A welcome sign for the village of Southampton, established in 1640, with a cyclist on the road.

Southampton Vacation Rentals

Dates

November 2026

December 2026

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Our top choices for Southampton vacation rentals

A modern living room with a sofa, armchairs, a coffee table, and a TV.

1. Minutes from the beach, brand new 3 bedroom

Southampton

Kathy B.

AED 4,008 total

includes taxes & fees

9 Dec - 10 Dec

A spacious living room with a grey sectional sofa, a round coffee table, and a white armchair.

2. Minutes from the beach, brand new 4 bedroom

Southampton

Okito H.

AED 3,873 total

includes taxes & fees

9 Nov - 10 Nov

A modern kitchen with white cabinets, a stainless steel sink, and a dishwasher.

3. Newly Renovated Pristine Southampton Colonial

Southampton

Brian M.

AED 5,372 total

includes taxes & fees

9 Nov - 10 Nov

A wooden house with a front porch, white railings, and a double door.

4. COLONIAL COMPOUND WITH OVERSIZED LIVING ROOMS, GYM, AND ARCADE ROOM, CLOSE...

Southampton

Melissa

AED 10,780 total

includes taxes & fees

9 Nov - 10 Nov

A dining area with a round table and chairs, surrounded by bookshelves filled with books and decorative items.

5. Contemporary Southampton Village Home Walking Distance to Town, Pool,...

Southampton

Sarah

AED 10,126 total

includes taxes & fees

6 Dec - 7 Dec

A single-story house with a gabled roof, a front porch, and a well-maintained garden.

6. Walk to Beach | Seabreeze Cottage #4

Hampton Bays

Weston B.

AED 1,766 total

includes taxes & fees

30 Nov - 1 Dec

A brick patio with outdoor seating, a wooden staircase, and a house with a window and door.

7. Cozy Cottage by the beach - Seabreeze #1

Hampton Bays

AED 1,644 total

includes taxes & fees

16 Nov - 17 Nov

A spacious living area with a white sofa, a white armchair, and a dining table. There is a staircase leading to an upper level.

8. Steps to the beach | Seabreeze Cottage #3

Hampton Bays

"The property needs a major cleaning and repairs. The floors were sticky, and the carpet was dirty. Furniture was dirty and soiled. There was dried food on the utensils. The pipes groaned at all hours, several times an hour. The bed creaked with every movement. Bedroom blinds were broken and wouldn’t close all the way. The bedside lamp on the wall was falling off. The last straw was the huge spider that jumped down from the closet onto me. We ended up leaving after less than 24 hours and...

Lydia

AED 1,668 total

includes taxes & fees

15 Nov - 16 Nov

A modern building with large windows overlooking a beach.

9. Beachfront Jacuzzi All Year - Black Swan Home

Hampton Bays

John M.

AED 4,565 total

includes taxes & fees

9 Nov - 10 Nov

A hot tub with a checkered roof structure and surrounding greenery.

10. Jacuzzi year-round - Villa Luz Private Home

Hampon Bays

Annie B.

AED 3,986 total

includes taxes & fees

9 Nov - 10 Nov

A balcony with a view of the ocean, a lawn, and a house in the background.

11. Cliffside Resort Condominiums

Greenport

William

AED 1,129 total

includes taxes & fees

30 Nov - 1 Dec

12. Windward Shores Ocean Resort

Napeague

Banessa

AED 653 total

includes taxes & fees

9 Nov - 10 Nov

A small cabin with a porch, surrounded by trees and a fenced area.

13. Lovely studio with AC in charming Sag Harbor

Sag Harbor

"For a last minute trip, we couldn't beat the location. Less than 10 minutes from Sag Harbor and Bridgehampton main streets as well as from Sagaponack beaches. The space is quaint and offers everything you need, a small kitchenette, a work desk, outdoor space. There was several communications sent regarding privacy and not interacting with other guests on property which I can appreciate but felt excessive.My two biggest complaints and likely why I would not rebook was first the cleanliness of the...

Emily t.

AED 1,737 total

includes taxes & fees

9 Nov - 10 Nov

14. Hamptons Oceanfront Oasis - Cozy 1-bedroom cottage

Hampton Bays

AED 1,486 total

includes taxes & fees

15 Nov - 16 Nov

A modern kitchen with a stainless steel refrigerator, white cabinets, a window with a view, and a chandelier.

15. Charming Accommodations in the Hamptons

Sag Harbor

AED 1,737 total

includes taxes & fees

9 Nov - 10 Nov

A modern kitchen with a central island, white cabinetry, and a dining area with a table set for two.

16. Immaculate Waterfront 2 bedroom!

Hampton Bays

Michael L.

AED 2,006 total

includes taxes & fees

9 Nov - 10 Nov

A modern living room with a wooden accent wall, a flat-screen TV, a fireplace, and a dining area with a chair and table.

17. Bridgehampton, NY cottage near Sag Harbor, NY. Elegant and modern.

Bridgehampton

Katie B.

AED 2,700 total

includes taxes & fees

19 Nov - 20 Nov

A dining area with a wooden table, chairs, and a decorative wall with a cityscape picture.

18. Nicely Furnished apartment; Ideal for Travelling nurses, Resident doctors, etc,

Flanders

Sherri K.

AED 1,175 total

includes taxes & fees

9 Dec - 10 Dec

A modern house with a deck, outdoor seating, and a fire pit.

19. North Fork Resort

Greenport

Altynai

AED 1,308 total

includes taxes & fees

9 Nov - 10 Nov

A two-story house with a white staircase, a covered patio with outdoor furniture, and a fenced yard.

20. Harbor Heights

Pipes Cove

Steven R.

AED 846 total

includes taxes & fees

9 Nov - 10 Nov

View all properties

Find vacation rentals that suit your style

Top Southampton Hotel Reviews

A tented area with a pool view, wooden lounge chairs, and a table with a drink and food.

Canoe Place Inn and Cottages

Hampton Bays

10/10 Excellent

Quinne

A modern bathroom with a large mirror, wooden vanity, and a sink. There is a chair and a small table in the adjacent living area, with a sofa and a view of the outdoors.

The Bentley Hotel Southampton

Southampton

10/10 Excellent

Jennifer

Southampton Inn

Southampton

10/10 Excellent

Anonymous traveler

A staircase with a white railing, a white chandelier, and framed artwork on the walls.

Harpoon House

Southampton

10/10 Excellent

The location is great for walking around downtown. Close to shops, restaurants and a quick drive to the beach. I came here off season and it was chilly but during the summer you could easily ride a bike over to the beach. The room was clean, comfortable and very Hamptons feeling. Parking on site which was nice and I highly recommend the coffee shop on the corner. During the summer sitting on the big front porch would be nice. The water in the shower was a bit tricky to get the right temp but I...

Candy

A living room with a fireplace, a television mounted above it, and a dining area in the background.

The 1770 House Restaurant & Inn

East Hampton

10/10 Excellent

Anonymous traveler

A modern kitchen with a central island, bar stools, pendant lighting, and a seating area with a sofa and coffee table.

The Hampton Maid

Hampton Bays

10/10 Excellent

Such a beautiful property, lots of trees, lovely landscaping. They keep Crassula in pots on all of the porches as long as weather permits. The room I stayed in (double queen) was very spacious. Wood beamed ceiling with a ceiling fan, walk in shower. Loved the restaurant that was open for breakfast daily. Open for dinner Tuesday - Saturday while I was there. It's still family owned and run after 69 years. Great dining options all around, and lots to see and do on the island - although you...

ALIX

A bedroom with a wooden headboard, a bedside table with a lamp, and a bed with a grey blanket.

Bridgehampton Inn

Bridgehampton

10/10 Excellent

The Speights

A rooftop deck with outdoor seating, fire pits, and a view of a body of water.

The Menhaden

Greenport

10/10 Excellent

Anonymous traveler

A spacious hallway with a fireplace, a large window, and a built-in shelving unit.

Sag Harbor Inn

Sag Harbor

10/10 Excellent

Anonymous traveler

A large, multi-story building with a swimming pool, outdoor seating, and a well-maintained garden.

East Hampton Art House Bed & Breakfast

Clearwater Beach

10/10 Excellent

Anonymous traveler

Frequently Asked Questions

Can I find vacation rentals in Southampton?

Yes, you can find vacation rentals in Southampton close to Southampton Arts Center, or you can select a more secluded option if you're looking for a relaxing stay. 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?

Private 2.1 acre gated home with heated pool and tennis & pickleball court: Visitors like this Southampton vacation home rental. It is located near the beach and has an outdoor pool, a fireplace, and a barbecue grill to put you at ease 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 balcony, a garden, and an arcade game room so you can immerse yourself in your vacation. Some other top choices in Southampton are Spacious Southampton Home in Shinnecock Hills, Central Between Southampton,... and Delightful Southampton Retreat with Heated Pool & Jacuzzi, Near Beach & Shopping.

How many vacation rentals are there in Southampton?

Expedia has 481 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 Southampton Historical Museum and Halsey House. Other places in town to visit include Southampton Arts Center and Shinnecock Hills Golf Course.

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.

Southampton Vacation Rentals

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Southampton vacation rentals

1. Minutes from the beach, brand new 3 bedroom

2. Minutes from the beach, brand new 4 bedroom

3. Newly Renovated Pristine Southampton Colonial

4. COLONIAL COMPOUND WITH OVERSIZED LIVING ROOMS, GYM, AND ARCADE ROOM, CLOSE...

5. Contemporary Southampton Village Home Walking Distance to Town, Pool,...

6. Walk to Beach | Seabreeze Cottage #4

7. Cozy Cottage by the beach - Seabreeze #1

8. Steps to the beach | Seabreeze Cottage #3

9. Beachfront Jacuzzi All Year - Black Swan Home

10. Jacuzzi year-round - Villa Luz Private Home

11. Cliffside Resort Condominiums

12. Windward Shores Ocean Resort

13. Lovely studio with AC in charming Sag Harbor

14. Hamptons Oceanfront Oasis - Cozy 1-bedroom cottage

15. Charming Accommodations in the Hamptons

16. Immaculate Waterfront 2 bedroom!

17. Bridgehampton, NY cottage near Sag Harbor, NY. Elegant and modern.

18. Nicely Furnished apartment; Ideal for Travelling nurses, Resident doctors, etc,

19. North Fork Resort

20. Harbor Heights

Find vacation rentals that suit your style

Top Southampton Hotel Reviews

Canoe Place Inn and Cottages

10/10 Excellent

Frequently Asked Questions

Can I find vacation rentals in Southampton?

What are some of the best vacation rentals in Southampton?

How many vacation rentals are there in Southampton?

What can I see and do in Southampton?

What are vacation rentals like in Southampton?