Vacation Rentals with Pool in Osprey's Dominion, NY: Compare 10+ Sites & Save

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  2. Vacation Rentals with Pool
  3.  USA

  4.  New York

  5.  Southold
  6.  Osprey's Dominion

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128 Best Vacation Rentals with Pool in Osprey's Dominion (Starting from $304)

Steve's Place: Heated Pool, 3BR Southold Home, Beach
Steve's Place: Heated Pool, 3BR Southold Home, Beach
House
Southold, NY, USA
2.3k from Osprey's Dominion 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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Newly Renovated, Stylish Peconic Retreat with Private Pool, Lush Grounds,...
Newly Renovated, Stylish Peconic Retreat with Private Pool, Lush Grounds,...
House
Peconic, NY, 11958, United States
1.0k from Osprey's Dominion center

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

4 Bedrooms8 Guests
10.0

Exceptional

3 reviews

$1506
Average price / night
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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
7.2k from Osprey's Dominion 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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A  cozy and family-friendly haven with heated pool, minutes from the beach
A cozy and family-friendly haven with heated pool, minutes from the beach
House
Southold, NY, 11971, United States
1.2k from Osprey's Dominion center

AC, Barbecue, Crib, Dryer, Heater, Internet, Kitchen, Laundry, Living Area

4 Bedrooms13 Guests
New to Booking
$1395
Average price / night
Check Availability
Respite Ranch: Private Pool, Hot Tub, Beach Access
Respite Ranch: Private Pool, Hot Tub, Beach Access
House
Mattituck, NY, USA
7.4k from Osprey's Dominion center

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

3 Bedrooms6 Guests
New to Booking
$679
Average price / night
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North Fork Family Villa- large family home with fenced in pool
North Fork Family Villa- large family home with fenced in pool
House
Peconic, NY, 11958, United States
1.3k from Osprey's Dominion center

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

5 Bedrooms10 Guests
8.0

Good

2 reviews

$1176
Average price / night
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The Cliffside Resort Condominiums
The Cliffside Resort Condominiums
Apartment
Greenport, NY, USA
8.0k from Osprey's Dominion 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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Historic House Getaway
Historic House Getaway
House
Peconic, NY, 11958, United States
1.4k from Osprey's Dominion center

AC, Dryer, Fireplace, Free Parking, Heater, Hot Tub, Internet, Kitchen, Laundry

6 Bedrooms9 Guests
9.6

Exceptional

139 reviews

$1076
Average price / night
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Cozy Greenport Cottage
Cozy Greenport Cottage
House
Greenport, NY, USA
9.4k from Osprey's Dominion 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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Heated pool on Goose Creek, private dock, massive yard walk to beach, wineries
Heated pool on Goose Creek, private dock, massive yard walk to beach, wineries
House
Southold, NY, 11971, United States
1.4k from Osprey's Dominion center

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

3 Bedrooms7 Guests
9.6

Exceptional

24 reviews

$718
Average price / night
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Villa Ebrar - Luxury with pool
Villa Ebrar - Luxury with pool
Villa
Sag Harbor, NY, USA
9.6k from Osprey's Dominion 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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4BR+ Newly renovated home mins to top beaches and vineyards, new heated pool!
4BR+ Newly renovated home mins to top beaches and vineyards, new heated pool!
House
Southold, NY, 11971, United States
1.4k from Osprey's Dominion center

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

4 Bedrooms10 Guests
10.0

Exceptional

4 reviews

$587
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
9.7k from Osprey's Dominion 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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Newly Constructed Modern Vacation Villa Minutes to some of the best...
Newly Constructed Modern Vacation Villa Minutes to some of the best...
House
Southold, NY, 11971, United States
2.1k from Osprey's Dominion center

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

4 Bedrooms8 Guests
10.0

Exceptional

2 reviews

$722
Average price / night
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Perfect Retreat for Families - Close to Amazing Wineries, Beaches, and Dining!
Perfect Retreat for Families - Close to Amazing Wineries, Beaches, and Dining!
House
Southold, NY, 11971, United States
2.1k from Osprey's Dominion center

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

4 Bedrooms9 Guests
9.8

Exceptional

6 reviews

$935
Average price / night
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NORTH FORK DREAM HOME, 4,000 Sq Ft, 1 Acre, Heated Pool!
NORTH FORK DREAM HOME, 4,000 Sq Ft, 1 Acre, Heated Pool!
House
Southold, NY, 11971, United States
2.1k from Osprey's Dominion center

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

4 Bedrooms12 Guests
9.8

Exceptional

7 reviews

$1828
Average price / night
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Modern & Spacious, Heated Pool, Kenneys Beach
Modern & Spacious, Heated Pool, Kenneys Beach
House
Southold, NY, 11971, United States
2.1k from Osprey's Dominion center

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

4 Bedrooms9 Guests
New to Booking
$642
Average price / night
Check Availability
HEATED POOL waterfront HOT TUB, GYM, Watersports, BOATER DELIGHT luxury modern
HEATED POOL waterfront HOT TUB, GYM, Watersports, BOATER DELIGHT luxury modern
House
Southold, NY, 11971, United States
2.1k from Osprey's Dominion center

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

6 Bedrooms14 Guests
10.0

Exceptional

12 reviews

$3783
Average price / night
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Cozy North Fork Home with Direct Water Access, Private Dock, Close to Wineries
Cozy North Fork Home with Direct Water Access, Private Dock, Close to Wineries
House
Southold, NY, 11971, United States
2.3k from Osprey's Dominion center

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

4 Bedrooms8 Guests
New to Booking
$1072
Average price / night
Check Availability
Steve’s Place | Heated Pool Southold Retreat
Steve’s Place | Heated Pool Southold Retreat
House
Southold, NY, 11971, United States
2.3k from Osprey's Dominion center

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

3 Bedrooms6 Guests
10.0

Exceptional

6 reviews

$643
Average price / night
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Mid-Century Southold Retreat: Heated Pool + Woods
Mid-Century Southold Retreat: Heated Pool + Woods
House
North Fork, NY, 11971, United States
2.4k from Osprey's Dominion center

AC, Barbecue, Dryer, Heater, Internet, Kitchen, Microwave, No Smoking, Pool

3 Bedrooms6 Guests
New to Booking
$734
Average price / night
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Spacious New 4 Bedroom Home With Pool on 2 Acre Property
Spacious New 4 Bedroom Home With Pool on 2 Acre Property
House
Cutchogue, NY, 11935, United States
2.5k from Osprey's Dominion center

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

4 Bedrooms10 Guests
10.0

Exceptional

24 reviews

$1134
Average price / night
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Luxury north fork estate
Luxury north fork estate
House
Southold, NY, 11971, United States
2.6k from Osprey's Dominion center

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

3 Bedrooms6 Guests
10.0

Exceptional

3 reviews

$2513
Average price / night
Check Availability
 New Modern Farmhouse Estate Living in the heart of Southold with a pool!!!
New Modern Farmhouse Estate Living in the heart of Southold with a pool!!!
House
Southold, NY, 11971, United States
2.7k from Osprey's Dominion center

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

8 Bedrooms12 Guests
10.0

Exceptional

10 reviews

$1480
Average price / night
Check Availability
Modern North Fork Retreat: Beachfront, Heated Pool
Modern North Fork Retreat: Beachfront, Heated Pool
House
Southold, NY, 11971, United States
2.9k from Osprey's Dominion center

AC, Balcony, Dryer, Extra Bed, Free Parking, Heater, Internet, Kitchen, Laundry

4 Bedrooms9 Guests
New to Booking
$1625
Average price / night
Check Availability
Panoramic Water Views, Plunge Pool, Hot Tub, Fire Pit & Walk to Beach
Panoramic Water Views, Plunge Pool, Hot Tub, Fire Pit & Walk to Beach
House
Southold, NY, 11971, United States
2.9k from Osprey's Dominion center

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

4 Bedrooms11 Guests
10.0

Exceptional

15 reviews

$2456
Average price / night
Check Availability
Spacious  and Renovated Summer Home with w/ Pool & Hot tub
Spacious and Renovated Summer Home with w/ Pool & Hot tub
House
Cutchogue, NY, 11935, United States
3.0k from Osprey's Dominion center

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

4 Bedrooms8 Guests
10.0

Exceptional

2 reviews

$856
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 Osprey's Dominion.

Where to stay in Osprey's Dominion? Best neighborhoods & areas

Osprey's Dominion Vacation Rentals with Pool on the Map

Frequently Asked Questions

You can explore 128 verified vacation rentals with a pool in Osprey's Dominion. 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 Osprey's Dominion 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 Osprey's Dominion 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 Osprey's Dominion welcome pets. Currently, 20 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 Osprey's Dominion 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 Osprey's Dominion 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.