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

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  2. Vacation Rentals with Pool
  3.  USA

  4.  New York

  5.  Shelter Island Heights
  6.  Shelter Island Tennis Club

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177 Best Vacation Rentals with Pool in Shelter Island Tennis Club (Starting from $304)

Sandpoint by Rove Travel Modern 5BR Family Home with Pool
Sandpoint by Rove Travel Modern 5BR Family Home with Pool
House
Shelter Island, NY, USA
1.7k from Shelter Island Tennis Club center

Accommodations, Pools, Parking, Villas, Vacation homes, Cottages, Lodgings, Places to stay

1 Bedroom12 Guests
New to Booking
$1760
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
1.2k from Shelter Island Tennis 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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Cozy Greenport Cottage
Cozy Greenport Cottage
House
Greenport, NY, USA
3.7k from Shelter Island Tennis Club center

Accommodations, Pools, Villas, Vacation homes, Cottages, Lodgings, Vacation rentals, Places to stay

3 Bedrooms10 Guests
New to Booking
$559
Average price / night
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Shelter Island Waterfront Home!
Shelter Island Waterfront Home!
House
Shelter Island, NY, 11964, United States
1.4k from Shelter Island Tennis 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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The Cliffside Resort Condominiums
The Cliffside Resort Condominiums
Apartment
Greenport, NY, USA
3.7k from Shelter Island Tennis Club center

Apartments, Cheap, Accommodations, Pools, Parking, 3-star, Lodgings, Vacation rentals, Beach

130 Bedrooms391 Guests
8.6

Fabulous

233 reviews

$405
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
1.4k from Shelter Island Tennis 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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Steve's Place: Heated Pool, 3BR Southold Home, Beach
Steve's Place: Heated Pool, 3BR Southold Home, Beach
House
Southold, NY, USA
5.0k from Shelter Island Tennis Club center

Accommodations, Pools, Parking, Villas, Vacation homes, Cottages, Pet-friendly, Lodgings, Places to stay

3 Bedrooms6 Guests
New to Booking
$304
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
1.4k from Shelter Island Tennis 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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Shelter Island Retreat with Outdoor Pool!
Shelter Island Retreat with Outdoor Pool!
House
Shelter Island, NY, USA
8.0k from Shelter Island Tennis Club center

Cheap, Accommodations, Pools, Parking, Villas, Vacation homes, Spa, Cottages, Lodgings

5 Bedrooms8 Guests
10.0

Exceptional

1 reviews

$1119
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
1.4k from Shelter Island Tennis 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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Coves Bay Beauty
Coves Bay Beauty
House
Sag Harbor, NY, USA
8.4k from Shelter Island Tennis Club center

Laundry, Wheelchair Accessible, Pool, Parking, Internet, Child Friendly

5 Bedrooms10 Guests
New to Booking
$3853
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 Tennis 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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Villa Ebrar - Luxury with pool
Villa Ebrar - Luxury with pool
Villa
Sag Harbor, NY, USA
8.6k from Shelter Island Tennis 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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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
1.5k from Shelter Island Tennis 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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Dumar Villa by Rove - 6BR Family Home with Pool & Outdoor Spaces
Dumar Villa by Rove - 6BR Family Home with Pool & Outdoor Spaces
House
Sag Harbor, NY, USA
8.9k from Shelter Island Tennis Club center

Accommodations, Pools, Parking, Villas, Vacation homes, Cottages, Pet-friendly, Lodgings, Places to stay

6 Bedrooms12 Guests
New to Booking
$1716
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
1.5k from Shelter Island Tennis 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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Entertainment Galore, Meadowood Manor by RoveTravel
Entertainment Galore, Meadowood Manor by RoveTravel
House
Sag Harbor, USA
9.3k from Shelter Island Tennis Club center

Accommodations, Pools, Parking, Villas, Vacation homes, Cottages, Pet-friendly, Lodgings, Vacation rentals

1 Bedroom12 Guests
New to Booking
$1778
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
1.6k from Shelter Island Tennis 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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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
1.7k from Shelter Island Tennis 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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 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
1.7k from Shelter Island Tennis 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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Relax and Enjoy!
Relax and Enjoy!
House
Shelter Island, NY, 11965, United States
1.7k from Shelter Island Tennis 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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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
1.7k from Shelter Island Tennis 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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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
1.8k from Shelter Island Tennis 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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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
1.8k from Shelter Island Tennis 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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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
2.0k from Shelter Island Tennis 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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Waterfront Victorian farmhouse with heated pool and deepwater dock
Waterfront Victorian farmhouse with heated pool and deepwater dock
House
Shelter Island, NY, 11964, United States
2.0k from Shelter Island Tennis Club center

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

6 Bedrooms16 Guests
New to Booking
$1723
Average price / night
Check Availability
NEWLY RENOVATED WITH POOL, HOT TUB, AND FIREPLACE!
NEWLY RENOVATED WITH POOL, HOT TUB, AND FIREPLACE!
House
Shelter Island, NY, 11965, United States
2.1k from Shelter Island Tennis 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
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 Pool in Shelter Island Tennis Club.

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

Shelter Island Tennis Club Vacation Rentals with Pool on the Map

Frequently Asked Questions

You can explore 177 verified vacation rentals with a pool in Shelter Island Tennis Club. These include a wide range of private homes, villas, and condos that offer on-site swimming facilities for a more relaxing stay.

Prices for vacation rentals with a pool in Shelter Island Tennis Club vary depending on the season, property size, and whether the pool is private or shared. Rates typically start from around $304 per night, with private pool homes and peak travel periods often costing more.

Many rentals in Shelter Island Tennis Club offer private pools for exclusive use, while others provide access to shared or community pools. You can use filters to specifically find properties with private pools if that is your preference.

Yes, some vacation rentals with pools in Shelter Island Tennis Club welcome pets. Currently, 24 listings allow pets, although policies may vary by property. It’s a good idea to review any rules related to pets around pool areas before booking.

Properties with pools are often in high demand, especially during warmer months and holidays, so booking 90 to 120 days in advance is recommended for the best selection. During off-peak seasons, you may still find availability closer to your travel dates.

Vacation rentals with pools in Shelter Island Tennis Club often include additional outdoor features such as Pool, Fireplace/Heating, and View. These amenities enhance comfort and make it easier to enjoy outdoor living during your stay.

Some vacation rentals in Shelter Island Tennis Club offer heated pools, which can be especially useful during cooler months. In certain cases, pool heating may be available for an additional fee, so it’s best to check the property details before booking.