
Holiday rentals near Amagansett Square
We found 3,381 holiday rentals — enter your dates for availability
If you want to to stay within easy reach of Amagansett Square, scroll through and discover private holiday rentals to find the perfect home base for your trip. Whether you’re staying in a holiday home with family, friends or just your furry companion, you'll have the best amenities for spending time at your home away from home, such as Wi-Fi and cable TV. Whatever you're looking for, you'll be sure to find a property to rent to meet everyone's needs, including a place that's non-smoking or offers accessibility.
Holiday rentals with weekly discounts - Amagansett Square
Showing deals for:17 Oct - 24 Oct
Image gallery for Private Waterfront Home: Dock, Kayaks

9.29.2 out of 10 rating
Wonderful
(17 reviews)
Private Waterfront Home: Dock, Kayaks
Southold, New York
7% off
Price is NZ$7,015
NZ$7,015
NZ$1,002 per night
includes taxes & fees
Image gallery for Everything in Hamptons special discount available for weekly and monthly renters

1010 out of 10 rating
Exceptional
(7 reviews)
Everything in Hamptons special discount available for weekly and monthly renters
Water Mill, NY
8% off
Price is NZ$109,676
NZ$109,676
NZ$15,668 per night
includes taxes & fees
Image gallery for Beautiful home with spectacular views of the ocean.

1010 out of 10 rating
Exceptional
(8 reviews)
Beautiful home with spectacular views of the ocean.
Montauk, NY
8% off
Price is NZ$26,776
NZ$26,776
NZ$3,825 per night
includes taxes & fees
Image gallery for Beachfront Heated Pool Hot Tub Orient Village Modern Dream Home

9.49.4 out of 10 rating
Exceptional
(6 reviews)
Beachfront Heated Pool Hot Tub Orient Village Modern Dream Home
Orient, NY
8% off
Price is NZ$27,273
NZ$27,273
NZ$3,896 per night
includes taxes & fees
Image gallery for East Hampton NEW home with Pool: 5 minutes from town and beaches. Kid friendly

9.89.8 out of 10 rating
Exceptional
(8 reviews)
East Hampton NEW home with Pool: 5 minutes from town and beaches. Kid friendly
East Hampton, NY
8% off
Price is NZ$9,879
NZ$9,879
NZ$1,411 per night
includes taxes & fees
Image gallery for PRIVATE POOL ~ PERFECT HAMPTONS GETAWAY ~ WBH

1010 out of 10 rating
Exceptional
(12 reviews)
PRIVATE POOL ~ PERFECT HAMPTONS GETAWAY ~ WBH
East Hampton, NY
7% off
Price is NZ$15,533
NZ$15,533
NZ$2,219 per night
includes taxes & fees
Image gallery for HEATED POOL waterfront HOT TUB, GYM, Watersports, BOATER DELIGHT luxury modern

9.89.8 out of 10 rating
Exceptional
(9 reviews)
HEATED POOL waterfront HOT TUB, GYM, Watersports, BOATER DELIGHT luxury modern
Southold, NY
8% off
Price is NZ$40,088
NZ$40,088
NZ$5,727 per night
includes taxes & fees
Image gallery for Hamptons Compound w/ Golf, Tennis, Pool, Basketball, Bocce, and much more!

9.69.6 out of 10 rating
Exceptional
(20 reviews)
Hamptons Compound w/ Golf, Tennis, Pool, Basketball, Bocce, and much more!
East Hampton, NY
8% off
Price is NZ$54,658
NZ$54,658
NZ$7,808 per night
includes taxes & fees
Image gallery for New Fully Remodeled Post Modern Home, Perfect getaway for a family!

1010 out of 10 rating
Exceptional
(14 reviews)
New Fully Remodeled Post Modern Home, Perfect getaway for a family!
Water Mill, NY
7% off
Price is NZ$13,003
NZ$13,003
NZ$1,858 per night
includes taxes & fees
Image gallery for Book your vacation at our EH retreat on the water!

1010 out of 10 rating
Exceptional
(29 reviews)
Book your vacation at our EH retreat on the water!
East Hampton, NY
8% off
Price is NZ$24,347
NZ$24,347
NZ$3,478 per night
includes taxes & fees
Image gallery for Southampton Pickleball Walk to beach. Kayaks on lake Park-like grounds Pool

9.89.8 out of 10 rating
Exceptional
(25 reviews)
Southampton Pickleball Walk to beach. Kayaks on lake Park-like grounds Pool
Southampton, NY
12% off
Price is NZ$28,680
NZ$28,680
NZ$4,097 per night
includes taxes & fees
Image gallery for Traditional Immaculate Updated Home- Heated Pool, Gym, Yard- Close to EH and Sag

1010 out of 10 rating
Exceptional
(8 reviews)
Traditional Immaculate Updated Home- Heated Pool, Gym, Yard- Close to EH and Sag
East Hampton, NY
16% off
Price is NZ$24,687
NZ$24,687
NZ$3,527 per night
includes taxes & fees
Image gallery for Steps from Cedar Beach ! Tranquil Retreat in the Heart of Wine Country

9.89.8 out of 10 rating
Exceptional
(12 reviews)
Steps from Cedar Beach ! Tranquil Retreat in the Heart of Wine Country
Southold, NY
8% off
Price is NZ$7,598
NZ$7,598
NZ$1,085 per night
includes taxes & fees
Image gallery for Peconic Sound Beach Home: Backyard & Vineyards

9.69.6 out of 10 rating
Exceptional
(9 reviews)
Peconic Sound Beach Home: Backyard & Vineyards
Peconic, New York
7% off
Price is NZ$8,241
NZ$8,241
NZ$1,177 per night
includes taxes & fees
Image gallery for Just renovated, Amazing oasis, heated pool-spa, between Sag Harbor -Southampton

1010 out of 10 rating
Exceptional
(9 reviews)
Just renovated, Amazing oasis, heated pool-spa, between Sag Harbor -Southampton
Southampton, NY
7% off
Price is NZ$20,414
NZ$20,414
NZ$2,916 per night
includes taxes & fees
Image gallery for Newly Renovated Gem on the Cedar Beach Peninsula!

1010 out of 10 rating
Exceptional
(28 reviews)
Newly Renovated Gem on the Cedar Beach Peninsula!
Southold, NY
8% off
Price is NZ$12,803
NZ$12,803
NZ$1,829 per night
includes taxes & fees
Image gallery for Delightful Southampton Retreat with Heated Pool & Jacuzzi, Near Beach & Shopping

1010 out of 10 rating
Exceptional
(25 reviews)
Delightful Southampton Retreat with Heated Pool & Jacuzzi, Near Beach & Shopping
Southampton, NY
7% off
Price is NZ$13,991
NZ$13,991
NZ$1,999 per night
includes taxes & fees
Image gallery for Summer in the Hamptons

9.29.2 out of 10 rating
Wonderful
(12 reviews)
Summer in the Hamptons
East Hampton, NY
7% off
Price is NZ$9,343
NZ$9,343
NZ$1,335 per night
includes taxes & fees
Image gallery for Newly renovated Modern East Hampton Home / Pets welcome

9.89.8 out of 10 rating
Exceptional
(7 reviews)
Newly renovated Modern East Hampton Home / Pets welcome
East Hampton, NY
16% off
Price is NZ$14,364
NZ$14,364
NZ$2,052 per night
includes taxes & fees
Image gallery for Luxury Home with Private Tennis, Basketball, Pool & Jacuzzi

9.69.6 out of 10 rating
Exceptional
(9 reviews)
Luxury Home with Private Tennis, Basketball, Pool & Jacuzzi
Southampton, NY
7% off
Price is NZ$11,754
NZ$11,754
NZ$1,679 per night
includes taxes & fees
Image gallery for Newly renovated modern cottage, 5 minutes from town, beaches, and trailheads.

1010 out of 10 rating
Exceptional
(5 reviews)
Newly renovated modern cottage, 5 minutes from town, beaches, and trailheads.
Bridgehampton, NY
8% off
Price is NZ$6,870
NZ$6,870
NZ$981 per night
includes taxes & fees
Image gallery for Modern East Hampton Getaway

9.89.8 out of 10 rating
Exceptional
(10 reviews)
Modern East Hampton Getaway
East Hampton, NY
8% off
Price is NZ$16,503
NZ$16,503
NZ$2,358 per night
includes taxes & fees
Image gallery for Southampton Luxury Waterfront Villa Rental

9.29.2 out of 10 rating
Wonderful
(18 reviews)
Southampton Luxury Waterfront Villa Rental
Southampton, NY
31% off
Price is NZ$20,966
NZ$20,966
NZ$2,995 per night
includes taxes & fees
Image gallery for Huge private house, IG heated pool, fire pit, sleeps 10, 5 bath,Walk to Gurneys!

9.89.8 out of 10 rating
Exceptional
(22 reviews)
Huge private house, IG heated pool, fire pit, sleeps 10, 5 bath,Walk to Gurneys!
Montauk, NY
8% off
Price is NZ$15,796
NZ$15,796
NZ$2,257 per night
includes taxes & fees
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Find the best place to stay - Amagansett Square
Newly Renovated, 5BR Private Getaway with Pool
Sleeps 12 · 5 bedrooms · 3+ bathrooms
9.29.2 out of 10
Wonderfulwonderful
7 reviews(7 reviews)
- Peace of mindOur Book with Confidence guarantee gives you 24/7 support
- More quality timeFrom booking to staying, the whole process is simple and enjoyable
- All the privacy of homeEnjoy full kitchens, laundry, pools, gardens and more
- More for lessMore space, more privacy, more amenities — more value