Amagansett Vacation Rentals

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Check prices for these dates

In two weeks
Jan 30 - Feb 1
In two months
Mar 13 - Mar 15
In three months
Apr 10 - Apr 12
In four months
May 8 - May 10

Our top choices for Amagansett vacation rentals

WiFi

Apartment in Napeague

White Studio Apt w/ Balcony, Tub & Ocean view!
8.0 out of 10, Very Good, (1 review)
The price is ￥70,048
￥133,696 total
includes taxes & fees
Jan 28 - Jan 29
White Studio Apt w/ Balcony, Tub & Ocean view!
Exterior

Apartment in Napeague

Modern 1BR Apt w/ private balcony!
6.0 out of 10, (1 review)
"Check in - out unit was given to another group so had to wait for that to be sorted out. Several things in our unit were broken (ex. TV, fan, blinds) and some attention to cleaning details (ex. Toilet, stains in upholstery). But great location and beach. Helpful staff on the beach to help you get chairs and umbrellas set up. "
Canada
Brynne B.
The price is ￥70,035
￥133,478 total
includes taxes & fees
Jan 25 - Jan 26
Modern 1BR Apt w/ private balcony!
Lobby

Aparthotel in Montauk

Montauk Manor
3.5 star property
9.2 out of 10, Wonderful, (1,281 reviews)
"Very beautiful place, staff are amazing. Thank you"
United States
Frank
The price is ￥21,961
￥28,191 total
includes taxes & fees
Jan 20 - Jan 21
Montauk Manor
Beach

Cottage in Hampton Bays

Seabreeze #4: Charming Cottage Footsteps to the Beach
8.8 out of 10, Excellent, (3 reviews)
"Great location. Walk to the beautiful beach. However, the couch was broken, tub did not drain. Off season price is still quite high for dated amenities, but that's the price in the Hamptons you pay."
United States
Karl L.
The price is ￥8,715
￥70,422 total
includes taxes & fees
Jan 20 - Jan 21
Seabreeze #4: Charming Cottage Footsteps to the Beach
Fridge, microwave, oven, stovetop

Vacation Home in East Hampton

Blackberry: Private home with jacuzzi year-round
9.0 out of 10, Wonderful, (4 reviews)
"We had a great time staying here. The home is well worn and there are some fixtures that should be replaced "
United States
Suzanne R.
The price is ￥15,687
￥154,963 total
includes taxes & fees
Feb 12 - Feb 13
Blackberry: Private home with jacuzzi year-round
Interior

Vacation Home in Bay Point

Sag Harbor Water View w Dock 1.5ml from town
The price is ￥713,025
￥1,012,678 total
includes taxes & fees
Jan 27 - Jan 28
Sag Harbor Water View w Dock 1.5ml from town
Smart TV

Cottage in Hampton Bays

Seabreeze #3: Cozy Cottage by the beach
10.0 out of 10, Exceptional, (1 review)
The price is ￥8,756
￥72,210 total
includes taxes & fees
Jan 29 - Jan 30
Seabreeze #3: Cozy Cottage by the beach
Smart TV, fireplace

Vacation Home in Sag Harbor

Spacious 5-bedroom house with water views and 2 houses from the bay.
The price is ￥633,800
￥1,021,730 total
includes taxes & fees
Feb 14 - Feb 15
Spacious 5-bedroom house with water views and 2 houses from the bay.
Terrace/patio

Vacation Home in Greenport

American Beech in Greenport - Petite King Room 7
9.0 out of 10, Wonderful, (4 reviews)
"Great job "
United States
emilio
The price is ￥22,025
￥35,845 total
includes taxes & fees
Jan 22 - Jan 23
American Beech in Greenport - Petite King Room 7
Smart TV, fireplace, table tennis, books

Vacation Home in Water Mill

NEW Luxury 7BR Water Mill Estate – Salt Pool, Sauna & Cold Plunge, Mins to Beach
10.0 out of 10, Exceptional, (6 reviews)
"A few of us moms plan a midweek getaway every year — and this trip to Water Mill/Southampton was our favorite yet. We’ve stayed in some stunning homes over the years, but this one truly exceeded all expectations. Unlike many properties, it’s even more beautiful in person — spacious, serene, and clearly designed with care and intention.Each bedroom was thoughtfully furnished and incredibly comfortable, with its own bathroom, giving everyone plenty of privacy and space to unwind. The layout is...
United States
Michele L.
The price is ￥664,254
￥1,170,933 total
includes taxes & fees
Jan 16 - Jan 17
NEW Luxury 7BR Water Mill Estate – Salt Pool, Sauna & Cold Plunge, Mins to Beach
One Bedroom Condo King with Ocean view | Living area | 55-inch Smart TV with digital channels, Netflix, Hulu

Condo in Downtown Montauk

Offshore Residences
4.5 star property
The price is ￥73,073
￥101,673 total
includes taxes & fees
Jan 18 - Jan 19
Offshore Residences
Smart TV, books

Cottage in Greenport

The Greenport Beach Cottage: 3 Min Walk to Beach, 1 mile to Town
10.0 out of 10, Exceptional, (1 review)
"Wonderful house. Immaculate with all the provisions you can hope for. Perfect location and beautifully done!"
United States
Jeannette M.
The price is ￥46,964
￥97,491 total
includes taxes & fees
Feb 5 - Feb 6
The Greenport Beach Cottage: 3 Min Walk to Beach, 1 mile to Town
Smart TV, fireplace

Vacation Home in Greenport

Renovated Townhouse walk to all
9.6 out of 10, Exceptional, (9 reviews)
"What a wonderful spot! We could walk to town, and a beach. We loved our stay in Greenport! "
United States
Laura B.
The price is ￥42,268
￥92,671 total
includes taxes & fees
Jan 18 - Jan 19
Renovated Townhouse walk to all
Living area

Vacation Home in Sag Harbor

Newly Renovated Sag Harbor Beach House with Pool
2.0 star property
The price is ￥73,652
￥148,172 total
includes taxes & fees
Jan 20 - Jan 21
Newly Renovated Sag Harbor Beach House with Pool
Dining

Vacation Home in Greenport

Northfork Townhouse walk to all
10.0 out of 10, Exceptional, (5 reviews)
"Five of us wound up staying. We were celebrating birthdays and just wanted somewhere to enjoy each other‘s company and relax. Originally planned for six people it would have been two in the full size bed so five was just right actually. The place is comfortable and on a quiet street close to everything. This owner was very prompt with responses and helpful with information. It was really very nice. "
United States
Doreen J.
The price is ￥46,566
￥96,856 total
includes taxes & fees
Jan 21 - Jan 22
Northfork Townhouse walk to all
Living area

Vacation Home in Wainscott

Cozy 5 Bedroom With Wi-fi And Air Condition
The price is ￥236,724
￥307,748 total
includes taxes & fees
Jan 19 - Jan 20
Cozy 5 Bedroom With Wi-fi And Air Condition
Exterior

Vacation Home in Southold

Beautifully farmhouse
10.0 out of 10, Exceptional, (3 reviews)
"We spent a few days to attend a family wedding. We were 7 and the house was extremely comfortable for all of us. The house is 2 floors and there is no bathroom upstairs so keep that in mind when assigning sleeping arrangements. We found a well stocked welcome basket and a bottle of wine which were very much appreciated. The location is perfect as it is in the middle of wine country, less than 2 miles from the beach and near quaint little towns. We would definitely stay there again. "
United States
josie c.
The price is ￥95,070
￥186,100 total
includes taxes & fees
Jan 27 - Jan 28
Beautifully farmhouse
Property grounds

Vacation Home in Greenport

Beachfront Greenport Villa
9.6 out of 10, Exceptional, (10 reviews)
"Great views! The deck looks as though it is collapsing. The doors to the sunroom do not open easy and seem mostly broken. Also, loud traffic in the morning. Good house not a great house."
United States
Claudine F.
Beachfront Greenport Villa
Smart TV, fireplace, stereo

Vacation Home in Southampton

Minutes from the beach, brand new 4 bedroom
10.0 out of 10, Exceptional, (3 reviews)
"perfect for families"
United States
Okito H.
The price is ￥71,303
￥175,780 total
includes taxes & fees
Jan 17 - Jan 18
Minutes from the beach, brand new 4 bedroom
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Amagansett Hotel Reviews

The Harbor Front Inn

The Harbor Front Inn

10/10 Excellent
"The staff was wonderful and the room and views fantastic."
Cathleen 2-night trip
Posted 3 days ago
The Harbor Front Inn

Find out more about Amagansett

Search for holiday rentals in Amagansett on Expedia! You can easily find your home rentals, villas, holiday apartments in Amagansett using one of the methods below:

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Frequently asked questions

Can I find vacation rentals in Amagansett?

Yes, we offer vacation rentals near well known sights in Amagansett, or you can select a more remote option if you're looking for a relaxing stay. Nature enthusiasts will enjoy the beaches in Amagansett. Make sure you have time to check out the seafood restaurants and coffeehouses during your trip.

What are some of the best vacation rentals in Amagansett?

Summer 2026 Now Available! Grab an amazing property in the heart of the Hamptons: You might want to consider this vacation rental near Amagansett, which is located near the beach and has an outdoor pool, a fireplace, and a barbecue grill to put you at ease in your new surroundings. It has 7 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. It offers a patio, a garden, and a selection of games so you can immerse yourself in your vacation.

How many vacation rentals are there in Amagansett?

With 124 Expedia vacation rentals, you're sure to find just the right place for your Amagansett stay.

What can I see and do in Amagansett?

Indian Wells Beach and Amagansett Beach are a couple of scenic spots to enjoy the outdoors, whereas Amelia Cottage Museum is one of the cultural attractions. While here, Hither Hills State Park and The Hamptons Beaches are other places worth a visit.

What are vacation rentals like in Amagansett?

Vacation rentals are private accommodations you can reserve for a few days or a quick weekend in Amagansett. Vacation rentals offer extras such as patios, hot tubs, and fire pits so you'll be comfy for your stay. If you're concerned about cleanliness, vacation rentals can provide a sense of safety away from shared hotel elevators and busy reception areas while still allowing you the experience of travel. You'll also find more space in a vacation rental than in a standard hotel, which makes a vacation rental a popular option for small groups.