night
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Beautiful Shelter Island Getaway on over an acre, minutes from the ferry!
Beautiful Shelter Island Getaway on over an acre, minutes from the ferry!
House
Shelter Island, NY, 11964, United States
2.5k from Shelter Island Heights center

AC, Barbecue, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry, Microwave

5 Bedrooms10 Guests
New to Booking
$972
Average price / night
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Cozy Shelter Island Cottage, walk to beaches and Mashomack Preserve
Cozy Shelter Island Cottage, walk to beaches and Mashomack Preserve
House
Shelter Island, NY, 11964, United States
2.6k from Shelter Island Heights center

AC, Balcony, Barbecue, Dryer, Fireplace, Free Parking, Heater, Internet, Kitchen

3 Bedrooms6 Guests
9.8

Exceptional

29 reviews

$471
Average price / night
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Shelter Island Retreat With Pool ...Close To Beach & Pet Friendly
Shelter Island Retreat With Pool ...Close To Beach & Pet Friendly
House
Shelter Island, NY, 11964, United States
2.6k from Shelter Island Heights center

AC, Arcade, Barbecue, Dryer, Fireplace, Fitness Equipment, Free Parking, Heater, Internet

3 Bedrooms9 Guests
10.0

Exceptional

16 reviews

$859
Average price / night
Check Availability
Explore the Hampton in this Shelter Island Getaway.  Weekly Bookings
Explore the Hampton in this Shelter Island Getaway. Weekly Bookings
House
Shelter Island, NY, 11964, United States
2.7k from Shelter Island Heights center

AC, Barbecue, Dryer, Fireplace, Fitness Equipment, Free Parking, Heater, Internet, Kitchen

3 Bedrooms6 Guests
10.0

Exceptional

13 reviews

$855
Average price / night
Check Availability
Charming updated home with pool on quiet street.  Near Silver Beach
Charming updated home with pool on quiet street. Near Silver Beach
House
Shelter Island, NY, 11964, United States
2.7k from Shelter Island Heights center

AC, Barbecue, Dryer, Fireplace, Free Parking, Heater, Internet, Kitchen, Laundry

3 Bedrooms8 Guests
10.0

Exceptional

17 reviews

$534
Average price / night
Check Availability
Congdon's Point Shelter Island
Congdon's Point Shelter Island
House
Shelter Island, NY, 11964, United States
2.7k from Shelter Island Heights center

AC, Balcony, Barbecue, Dryer, Fireplace, Free Parking, Heater, Hot Tub, Internet

5 Bedrooms11 Guests
New to Booking
$4077
Average price / night
Check Availability
Private heated pool and spacious yard. 5 minute walk to the beach.
Private heated pool and spacious yard. 5 minute walk to the beach.
House
Shelter Island, NY, 11964, United States
2.7k from Shelter Island Heights center

AC, Barbecue, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry, Microwave

4 Bedrooms7 Guests
10.0

Exceptional

8 reviews

$1098
Average price / night
Check Availability
Coastal 3-bedroom house with pool, bocce court on Shelter Island
Coastal 3-bedroom house with pool, bocce court on Shelter Island
House
Shelter Island Heights, NY, 11965, United States
2.8k from Shelter Island Heights center

AC, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry, No Smoking, Outdoor Space

3 Bedrooms6 Guests
New to Booking
$908
Average price / night
Check Availability
Sandpoint by Rove Travel | 6BR Family Home w/ Pool
Sandpoint by Rove Travel | 6BR Family Home w/ Pool
House
Shelter Island, NY, 11964, United States
2.9k from Shelter Island Heights center

AC, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry, Microwave, No Smoking

6 Bedrooms12 Guests
New to Booking
$1520
Average price / night
Check Availability
Waterfront Home Plus Separate Cottage/Dock
Waterfront Home Plus Separate Cottage/Dock
House
Shelter Island, NY, 11964, United States
2.9k from Shelter Island Heights center

AC, Barbecue, Dryer, Fireplace, Free Parking, Heater, Internet, Kitchen, Laundry

4 Bedrooms9 Guests
10.0

Exceptional

9 reviews

$1075
Average price / night
Check Availability

Pro Tip:
VacationByOwnerRentals 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 Heights.

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Shelter Island Heights Vacation Rentals with Private Pool on the Map

Frequently Asked Questions

You can explore 134 verified vacation rentals with a private pool in Shelter Island Heights. 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 Heights vary depending on the property size, location, and travel season. Rates typically start from around $471 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 Heights also welcome pets. Currently, 23 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 Heights 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 Shelter Island Heights 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.