Holiday rentals in Southampton

Charming House In The Village

Keep it simple at this peaceful and centrally-located place in the Heart of Southampton Village Escape to this delightful house nestled in the heart of Southampton Village, offering a perfect blend of charm, comfort, and convenience. Situated just moments away from the beach, and walking distance to restaurants and entertainment. 🏠 Entire First Floor (Private) 🛏️ Bedrooms: 2
🛁 Bathrooms: 1
🌳 Outdoor Space: Private Garden 
🔥 Fire Pit and BBQ 🚘 Two Parking Spaces 👨‍🍳 Fully Stocked Kitchen

Modern Southampton home, heated pool, pickleball

A modern style and freshly renovated Southampton home with waterfront views. 5 minutes from Southampton village & Coopers Beach. The house features 5 bedrooms, 4 bathrooms, including 2 ensuites. Brand-new kitchen with large Restoration Hardware dining table that seats 12 (+8 around the oversized counter). Expertly styled. Two fireplaces. Perfect for couples and/or families (equipped with 2 cribs, pack and play,xl playpen,toys,high chair). Total beach vibes with a heated pool and new patio area.

Southampton Charmer, 5 bedrooms w pool - Location

This 5-bedroom home boasts en-suite baths and elegant furnishings. The gourmet kitchen features marble countertops and stainless steel appliances, leading to a dining area. The lower level includes a spacious seating area and a game room with toys. The second floor houses a master suite with stunning views and three additional en-suite bedrooms. Located minutes from the village center, with restaurants, shops, and beaches nearby. A heated pool invites you to relax and enjoy the comfort of home.

Chic Southampton Home. Mins to Village and Beach!

Welcome to your perfect Hamptons getaway! This sun-filled, architecturally unique home is ideal for a summer retreat or a cozy weekend escape. Offering modern furnishings, and an open floor plan, this space is perfect for small groups. Whether you're enjoying the crisp evenings of early spring, sun-drenched summer days, or the vibrant fall season, this home is a serene escape year-round. Cozy up by the fire, relax on the sun-soaked balconies, or unwind in the beautifully renovated pool house.

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.

3 Bedroom Guest House in Southampton

This magical getaway delivers peace and relaxation. Curl up to the wood burning fireplace. Wake up to coffee on the porch with a view of the pool. Play in your heated, saltwater pool, (Open April 17-October 23) and relax under the stars in your hot tub. Get a workout in on the Peloton bike or the Cybex Arc Trainer. The gym is equipped with REP Fitness weights and squat rack. You can also drive 12 minutes to Southampton Village for shopping, restaurants, art galleries and Ocean Beaches.

Luxury Hamptons Poolside Paradise w/ Outdoor Sauna

Chic, 5-bedroom, 3.5 half-bath home is close to the water and the village of Southampton. The sparkling pool has a beautiful backdrop of a lushly landscaped garden. Southern exposure in the backyard brings an abundance of sunshine inside and out. The home includes an outdoor sauna, fire pit and rock garden perched above the pool for your very own spa retreat. The inside of the home is thoughtfully designed with a relaxed, chic & luxury feel making it the perfect Hamptons getaway.

Stunning Hamptons Waterfront Escape w/ Sunset View

Experience an unforgettable trip in the Hamptons at our waterfront haven! Savor the views and sunset from our spacious deck. Vaulted ceilings and large windows flood the space with natural light. Brand new Weber Grill (2025). We have completed renovations of 3 bathrooms, 2 kitchens, and the entire pool house over the last 18 months. Our home is <10 minutes drive to the beach, groceries, and restaurants! Our pool will close on September 15th, 2026 and will reopen May 29, 2027.

Brand New Sun Filled Home

OUR HOUSE A beautiful newly renovated Southampton two story home with spectacular light, offering the best of indoor-outdoor living. A large deck off of the kitchen with small porches off of two primary suites and a small sitting area off the first floor junior suite. On almost one acre of land, there is plenty of peaceful space. Very central - two miles from the beach and town. Two car garage with built in electric vehicle charger. Gas fireplace. All appliances are brand new.

Southampton apt walk to village

Enjoy easy access to everything from this perfectly located apartment in Southampton Village. You are just a 10-minute walk to downtown and 1.5 miles to our glorious village beaches. We are centrally located to all of the Hamptons, Sag Harbor, Montauk, and the North Fork. Ideal for nature lovers, our garden is a pollinator sanctuary home to birds, 🐝, 🦋, and other wildlife. We love pets, so your furry baby is welcome!

Southampton Village Escape

Welcome to 86 Hildreth St, a 3BR, 3.5BA gem steps from Main St. Built in 1930 and thoughtfully updated with central AC and bright, sun-filled interiors, it blends charm and comfort. The yard features a gunite pool and bluestone patio. Bike to Coopers Beach, grab lunch at Citarella, hit SLT, and make it to Sant Ambroeus for dinner. It’s walkable village life with a great Hamptons vibe.

Beach Barn w/ Heated Pool & Sauna - Dog Friendly

@WaterMillBeachBarn Dog friendly (upon approval) Hampton Beach Barn with pool and infrared sauna. POOL OPEN - May 1st - October 23, 2026 This impressive house, nestled within a rustic, woodland plot, promises a tranquil stay. Eclectic designer decor is complemented by striking rustic touches, such as Dutch-style farm doors, exposed beams, and vintage wood-burning stove.