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Holiday Rentals in Southampton

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Bedrooms

Bathrooms

Amenities

Suitability

Property type

Distinctive Features

Distance from

5 km
833 rentals in Southampton.
Beachy Chic South of the Hwy in Southampton Village 3blks to town/Bike to, holiday rental in Southampton
Beachy Chic South of the Hwy in Southampton Village 3blks to town/Bike to, holiday rental in Southampton
Beachy Chic South of the Hwy in Southampton Village 3blks to town/Bike to, holiday rental in Southampton

Beachy Chic South of the Hwy in Southampton Village 3blks to town/Bike to

Holiday Rental House
3 bedrooms
4 bathrooms
Sleeps 6
Match: Sleeps
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Gorgeous private Hamptons house with pool and volleyball court, holiday rental in Southampton
Gorgeous private Hamptons house with pool and volleyball court, holiday rental in Southampton
Gorgeous private Hamptons house with pool and volleyball court, holiday rental in Southampton

Gorgeous private Hamptons house with pool and volleyball court

Holiday Rental House
5 bedrooms
4 bathrooms
Sleeps 15
Match: Sleeps
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Come to the Hamptons and Getaway!, holiday rental in Southampton
Come to the Hamptons and Getaway!, holiday rental in Southampton
Come to the Hamptons and Getaway!, holiday rental in Southampton

Come to the Hamptons and Getaway!

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
More info
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Cozy Hamptons get away, pool, minutes from beaches, shops, restaurants and more!, holiday rental in Southampton
Cozy Hamptons get away, pool, minutes from beaches, shops, restaurants and more!, holiday rental in Southampton
Cozy Hamptons get away, pool, minutes from beaches, shops, restaurants and more!, holiday rental in Southampton

Cozy Hamptons get away, pool, minutes from beaches, shops, restaurants and more!

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps
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Entire House in Southampton Village, Heated Pool, 2 Fireplaces, Walk Everywhere, holiday rental in Southampton
Entire House in Southampton Village, Heated Pool, 2 Fireplaces, Walk Everywhere, holiday rental in Southampton
Entire House in Southampton Village, Heated Pool, 2 Fireplaces, Walk Everywhere, holiday rental in Southampton

Entire House in Southampton Village, Heated Pool, 2 Fireplaces, Walk Everywhere

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
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Five ⭐️ Beach Bungalow, New Jacuzzi, Steps to Water, Tennis Southampton Shores!, holiday rental in Southampton
Five ⭐️ Beach Bungalow, New Jacuzzi, Steps to Water, Tennis Southampton Shores!, holiday rental in Southampton
Five ⭐️ Beach Bungalow, New Jacuzzi, Steps to Water, Tennis Southampton Shores!, holiday rental in Southampton

Five ⭐️ Beach Bungalow, New Jacuzzi, Steps to Water, Tennis Southampton Shores!

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
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Picturesque 5 Bedroom Hamptons Villa with pool 3 min from beach, holiday rental in Southampton
Picturesque 5 Bedroom Hamptons Villa with pool 3 min from beach, holiday rental in Southampton
Picturesque 5 Bedroom Hamptons Villa with pool 3 min from beach, holiday rental in Southampton

Picturesque 5 Bedroom Hamptons Villa with pool 3 min from beach

Holiday Rental House
5 bedrooms
5 bathrooms
Sleeps 10
Match: Sleeps
More info
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Beautiful Garden with pool & koi fish pond - 2 cottages fully renovated, holiday rental in Southampton
Beautiful Garden with pool & koi fish pond - 2 cottages fully renovated, holiday rental in Southampton
Beautiful Garden with pool & koi fish pond - 2 cottages fully renovated, holiday rental in Southampton

Beautiful Garden with pool & koi fish pond - 2 cottages fully renovated

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Luxury living meets Hamptons charm in this Award-Winning Carriage House, holiday rental in Southampton
Luxury living meets Hamptons charm in this Award-Winning Carriage House, holiday rental in Southampton
Luxury living meets Hamptons charm in this Award-Winning Carriage House, holiday rental in Southampton

Luxury living meets Hamptons charm in this Award-Winning Carriage House

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Walk to the Village! Charming modern farmhouse., holiday rental in Southampton
Walk to the Village! Charming modern farmhouse., holiday rental in Southampton
Walk to the Village! Charming modern farmhouse., holiday rental in Southampton

Walk to the Village! Charming modern farmhouse.

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Charming Southampton Village Home  4 Bedroom, 2 Bath 
5 minutes from the beach, holiday rental in Southampton
Charming Southampton Village Home  4 Bedroom, 2 Bath 
5 minutes from the beach, holiday rental in Southampton
Charming Southampton Village Home  4 Bedroom, 2 Bath 
5 minutes from the beach, holiday rental in Southampton

Charming Southampton Village Home 4 Bedroom, 2 Bath 5 minutes from the beach

Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Charming Hampton Bays Home 5 Mi to Cooper’s Beach, holiday rental in Southampton
Charming Hampton Bays Home 5 Mi to Cooper’s Beach, holiday rental in Southampton
Charming Hampton Bays Home 5 Mi to Cooper’s Beach, holiday rental in Southampton

Charming Hampton Bays Home 5 Mi to Cooper’s Beach

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
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Beautiful Vacation Home in Hampton Bays walking distance to Peconic Bay Beaches!, holiday rental in Southampton
Beautiful Vacation Home in Hampton Bays walking distance to Peconic Bay Beaches!, holiday rental in Southampton
Beautiful Vacation Home in Hampton Bays walking distance to Peconic Bay Beaches!, holiday rental in Southampton

Beautiful Vacation Home in Hampton Bays walking distance to Peconic Bay Beaches!

Holiday Rental House
6 bedrooms
4 bathrooms
Sleeps 14
Match: Sleeps
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Bayfront 5 bedrooms family home. Panoramic sea view from all rooms, holiday rental in Southampton
Bayfront 5 bedrooms family home. Panoramic sea view from all rooms, holiday rental in Southampton
Bayfront 5 bedrooms family home. Panoramic sea view from all rooms, holiday rental in Southampton

Bayfront 5 bedrooms family home. Panoramic sea view from all rooms

Holiday Rental House
5 bedrooms
5 bathrooms
Sleeps 10
Match: Sleeps
More info
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Cozy home in Hampton Bays near Ponquogue beach, holiday rental in Southampton
Cozy home in Hampton Bays near Ponquogue beach, holiday rental in Southampton
Cozy home in Hampton Bays near Ponquogue beach, holiday rental in Southampton

Cozy home in Hampton Bays near Ponquogue beach

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
More info
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Newly Listed - Updated Carriage House Apt - Centrally Located, holiday rental in Southampton
Newly Listed - Updated Carriage House Apt - Centrally Located, holiday rental in Southampton
Newly Listed - Updated Carriage House Apt - Centrally Located, holiday rental in Southampton

Newly Listed - Updated Carriage House Apt - Centrally Located

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
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1Bd, 1.5Ba Cottage with Waterviews in Hampton Bays, holiday rental in Southampton
1Bd, 1.5Ba Cottage with Waterviews in Hampton Bays, holiday rental in Southampton
1Bd, 1.5Ba Cottage with Waterviews in Hampton Bays, holiday rental in Southampton

1Bd, 1.5Ba Cottage with Waterviews in Hampton Bays

Holiday Rental House
1 bedroom
2 bathrooms
Sleeps 4
Match: Sleeps
More info
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Hamptons Waterfront- On A Sandy Beach- Relax & Getaway! (SH), holiday rental in Southampton
Hamptons Waterfront- On A Sandy Beach- Relax & Getaway! (SH), holiday rental in Southampton
Hamptons Waterfront- On A Sandy Beach- Relax & Getaway! (SH), holiday rental in Southampton

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

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
More info
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enjoy the beach/ wineries  and  hot tub, holiday rental in Southampton
enjoy the beach/ wineries  and  hot tub, holiday rental in Southampton
enjoy the beach/ wineries  and  hot tub, holiday rental in Southampton

enjoy the beach/ wineries and hot tub

Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
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Stunning Bayfront Views, holiday rental in Southampton
Stunning Bayfront Views, holiday rental in Southampton
Stunning Bayfront Views, holiday rental in Southampton

Stunning Bayfront Views

Holiday Rental House
6 bedrooms
5 bathrooms
Sleeps 12
Match: Sleeps
More info
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Luxury Southampton Village House, holiday rental in Southampton
Luxury Southampton Village House, holiday rental in Southampton
Luxury Southampton Village House, holiday rental in Southampton

Luxury Southampton Village House

Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
More info
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VILLAGE RARE WATER VIEWS SO. OF HWY NEW PHOTOS
Oct. 6-15 Intl. Film Festival, holiday rental in Southampton
VILLAGE RARE WATER VIEWS SO. OF HWY NEW PHOTOS
Oct. 6-15 Intl. Film Festival, holiday rental in Southampton
VILLAGE RARE WATER VIEWS SO. OF HWY NEW PHOTOS
Oct. 6-15 Intl. Film Festival, holiday rental in Southampton

VILLAGE RARE WATER VIEWS SO. OF HWY NEW PHOTOS Oct. 6-15 Intl. Film Festival

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
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Hampton's Retreat, holiday rental in Southampton
Hampton's Retreat, holiday rental in Southampton
Hampton's Retreat, holiday rental in Southampton

Hampton's Retreat

Holiday Rental House
5 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
More info
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HAMPTON HAVEN- Gorgeous home in Hampton Bays New York (sleeps 6), holiday rental in Southampton
HAMPTON HAVEN- Gorgeous home in Hampton Bays New York (sleeps 6), holiday rental in Southampton
HAMPTON HAVEN- Gorgeous home in Hampton Bays New York (sleeps 6), holiday rental in Southampton

HAMPTON HAVEN- Gorgeous home in Hampton Bays New York (sleeps 6)

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
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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, holiday rental in Southampton
Southampton Estate, Newly Renovated , Excellent For Families! Sleeps 12-14, holiday rental in Southampton

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

Holiday Rental House
5 bedrooms
4 bathrooms
Sleeps 15
Match: Sleeps
More info
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Modern Beach house-5 minutes from the beach!, holiday rental in Southampton
Modern Beach house-5 minutes from the beach!, holiday rental in Southampton
Modern Beach house-5 minutes from the beach!, holiday rental in Southampton

Modern Beach house-5 minutes from the beach!

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
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Brand new fully renovated backyard paradise! Come relax at our family resort., holiday rental in Southampton
Brand new fully renovated backyard paradise! Come relax at our family resort., holiday rental in Southampton
Brand new fully renovated backyard paradise! Come relax at our family resort., holiday rental in Southampton

Brand new fully renovated backyard paradise! Come relax at our family resort.

Holiday Rental House
5 bedrooms
2 bathrooms
Sleeps 14
Match: Sleeps
More info
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Spacious Hamptons Oasis 4BD/2.5BA with private pool & massive desk, holiday rental in Southampton
Spacious Hamptons Oasis 4BD/2.5BA with private pool & massive desk, holiday rental in Southampton
Spacious Hamptons Oasis 4BD/2.5BA with private pool & massive desk, holiday rental in Southampton

Spacious Hamptons Oasis 4BD/2.5BA with private pool & massive desk

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
More info
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Private Beach front Home, holiday rental in Southampton
Private Beach front Home, holiday rental in Southampton
Private Beach front Home, holiday rental in Southampton

Private Beach front Home

Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
More info
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Studio on Tianna Bay (Memorial Day - Labor Day), holiday rental in Southampton
Studio on Tianna Bay (Memorial Day - Labor Day), holiday rental in Southampton
Studio on Tianna Bay (Memorial Day - Labor Day), holiday rental in Southampton

Studio on Tianna Bay (Memorial Day - Labor Day)

Condo/Apartment
0 bedrooms
1 bathroom
Sleeps 2
Match: Sleeps
More info
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Southampton Home #5, holiday rental in Southampton
Southampton Home #5, holiday rental in Southampton
Southampton Home #5, holiday rental in Southampton

Southampton Home #5

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
More info
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Beautiful Beach Front 1 Bedroom Triplex, holiday rental in Southampton
Beautiful Beach Front 1 Bedroom Triplex, holiday rental in Southampton
Beautiful Beach Front 1 Bedroom Triplex, holiday rental in Southampton

Beautiful Beach Front 1 Bedroom Triplex

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
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Southampton Home #1, holiday rental in Southampton
Southampton Home #1, holiday rental in Southampton
Southampton Home #1, holiday rental in Southampton

Southampton Home #1

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
More info
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Southampton Home #2, holiday rental in Southampton
Southampton Home #2, holiday rental in Southampton
Southampton Home #2, holiday rental in Southampton

Southampton Home #2

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
More info
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Southampton Home #3, holiday rental in Southampton
Southampton Home #3, holiday rental in Southampton
Southampton Home #3, holiday rental in Southampton

Southampton Home #3

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
More info
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Hampton Chic3 Bedroom 2 Bathrooms with Pool, holiday rental in Southampton
Hampton Chic3 Bedroom 2 Bathrooms with Pool, holiday rental in Southampton
Hampton Chic3 Bedroom 2 Bathrooms with Pool, holiday rental in Southampton

Hampton Chic3 Bedroom 2 Bathrooms with Pool

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
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Tiny Southampton House on the Bay, holiday rental in Southampton
Tiny Southampton House on the Bay, holiday rental in Southampton
Tiny Southampton House on the Bay, holiday rental in Southampton

Tiny Southampton House on the Bay

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
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Million Dollar Sunsets Overlooking Bayfront Beach, holiday rental in Southampton
Million Dollar Sunsets Overlooking Bayfront Beach, holiday rental in Southampton
Million Dollar Sunsets Overlooking Bayfront Beach, holiday rental in Southampton

Million Dollar Sunsets Overlooking Bayfront Beach

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
More info
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Hamptons getaway - let’s go ! Close to ocean beach-family friendly-walk to bay, holiday rental in Southampton
Hamptons getaway - let’s go ! Close to ocean beach-family friendly-walk to bay, holiday rental in Southampton
Hamptons getaway - let’s go ! Close to ocean beach-family friendly-walk to bay, holiday rental in Southampton

Hamptons getaway - let’s go ! Close to ocean beach-family friendly-walk to bay

Holiday Rental House
5 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
More info
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New Duplex Apartment, holiday rental in Southampton
New Duplex Apartment, holiday rental in Southampton
New Duplex Apartment, holiday rental in Southampton

New Duplex Apartment

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
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Southampton Village Walk to All, holiday rental in Southampton
Southampton Village Walk to All, holiday rental in Southampton
Southampton Village Walk to All, holiday rental in Southampton

Southampton Village Walk to All

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
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Minutes to private bay beach, Ponquogue Beach, Rumba and Cowfish, restaurants., holiday rental in Southampton
Minutes to private bay beach, Ponquogue Beach, Rumba and Cowfish, restaurants., holiday rental in Southampton
Minutes to private bay beach, Ponquogue Beach, Rumba and Cowfish, restaurants., holiday rental in Southampton

Minutes to private bay beach, Ponquogue Beach, Rumba and Cowfish, restaurants.

Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
More info
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Large 1 bedroom apt on 9 acre estate property, holiday rental in Southampton
Large 1 bedroom apt on 9 acre estate property, holiday rental in Southampton
Large 1 bedroom apt on 9 acre estate property, holiday rental in Southampton

Large 1 bedroom apt on 9 acre estate property

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
More info
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Expansive Hamptons Mansion!, holiday rental in Southampton
Expansive Hamptons Mansion!, holiday rental in Southampton
Expansive Hamptons Mansion!, holiday rental in Southampton

Expansive Hamptons Mansion!

Condo/Apartment
0 bedrooms
0 bathrooms
Sleeps 16
Match: Sleeps
More info
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Hamptons 2 bedroom with heated pool, holiday rental in Southampton
Hamptons 2 bedroom with heated pool, holiday rental in Southampton
Hamptons 2 bedroom with heated pool, holiday rental in Southampton

Hamptons 2 bedroom with heated pool

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
More info
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Hidden Hideaway - Close to All, holiday rental in Southampton
Hidden Hideaway - Close to All, holiday rental in Southampton
Hidden Hideaway - Close to All, holiday rental in Southampton

Hidden Hideaway - Close to All

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
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Retro Mid-Century Cottage 1/2 mile to CPI, holiday rental in Southampton
Retro Mid-Century Cottage 1/2 mile to CPI, holiday rental in Southampton
Retro Mid-Century Cottage 1/2 mile to CPI, holiday rental in Southampton

Retro Mid-Century Cottage 1/2 mile to CPI

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
More info
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Pool House, holiday rental in Southampton
Pool House, holiday rental in Southampton
Pool House, holiday rental in Southampton

Pool House

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
More info
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Hampton Bay Home 2 Miles from Beach & Dune Road, holiday rental in Southampton
Hampton Bay Home 2 Miles from Beach & Dune Road, holiday rental in Southampton
Hampton Bay Home 2 Miles from Beach & Dune Road, holiday rental in Southampton

Hampton Bay Home 2 Miles from Beach & Dune Road

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
More info
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Payment Protection
Stunning Waterfront Beach House, holiday rental in Southampton
Stunning Waterfront Beach House, holiday rental in Southampton
Stunning Waterfront Beach House, holiday rental in Southampton

Stunning Waterfront Beach House

Condo/Apartment
0 bedrooms
1 bathroom
Sleeps 7
Match: Sleeps
More info
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Showing results 1-50 of 833
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