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

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  2. Vacation Rentals with Pool
  3.  USA

  4.  New York

  5.  Shelter Island
  6.  Shorewood

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314 Best Vacation Rentals with Pool in Shorewood (Starting from $471)

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
3.4k from Shorewood center

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

1 Bedroom12 Guests
New to Booking
$1760
Average price / night
Check Availability
Work and Play Special!  Extended Stay Discount
Work and Play Special! Extended Stay Discount
House
Shelter Island, NY, 11964, United States
0.6k from Shorewood center

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

5 Bedrooms10 Guests
10.0

Exceptional

53 reviews

$1308
Average price / night
Check Availability
Coves Bay Beauty
Coves Bay Beauty
House
Sag Harbor, NY, USA
4.3k from Shorewood center

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

5 Bedrooms10 Guests
New to Booking
$3853
Average price / night
Check Availability
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
0.8k from Shorewood 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 Outdoor Pool!
Shelter Island Retreat with Outdoor Pool!
House
Shelter Island, NY, USA
5.1k from Shorewood 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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 Contemporary Home with heated pool and waterviews on Shelter Island
Contemporary Home with heated pool and waterviews on Shelter Island
House
Shelter Island, NY, 11964, United States
0.9k from Shorewood center

AC, Barbecue, Free Parking, Heater, Internet, Laundry, Microwave, No Smoking, Pool

4 Bedrooms8 Guests
10.0

Exceptional

12 reviews

$1640
Average price / night
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Heated Pool, Grill, Breakwater by RoveTravel
Heated Pool, Grill, Breakwater by RoveTravel
House
Shorewood, Shelter Island, New York, USA
6.4k from Shorewood 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
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
1.1k from Shorewood center

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

5 Bedrooms10 Guests
New to Booking
$972
Average price / night
Check Availability
Villa Ebrar - Luxury with pool
Villa Ebrar - Luxury with pool
Villa
Sag Harbor, NY, USA
6.7k from Shorewood 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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Scandinavian family home on the water
Scandinavian family home on the water
House
Shelter Island, NY, 11964, United States
1.2k from Shorewood center

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

3 Bedrooms6 Guests
New to Booking
$1051
Average price / night
Check Availability
Cozy Greenport Cottage
Cozy Greenport Cottage
House
Greenport, NY, USA
7.0k from Shorewood 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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Updated Greek Revival home minutes to beaches and amenities
Updated Greek Revival home minutes to beaches and amenities
House
Shelter Island, NY, 11964, United States
1.4k from Shorewood center

AC, Dryer, Internet, Laundry, No Smoking, Pool, Washer

5 Bedrooms7 Guests
New to Booking
$744
Average price / night
Check Availability
Villa KeyLime
Villa KeyLime
Villa
Sag Harbor, NY, USA
7.0k from Shorewood center

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

5 Bedrooms9 Guests
New to Booking
$1241
Average price / night
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Private Sag Harbor estate on expansive property with sprawling manicured lawns
Private Sag Harbor estate on expansive property with sprawling manicured lawns
House
Sag Harbor, NY, 11963, United States
1.8k from Shorewood center

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

6 Bedrooms14 Guests
New to Booking
$4341
Average price / night
Check Availability
Villa Kimaal - Luxury with pool
Villa Kimaal - Luxury with pool
Villa
Sag Harbor, NY, USA
7.0k from Shorewood center

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

5 Bedrooms8 Guests
New to Booking
$5693
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
1.9k from Shorewood 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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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
7.1k from Shorewood 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
 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
2.0k from Shorewood 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
Entertainment Galore, Meadowood Manor by RoveTravel
Entertainment Galore, Meadowood Manor by RoveTravel
House
Sag Harbor, USA
7.3k from Shorewood 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
Stunning Contemporary Sag Harbor Estate, Minutes to Sag Harbor Village,...
Stunning Contemporary Sag Harbor Estate, Minutes to Sag Harbor Village,...
House
Sag Harbor, NY, 11963, United States
2.1k from Shorewood center

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

4 Bedrooms8 Guests
10.0

Exceptional

1 reviews

$1121
Average price / night
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Lux Designer Home- 6 Ensuite Beds, Salt Pool, Media Room, 2 Week Min Rental Only
Lux Designer Home- 6 Ensuite Beds, Salt Pool, Media Room, 2 Week Min Rental Only
House
Sag Harbor, NY, 11963, United States
2.1k from Shorewood center

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

6 Bedrooms10 Guests
10.0

Exceptional

2 reviews

$4260
Average price / night
Check Availability
Endless Water Views, Full Spa with Gym and Sauna, Direct Water Access,...
Endless Water Views, Full Spa with Gym and Sauna, Direct Water Access,...
House
Sag Harbor, NY, 11963, United States
2.2k from Shorewood center

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

6 Bedrooms6 Guests
New to Booking
$3678
Average price / night
Check Availability
Bluffside Cove by Rove Travel - Villa with Pool & Sauna
Bluffside Cove by Rove Travel - Villa with Pool & Sauna
House
Sag Harbor, NY, 11963, United States
2.2k from Shorewood center

AC, Balcony, Barbecue, Dryer, Fireplace, Fitness Equipment, Heater, Hot Tub, Internet

6 Bedrooms12 Guests
New to Booking
$4033
Average price / night
Check Availability
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
2.2k from Shorewood center

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

4 Bedrooms8 Guests
New to Booking
$1176
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
2.2k from Shorewood 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
Majestic estate in coveted Private North Haven Community, 2 acres of lush...
Majestic estate in coveted Private North Haven Community, 2 acres of lush...
House
Sag Harbor, NY, 11963, United States
2.2k from Shorewood center

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

6 Bedrooms12 Guests
New to Booking
$7594
Average price / night
Check Availability
Sag Harbor Retreat - 4BR Home with Heated Pool + Game Room
Sag Harbor Retreat - 4BR Home with Heated Pool + Game Room
House
Sag Harbor, NY, 11963, United States
2.3k from Shorewood center

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

4 Bedrooms8 Guests
New to Booking
$1394
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 Shorewood.

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Shorewood Vacation Rentals with Pool on the Map

Frequently Asked Questions

You can explore 314 verified vacation rentals with a pool in Shorewood. 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 Shorewood vary depending on the season, property size, and whether the pool is private or shared. Rates typically start from around $471 per night, with private pool homes and peak travel periods often costing more.

Many rentals in Shorewood 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 Shorewood welcome pets. Currently, 30 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 Shorewood often include additional outdoor features such as Pool, Fireplace/Heating, and Laundry. These amenities enhance comfort and make it easier to enjoy outdoor living during your stay.

Some vacation rentals in Shorewood 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.