Southampton Vacation Home Rentals from CA $86: Search Top Private Vacation Homes for Rent

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Our top choices for Southampton vacation homes

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.

CA $1,571 total

includes taxes & fees

Nov 16 - Nov 17

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.

CA $1,483 total

includes taxes & fees

Nov 15 - Nov 16

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

3. Newly Renovated Pristine Southampton Colonial

Southampton

Brian M.

CA $2,075 total

includes taxes & fees

Nov 15 - Nov 16

A wooden gate partially covered by lush green ivy.

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

Southampton

Sarah

CA $4,111 total

includes taxes & fees

Nov 13 - Nov 14

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

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

Southampton

Melissa

CA $4,164 total

includes taxes & fees

Nov 15 - Nov 16

A modern building with large windows overlooking a beach.

6. Beachfront Jacuzzi All Year - Black Swan Home

Hampton Bays

John M.

CA $1,819 total

includes taxes & fees

Nov 15 - Nov 16

A residential property with a covered patio, outdoor seating, and a hot tub.

7. Jacuzzi year-round - Villa Luz Private Home

Hampon Bays

Annie B.

CA $1,608 total

includes taxes & fees

Nov 13 - Nov 14

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

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

Bridgehampton

Katie B.

CA $793 total

includes taxes & fees

Nov 15 - Nov 16

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

9. Immaculate Waterfront 2 bedroom!

Hampton Bays

Michael L.

CA $775 total

includes taxes & fees

Nov 13 - Nov 14

A house with a sliding glass door, a white door, and a small porch with potted plants.

10. Designer Sag Harbor Home w/ Pool + Fire Pit + Yard

Sag Harbor

maria m.

CA $867 total

includes taxes & fees

Nov 13 - Nov 14

A kitchen with a central island, white cabinetry, and a brick accent wall.

11. Rare Two-House Wainscott Estate: Hot Tub, Pool, Walk to Beach!!

Wainscott

Suzanne B.

CA $2,903 total

includes taxes & fees

Nov 16 - Nov 17

A beach with people sunbathing, a pier extending into the water, and a clear blue sky.

12. The SandPiper

Pipes Cove

Manuela C.

CA $344 total

includes taxes & fees

Nov 30 - Dec 1

A beach with people relaxing under umbrellas, a dock extending into the water, and a forested hill in the background.

13. Aqua Vista

Pipes Cove

Carey D.

CA $342 total

includes taxes & fees

Nov 18 - Nov 19

A beach with people relaxing, a pier extending into the water, and a clear sky.

14. Blue Bay Dream w/ Seasonal Outdoor Jacuzzi, Cabana + Office

Pipes Cove

Callie E.

CA $494 total

includes taxes & fees

Nov 15 - Nov 16

A modern living room with a television, a glass coffee table, and a view of the sea.

15. Spacious 5-bedroom house with Private Beach and Wide Open Bay Views

Hampton Bays

CA $3,039 total

includes taxes & fees

Nov 18 - Nov 19

A wooden pathway leading to a beach with scattered rocks and greenery.

16. Beach Block Hideaway

Pipes Cove

Teresa C.

CA $608 total

includes taxes & fees

Nov 15 - Nov 16

A swimming pool with a white deck, surrounded by lush greenery and a swan inflatable float.

17. Elegant 5-Bedroom Hamptons Home with Private Pool

Hampton Bays

Christina M.

CA $2,428 total

includes taxes & fees

Nov 16 - Nov 17

An outdoor dining area with hanging lights, palm trees, and a bar.

18. American Beech in Greenport - Petite King Room 7

Greenport

Paul F.

CA $412 total

includes taxes & fees

Nov 16 - Nov 17

A modern kitchen with white cabinets, a stainless steel refrigerator, and a dining area with a black table set for four.

19. Lovely & Spacious Sag Harbor escape with heated pool

Sag Harbor

CA $2,861 total

includes taxes & fees

Nov 13 - Nov 14

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Learn more about Southampton

Pristine beaches stretch for miles along this Hamptons gem where celebrities and locals mingle at waterfront seafood spots. Explore historic mansions and boutique shops in the village, then catch a spectacular sunset from Cooper's Beach with a local lobster roll.

See all hotels in Southampton

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

Top reviews in Southampton

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

Corrado

An outdoor dining area with trees and tables under string lights.

The 1770 House Restaurant & Inn

East Hampton

10/10 Excellent

Anonymous traveller

A modern two-story building with a pool area featuring sun loungers and umbrellas.

Seven Beach Lane

Westhampton Beach

10/10 Excellent

My stay was absolutely incredible! From the moment I arrived, Jen made me feel so welcome. After an early travel day, her warmth and kindness immediately made me feel comfortable and at home. She gave me so many great recommendations and was incredibly attentive, making everything over the last two days feel completely seamless and enjoyable. As a solo traveler, I also felt incredibly safe on the property, which was so important to me. The location is amazing and within easy walking distance of...

Mel

A dining area with a fireplace, bookshelves, and a view of the bar area.

Bridgehampton Inn

Bridgehampton

10/10 Excellent

We had a wonderful stay at the Bridgehampton Inn from the moment we were welcomed at the entrance. Charming rooms, beautiful property and gardens, walkable to the shops and restaurants in town. Their store Loaves and Fishes is filled with great kitchen treasures. Breakfast which was included daily was amazing as was the dinner we enjoyed one evening. Great location to explore all of the Hamptons which we did! Can’t say enough about the staff. Every one of them went out of their way to...

Liliana