Villa holiday rentals in East Hampton

Year-Round Heated Pool Villa - 3 blocks from town

Pool heated to hot tub temperatures & open year round! This brand new construction house is perfect for large groups. Gather with friends and family in the double height ceiling open concept living room/dining room/kitchen area. Soak up the sun lounging by the pool. Take a super short walk to town to enjoy the incredible local shops, restaurants, and bars. Then end with a nightcap relaxing in the heated hot tub seating section of the pool. There's no better place to stay in Greenport Village.

Location · Value · Air conditioning

Just renovated Southampton retreat w/ heated pool

JUST RENOVATED! INQUIRE ABOUT MONTHLY RENTALS! Come and enjoy with family and friends your own beautiful house in Southampton. 5-minute drive to Cooper’s Beach and to Southampton Village. Enjoy beautiful ocean beaches, have brunch in the Village, swim in your 32’ heated salt water pool, enjoy a BBQ on your patio under the shadow of a Japanese Maple, indulge in a quiet evening with a book by the fireplace, or take advantage of the home office while your family & friends enjoy the property.

Family · Value · Walkability

Luxe|Pool|BeachCar|Games|Movie|HotTub|Firepit

SERENITY AT SHOREWOOD Pool is Open April 1 - November 1. Must be 25+ to book. Luxurious Newly Renovated Mid Century Modern Home in East Hampton with Beach Car! Peaceful and stylish with three bedrooms, 3 1/2 baths, spectacular great room, huge deck, heated pool and more, less than four miles to the heart of East Hampton Village, world renowned for its restaurants, shopping and ocean beaches. A designer-curated architectural gem! Kick back and relax in this calm, stylish space.

Location · Value · Check-in

Pool|Golf Sim|HotTub|Movie|Games|Firepit|Golf Open

Insta: @staywithhamptonsmama PINKWOOD PLAYHOUSE is the perfect spot for your Hamptons stay, offering elevated design and relaxed luxury with laid back beach vibes. Perfect for families, friends or couples. This stylish and serene home features 4 bedrooms, 2.5 bathrooms, a fully equipped kitchen, soaring ceilings, games room and movie room. Bring the outdoors in with oversized windows and over 1000 square feet of deck space overlooking the gorgeous pool (can be heated for a fee).

Location · Value · Hospitality

Hamptons WaterLiving-Dock, Kayak, Beach, EV charge

[FOLLOW US on INSTA @29watersedge] 1-mile from the beach, this child-friendly waterfront Southampton home is a perfect family getaway. Ready for watersports: kayak, paddleboard, boat, or jet ski. Walk down to the beach for a swim in the bay. At home, the backyard has it all: large dock, fire pit, swing/playset, hammock, grill, & oversized deck to take in the views. Surrounded by nature and water, you are just minutes from restaurants and shopping in Southampton Village &Sag Harbor.

Location · Family · Laundry

Hamptons Retreat | Pool, Hot Tub, Sleeps 10

Spacious 5-bedroom Hamptons retreat designed for families and groups, featuring a heated pool, brand-new 9-person hot tub, and a newly renovated outdoor living space just minutes from Southampton Village and the beaches. Perfect for summer getaways or long weekends, this home comfortably sleeps 10 and is designed for both relaxing and entertaining. Centrally located: • 6 min to LIRR/Jitney • 2 min to bay beaches • 10 min to ocean beaches & Southampton Village • 20 min to wineries

Value · Family · Air conditioning

Farm reserve sunset views

Beautiful villa in beginning part of the Hamptons for a more convenient commute. A private hideaway surrounded by nature where you can relax. It’s perfect for families and friends who love nature, horses and beautiful sunsets. Since our property is spread out over an acre (and surrounded by greater than acre properties), we have the space to allow our guests the ability to maintain a safe distance while still being able to relax comfortably during their stay.

Value · Location · Backyard

Superb Shelter Island 4 bed Designer with a Pool

This contemporary, designer-updated residence provides an idyllic Shelter Island retreat. With 4 delightful bedrooms, 3 sleek bathrooms, and a seasonal heated salt wayer pool amidst mature landscaping, you're promised a calming respite. We kindly ask that you familiarize yourself with the detailed disclosures, & guidelines. Around the corner from Sunset beach, Silver beach and Shell beach, and located on a quiet street. Easily accessible to the ferries.

Location · Family · Beach

East Hampton Villa | Heated Saltwater Pool & Beach

A 'Guest Favourite' 4-bedroom East Hampton bungalow with a heated saltwater pool (87°F, May–September) and walking access to the private Clearwater Beach. Twelve minutes from East Hampton village and its restaurants — Roudy Hall and Citta Nova both a short drive. Inside: open-plan living, a marbled primary bath with claw foot tub, and a built-in outdoor grill set among professionally landscaped grounds with multiple dining areas.

Location · Family · Sleep quality

Newly Renovated Villa w/ Pool And Tennis Court

Enjoy a summer sojourn in style in our beautifully renovated home with pool and tennis court that's close to the beach. Located on an acre in the bucolic Red Creek area of Hampton Bays, the home is your own private retreat providing 2,400+/- sq. ft. of living space with 4 bedrooms and 2.5 baths. Meanwhile, all of Southampton is minutes from you: Red Creek Park The Bay Beach The Hamlet Center Good Ground Park

Location · Family · Hospitality

Hampton stay near by the beach

Welcome to the Hampton. Summer time. home Location just 2 block from Southampton town. Nice and quiet neighborhood.. 2 miles from the beach Your lovely private bedroom with the view of the backyard garden and the Pool.. Bathroom just outside your room .. Swimming Pool is open during summer Send us some note before booking the room. Thank you !!

Family · Value · Nearby

Hamptons Bungalow with Pool

11 minutes from US OPEN PGA TOUR. Escape to a contemporary, minimalist, dream in Hampton Bays! The bungalow is a 5 minute drive or a 15 minute bike ride to multiple beaches, farm stands, restaurants and village center. This slice of heaven is truly a special get away.

Family · Location · Wi-Fi