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Cheap Southampton Holiday Rentals

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243 rentals in Southampton.
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Hampton Bays, south of 27A
4 bedrooms
3 bathrooms
Sleeps 8
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31 other travellers have booked this property
Southampton House Perfect for Families and Entertaining
5 bedrooms
5 bathrooms
Sleeps 12
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Southampton Village Clean Renovated Sun Filled Charm, Gunite Heated Salt Pool
4 bedrooms
4 bathrooms
Sleeps 10
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Waterfront hidden gem with dock
3 bedrooms
4 bathrooms
Sleeps 6
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Southampton House South of Highway Perfect for Families
4 bedrooms
5 bathrooms
Sleeps 10
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Relax in Hampton Bays...
3 bedrooms
3 bathrooms
Sleeps 6
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Huge Children’s Playground Set, swings and Fenced-in and Heated Pool!
4 bedrooms
3 bathrooms
Sleeps 9
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Hamptons Cousy, Spacious, Family Home by the beach
4 bedrooms
3 bathrooms
Sleeps 10
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Relax on Big Fresh Pond -Southampton
4 bedrooms
2 bathrooms
Sleeps 8
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Gorgeous, Private, Water View New Home! New Pool and Hot Tub- Bay 1 Street away!
3 bedrooms
3 bathrooms
Sleeps 8
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The cleanest rental in the Hamptons. Quiet street. 3 mi to Ocean. Heated Pool.
4 bedrooms
4 bathrooms
Sleeps 8
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Sleek Hampton Bays Getaway on a Half-Acre, Well-Stocked w/ Beach Gear,...
3 bedrooms
3 bathrooms
Sleeps 6
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3 bedroom Hamptons home near beach, vineyards, shopping, golf
3 bedrooms
2 bathrooms
Sleeps 6
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Great Rates in 2019- No Increases In Rates and Over Holiday Weeks
3 bedrooms
2 bathrooms
Sleeps 6
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Charming Water Mill Getaway
5 bedrooms
3 bathrooms
Sleeps 8
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14 day min Hot tub / wine / drinks / relax.
4 bedrooms
2 bathrooms
Sleeps 7
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Stunning Shinnecock View
4 bedrooms
2 bathrooms
Sleeps 6
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Majestic Southampton Waterfront Estate
7 bedrooms
5 bathrooms
Sleeps 18
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Spacious Southampton Escape, Mins. from Town, Private Pool, Sunny and Open...
5 bedrooms
5 bathrooms
Sleeps 12
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Southampton Estate, Newly Renovated , Excellent For Families! Sleeps 12-14
5 bedrooms
4 bathrooms
Sleeps 15
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Please come and enjoy our newly renovated home perfectly designed for families.
5 bedrooms
2 bathrooms
Sleeps 14
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Beautiful Dream Home
5 bedrooms
5 bathrooms
Sleeps 10
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Gorgeous Family Home in Heart of Art Village w/ Guest House on One Acre w/...
6 bedrooms
8 bathrooms
Sleeps 12
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Private & Pristine in Southampton NY
3 bedrooms
4 bathrooms
Sleeps 6
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New Construction Southampton 6 BR, 6.5 Bath, 5 Fireplace Masterpiece.
6 bedrooms
7 bathrooms
Sleeps 12
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Modern Southampton Cottage | Prime Location
3 bedrooms
2 bathrooms
Sleeps 6
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FANTASTIC HAMPTONS GETAWAY
4 bedrooms
3 bathrooms
Sleeps 8
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Cool Hamptons Home minutes from Southampton Village. US Open '18 still available
3 bedrooms
2 bathrooms
Sleeps 5
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Home w/ Heated Pool & Boat Dock - Expansive Water View Family Friendly Renovated
4 bedrooms
5 bathrooms
Sleeps 10
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New Southampton Village ranch w/saltwater heated pool. Aug/fall availability
4 bedrooms
3 bathrooms
Sleeps 12
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*NEW LISTING - Beachy Chic Hamptons House
4 bedrooms
4 bathrooms
Sleeps 8
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NEW LISTING! Sun-drenched 4 bdrm cottage in the Hamptons, minutes from beach
4 bedrooms
2 bathrooms
Sleeps 8
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Waterfront View, Great Location
3 bedrooms
3 bathrooms
Sleeps 6
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Direct Bayfront in Hampton Bays
2 bedrooms
1 bathroom
Sleeps 4
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Historic Elegance in Southampton For 20 Guests at a 200-Year-Old Former B&B...
9 bedrooms
8 bathrooms
Sleeps 20
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A Classic Hamptons Retreat in Water Mill w/ Private Pool, Laid-back Living...
4 bedrooms
2 bathrooms
Sleeps 8
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Spectacular Family Resort in Hampton Bays, NY
7 bedrooms
5 bathrooms
Sleeps 18
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Very Private and Tranquil House in wooded estate.
4 bedrooms
3 bathrooms
Sleeps 8
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1 other traveller has booked this property
Hampton Private Retreat
5 bedrooms
6 bathrooms
Sleeps 10
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Newly Renovated Haven for Multi-Generational Family Vacations Near Bay & Ocean
5 bedrooms
3 bathrooms
Sleeps 10
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Perfect Southampton Getaway - Pristine Home with Water Views
3 bedrooms
2 bathrooms
Sleeps 8
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MODERN Hampton Bays Retreat with WATER VIEW
4 bedrooms
3 bathrooms
Sleeps 8
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Amazing Southampton 5 bedrm/3 bath/sleeps 13+, pool, poolhouse .5 mi private BCH
6 bedrooms
4 bathrooms
Sleeps 12
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6BR Southampton Home Pool Jacuz Coopers beach town Classic
6 bedrooms
3 bathrooms
Sleeps 12
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OVERSIZED BEACH HOUSES ON FIELDS OF GREEN
5 bedrooms
4 bathrooms
Sleeps 12
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Family Fun Compound with Full Gym and Huge Game-room!
8 bedrooms
6 bathrooms
Sleeps 16
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The Perfect Southampton Summer Rental for Your Vacation
4 bedrooms
3 bathrooms
Sleeps 9
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Amenities Galore: Southampton Home at the Edge of a 200-Acre Preserve, Huge...
5 bedrooms
3 bathrooms
Sleeps 16
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Sprawling Southampton home with pool & jacuzzi room for entire family
4 bedrooms
4 bathrooms
Sleeps 14
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Cottage by Shinnecock canal and 2 min to Meschutt beach!
3 bedrooms
3 bathrooms
Sleeps 7
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