Vacation rentals in Amagansett

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Top-rated vacation 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, 476 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

Top guest favourite
An enclosed outdoor living space features a wooden deck overlooking a heated pool. Furnished with a large round table and comfortable seating, natural light floods through the screens, creating an airy atmosphere. Elegant trees and lounge chairs visible outside enhance the serene environment.
Home in The Hamptons
4.94 out of 5 average rating, 318 reviews

Amazing Home close to Everything -

Elegantly designed home featuring modern appliances, a seasonal heated pool, and situated just moments away from ocean beaches, Wolffer Vineyard, and the vibrant Bridgehampton/Sag Harbor villages. Set within meticulously curated landscaping, this property embodies perfection and meticulous attention to detail. Familiarize yourself with our disclosures, guidelines, and house rules. We maintain a strict no events, no parties, and no smoking policy — our home and property grouds are smoke-free.

Guest favourite
An open-concept living space features a dining area with a rectangular wooden table adorned with a decorative bowl. A spacious couch is positioned near a fireplace, with large windows allowing ample natural light. A stylish chandelier hangs above, complementing the high, pitched ceiling.
Villa in The Hamptons
4.99 out of 5 average rating, 111 reviews

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.

Top guest favourite
Place to stay in The Hamptons
4.97 out of 5 average rating, 145 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.

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, 102 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

Guest favourite
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.

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!

Guest favourite
A wide sandy beach stretches towards the horizon, where soft waves gently lap at the shore. Tall lifeguard stands are positioned along the beach, with a few distant figures walking. The sky features a gradient of muted colors as the sun sets, creating a serene atmosphere.
Apartment in The Hamptons
4.95 out of 5 average rating, 224 reviews

Sunny Southampton Studio

Newly renovated sun drenched, spacious studio in Southampton. Five minute drive to Main Street, while still in close proximity to some of the most beautiful beaches. Queen size bed and queen size pull out couch. Full kitchen with new appliances and full bathroom. BEACH PASS for Coopers beach is available upon advanced request—please let me know the day before you arrive

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, 354 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).

Top guest favourite
Home in The Hamptons
4.99 out of 5 average rating, 233 reviews

Designer East Hampton Farmhouse -Cozy Fall Getaway

Tucked away on a private lot, just minutes from East Hampton Village, Amagansett Village, and Ocean Beaches this 3-bedroom, 2.5-bath cottage features a heated saltwater pool & Mahogany outdoor shower, outdoor lounge area, and charming children’s playhouse - creating the perfect setting for relaxing days spent at home.

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, 125 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
Home in The Hamptons
4.93 out of 5 average rating, 170 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 vacation rentals

When is the best time to visit Amagansett?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. price$1,132 CAD$1,123 CAD$1,053 CAD$1,259 CAD$1,056 CAD$1,362 CAD$1,537 CAD$1,605 CAD$1,167 CAD$795 CAD$842 CAD$837 CAD
Avg. temp-2 °C-1 °C3 °C8 °C13 °C18 °C21 °C21 °C17 °C11 °C6 °C1 °C

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 cottage rentals in Amagansett?

    Experience the best of Amagansett with our cottage rentals, starting at about $260 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.

  • Do cottage rentals in Amagansett have a bbq area?

    Absolutely! We offer over 10 cottage 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 vacation rentals in Amagansett

  • Total vacation rentals

    Explore 380 vacation rentals in Amagansett

  • Nightly prices starting at

    Amagansett vacation rentals start at $168 CAD per night before taxes and fees

  • Verified guest reviews

    Over 5,110 verified reviews to help you choose

  • Family-friendly vacation rentals

    320 properties offer extra space and kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 160 rentals that welcome pets

  • Vacation rentals with a pool

    240 properties feature pools

  • Rentals with dedicated workspaces

    200 properties have a dedicated workspace

  • Wifi availability

    380 of Amagansett vacation 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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