Villa holiday rentals in Suffolk County

East Hampton Escape | Heated Pool + Outdoor Living

Escape to a 5* rated Hamptons retreat designed for effortless summer living. Set on a quiet property surrounded by mature landscapes, this light-filled designer home offers the perfect balance of privacy, comfort, and indoor-outdoor flow. The open concept layout is filled with natural light, feat a modern kitchen, multiple living areas, and thoughtfully designed bedrooms for a relaxed, and comfortable stay. Ideal for small groups looking for elevated escape minutes from beaches and town.

Value · Family · View

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.

Value · Family · Amenities

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.

Location · Value · Walkability

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).

Value · Location · Cleanliness

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

Family · Value · Cleanliness

Indulge in Prime Luxury 3BR 3-7 Guest

Experience luxury and convenience at our stunning villa! Whether you're planning a group retreat or a family escape, our exquisite property is your ideal haven. Located just moments away from major hospitals, universities, and transportation hubs, our villa provides unmatched accessibility to all your needs. Note: lower level unit listing it might be someone staying/living on the lower unit. They will not be able to disturb or enter the listing separately entrance

Location · Family · Cleanliness

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 · Checkout

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.

Family · Location · Kitchen

Private Luxury Waterfront Home

With uninterrupted and unequaled coastal views, this home is a haven of tranquility. It sits on a special stretch of the Connecticut coast, with spectacular bird and wild life-watching year-round. Enjoy great shopping in Guilford's boutiques around the historic town green. On chilly nights, you can light the fire in the great room and watch the sun set over the water, then hit the hot tub for some star gazing. A slice of pure heaven.

Family · Location · Comfort

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.

Family · Location · Condition

TREETOPS! An upscale, unique 5 bdrm home with POOL

TREETOPS is a 4850 square ft 5 bedroom house perched on an outcropping of granite cliffs, on 2 acres of beautiful forest. *Property not suitable for children under 8 years old* Sit in the garden, have a fire in the fire pit, or relax and get some sun by the marine-blue, stone-decked pool! Birdwatching, breakfast, and evening cocktails are best on the spacious wrap-around deck. Hiking is just steps away at "Westwoods Trailhead".

Location · Family · Hiking

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

Family · Location · Hospitality