Southampton Vacation Rentals

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Sep 24 - Sep 25
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Vacation Rentals in Southampton

Our top choices for Southampton vacation rentals

Delightful Southampton Retreat with Heated Pool & Jacuzzi, Near Beach & Shopping
Outdoor pool, a heated pool

Delightful Southampton Retreat with Heated Pool & Jacuzzi, Near Beach & Shopping

9.8 out of 10, Exceptional, (31)
"Our trip was amazing, the pool was in perfect condition and the house had everything we needed. Would definitely stay here again!!"
Delightful Southampton Retreat with Heated Pool & Jacuzzi, Near Beach & Shopping
Quintessential Hamptons home with 6 bedrooms (all ensuite bathrooms), open...
Terrace/patio

Quintessential Hamptons home with 6 bedrooms (all ensuite bathrooms), open...

9.8 out of 10, Exceptional, (16)
"Had an amazing stay here and would definitely recommend to others!! Only issue was the heat did not work in certain areas. House and backyard / pool area was spacious and beautiful. Perfect for large groups. Would definitely stay again."
Quintessential Hamptons home with 6 bedrooms (all ensuite bathrooms), open...
Luxurious Waterfront Retreat in Southampton: Breathtaking Views, Pool, and More!
Outdoor pool, a heated pool

Luxurious Waterfront Retreat in Southampton: Breathtaking Views, Pool, and More!

10.0 out of 10, Exceptional, (31)
"Great home. As advertised"
Luxurious Waterfront Retreat in Southampton: Breathtaking Views, Pool, and More!
Mansion Near the Bay. 7 bedrooms! Chef’s kitchen.
Terrace/patio

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

9.8 out of 10, Exceptional, (53)
"Our family (16) spent a week at the property and found the house and property in good order, comfortable and convenient to the bay and other attractions. I would definitely recommend it as a great family vacation."
Mansion Near the Bay. 7 bedrooms! Chef’s kitchen.
Cozy Southampton Home with Private Pool, Outdoor Dining, Perfect for Families
Outdoor dining

Cozy Southampton Home with Private Pool, Outdoor Dining, Perfect for Families

9.4 out of 10, Exceptional, (6)
"Loved it! "
Cozy Southampton Home with Private Pool, Outdoor Dining, Perfect for Families
Wooded Oasis and Guest House in Hamptons!
Pool

Wooded Oasis and Guest House in Hamptons!

10.0 out of 10, Exceptional, (25)
"Perfect setup for a guys golf trip. Clean and comfortable stay. Close to great golf. Easy communication with owners. Will stay here again."
Wooded Oasis and Guest House in Hamptons!
Southampton Pickleball Walk to beach. Kayaks on lake Park-like grounds Pool
Fridge, microwave, oven, stovetop

Southampton Pickleball Walk to beach. Kayaks on lake Park-like grounds Pool

9.6 out of 10, Exceptional, (26)
"Ken was great and easy to work with. The house was nice and perfect for our stay!"
Southampton Pickleball Walk to beach. Kayaks on lake Park-like grounds Pool
Entire House in Southampton Village, Pool, 2 Fireplaces, Walk Everywhere, Pets!
Pool

Entire House in Southampton Village, Pool, 2 Fireplaces, Walk Everywhere, Pets!

9.0 out of 10, Wonderful, (10)
"Enjoyed our time. House was clean, pool was a bonus for the family after a day at the beach. House was spacious and welcoming. Beds were very comfortable.Location was perfect! Would definitely come back!"
The price is ￥87,607
￥170,294 total
includes taxes & fees
Sep 28 - Sep 29
Entire House in Southampton Village, Pool, 2 Fireplaces, Walk Everywhere, Pets!
Beachy Chic South of the Hwy in SH Village just 3blks to shops, food and fun!!!🏖️
Outdoor dining

Beachy Chic South of the Hwy in SH Village just 3blks to shops, food and fun!!!🏖️

10.0 out of 10, Exceptional, (106)
"Very comfortable place. Host very easy and accommodating "
Beachy Chic South of the Hwy in SH Village just 3blks to shops, food and fun!!!🏖️
Stunning Private Sunny Modern Southampton home-5 beds Last minute discounts
Fridge, microwave, oven, stovetop

Stunning Private Sunny Modern Southampton home-5 beds Last minute discounts

9.8 out of 10, Exceptional, (19)
"House was perfectly appointed in Southampton! Close to all the spots--Southampton town, Bridgehampton shopping and quaint Sag Harbor"
Stunning Private Sunny Modern Southampton home-5 beds Last minute discounts
Charming Two-Story Retreat in Southampton Village walk to town, beach and train.
Terrace/patio

Charming Two-Story Retreat in Southampton Village walk to town, beach and train.

10.0 out of 10, Exceptional, (15)
"Great property for two people right next to the downtown. Our stay was comfortable and clean!"
Charming Two-Story Retreat in Southampton Village walk to town, beach and train.
Southampton Home with Heated Pool,6 minutes from beach’s
Terrace/patio

Southampton Home with Heated Pool,6 minutes from beach’s

8.0 out of 10, Very Good, (5)
"Good location close to everything "
Southampton Home with Heated Pool,6 minutes from beach’s
Southampton Village Luxury with Pool House Spa - Guest Cottage. Walk to Town!
Fridge, microwave, oven, stovetop

Southampton Village Luxury with Pool House Spa - Guest Cottage. Walk to Town!

10.0 out of 10, Exceptional, (18)
"For the 2nd consecutive summer Michael and Julie were the perfect hosts. Our family loved the pool, the pool house, the yard and the beautiful home. We can’t wait to return again soon. "
Southampton Village Luxury with Pool House Spa - Guest Cottage. Walk to Town!
Hamptons Modern Retreat NEW CONS
Pool

Hamptons Modern Retreat NEW CONS

10.0 out of 10, Exceptional, (12)
"Property was was everything and more than described!"
Hamptons Modern Retreat NEW CONS
Southampton - Walk to water/10 min drive to area beaches and Southampton Village
Beach nearby, beach towels

Southampton - Walk to water/10 min drive to area beaches and Southampton Village

10.0 out of 10, Exceptional, (2)
"Had a great stay for a long weekend in the Hamptons. House was cozy and comfortable and in a good location."
Southampton - Walk to water/10 min drive to area beaches and Southampton Village
New Construction Modern Luxury Retreat w 6 Beds
Exterior

New Construction Modern Luxury Retreat w 6 Beds

10.0 out of 10, Exceptional, (7)
"Had the best weekend! Elevate was very communicative and the house was great. Would definitely stay again!"
New Construction Modern Luxury Retreat w 6 Beds
Stunning House: Tennis & Pool in Southampton Estate section
Outdoor pool, a heated pool

Stunning House: Tennis & Pool in Southampton Estate section

10.0 out of 10, Exceptional, (38)
"Great home, the owner was wonderful to work with."
Stunning House: Tennis & Pool in Southampton Estate section
Resort Style backyard including professional PICKLEBALL COURT and HOT TUB.
Terrace/patio

Resort Style backyard including professional PICKLEBALL COURT and HOT TUB.

9.8 out of 10, Exceptional, (64)
"House was very clean! Owner was attentive. Highly recommend for a family vacation! Kids were never bored! "
Resort Style backyard including professional PICKLEBALL COURT and HOT TUB.
Hampton Private Retreat - last minute offer June 23-
Exterior

Hampton Private Retreat - last minute offer June 23-

10.0 out of 10, Exceptional, (19)
"We enjoyed Connie’s beautiful home. The kitchen was fully stocked, the bedrooms were very comfortable and the location was perfect. My family would definitely stay here again!"
Hampton Private Retreat - last minute offer June 23-
Beautifully renovated home, entertainers dream, saltwater pool and spa,...
Interior

Beautifully renovated home, entertainers dream, saltwater pool and spa,...

9.6 out of 10, Exceptional, (15)
"What a great experience we had! We will definitely be going back. The house was clean very well managed"
Beautifully renovated home, entertainers dream, saltwater pool and spa,...
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Southampton Hotel Reviews

Beachy Chic South of the Hwy in SH Village just 3blks to shops, food and fun!!!🏖️

Beachy Chic South of the Hwy in SH Village just 3blks to shops, food and fun!!!🏖️

10/10 Excellent
"Great location. "
Lauren H. 2-night trip
Posted 2 days ago
Beachy Chic South of the Hwy in SH Village just 3blks to shops, food and fun!!!🏖️

Find out more about Southampton

Find out more about Southampton

Search for holiday rentals in Southampton on Expedia! You can easily find your home rentals, villas, holiday apartments in Southampton using one of the methods below:

  • View our selection of featured holiday rentals in Southampton
  • Use the map to find apartments and other holiday homes in the Southampton neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Southampton while they last

Look no further and take a look at our great range of rental properties in Southampton!

Explore a world of travel with Expedia

Explore a world of travel with Expedia

Frequently asked questions

Can I find vacation rentals in Southampton?

Yes, you can find vacation rentals close to top local attractions in Southampton, or you can select a more secluded option if you're looking for relaxation. Nature enthusiasts will enjoy the beaches in Southampton. Make sure you have time to check out the museums and festivals during your trip.

What are some of the best vacation rentals in Southampton?

Delightful Southampton Retreat with Heated Pool & Jacuzzi, Near Beach & Shopping: Visitors like this Southampton vacation home rental. It offers an outdoor pool, a patio, and a barbecue grill to help you feel perfectly comfortable in your new surroundings. It has 5 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. It offers a garden, a selection of games, and a hot tub so you can immerse yourself in your vacation. Some other top choices in Southampton are Mansion Near the Bay. 7 bedrooms! Chef’s kitchen. and Cozy Southampton Home with Private Pool, Outdoor Dining, Perfect for Families.

How many vacation rentals are there in Southampton?

Expedia has 476 vacation rentals for your stay in Southampton.

What can I see and do in Southampton?

Enjoy the outdoors at Cooper's Beach and The Hamptons Beaches, or simply take in cultural attractions like Shinnecock Nation Cultural Center and Museum and Southampton Historical Museum. Other places in town to visit include Southampton Arts Center and Southampton Cultural Center.

What are vacation rentals like in Southampton?

Vacation rentals are private properties you can reserve for a short or long stay in Southampton. Vacation rentals feature amenities like WiFi and washers and dryers so you'll feel just like you're staying in your own home. If you're concerned about a clean environment, vacation rentals can provide a sense of security away from shared hotel elevators and busy concierge desks while still allowing you the enjoyment of travel. You'll also have more space in a vacation rental than in a hotel, which makes a vacation rental an attractive option for a family getaway.