Holiday rentals in Napeague

5.0 out of 5 average rating, 19 reviews

A modern home is set against a twilight sky, accessible via a well-lit stone pathway lined with greenery. The landscaped garden features low shrubs and ornamental grasses, while the house is designed with large windows that provide a glimpse of the inviting interior.

Home in Montauk

Modern beach getaway ocean views

Newly built modern and stylish home, nestled hilltop behind Fort Pond with panoramic rooftop views from the ocean to the Long Island Sound. A 15 minute walk or just a few minutes drive to town and the ocean beaches, close to Surf Lodge, Navy Beach, Duryeas, Montauket. The house has 4 beds, 3-1/2 baths, large open plan kitchen, dining, living, and a second living room / den off the downstairs deck. Outside enjoy the large gunnite pool, lawn, and wooden decks at three levels! Pool open may-Oct.

The living room features a cozy seating arrangement, including a spacious sofa and armchairs. A round coffee table centers the room, and large windows allow natural light to brighten the space. A textured area rug adds warmth, while a chandelier complements the high ceiling.

4.96 out of 5 average rating, 111 reviews

Casa Amagansett

*REMODELED FEB 2022* Casa Amagansett is a classic Hamptons bungalow, 3 minutes from the beach. Our 3br/2b home features a beautiful kitchen with 2 sinks, a laundry room, a truly sunny Sunroom, and gorgeous outdoor space. We are perfectly situated minutes from the beach, the Amagansett LIRR train station, grocery stores, and great shops & dining. There are four bicycles available for easy breezy access to everything nearby. Suitable for couples, families, business travelers, and friends.

5.0 out of 5 average rating, 34 reviews

A spacious outdoor deck features a dining table accompanied by seating and an umbrella. The deck is surrounded by sand and greenery, with a grill positioned nearby. A flowering tree adds a pop of color, enhancing the outdoor space's ambiance.

Cottage in Amagansett

Amagansett Beach Cottage - Short Walk to the Ocean

Escape to our charming, contemporary beach cottage nestled in the Napeague Dunes. South of the highway with a semi-private ocean beach only two short blocks away. Our well-appointed home, also cherished by us, the owners, is thoughtfully stocked to ensure a comfortable stay. Grille, dine on the back porch, surrounded by tree-lined privacy, or cook in the nicely equipped kitchen. The Lobster Roll, and Goldberg's Bagels are a walk or bike away. Located 8-minutes between Amagansett and Montauk.

5.0 out of 5 average rating, 48 reviews

A spacious living area features large windows dressed with natural shades, allowing ample light to filter in. Comfortable seating includes a plush sofa with blue accents, woven chairs, and a wooden coffee table. A modern kitchen area with a wine fridge is visible in the background.

Home in East Hampton

Stunning Central E. Hampton Home w/ gunite pool.

EH Registry #24-65. One of the top rentals in East Hampton, this beautifully remodeled 2,800 sq. ft. home is ideally located between East Hampton and Amagansett villages, close to beaches, dining and shopping. Features include 10' ceilings, a remodeled kitchen and baths, 4 bedrooms with new mattresses, dining for 10, beautiful landscaping, private fenced yard and large deck. Pool open mid-May–early Oct.; heat extra fee. NO PETS. No content creators, filming or commercial photography.

Luxe

An aerial view of the Mid Century Modern home is showcased, surrounded by lush greenery. The spacious yard features a heated pool, deck chairs, and a large checkered game board. A shaded seating area is positioned nearby, offering a perfect gathering spot amidst the natural landscape.

Villa in East Hampton

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.

4.99 out of 5 average rating, 70 reviews

5.0 out of 5 average rating, 28 reviews

Flat in Montauk

Renovated Oceanfront Montauk Studio Retreat

Experience the ultimate Montauk getaway in this stylish, renovated oceanfront studio. Perched on the 2nd floor, your private balcony offers front row seats to the Atlantic-keep your eyes peeled for dolphins and whales which are frequently spotted right from the unit! Whether you're grabbing a lobster roll from the award winning food truck, dipping into the indoor pool or ending your night with a private bonfire on the beach, this is the perfect place for your east end escape.

5.0 out of 5 average rating, 57 reviews

The charming cottage exterior is framed by lush greenery, with a welcoming front porch featuring two chairs. Vibrant white flowers line the pathway leading to the entrance, while a neatly manicured lawn enhances the inviting appeal of the home.

Cottage in East Hampton

Storybook Cottage Seconds to East Hampton Village

Beach Cottage at edge of East Hampton Village. This fresh and bright cottage with three bedrooms and two new bathrooms is a compact and convenient jewel box with everything you'd expect in the Hamptons - including a beautiful pool. Just blocks from the heart of East Hampton on a quiet no-traffic cul-de-sac, not far from beach, shopping, dining and train... sparkling kitchen with new 'retro style' appliances, gleaming hardwood floors throughout, and a cozy front porch.

4.9 out of 5 average rating, 20 reviews

Cabin in East Hampton

Close to all! Peaceful Fall Monthly *Heated Pool!

Village Fringe, Close to All, Comfortable 3+ bedroom, 2 Bath log home w/ *Heated pool (*heat option May - mid Sept ). Sun filled.. Located on quiet cul-de-sac close to Ocean Beaches & EH Village! Includes *Pool (Open 5/22 ) w/ outdoor shower & changing area. Relax in teak furniture / hammock after a swim in the 20x40 *pool! Peaceful setting. All amenities one would expect. High speed wireless internet 3 Smart TVs. Monthly Rental Registration # 20-1005.

4.87 out of 5 average rating, 71 reviews

Home in Springs

Spacious East Hampton house with heated pool + WFH

This 4 bed 3 bath East Hampton home is ideal for families and groups who want room to relax. The home has a heated pool (open 5/15–10/4), outdoor grill, and finished basement. You're also ideally set up for WFH with 300 Mbps fiber WiFi and 3 desks. You're a 5-min drive to bay beaches, 15 min to ocean beaches, and 10–12 min from the shops and restaurants of Amagansett and East Hampton Village. The driveway fits up to 4 cars. (RR #21-807)

5.0 out of 5 average rating, 30 reviews

Bungalow in Springs

Charming Bungalow on the Bay

This newly remodeled 1960’s bungalow is the perfect getaway for couples and families alike. Located right on Gardiner’s Bay, there’s a gorgeous view of the water from the large windows and front porch. From the front steps you can follow the 300 yard path to your own private beach where you can wade, swim, snorkel, paddleboard, or just enjoy the amazing view and salt air. (East Hampton Rental Registry Certificate Number: 24-234)

4.85 out of 5 average rating, 55 reviews

Home in Springs

Historic Home + Private Waterfront Access

A rare piece of East Hampton architectural history. Designed in 1958 by Kaneji Domoto, a student of Frank Lloyd Wright, this mid-century home celebrates indoor-outdoor living with walls of glass, abundant natural light, and panoramic views of Three Mile Harbor. Set among mature trees with a private staircase down to the water, the home offers a truly unique Hamptons experience - from sunrise coffees to unforgettable sunsets.

Superhost

Home in East Hampton

Contemporary house East Hampton with heated pool

Recently renovated contemporary house with 3 bedrooms and 2.5 baths has a nice and clean design. The house has a heated pool with outdoor entertaining area, a large and bright living room with a wood burning fireplace, renovated kitchen with open dining space, 2 guest rooms sharing a full bath and a master suite. It is a perfect retreat in East Hampton.

5.0 out of 5 average rating, 8 reviews

Popular amenities for Napeague holiday rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Other great holiday rentals in Napeague

Superhost

A relaxing outdoor space features a white jacuzzi surrounded by a wooden deck. A dining table and chairs are positioned adjacent to the jacuzzi. Lush greenery and trees provide a natural backdrop, creating a tranquil environment for guests.

Home in Springs

Year round Jacuzzi - Blackberry Home

4.76 out of 5 average rating, 192 reviews

4.94 out of 5 average rating, 53 reviews

A spacious backyard features a large pool surrounded by a wooden deck. Two lounge chairs are positioned beside the pool, and an umbrella provides shade nearby. Lush greenery lines the property, creating a serene and private environment for relaxation and recreation.

Home in East Hampton

Sunny, walk to beach, large pool

Guest suite in East Hampton

Peaceful Suite w/Pool, Hot tub, Private Entry.

5.0 out of 5 average rating, 30 reviews

4.88 out of 5 average rating, 223 reviews

A serene view of a spacious barn with a deck illuminated by the golden light of sunset. Surrounded by lush foliage, the barn features large windows and a welcoming porch, providing a glimpse of modern yet comfortable architecture.

Guest house in Springs

Beautiful Airy Barn in Springs

5.0 out of 5 average rating, 3 reviews

Unit 211: Cottage | Ocean View | Striper

5.0 out of 5 average rating, 21 reviews

"The Place of Good Water"

A serene waterfront view captures a gradient sky transitioning from deep blue to vibrant orange and yellow at sunset. The calm water reflects these warm hues, while silhouettes of wooden structures outline the shoreline, offering a peaceful and picturesque setting.

4.95 out of 5 average rating, 19 reviews

Amagansett, Waterfront retreat