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Southampton Cottages

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850 rentals in Southampton.
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Southampton House Perfect for Families and Entertaining, vacation rental in Southampton
Southampton House Perfect for Families and Entertaining, vacation rental in Southampton
Southampton House Perfect for Families and Entertaining, vacation rental in Southampton

Southampton House Perfect for Families and Entertaining

Rental Home
5 bedrooms
5 bathrooms
Sleeps 10
Match: Sleeps
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Southamp Water-View, Pool,  Dogs Stay FREE!  Kayaks+Bikes+PingPong, vacation rental in Southampton
Southamp Water-View, Pool,  Dogs Stay FREE!  Kayaks+Bikes+PingPong, vacation rental in Southampton
Southamp Water-View, Pool,  Dogs Stay FREE!  Kayaks+Bikes+PingPong, vacation rental in Southampton

Southamp Water-View, Pool, Dogs Stay FREE! Kayaks+Bikes+PingPong

Rental Home
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Southampton Village Clean/Renovated Sun-filled Charming Home, Heated Salt Pool, vacation rental in Southampton
Southampton Village Clean/Renovated Sun-filled Charming Home, Heated Salt Pool, vacation rental in Southampton
Southampton Village Clean/Renovated Sun-filled Charming Home, Heated Salt Pool, vacation rental in Southampton

Southampton Village Clean/Renovated Sun-filled Charming Home, Heated Salt Pool

Rental Home
4 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
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Cosy  6 bedrooms, 5 baths, 45 ' Salt Water Pool, vacation rental in Southampton
Cosy  6 bedrooms, 5 baths, 45 ' Salt Water Pool, vacation rental in Southampton
Cosy  6 bedrooms, 5 baths, 45 ' Salt Water Pool, vacation rental in Southampton

Cosy 6 bedrooms, 5 baths, 45 ' Salt Water Pool

Rental Home
6 bedrooms
5 bathrooms
Sleeps 12
Match: Sleeps
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Hamptons Cousy, Spacious, Family Home by the beach, vacation rental in Southampton
Hamptons Cousy, Spacious, Family Home by the beach, vacation rental in Southampton
Hamptons Cousy, Spacious, Family Home by the beach, vacation rental in Southampton

Hamptons Cousy, Spacious, Family Home by the beach

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

Southampton House South of Highway Perfect for Families

Rental Home
5 bedrooms
5 bathrooms
Sleeps 10
Match: Sleeps
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Huge Children’s Playground, Swings,  Fenced-In and Heated Pool!, vacation rental in Southampton
Huge Children’s Playground, Swings,  Fenced-In and Heated Pool!, vacation rental in Southampton
Huge Children’s Playground, Swings,  Fenced-In and Heated Pool!, vacation rental in Southampton

Huge Children’s Playground, Swings, Fenced-In and Heated Pool!

Rental Home
3 bedrooms
3 bathrooms
Sleeps 7
Match: Sleeps
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SOUTHAMPTON LUXURY 6 BEDROOM GETAWAY !!!, vacation rental in Southampton
SOUTHAMPTON LUXURY 6 BEDROOM GETAWAY !!!, vacation rental in Southampton
SOUTHAMPTON LUXURY 6 BEDROOM GETAWAY !!!, vacation rental in Southampton

SOUTHAMPTON LUXURY 6 BEDROOM GETAWAY !!!

Rental Home
6 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Relax in Hampton Bays..., vacation rental in Southampton
Relax in Hampton Bays..., vacation rental in Southampton
Relax in Hampton Bays..., vacation rental in Southampton

Relax in Hampton Bays...

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

Waterfront hidden gem with dock

Rental Home
3 bedrooms
4 bathrooms
Sleeps 6
Match: Sleeps
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Charming Hampton Bays colonial on quiet cul de sac, vacation rental in Southampton
Charming Hampton Bays colonial on quiet cul de sac, vacation rental in Southampton
Charming Hampton Bays colonial on quiet cul de sac, vacation rental in Southampton

Charming Hampton Bays colonial on quiet cul de sac

Rental Home
4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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SPACIOUS, IMMACULATE 5 BEDROOM SOUTHAMPTON BEAUTY!!!, vacation rental in Southampton
SPACIOUS, IMMACULATE 5 BEDROOM SOUTHAMPTON BEAUTY!!!, vacation rental in Southampton
SPACIOUS, IMMACULATE 5 BEDROOM SOUTHAMPTON BEAUTY!!!, vacation rental in Southampton

SPACIOUS, IMMACULATE 5 BEDROOM SOUTHAMPTON BEAUTY!!!

Rental Home
5 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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3 bedroom Hamptons home near beach, vineyards, shopping, golf, vacation rental in Southampton
3 bedroom Hamptons home near beach, vineyards, shopping, golf, vacation rental in Southampton
3 bedroom Hamptons home near beach, vineyards, shopping, golf, vacation rental in Southampton

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

Rental Home
3 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
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Private Bayfront Living, Water Views, vacation rental in Southampton
Private Bayfront Living, Water Views, vacation rental in Southampton
Private Bayfront Living, Water Views, vacation rental in Southampton

Private Bayfront Living, Water Views

Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Fantastic Shinnecock View, vacation rental in Southampton
Fantastic Shinnecock View, vacation rental in Southampton
Fantastic Shinnecock View, vacation rental in Southampton

Fantastic Shinnecock View

Rental Home
4 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Hampton's, Bridgehampton South Grand Estate Home, Newly Decorated Close To Ocean, vacation rental in Southampton
Hampton's, Bridgehampton South Grand Estate Home, Newly Decorated Close To Ocean, vacation rental in Southampton
Hampton's, Bridgehampton South Grand Estate Home, Newly Decorated Close To Ocean, vacation rental in Southampton

Hampton's, Bridgehampton South Grand Estate Home, Newly Decorated Close To Ocean

Rental Home
6 bedrooms
6 bathrooms
Sleeps 15
Match: Sleeps
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Hamptons Waterfront- Great Location!, vacation rental in Southampton
Hamptons Waterfront- Great Location!, vacation rental in Southampton
Hamptons Waterfront- Great Location!, vacation rental in Southampton

Hamptons Waterfront- Great Location!

Rental Home
2 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
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Charming Southampton Village Rental walking distance to both shops and beach, vacation rental in Southampton
Charming Southampton Village Rental walking distance to both shops and beach, vacation rental in Southampton
Charming Southampton Village Rental walking distance to both shops and beach, vacation rental in Southampton

Charming Southampton Village Rental walking distance to both shops and beach

Rental Home
5 bedrooms
4 bathrooms
Sleeps 9
Match: Sleeps
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Mint 5-BR Gem in Southampton Village, Heated Gunite Pool, walk to beach and town, vacation rental in Southampton
Mint 5-BR Gem in Southampton Village, Heated Gunite Pool, walk to beach and town, vacation rental in Southampton
Mint 5-BR Gem in Southampton Village, Heated Gunite Pool, walk to beach and town, vacation rental in Southampton

Mint 5-BR Gem in Southampton Village, Heated Gunite Pool, walk to beach and town

Rental Home
5 bedrooms
5 bathrooms
Sleeps 10
Match: Sleeps
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Beautiful Dream Home, vacation rental in Southampton
Beautiful Dream Home, vacation rental in Southampton
Beautiful Dream Home, vacation rental in Southampton

Beautiful Dream Home

Rental Home
5 bedrooms
6 bathrooms
Sleeps 10
Match: Sleeps
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Southampton secluded Beauty on Big Fresh Pond, vacation rental in Southampton
Southampton secluded Beauty on Big Fresh Pond, vacation rental in Southampton
Southampton secluded Beauty on Big Fresh Pond, vacation rental in Southampton

Southampton secluded Beauty on Big Fresh Pond

Rental Home
4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Charming Water Mill Getaway, vacation rental in Southampton
Charming Water Mill Getaway, vacation rental in Southampton
Charming Water Mill Getaway, vacation rental in Southampton

Charming Water Mill Getaway

Rental Home
5 bedrooms
3 bathrooms
Sleeps 9
Match: Sleeps
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Gorgeous, Private, Water View New Home! New Pool and Hot Tub- Bay 1 Street away!, vacation rental in Southampton
Gorgeous, Private, Water View New Home! New Pool and Hot Tub- Bay 1 Street away!, vacation rental in Southampton
Gorgeous, Private, Water View New Home! New Pool and Hot Tub- Bay 1 Street away!, vacation rental in Southampton

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

Rental Home
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
More info
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Private & Pristine in Southampton NY, vacation rental in Southampton
Private & Pristine in Southampton NY, vacation rental in Southampton
Private & Pristine in Southampton NY, vacation rental in Southampton

Private & Pristine in Southampton NY

Rental Home
3 bedrooms
4 bathrooms
Sleeps 3
Match: Sleeps
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Southampton 6 BR, 6.5 Bath, 5 Fireplace Masterpiece., vacation rental in Southampton
Southampton 6 BR, 6.5 Bath, 5 Fireplace Masterpiece., vacation rental in Southampton
Southampton 6 BR, 6.5 Bath, 5 Fireplace Masterpiece., vacation rental in Southampton

Southampton 6 BR, 6.5 Bath, 5 Fireplace Masterpiece.

Rental Home
6 bedrooms
7 bathrooms
Sleeps 12
Match: Sleeps
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Cool Hamptons Home minutes from Southampton Village., vacation rental in Southampton
Cool Hamptons Home minutes from Southampton Village., vacation rental in Southampton
Cool Hamptons Home minutes from Southampton Village., vacation rental in Southampton

Cool Hamptons Home minutes from Southampton Village.

Rental Home
3 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
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SAFE AND SANITIZED BY MEDICAL PROFESSIONAL-RELAX, WORK IN SPACIOUS  HAVEN., vacation rental in Southampton
SAFE AND SANITIZED BY MEDICAL PROFESSIONAL-RELAX, WORK IN SPACIOUS  HAVEN., vacation rental in Southampton
SAFE AND SANITIZED BY MEDICAL PROFESSIONAL-RELAX, WORK IN SPACIOUS  HAVEN., vacation rental in Southampton

SAFE AND SANITIZED BY MEDICAL PROFESSIONAL-RELAX, WORK IN SPACIOUS HAVEN.

Rental Home
5 bedrooms
5 bathrooms
Sleeps 13
Match: Sleeps
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Mansion Near the Bay. 7 bedrooms! Chef’s kitchen., vacation rental in Southampton
Mansion Near the Bay. 7 bedrooms! Chef’s kitchen., vacation rental in Southampton
Mansion Near the Bay. 7 bedrooms! Chef’s kitchen., vacation rental in Southampton

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

Rental Home
7 bedrooms
10 bathrooms
Sleeps 7
Match: Sleeps
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Please come and enjoy our newly renovated home perfectly designed for families., vacation rental in Southampton
Please come and enjoy our newly renovated home perfectly designed for families., vacation rental in Southampton
Please come and enjoy our newly renovated home perfectly designed for families., vacation rental in Southampton

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

Rental Home
5 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
More info
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Architect Designed Home with Heated Pool near Bridgehampton Village, vacation rental in Southampton
Architect Designed Home with Heated Pool near Bridgehampton Village, vacation rental in Southampton
Architect Designed Home with Heated Pool near Bridgehampton Village, vacation rental in Southampton

Architect Designed Home with Heated Pool near Bridgehampton Village

Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
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Hamptons Waterfront- On A Sandy Beach- Relax & Getaway! (SH), vacation rental in Southampton
Hamptons Waterfront- On A Sandy Beach- Relax & Getaway! (SH), vacation rental in Southampton
Hamptons Waterfront- On A Sandy Beach- Relax & Getaway! (SH), vacation rental in Southampton

Hamptons Waterfront- On A Sandy Beach- Relax & Getaway! (SH)

Rental Home
1 bedroom
2 bathrooms
Sleeps 3
Match: Sleeps
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Spacious Master Bedroom Suite, Stone Chef's Eat-In Kitchen, Close to..., vacation rental in Southampton
Spacious Master Bedroom Suite, Stone Chef's Eat-In Kitchen, Close to..., vacation rental in Southampton
Spacious Master Bedroom Suite, Stone Chef's Eat-In Kitchen, Close to..., vacation rental in Southampton

Spacious Master Bedroom Suite, Stone Chef's Eat-In Kitchen, Close to...

Rental Home
5 bedrooms
5 bathrooms
Sleeps 12
Match: Sleeps
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Walk to Bay and Bike to Ocean - Perfect Location!, vacation rental in Southampton
Walk to Bay and Bike to Ocean - Perfect Location!, vacation rental in Southampton
Walk to Bay and Bike to Ocean - Perfect Location!, vacation rental in Southampton

Walk to Bay and Bike to Ocean - Perfect Location!

Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Southampton Village home/Heated pool, vacation rental in Southampton
Southampton Village home/Heated pool, vacation rental in Southampton
Southampton Village home/Heated pool, vacation rental in Southampton

Southampton Village home/Heated pool

Rental Home
4 bedrooms
3 bathrooms
Sleeps 12
Match: Sleeps
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Amazing Southampton 5 bedrm/3 bath/sleeps 12, pool, poolhouse ~.5 mi private BCH, vacation rental in Southampton
Amazing Southampton 5 bedrm/3 bath/sleeps 12, pool, poolhouse ~.5 mi private BCH, vacation rental in Southampton
Amazing Southampton 5 bedrm/3 bath/sleeps 12, pool, poolhouse ~.5 mi private BCH, vacation rental in Southampton

Amazing Southampton 5 bedrm/3 bath/sleeps 12, pool, poolhouse ~.5 mi private BCH

Rental Home
5 bedrooms
6 bathrooms
Sleeps 12
Match: Sleeps
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Southampton Estate, Newly Renovated , Excellent For Families! Sleeps 12-14, vacation rental in Southampton
Southampton Estate, Newly Renovated , Excellent For Families! Sleeps 12-14, vacation rental in Southampton
Southampton Estate, Newly Renovated , Excellent For Families! Sleeps 12-14, vacation rental in Southampton

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

Rental Home
5 bedrooms
4 bathrooms
Sleeps 15
Match: Sleeps
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Stunning House: Tennis & Pool in Southampton Estate section, vacation rental in Southampton
Stunning House: Tennis & Pool in Southampton Estate section, vacation rental in Southampton
Stunning House: Tennis & Pool in Southampton Estate section, vacation rental in Southampton

Stunning House: Tennis & Pool in Southampton Estate section

Rental Home
6 bedrooms
7 bathrooms
Sleeps 10
Match: Sleeps
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Modern Southampton Cottage | Prime Location with Heated Pool and Peloton, vacation rental in Southampton
Modern Southampton Cottage | Prime Location with Heated Pool and Peloton, vacation rental in Southampton
Modern Southampton Cottage | Prime Location with Heated Pool and Peloton, vacation rental in Southampton

Modern Southampton Cottage | Prime Location with Heated Pool and Peloton

Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Home w/ Heated Pool & Boat Dock - Expansive Water View Family Friendly Renovated, vacation rental in Southampton
Home w/ Heated Pool & Boat Dock - Expansive Water View Family Friendly Renovated, vacation rental in Southampton
Home w/ Heated Pool & Boat Dock - Expansive Water View Family Friendly Renovated, vacation rental in Southampton

Home w/ Heated Pool & Boat Dock - Expansive Water View Family Friendly Renovated

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

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

Rental Home
3 bedrooms
4 bathrooms
Sleeps 6
Match: Sleeps
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Manicured Grounds in Art Village, Expansive Eat-In Chef's Kitchen, Living..., vacation rental in Southampton
Manicured Grounds in Art Village, Expansive Eat-In Chef's Kitchen, Living..., vacation rental in Southampton
Manicured Grounds in Art Village, Expansive Eat-In Chef's Kitchen, Living..., vacation rental in Southampton

Manicured Grounds in Art Village, Expansive Eat-In Chef's Kitchen, Living...

Rental Home
5 bedrooms
6 bathrooms
Sleeps 12
Match: Sleeps
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Perfect Southampton Getaway - Pristine Home with Water Views, vacation rental in Southampton
Perfect Southampton Getaway - Pristine Home with Water Views, vacation rental in Southampton
Perfect Southampton Getaway - Pristine Home with Water Views, vacation rental in Southampton

Perfect Southampton Getaway - Pristine Home with Water Views

Rental Home
4 bedrooms
5 bathrooms
Sleeps 10
Match: Sleeps
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Stunning Private 4 acre Estate on Preserve near Village/Beach with Heated Pool., vacation rental in Southampton
Stunning Private 4 acre Estate on Preserve near Village/Beach with Heated Pool., vacation rental in Southampton
Stunning Private 4 acre Estate on Preserve near Village/Beach with Heated Pool., vacation rental in Southampton

Stunning Private 4 acre Estate on Preserve near Village/Beach with Heated Pool.

Rental Home
4 bedrooms
5 bathrooms
Sleeps 4
Match: Sleeps
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Stylish Southampton Village Charmer with Pool and Studio, vacation rental in Southampton
Stylish Southampton Village Charmer with Pool and Studio, vacation rental in Southampton
Stylish Southampton Village Charmer with Pool and Studio, vacation rental in Southampton

Stylish Southampton Village Charmer with Pool and Studio

Rental Home
3 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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Majestic Southampton Waterfront Estate, vacation rental in Southampton
Majestic Southampton Waterfront Estate, vacation rental in Southampton
Majestic Southampton Waterfront Estate, vacation rental in Southampton

Majestic Southampton Waterfront Estate

Rental Home
7 bedrooms
5 bathrooms
Sleeps 18
Match: Sleeps
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Hampton Private Retreat, vacation rental in Southampton
Hampton Private Retreat, vacation rental in Southampton
Hampton Private Retreat, vacation rental in Southampton

Hampton Private Retreat

Rental Home
5 bedrooms
6 bathrooms
Sleeps 5
Match: Sleeps
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Southampton Newly-renovated Home / Heated Pool!, vacation rental in Southampton
Southampton Newly-renovated Home / Heated Pool!, vacation rental in Southampton
Southampton Newly-renovated Home / Heated Pool!, vacation rental in Southampton

Southampton Newly-renovated Home / Heated Pool!

Rental Home
5 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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Perfect Southampton Getaway and Family Reunion, vacation rental in Southampton
Perfect Southampton Getaway and Family Reunion, vacation rental in Southampton
Perfect Southampton Getaway and Family Reunion, vacation rental in Southampton

Perfect Southampton Getaway and Family Reunion

Rental Home
6 bedrooms
7 bathrooms
Sleeps 12
Match: Sleeps
More info
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Luxury Hampton Bays Home - Walk to Shinnecock Bay, vacation rental in Southampton
Luxury Hampton Bays Home - Walk to Shinnecock Bay, vacation rental in Southampton
Luxury Hampton Bays Home - Walk to Shinnecock Bay, vacation rental in Southampton

Luxury Hampton Bays Home - Walk to Shinnecock Bay

Rental Home
3 bedrooms
4 bathrooms
Sleeps 9
Match: Sleeps
More info
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Southampton Luxury.  Walk to beach, kayaks on lake!  Hamptons House Rental, vacation rental in Southampton
Southampton Luxury.  Walk to beach, kayaks on lake!  Hamptons House Rental, vacation rental in Southampton
Southampton Luxury.  Walk to beach, kayaks on lake!  Hamptons House Rental, vacation rental in Southampton

Southampton Luxury. Walk to beach, kayaks on lake! Hamptons House Rental

Rental Home
6 bedrooms
4 bathrooms
Sleeps 13
Match: Sleeps
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