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

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  2. Vacation Rentals with Private Pool
  3.  USA

  4.  New York

  5.  Shelter Island Heights
  6.  Shelter Island Country Club

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111 Best Vacation Rentals with Private Pool in Shelter Island Country Club (Starting from $500)

Villa Ebrar - Luxury with pool
Villa Ebrar - Luxury with pool
Villa
Sag Harbor, NY, USA
9.4k from Shelter Island Country Club 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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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
0.2k from Shelter Island Country Club 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
0.3k from Shelter Island Country Club 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
0.3k from Shelter Island Country Club 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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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
0.5k from Shelter Island Country Club 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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 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
0.6k from Shelter Island Country Club 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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NEWLY RENOVATED WITH POOL, HOT TUB, AND FIREPLACE!
NEWLY RENOVATED WITH POOL, HOT TUB, AND FIREPLACE!
House
Shelter Island, NY, 11965, United States
0.6k from Shelter Island Country Club 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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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
0.6k from Shelter Island Country Club 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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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 Country Club 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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 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
1.2k from Shelter Island Country Club 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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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 Country Club 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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Shelter Island, NY Fully Renovated Farmhouse with Pool
Shelter Island, NY Fully Renovated Farmhouse with Pool
House
Shelter Island, NY, 11964, United States
1.9k from Shelter Island Country Club 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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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
1.9k from Shelter Island Country Club 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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Spacious North Fork Home in Greenport, Heated Pool, Perfect for Families
Spacious North Fork Home in Greenport, Heated Pool, Perfect for Families
House
Greenport, NY, 11944, United States
2.0k from Shelter Island Country Club center

AC, Barbecue, Dryer, Fireplace, Fitness Equipment, Free Parking, Heater, Hot Tub, Kitchen

4 Bedrooms8 Guests
10.0

Exceptional

4 reviews

$1559
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
2.1k from Shelter Island Country Club 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 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
2.1k from Shelter Island Country Club center

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

3 Bedrooms9 Guests
10.0

Exceptional

16 reviews

$859
Average price / night
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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
2.2k from Shelter Island Country Club center

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

3 Bedrooms8 Guests
10.0

Exceptional

17 reviews

$534
Average price / night
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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
2.2k from Shelter Island Country Club center

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

4 Bedrooms7 Guests
10.0

Exceptional

8 reviews

$1098
Average price / night
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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
2.3k from Shelter Island Country Club center

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

3 Bedrooms6 Guests
10.0

Exceptional

13 reviews

$855
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
2.4k from Shelter Island Country Club center

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

3 Bedrooms6 Guests
New to Booking
$997
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
2.5k from Shelter Island Country Club center

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

6 Bedrooms12 Guests
New to Booking
$1520
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
2.5k from Shelter Island Country Club center

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

4 Bedrooms10 Guests
10.0

Exceptional

22 reviews

$579
Average price / night
Check Availability
Shelter Island Waterfront Home!
Shelter Island Waterfront Home!
House
Shelter Island, NY, 11964, United States
2.6k from Shelter Island Country Club center

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

5 Bedrooms10 Guests
9.8

Exceptional

9 reviews

$860
Average price / night
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Greenport Getaway the perfect blend of relaxation, nature, and North Fork charm.
Greenport Getaway the perfect blend of relaxation, nature, and North Fork charm.
House
Greenport, NY, 11944, United States
2.7k from Shelter Island Country Club center

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

5 Bedrooms10 Guests
9.8

Exceptional

79 reviews

$939
Average price / night
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Waterfront Home Plus Separate Cottage/Dock
Waterfront Home Plus Separate Cottage/Dock
House
Shelter Island, NY, 11964, United States
2.9k from Shelter Island Country Club 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
New Construction Greenport Pool House - 3 Blocks from Town
New Construction Greenport Pool House - 3 Blocks from Town
Villa
Greenport, NY, 11944, United States
2.9k from Shelter Island Country Club center

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

4 Bedrooms16 Guests
10.0

Exceptional

3 reviews

$1053
Average price / night
Check Availability
Cozy Greenport Cottage | House in Greenport with a private pool & sauna
Cozy Greenport Cottage | House in Greenport with a private pool & sauna
House
Greenport, NY, 11944, United States
2.9k from Shelter Island Country Club center

AC, Barbecue, Dryer, Extra Bed, Fitness Equipment, Free Parking, Kitchen, Laundry, Microwave

3 Bedrooms10 Guests
9.0

Fabulous

2 reviews

$762
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 Country Club.

Where to stay in Shelter Island Country Club? Best neighborhoods & areas

Shelter Island Country Club Vacation Rentals with Private Pool on the Map

Frequently Asked Questions

You can explore 111 verified vacation rentals with a private pool in Shelter Island Country Club. 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 Country Club 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 Shelter Island Country Club 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 Shelter Island Country Club often include additional features such as Pool, Private Pool, and Laundry. These amenities enhance comfort and create a more relaxing, self-contained stay.

Some family-friendly vacation rentals in Shelter Island Country Club 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.