Vacation Rentals with Pool in Silver Beach, NY: Compare 10+ Sites & Save

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  2. Vacation Rentals with Pool
  3.  USA

  4.  New York

  5.  Shelter Island Heights
  6.  Silver Beach

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258 Best Vacation Rentals with Pool in Silver Beach (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
0.5k from Silver Beach center

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

1 Bedroom12 Guests
New to Booking
$1760
Average price / night
Check Availability
Cozy Shelter Island all season Rental
Cozy Shelter Island all season Rental
House
Shelter Island, NY, 11964, United States
0.3k from Silver Beach center

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

3 Bedrooms6 Guests
10.0

Exceptional

1 reviews

$685
Average price / night
Check Availability
Steve's Place: Heated Pool, 3BR Southold Home, Beach
Steve's Place: Heated Pool, 3BR Southold Home, Beach
House
Southold, NY, USA
5.3k from Silver Beach center

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

3 Bedrooms6 Guests
New to Booking
$304
Average price / night
Check Availability
Waterfront Home Plus Separate Cottage/Dock
Waterfront Home Plus Separate Cottage/Dock
House
Shelter Island, NY, 11964, United States
0.4k from Silver Beach 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
Cozy Greenport Cottage
Cozy Greenport Cottage
House
Greenport, NY, USA
5.6k from Silver Beach center

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

3 Bedrooms10 Guests
New to Booking
$559
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
0.5k from Silver Beach center

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

6 Bedrooms12 Guests
New to Booking
$1520
Average price / night
Check Availability
The Cliffside Resort Condominiums
The Cliffside Resort Condominiums
Apartment
Greenport, NY, USA
5.9k from Silver Beach 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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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
0.7k from Silver Beach 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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Coves Bay Beauty
Coves Bay Beauty
House
Sag Harbor, NY, USA
6.2k from Silver Beach center

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

5 Bedrooms10 Guests
New to Booking
$3853
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
0.7k from Silver Beach 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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Villa Ebrar - Luxury with pool
Villa Ebrar - Luxury with pool
Villa
Sag Harbor, NY, USA
6.6k from Silver Beach 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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unbelievable water views, 50' heated pool and private beach
unbelievable water views, 50' heated pool and private beach
House
Shelter Island, NY, 11964, United States
0.8k from Silver Beach center

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

3 Bedrooms6 Guests
New to Booking
$955
Average price / night
Check Availability
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
6.9k from Silver Beach center

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

6 Bedrooms12 Guests
New to Booking
$1716
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
0.8k from Silver Beach 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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Entertainment Galore, Meadowood Manor by RoveTravel
Entertainment Galore, Meadowood Manor by RoveTravel
House
Sag Harbor, USA
7.3k from Silver Beach center

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

1 Bedroom12 Guests
New to Booking
$1778
Average price / night
Check Availability
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
0.8k from Silver Beach 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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Shelter Island Retreat with Outdoor Pool!
Shelter Island Retreat with Outdoor Pool!
House
Shelter Island, NY, USA
7.4k from Silver Beach 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 Waterfront Home!
Shelter Island Waterfront Home!
House
Shelter Island, NY, 11964, United States
1.0k from Silver Beach 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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Heated Pool, Grill, Breakwater by RoveTravel
Heated Pool, Grill, Breakwater by RoveTravel
House
Silver Beach, Shelter Island Heights, New York, USA
8.6k from Silver Beach center

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

3 Bedrooms6 Guests
New to Booking
$3014
Average price / night
Check Availability
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
1.0k from Silver Beach 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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Year round family home on Shelter Island with indoor heated pool and dock.
Year round family home on Shelter Island with indoor heated pool and dock.
House
Shelter Island, NY, 11964, United States
1.1k from Silver Beach center

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

4 Bedrooms8 Guests
New to Booking
$1176
Average price / night
Check Availability
 Ideal for 2 families, private,  pool, close to beaches and marina  Sleeps 12
Ideal for 2 families, private, pool, close to beaches and marina Sleeps 12
House
Shelter Island, NY, 11964, United States
1.2k from Silver Beach center

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

6 Bedrooms12 Guests
10.0

Exceptional

1 reviews

$1042
Average price / night
Check Availability
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
1.5k from Silver Beach 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
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
1.5k from Silver Beach center

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

6 Bedrooms16 Guests
New to Booking
$1723
Average price / night
Check Availability
Shelter Island, NY Fully Renovated Farmhouse with Pool
Shelter Island, NY Fully Renovated Farmhouse with Pool
House
Shelter Island, NY, 11964, United States
1.6k from Silver Beach center

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

3 Bedrooms8 Guests
8.0

Good

1 reviews

$875
Average price / night
Check Availability
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
1.6k from Silver Beach center

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

4 Bedrooms8 Guests
10.0

Exceptional

30 reviews

$1035
Average price / night
Check Availability
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
1.7k from Silver Beach center

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

4 Bedrooms8 Guests
10.0

Exceptional

39 reviews

$942
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 Silver Beach.

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Silver Beach Vacation Rentals with Pool on the Map

Frequently Asked Questions

You can explore 258 verified vacation rentals with a pool in Silver Beach. 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 Silver Beach 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 Silver Beach 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 Silver Beach welcome pets. Currently, 28 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 Silver Beach 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 Silver Beach 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.