Villa holiday rentals in Southampton

Southampton Village Dream Walk to Beach & SAmbrose

Southampton Village Dream Two blocks from Main Street and Sant Ambroeus, and a short walk to the beach, this 7+ bedroom, 6 bath home has all modern conveniences in a beautifully landscaped private compound. Northstar is one of the original Southampton Village houses, over 350-year-old, rebuilt from the ground up, completely modernized and in pristine condition. This home delivers the perfect American dream summer vacation. IMPORTANT: Please read the guidelines and rules below before booking:

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.

East Hampton Village Fringe, Renovated with Pool

This remarkable East Hampton home, nestled along a quiet cul-de-sac, is just moments from shopping, restaurants, and ocean beaches. The residence features an abundance of natural light, crisp neutral color tones, and tall, pitched ceilings that enhance the sense of space. The calming, heated pool provides a perfect retreat for relaxation. Please review our disclosures and house manual to ensure this home meets your needs and expectations. We want to make sure it’s the perfect fit for you.

Stylish Beauty with Tennis

30% OFF for July 11-25th Peace and quiet awaits in this stylish modern house on the village fringe. Featuring a first floor Master suite with spa-style master bath, flatscreen TV and direct access to the pool and outdoor shower. The double height, 600 sqft great room is open towards the kitchen and perfect for entertaining. It is equipped with a stunning 82'' flatscreen TV. The south facing deck and heated pool (MD through September) overlook a 6 acre nature reserve.

Luxury Estate-Heated Pool, Fire Pit, Hot Tub

Escape to a private 1.5-acre East Hampton retreat with an Olympic-size pool, hot tub, pool-side gazebo, wrap-around porch, and secluded fire pit under the trees. This stylish 3BR home features a finished basement with ping pong and TV, a garage gym, and modern designer touches throughout. Just minutes from private beaches and both Amagansett and East Hampton village, it’s perfect for families, friends, or couples seeking luxury, privacy, and space to relax or entertain.

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.

Luxe| Pool|Game Room |Outdoor Movie|HotTub|Firepit

SERENITY AT SHOREWOOD 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.

balcony entrance to ensuite room with king bed +

Take it easy at this private beachfront. wake up to the sound of the waves and birds signing. 12 min from quaint town of Greenport. your room is in the back of my house, up the stairs to balcony entrance facing the ocean. your only neighbors are the seagulls. park in the driveway or pull you car right up on the lawn + sandy dune, stairs down to my private pebble beachfront. lots of waterfront dining.

Hamptons Bungalow With Pool

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.