Holiday houses 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, 483 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 cozy bedroom features a queen bed with a light blue quilt and a green loveseat nearby. Natural light enters through sliding glass doors, revealing a serene outdoor space. A decorative plant and framed artwork add a touch of interest to the room.
Guesthouse in The Hamptons
4.82 out of 5 average rating, 339 reviews

Detached bungalow w/ private bath

Cozy, simple living, in separate guest house w/ use of amenities (shared with our family of 4) including sauna & hot tub. The bungalow/guesthouse features a Queen bed, its own private bathroom (shower), small kitchenette (countertop oven, Keurig coffee maker & small fridge) and loveseat for relaxing. There is a dedicated separate outdoor seating area for 2 guests. 2 Adult guests ONLY, no children due to size of guesthouse and proximity to the pool. Please NO pets allowed since owners have pets

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, 122 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 contemporary house exterior features a combination of wood and metal finishes, set against a backdrop of lush greenery. Large glass windows provide ample natural light, and a pathway of stepping stones leads through a manicured lawn, enhancing the inviting atmosphere.
Home in The Hamptons
4.97 out of 5 average rating, 152 reviews

East Hampton (walking distance to village)

Relax by the hot tub and fire pit with local wines or walk to the village for shopping and dining. House is just a few blocks from Serafina and the famous Nick and Toni’s. Complimentary cruiser bikes included to get around town. IGA supermarket is around the corner and gas grill is on site and ready to use. The house is also walking distance to the train station if your coming from Manhattan. The second bedroom features a Murphy Bed that folds out of the wall and over the couch pictured.

Top Guest favourite
A cozy living area is shown with two comfortable sofas and a coffee table. Natural light enters through two windows adorned with bamboo shades. A flat-screen television is mounted on the wall, and a decorative rug adds warmth to the wooden flooring.
Apartment in The Hamptons
4.98 out of 5 average rating, 199 reviews

Updated apartment in historic village home

Quiet updated apartment close to Main St, boats and beaches. This second floor apartment has a private entrance and allows use of the front yard. Our home was built in 1880 but has just been renovated for a modern beach bungalow feel. The location is the perfect balance of a quiet neighborhood and close proximity to Marine Park, shops, restaurants, the Hampton Jitney and nightlife. The center of main street is less than a quarter mile from the apartment (4 minutes on foot). Walk to all!

Superhost
A bright living space features a classic sofa, two armchairs, and decorative lighting. A stone fireplace adds a cozy element, while a large window invites natural light. Indoor plants provide greenery, and a kitchen area with modern appliances is visible in the background.
Home in The Hamptons
4.85 out of 5 average rating, 133 reviews

Sag Harbor Wonder, 3 bedroom 2 Bath & Heated 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. 10 minute drive to Wolffer & ocean beaches. 3 bedrooms, 2 modern bathrooms and heated 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
Place to stay in The Hamptons
4.97 out of 5 average rating, 147 reviews

Walk-To-The-Beach House In The Dunes

(Weekly in season! Please inquire before booking!) This south-of-the highway artist residence is just three minutes by foot to the ocean. Up to 4 bedrooms + a queen sleeping loft, 2 full en site indoor bathrooms, one half off common room, 3 massive outdoor bathrooms, new central AC, multi-zone hi-fi, x2 two-person soaking hottubs. Fireplace, propane and charcoal grills, fiberoptic internet at blazing 500mbps! Only 6 mins to Montauk or Amagansett. Short walk to jitney stop.

Guest favourite
A spacious and heated swimming pool is surrounded by a brick patio and lush green landscaping. Two lounge chairs are positioned nearby, offering a tranquil spot to relax. The serene setting is enhanced by mature trees bordering the pool area.
Home in The Hamptons
4.87 out of 5 average rating, 115 reviews

Cheerful East Hampton home with Pool

Situated off of a quiet lane on one and a half-acres of land, this amazing residence offers a peaceful and quiet Hamptons getaway. The home consists of 4 wonderful bedrooms, 3.5 modern bathrooms, a heated pool & mature landscaping. Additionally, please read my disclosures and "rules". Not a party house. No Events, parties & No smoking will be permitted. The house is beautiful, tranquil and very comfortable. THANK YOU!

Guest favourite
A solar-heated pool is surrounded by a spacious bluestone patio, offering various lounge chairs and shaded areas. A brick fireplace is visible alongside a dining space, all framed by mature landscaping and trees, enhancing the outdoor relaxation experience.
Home in The Hamptons
4.97 out of 5 average rating, 198 reviews

Dream Home with a wonderful heated pool in SH

Situated on a half-acre of land, this designer, updated, modern residence offers a peaceful and quiet Hamptons getaway. 4 wonderful bedrooms 3 modern bathrooms and a solar heated pool with mature landscaping offers a relaxing escape. Please read the additional disclosures, guidelines, and rules. No events, no parties, no smoking –

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, 129 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.

Top Guest favourite
The exterior of a cottage is presented, featuring natural wood siding and a gabled roof. A solid front door is centered, with a small overhang extending above. A stone pathway leads to the entrance, framed by well-maintained landscaping and grass.
Cottage in The Hamptons
4.91 out of 5 average rating, 629 reviews

Montauk Oceanview

This fully furnished oceanview 1bd cottage steps to the beach with hardwood floors, an open beam ceiling, and a working fireplace allows you to enjoy Montauk throughout all seasons. There is a fully equipped kitchen,cable,central air,wireless,and an outside grill.

Popular amenities for Amagansett holiday rentals

When is the best time to visit Amagansett?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. price$1,206 AUD$1,197 AUD$1,122 AUD$1,342 AUD$1,125 AUD$1,451 AUD$1,638 AUD$1,710 AUD$1,243 AUD$847 AUD$897 AUD$891 AUD
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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 house rentals in Amagansett?

    Experience the best of Amagansett with our house rentals, starting at about $120 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 house rentals on Airbnb with pools?

    Yes! Dive into the perfect getaway at one of over 200 house 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 $179 AUD per night before taxes and fees

  • Verified guest reviews

    Over 5,270 verified reviews to help you choose

  • Family-friendly holiday rentals

    320 properties offer extra space and kid-friendly amenities

  • Pet-friendly accommodation

    Find 160 rentals that welcome pets

  • Holiday rentals with a pool

    240 properties feature pools

  • Rentals with dedicated workspaces

    190 properties have a dedicated workspace

  • Wi-Fi availability

    370 of Amagansett holiday rentals include Wi-Fi 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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