Holiday rentals in Amagansett

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Top-rated holiday rentals in Amagansett

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Guest favourite
A bright living area features a light grey sofa paired with two black chairs, positioned around a glass coffee table. Large windows allow natural light to fill the space, while a minimalist fireplace offers visual interest. A small desk is visible against the wall.
Home in The Hamptons
4.95 out of 5 average rating, 482 reviews

Silver House: 3BR Home with Private Beach Access

Located on a half-acre property surrounded by tall oak trees, this three-bedroom, two-bathroom home is the perfect getaway. The house is part of the Clearwater Beach community with private beach access. The recently renovated kitchen and bathrooms are modern and minimal. Natural light floods the space throughout the entire house. Here is your perfect getaway from the chaos of city life The fireplace is NOT available for guest use. Early check-in and late check-out are NOT available in season

Guest favourite
A serene pool area is surrounded by lush greenery and colorful hydrangea flowers. Lounge chairs offer relaxation under large umbrellas, while the inviting pool reflects the clear blue sky. A charming home stands in the background, adding to the peaceful setting.
Home in The Hamptons
4.92 out of 5 average rating, 121 reviews

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.

Guest favourite
A bright entryway is showcased, featuring a modern railing that overlooks a spacious living area. Large glass doors provide an unobstructed view of the pool and manicured outdoor space. Sunlight filters through the windows, enhancing the fresh ambiance and vibrant indoor plants.
Home in The Hamptons
4.94 out of 5 average rating, 137 reviews

Sag Harbor Village Cottage with Pool

Situated on a half-acre of land, this classic shingle cottage with brand new designer interiors offers the ideal Hamptons getaway. Located in the picturesque village of Sag Harbor, less than a mile from town, bay beaches, and tennis. 10 minute drive to Wolffer & ocean beaches. 4 bedrooms, 2 modern bathrooms and pool with mature landscaping offers a relaxing escape. Please read the additional disclosures, guidelines, and rules. No events, no parties, no smoking – no exceptions!

Top guest favourite
A cozy living area features a light-colored sofa adorned with blue and white throw pillows. Woven armchairs flank a wooden coffee table, while a stone fireplace adds warmth. Two large windows allow natural light to fill the space, complemented by greenery and decorative accents.
Home in The Hamptons
4.98 out of 5 average rating, 103 reviews

Sea Roost

This private, two-cottage property contains a few of the last remaining original fisherman cottages at Hither Hills built in the 1940s. Set on a lush, private knoll - South of the Highway - Sea Roost boasts mature landscaping and is located steps to Montauk's quiet and secluded Hither Hills Beach. The property consists of a 2 bed/2 bath cottage with separate artist studio (Qn bed, kitchenette & full bath). Dogs negotiable with pet fee. IG @searoosts

Superhost
A modern black-clad home is visible with large windows reflecting soft light. Lounge chairs line the pool area, accompanied by umbrellas providing shade. A playful inflatable is positioned in the sparkling aqua pool, framed by lush greenery creating a serene outdoor environment.
Cottage in The Hamptons
4.77 out of 5 average rating, 108 reviews

Spacious East Hampton Getaway with Pool

This bright and comfortable 3 bedroom, 2 bath Scandinavian home awaits! Located just a 5 minute drive Sag Harbor and 10 minutes to the heart of East Hampton to enjoy beaches, shopping, restaurants and bars. The light hardwood floors create a crisp feel that you have to witness. The first floor's two guest beds open out to a lovely eat-in kitchen with dining and living rooms featuring a wood-burning fireplace and pool to check every box for year-round fun.

Top guest favourite
An inviting living area is presented, featuring a white brick fireplace as a focal point. Comfortable seating includes light-colored sofas adorned with varying throw pillows. Large windows allow natural light to fill the space, and double doors lead to the outdoor area.
Holiday home in The Hamptons
4.99 out of 5 average rating, 111 reviews

2 BR apartment near ocean in Hither Hills

Relax and enjoy a peaceful stay that is a 3 block walk to one of the most beautiful ocean beaches in the Hampton's! This apartment is located in a beautiful, wooded, quiet neighborhood. Town is 1.5 miles away. This apartment has an open concept living space with a fully equipped kitchen. There are 2 cozy bedrooms and one bath with a walk in shower. We prefer families and mature adults. We supply beach towels, chairs, umbrella and beach wagon.

Guest favourite
A bright living room features tall windows that allow ample natural light. A modern sofa and coffee table are arranged on polished wooden floors. A large copper fireplace serves as the focal point, surrounded by minimalistic decor, creating a spacious and inviting atmosphere.
Home in The Hamptons
4.89 out of 5 average rating, 133 reviews

Light-filled Sag Harbor village gem

Midcentury style in the heart of Sag Harbor Historic district. Soaring 20-foot floor-to-ceiling windows and skylights throughout offer the ideal indoor-outdoor experience for enjoying all seasons. Featured in Home & Garden, the house is situated on sprawling grounds, one of the largest lots in Sag Harbor. In the winter, enjoy the Scandinavian sauna and lounge in front of the fireplace. Gunite pool open May 25 to Sept 3.

Superhost
A bright living area features a white sofa adorned with patterned blue pillows, positioned beside a rustic wooden coffee table. Large glass doors open to reveal a glimmering pool and lush outdoor landscaping, enhanced by vibrant potted plants and a shaded seating area.
Home in The Hamptons
4.89 out of 5 average rating, 134 reviews

Serene 3 Bed 2.5 Bath House w/Heated Pool

Situated off a quiet lane on a half-acre, this designer, updated, modern residence offers a peaceful and quiet Hamptons getaway. 3 wonderful bedrooms 2 modern bathroom and a heated saltwater pool ( See Pool heat and Pool Closure Details ) with mature landscaping offers a relaxing escape. Please read the additional disclosures, guidelines, and rules. No events, no parties, no smoking – no exceptions!

Top guest favourite
The living area features two comfortable sofas, a wooden coffee table, and a dining table set for four. A window allows natural light to fill the space, while decor accents create a relaxed environment. Air conditioning unit is visible on the wall.
Cottage in The Hamptons
4.97 out of 5 average rating, 357 reviews

Carriage House - Cottage in East Hampton Village

Darling cottage in East Hampton Village. Situated in a historic picturesque tree-canopied neighborhood. Easy stroll to Newtown Lane and Main Street shops. (1/2 mile). Classic atmosphere. Very comfortable, bright, and clean. A perfect place from which to enjoy East Hampton and the surrounding area. Fully renovated (2019).

Guest favourite
A spacious backyard features a heated swimming pool surrounded by a sun deck, adorned with loungers. Lush greenery and trees provide a natural backdrop to the inviting setting, while a charming house is visible in the distance.
Home in The Hamptons
4.88 out of 5 average rating, 128 reviews

4 BD w/ Heated Pool in E Hampton, Fully Furnished

Rent a beautiful and spacious 4 bedroom/3 bathroom property in East Hampton with a heated swimming pool in the backyard. This three level house with large kitchen, central A/C, BBQ in the backyard, and a garage is the perfect place to entertain guests or to relax and escape in East Hampton.

Guest favourite
A wooden deck features comfortable seating with white cushions, positioned around a small table set with tea and pastries. Lush green grass surrounds the area, dotted with tall trees, while a clear view of the harbor can be seen in the background.
Home in The Hamptons
4.83 out of 5 average rating, 41 reviews

Historic East Hampton Home - Private Beach Access

Experience breathtaking sunset views over the harbor from our beautiful mid-century modern home. Designed by Kaneji Domoto, a student of Frank Lloyd Wright, the house seamlessly blends with its stunning surroundings, offering abundant natural light and water views from nearly every room.

Guest favourite
Home in The Hamptons
4.94 out of 5 average rating, 172 reviews

1800 Historical EH Home, 1 Mile to Town!

This East Hampton cottage is conveniently located only 1 mile to Main Street, .5 miles to grocery shopping and restaurants and 2 miles to Main Beach. This 1800's farm house is possibly one of the most charming homes in all of East Hampton.

Popular amenities for Amagansett holiday rentals

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Frequently Asked Questions

  • Are there vacation rentals with a dedicated workspace in Amagansett?

    Yes! Work meets play with ease at over 200 vacation rentals in Amagansett featuring dedicated workspaces. Stay connected and productive in your home away from home.

  • Are there pet-friendly vacation rentals in Amagansett?

    Four-legged friends are welcome in Amagansett. Choose from more than 160 vacation rentals for guests traveling with pets.

  • How much does it cost to stay in apartment rentals in Amagansett?

    Experience the best of Amagansett with our apartment rentals, starting at about $150 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.

  • Do house rentals in Amagansett have a bbq area?

    Absolutely! We offer over 140 house rentals with a bbq area in Amagansett. Enjoy a tailored experience with all the comforts you desire.

  • Do house rentals in Amagansett have a gym?

    Absolutely! We offer over 70 house rentals with a gym in Amagansett. Enjoy a tailored experience with all the comforts you desire.

  • Are there Amagansett hotel rentals on Airbnb with pools?

    Yes! Dive into the perfect getaway at one of over 10 hotel rentals with pools in Amagansett, available on Airbnb. Make a splash and soak up the sun in style!

  • Do house rentals in Amagansett have self check-in?

    Absolutely! We offer over 60 house rentals with self check-in in Amagansett. Enjoy a tailored experience with all the comforts you desire.

  • Are there family-friendly cottage rentals in Amagansett?

    Amagansett has more than 10 family-friendly cottage rentals. Amenities on the property may include high chairs, travel cribs, or strollers.

Quick stats about holiday rentals in Amagansett

  • Total holiday rentals

    Explore 380 holiday rentals in Amagansett

  • Nightly prices starting at

    Amagansett holiday rentals start at £89 per night before taxes and fees

  • Verified guest reviews

    Over 5,110 verified reviews to help you choose

  • Family-friendly holiday rentals

    320 properties offer extra space & child-friendly amenities

  • Pet-friendly holiday rentals

    Find 160 rentals that welcome pets

  • Holiday rentals with a pool

    240 properties feature pools

  • Rentals with dedicated workspaces

    200 properties have a dedicated workspace

  • Wifi availability

    380 of Amagansett holiday rentals include wifi access

  • Popular amenities for guests

    Guests love Self check-in, Beachfront and Gym across Amagansett rentals

  • 4.9 Average rating

    Amagansett stays are highly rated by guests – averaging 4.9 out of 5!

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