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Southampton Holiday Rentals

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167 rentals in Southampton.
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Hampton Bays, south of 27A, holiday rental in Southampton

Hampton Bays, south of 27A

4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Southampton House Perfect for Families and Entertaining, holiday rental in Southampton

Southampton House Perfect for Families and Entertaining

5 bedrooms
5 bathrooms
Sleeps 12
Match: Sleeps
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Southampton Village Clean Renovated Sun Filled Charm,  Gunite Heated Salt Pool, holiday rental in Southampton

Southampton Village Clean Renovated Sun Filled Charm, Gunite Heated Salt Pool

4 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
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Hamptons Cousy, Spacious, Family Home by the beach, holiday rental in Southampton

Hamptons Cousy, Spacious, Family Home by the beach

4 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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Southampton House South of Highway Perfect for Families, holiday rental in Southampton

Southampton House South of Highway Perfect for Families

4 bedrooms
5 bathrooms
Sleeps 10
Match: Sleeps
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Huge Children’s Playground Set, swings and Fenced-in and Heated Pool!, holiday rental in Southampton

Huge Children’s Playground Set, swings and Fenced-in and Heated Pool!

4 bedrooms
3 bathrooms
Sleeps 9
Match: Sleeps
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Relax in Hampton Bays..., holiday rental in Southampton

Relax in Hampton Bays...

3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Waterfront hidden gem with dock, holiday rental in Southampton

Waterfront hidden gem with dock

3 bedrooms
4 bathrooms
Sleeps 6
Match: Sleeps
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3 bedroom Hamptons home near beach, vineyards, shopping, golf, holiday rental in Southampton

3 bedroom Hamptons home near beach, vineyards, shopping, golf

3 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
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Gorgeous, Private, Water View New Home! New Pool and Hot Tub- Bay 1 Street away!, holiday rental in Southampton

Gorgeous, Private, Water View New Home! New Pool and Hot Tub- Bay 1 Street away!

3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Beautiful Dream Home, holiday rental in Southampton

Beautiful Dream Home

5 bedrooms
5 bathrooms
Sleeps 10
Match: Sleeps
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Charming Water Mill Getaway, holiday rental in Southampton

Charming Water Mill Getaway

5 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Sleek Hampton Bays Getaway on a Half-Acre, Well-Stocked w/ Beach Gear,..., holiday rental in Southampton

Sleek Hampton Bays Getaway on a Half-Acre, Well-Stocked w/ Beach Gear,...

3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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New Construction Southampton 6 BR, 6.5 Bath, 5 Fireplace Masterpiece., holiday rental in Southampton

New Construction Southampton 6 BR, 6.5 Bath, 5 Fireplace Masterpiece.

6 bedrooms
7 bathrooms
Sleeps 12
Match: Sleeps
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Stunning Shinnecock View, holiday rental in Southampton

Stunning Shinnecock View

4 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Please come and enjoy our newly renovated home perfectly designed for families., holiday rental in Southampton

Please come and enjoy our newly renovated home perfectly designed for families.

5 bedrooms
2 bathrooms
Sleeps 14
Match: Sleeps
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Great Rates in 2019- No Increases In Rates and Over Holiday Weeks, holiday rental in Southampton

Great Rates in 2019- No Increases In Rates and Over Holiday Weeks

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Cool Hamptons Home minutes from Southampton Village. US Open '18 still available, holiday rental in Southampton

Cool Hamptons Home minutes from Southampton Village. US Open '18 still available

3 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
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Southampton Estate, Newly Renovated , Excellent For Families! Sleeps 12-14, holiday rental in Southampton

Southampton Estate, Newly Renovated , Excellent For Families! Sleeps 12-14

5 bedrooms
4 bathrooms
Sleeps 15
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Amazing Southampton 5 bedrm/3 bath/sleeps 13+, pool, poolhouse .5 mi private BCH, holiday rental in Southampton

Amazing Southampton 5 bedrm/3 bath/sleeps 13+, pool, poolhouse .5 mi private BCH

6 bedrooms
4 bathrooms
Sleeps 12
Match: Sleeps
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Mansion Near the Bay. 7 bedrooms! Chef’s kitchen., holiday rental in Southampton

Mansion Near the Bay. 7 bedrooms! Chef’s kitchen.

7 bedrooms
10 bathrooms
Sleeps 16
Match: Sleeps
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New Southampton Village ranch w/saltwater heated pool. Aug/fall availability, holiday rental in Southampton

New Southampton Village ranch w/saltwater heated pool. Aug/fall availability

4 bedrooms
3 bathrooms
Sleeps 12
Match: Sleeps
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Spacious Southampton Escape, Mins. from Town, Private Pool, Sunny and Open..., holiday rental in Southampton

Spacious Southampton Escape, Mins. from Town, Private Pool, Sunny and Open...

5 bedrooms
5 bathrooms
Sleeps 12
Match: Sleeps
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Private & Pristine in Southampton NY, holiday rental in Southampton

Private & Pristine in Southampton NY

3 bedrooms
4 bathrooms
Sleeps 6
Match: Sleeps
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Perfect Southampton Getaway - Pristine Home with Water Views, holiday rental in Southampton

Perfect Southampton Getaway - Pristine Home with Water Views

3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Majestic Southampton Waterfront Estate, holiday rental in Southampton

Majestic Southampton Waterfront Estate

7 bedrooms
5 bathrooms
Sleeps 18
Match: Sleeps
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Modern Southampton Cottage | Prime Location, holiday rental in Southampton

Modern Southampton Cottage | Prime Location

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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FANTASTIC HAMPTONS GETAWAY, holiday rental in Southampton

FANTASTIC HAMPTONS GETAWAY

4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Direct Bayfront in Hampton Bays, holiday rental in Southampton

Direct Bayfront in Hampton Bays

2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Hampton Private Retreat, holiday rental in Southampton

Hampton Private Retreat

5 bedrooms
6 bathrooms
Sleeps 10
Match: Sleeps
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Secluded Oasis with Pool, walk to beach, holiday rental in Southampton

Secluded Oasis with Pool, walk to beach

4 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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Very Private and Tranquil  House in wooded estate., holiday rental in Southampton

Very Private and Tranquil House in wooded estate.

4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Wooded Serenity, Big Heated Pool, 5BR, Beautiful Beach, holiday rental in Southampton

Wooded Serenity, Big Heated Pool, 5BR, Beautiful Beach

5 bedrooms
5 bathrooms
Sleeps 10
Match: Sleeps
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New Beach House! Heated saltwater pool, fun basement, < 5 min beach, walk to bay, holiday rental in Southampton

New Beach House! Heated saltwater pool, fun basement, < 5 min beach, walk to bay

4 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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Dreaming of summer fun or an off-season adventure? Enjoy both!, holiday rental in Southampton

Dreaming of summer fun or an off-season adventure? Enjoy both!

3 bedrooms
4 bathrooms
Sleeps 6
Match: Sleeps
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Southampton Water View, Modern Architecture House, holiday rental in Southampton

Southampton Water View, Modern Architecture House

5 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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5BR Southampton Home Pool Jacuz Coopers beach town Classic, holiday rental in Southampton

5BR Southampton Home Pool Jacuz Coopers beach town Classic

5 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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Sprawling Southampton home with pool & jacuzzi room for entire family, holiday rental in Southampton

Sprawling Southampton home with pool & jacuzzi room for entire family

4 bedrooms
4 bathrooms
Sleeps 14
Match: Sleeps
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The Perfect Southampton Summer Rental for Your Vacation, holiday rental in Southampton

The Perfect Southampton Summer Rental for Your Vacation

4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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OVERSIZED BEACH HOUSES ON FIELDS OF GREEN, holiday rental in Southampton

OVERSIZED BEACH HOUSES ON FIELDS OF GREEN

5 bedrooms
4 bathrooms
Sleeps 12
Match: Sleeps
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Hampton's Retreat - Just became available., holiday rental in Southampton

Hampton's Retreat - Just became available.

4 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps
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Quaint Seaside Retreat With Full Gym, holiday rental in Southampton

Quaint Seaside Retreat With Full Gym

4 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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Family Fun Compound with Full Gym and Huge Game-room!, holiday rental in Southampton

Family Fun Compound with Full Gym and Huge Game-room!

8 bedrooms
6 bathrooms
Sleeps 16
Match: Sleeps
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Spectacular Family Resort in Hampton Bays, NY, holiday rental in Southampton

Spectacular Family Resort in Hampton Bays, NY

7 bedrooms
5 bathrooms
Sleeps 18
Match: Sleeps
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Cottage by Shinnecock canal and 2 min to Meschutt beach!, holiday rental in Southampton

Cottage by Shinnecock canal and 2 min to Meschutt beach!

3 bedrooms
3 bathrooms
Sleeps 7
Match: Sleeps
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No weekly or biweekly  rentals. Southampton South of 27 near best beaches, holiday rental in Southampton

No weekly or biweekly rentals. Southampton South of 27 near best beaches

4 bedrooms
4 bathrooms
Sleeps 9
Match: Sleeps
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New Construction Wooded Oasis with Guesthouse in Southampton! 11 min to beach!, holiday rental in Southampton

New Construction Wooded Oasis with Guesthouse in Southampton! 11 min to beach!

5 bedrooms
6 bathrooms
Sleeps 10
Match: Sleeps
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Renovated Hamptons Heaven For Family Vacations By The Ocean - City Escape, holiday rental in Southampton

Renovated Hamptons Heaven For Family Vacations By The Ocean - City Escape

4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Enjoy More Summer at Stunning Beach Cottage! Shinnecock Hills, Southampton, NY, holiday rental in Southampton

Enjoy More Summer at Stunning Beach Cottage! Shinnecock Hills, Southampton, NY

2 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
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Monthly or Seasonal - Memorial thru Labor Day- Southampton Newly-renovated House, holiday rental in Southampton

Monthly or Seasonal - Memorial thru Labor Day- Southampton Newly-renovated House

5 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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