Vacation Rentals with Private Pool in Gardiner's Bay 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.  Gardiner's Bay Country Club

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96 Best Vacation Rentals with Private Pool in Gardiner's Bay Country Club (Starting from $504)

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
0.5k from Gardiner's Bay Country Club center

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

3 Bedrooms6 Guests
New to Booking
$908
Average price / night
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Elegant Treetop Modern Steps from Hay Beach, Heated Gunite Pool
Elegant Treetop Modern Steps from Hay Beach, Heated Gunite Pool
House
Shelter Island, NY, 11965, United States
0.7k from Gardiner's Bay Country Club center

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

4 Bedrooms5 Guests
9.8

Exceptional

7 reviews

$1087
Average price / night
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Resort Style Home- Family Friendly
Resort Style Home- Family Friendly
House
Shelter Island, NY, 11964, United States
1.1k from Gardiner's Bay Country Club center

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

4 Bedrooms6 Guests
8.8

Fabulous

6 reviews

$1222
Average price / night
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Tennis Court, Open and Spacious Living and Dining Areas, Close Proximity to...
Tennis Court, Open and Spacious Living and Dining Areas, Close Proximity to...
House
Shelter Island, NY, 11964, United States
1.2k from Gardiner's Bay Country Club center

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

5 Bedrooms10 Guests
New to Booking
$1470
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
2.2k from Gardiner's Bay Country Club 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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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
2.5k from Gardiner's Bay Country Club 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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Chic Shelter Island Home, Pool and Gardens
Chic Shelter Island Home, Pool and Gardens
House
Shelter Island, NY, 11965, United States
2.6k from Gardiner's Bay 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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NEWLY RENOVATED WITH POOL, HOT TUB, AND FIREPLACE!
NEWLY RENOVATED WITH POOL, HOT TUB, AND FIREPLACE!
House
Shelter Island, NY, 11965, United States
2.7k from Gardiner's Bay 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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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
2.7k from Gardiner's Bay 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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House by the Bay with Large In-ground Pool, Steps from Beach
House by the Bay with Large In-ground Pool, Steps from Beach
House
East Marion, NY, 11939, United States
2.8k from Gardiner's Bay Country Club center

AC, Barbecue, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry, Living Area

3 Bedrooms6 Guests
10.0

Exceptional

27 reviews

$741
Average price / night
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Greenport Gem: Private Saltwater Pool, Awesome Basement, Walk to Everything!
Greenport Gem: Private Saltwater Pool, Awesome Basement, Walk to Everything!
House
Greenport, NY, 11944, United States
2.8k from Gardiner's Bay Country Club center

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

3 Bedrooms8 Guests
9.8

Exceptional

12 reviews

$1119
Average price / night
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Congdon's Point Shelter Island
Congdon's Point Shelter Island
House
Shelter Island, NY, 11964, United States
2.8k from Gardiner's Bay Country Club center

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

5 Bedrooms11 Guests
New to Booking
$4077
Average price / night
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Relax and Enjoy!
Relax and Enjoy!
House
Shelter Island, NY, 11965, United States
3.0k from Gardiner's Bay 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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 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
3.1k from Gardiner's Bay 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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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
3.1k from Gardiner's Bay 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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SUMMER RETREAT: Beach, Dock & Pool overlooking the Peconic Bay in Greenport!
SUMMER RETREAT: Beach, Dock & Pool overlooking the Peconic Bay in Greenport!
House
Greenport, NY, 11944, United States
3.1k from Gardiner's Bay Country Club center

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

5 Bedrooms10 Guests
10.0

Exceptional

4 reviews

$1222
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
3.3k from Gardiner's Bay 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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New Construction Greenport Pool House - 3 Blocks from Town
New Construction Greenport Pool House - 3 Blocks from Town
Villa
Greenport, NY, 11944, United States
3.3k from Gardiner's Bay 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
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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
3.5k from Gardiner's Bay 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
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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
3.6k from Gardiner's Bay 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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POOL + Beach 1 mi. to Greenport Village! Ask about Winter DEALS for 3+ nights...
POOL + Beach 1 mi. to Greenport Village! Ask about Winter DEALS for 3+ nights...
House
East Marion, NY, 11939, United States
3.6k from Gardiner's Bay Country Club center

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

5 Bedrooms13 Guests
10.0

Exceptional

55 reviews

$1099
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
3.7k from Gardiner's Bay 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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Chic Coastal Farmhouse with Private Pool, Steps from the Water Your...
Chic Coastal Farmhouse with Private Pool, Steps from the Water Your...
House
Shelter Island, NY, 11964, United States
3.8k from Gardiner's Bay Country Club center

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

3 Bedrooms6 Guests
New to Booking
$1851
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
3.8k from Gardiner's Bay 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, NY Fully Renovated Farmhouse with Pool
Shelter Island, NY Fully Renovated Farmhouse with Pool
House
Shelter Island, NY, 11964, United States
3.8k from Gardiner's Bay 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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 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
3.8k from Gardiner's Bay 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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Newly renovated ranch w/ large Pool in quiet neighborhood\n 1 mile from Greenport
Newly renovated ranch w/ large Pool in quiet neighborhood\n 1 mile from Greenport
House
East Marion, NY, 11939, United States
3.9k from Gardiner's Bay Country Club center

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

3 Bedrooms8 Guests
10.0

Exceptional

8 reviews

$1127
Average price / night
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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 Gardiner's Bay Country Club.

Where to stay in Gardiner's Bay Country Club? Best neighborhoods & areas

Gardiner's Bay Country Club Vacation Rentals with Private Pool on the Map

Frequently Asked Questions

You can explore 96 verified vacation rentals with a private pool in Gardiner's Bay 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 Gardiner's Bay Country Club vary depending on the property size, location, and travel season. Rates typically start from around $504 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 Gardiner's Bay Country Club also welcome pets. Currently, 26 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 Gardiner's Bay Country Club often include additional features such as Bedding/Linens, Laundry, and Balcony/Terrace. These amenities enhance comfort and create a more relaxing, self-contained stay.

Some family-friendly vacation rentals in Gardiner's Bay 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.