A coastal sunset with a beach, ocean waves, and a road leading to a distant town.

Amagansett Holiday Rentals

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Our top choices for Amagansett holiday rentals

1. Windward Shores Ocean Resort

Windward Shores Ocean Resort
3.0 star property
Napeague
8.8 out of 10, Excellent, (324 reviews)
"Easy access to the beach. Perfect weather. Nicely furnished and updated rooms and bathrooms. The gym is tiny- not much equipment. The location is perfect for Montauk and Amagansett. The staff were very nice and hard working."
United States
Gaurang J
The price is NZ$290
includes taxes & fees
12 Oct - 13 Oct
Windward Shores Ocean Resort

2. Unit 1021: Studio | 2nd Floor-Pool View | Starfish

Unit 1021: Studio | 2nd Floor-Pool View | Starfish
Napeague
9.8 out of 10, Exceptional, (6 reviews)
"Comfortable accommodations, easy access to pool and beach, close to restaurants, quiet."
United States
Liana T.
The price is NZ$744
includes taxes & fees
5 Oct - 6 Oct
Unit 1021: Studio | 2nd Floor-Pool View | Starfish

3. Unit 811: Studio | 1st Floor-Garden View | Osprey

Unit 811: Studio | 1st Floor-Garden View | Osprey
Napeague
10.0 out of 10, Exceptional, (1 review)
"Great stay. Unfortunately, they told us there was pickleball but there wasn’t. "
United States
Kevin C.
The price is NZ$978
includes taxes & fees
31 Oct - 1 Nov
Unit 811: Studio | 1st Floor-Garden View | Osprey

4. Unit 1311: Cottage | Garden View | Deuce

Unit 1311: Cottage | Garden View | Deuce
Napeague
8.0 out of 10, Very good, (2 reviews)
"Great location a few steps always from the ocean and a few minutes away from town"
United States
Jessica S.
The price is NZ$1,092
includes taxes & fees
5 Oct - 6 Oct
Unit 1311: Cottage | Garden View | Deuce

5. Unit 1023: Studio | 2nd Floor-Pool View | Starfish

Unit 1023: Studio | 2nd Floor-Pool View | Starfish
Napeague
7.0 out of 10, Good, (2 reviews)
"Great spot! Nice to have beach access w/ chairs and umbrellas"
United States
Michael M.
The price is NZ$877
includes taxes & fees
7 Oct - 8 Oct
Unit 1023: Studio | 2nd Floor-Pool View | Starfish

6. Unit 1012: Studio | 1st Floor-Garden View | Starfish

Unit 1012: Studio | 1st Floor-Garden View | Starfish
Napeague
The price is NZ$877
includes taxes & fees
11 Oct - 12 Oct
Unit 1012: Studio | 1st Floor-Garden View | Starfish

7. Unit 823: Studio | 2nd Floor-Ocean View | Osprey

Unit 823: Studio | 2nd Floor-Ocean View | Osprey
Napeague
10.0 out of 10, Exceptional, (2 reviews)
"Loved having coffe on the deck enjoying the views. The location was perfect for us. Hope to be back!"
United States
Dianna L.
The price is NZ$877
includes taxes & fees
18 Oct - 19 Oct
Unit 823: Studio | 2nd Floor-Ocean View | Osprey

8. Unit 1817: 1-Bedroom | 1st Floor-Garden View | Dunes East

Unit 1817: 1-Bedroom | 1st Floor-Garden View | Dunes East
Napeague
9.6 out of 10, Exceptional, (4 reviews)
"Very clean, great location, and perfect place to spend a sunny weekend in the Hamptons!"
United States
Krista M.
Unit 1817: 1-Bedroom | 1st Floor-Garden View | Dunes East

9. Unit 1011: Studio | 1st Floor-Garden View | Starfish

Unit 1011: Studio | 1st Floor-Garden View | Starfish
Napeague
10.0 out of 10, Exceptional, (1 review)
"We very much enjoyed our stay, would definitely book again. "
United States
Mark F.
The price is NZ$877
includes taxes & fees
5 Oct - 6 Oct
Unit 1011: Studio | 1st Floor-Garden View | Starfish

10. Unit 1816: 1-Bedroom | 1st Floor-Garden View | Dunes East

Unit 1816: 1-Bedroom | 1st Floor-Garden View | Dunes East
Napeague
10.0 out of 10, Exceptional, (1 review)
"Love place to stay. The beach was amazing "
United States
Brett
The price is NZ$1,057
includes taxes & fees
31 Oct - 1 Nov
Unit 1816: 1-Bedroom | 1st Floor-Garden View | Dunes East

11. Unit 821: Studio | 2nd Floor-Ocean View | Osprey

Unit 821: Studio | 2nd Floor-Ocean View | Osprey
Napeague
8.0 out of 10, Very good, (1 review)
The price is NZ$877
includes taxes & fees
18 Oct - 19 Oct
Unit 821: Studio | 2nd Floor-Ocean View | Osprey

12. Unit 2014: 1-Bedroom | 1st Floor-Dune View | Court Side

Unit 2014: 1-Bedroom | 1st Floor-Dune View | Court Side
Napeague
10.0 out of 10, Exceptional, (1 review)
"Great"
United States
Anonymous traveller
The price is NZ$1,012
includes taxes & fees
7 Oct - 8 Oct
Unit 2014: 1-Bedroom | 1st Floor-Dune View | Court Side

13. Unit 2012: 1-Bedroom | 1st Floor-Dune View | Court Side

Unit 2012: 1-Bedroom | 1st Floor-Dune View | Court Side
Napeague
8.0 out of 10, Very good, (3 reviews)
"We had such a great stay here at the condo. The space was perfect and location was great. We came Columbus day weekend and would like to come back durijg summer season to use the facilities more. Everyone was very responsive during the process prior to arrival and the staff was excellent when on site. Highly recommend!!"
United States
Samantha R.
The price is NZ$811
includes taxes & fees
15 Oct - 16 Oct
Unit 2012: 1-Bedroom | 1st Floor-Dune View | Court Side

14. Unit 1022: Studio | 2nd Floor-Pool View | Starfish

Unit 1022: Studio | 2nd Floor-Pool View | Starfish
Napeague
6.0 out of 10, (1 review)
The price is NZ$877
includes taxes & fees
7 Oct - 8 Oct
Unit 1022: Studio | 2nd Floor-Pool View | Starfish

15. Unit 1912: 1-Bedroom | 1st Floor-Dune View | Dunes West

Unit 1912: 1-Bedroom | 1st Floor-Dune View | Dunes West
Napeague
10.0 out of 10, Exceptional, (1 review)
"Loved the unit and the grounds! Everything was as in description & super friendly staff!"
United States
cathleen f.
The price is NZ$978
includes taxes & fees
18 Oct - 19 Oct
Unit 1912: 1-Bedroom | 1st Floor-Dune View | Dunes West

16. Unit 1815: 1-Bedroom | 1st Floor-Garden View | Dunes East

Unit 1815: 1-Bedroom | 1st Floor-Garden View | Dunes East
Napeague
9.0 out of 10, Wonderful, (4 reviews)
"Overall, it was a great spot— the private beach, pool, and attentive staff were the cherry on top to the convenient location, and we’ll maintained unit and property"
United States
Michelle R.
The price is NZ$1,012
includes taxes & fees
7 Oct - 8 Oct
Unit 1815: 1-Bedroom | 1st Floor-Garden View | Dunes East

17. Unit 1825: 1-Bedroom with Loft | 2nd Floor-Partial Ocean View | Dunes East

Unit 1825: 1-Bedroom with Loft | 2nd Floor-Partial Ocean View | Dunes East
Napeague
10.0 out of 10, Exceptional, (1 review)
"Clean and very cute duplex. Great location."
United States
naz r.
The price is NZ$1,111
includes taxes & fees
31 Oct - 1 Nov
Unit 1825: 1-Bedroom with Loft | 2nd Floor-Partial Ocean View | Dunes East

18. Unit 1713: 1-Bedroom | 1st Floor-Ocean Front | Ocean Edge

Unit 1713: 1-Bedroom | 1st Floor-Ocean Front | Ocean Edge
Napeague
Unit 1713: 1-Bedroom | 1st Floor-Ocean Front | Ocean Edge

19. Unit 1822: 1-Bedroom with Loft | 2nd Floor-Partial Ocean View | Dunes East

Unit 1822: 1-Bedroom with Loft | 2nd Floor-Partial Ocean View | Dunes East
Napeague
10.0 out of 10, Exceptional, (3 reviews)
"We had a wonderful stay at this property! Very clean, just steps to the beach and close to everything we love in the Hamptons!"
United States
Pamela
The price is NZ$1,171
includes taxes & fees
18 Oct - 19 Oct
Unit 1822: 1-Bedroom with Loft | 2nd Floor-Partial Ocean View | Dunes East

20. Unit 1811: 1-Bedroom | 1st Floor-Garden View | Dunes East

Unit 1811: 1-Bedroom | 1st Floor-Garden View | Dunes East
Napeague
The price is NZ$811
includes taxes & fees
15 Oct - 16 Oct
Unit 1811: 1-Bedroom | 1st Floor-Garden View | Dunes East
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

Find out more about Amagansett

You always said you would go on a dream holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our Amagansett holiday rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your holiday just got upgraded.

As much as you love your vacation rental, it’s always good to get out and explore to soak up Amagansett. Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in Amagansett. Seeing all the best attractions is bound to make you fall in love with Amagansett. Who knows, you may even be tempted to extend your stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true. 

It’s your escape so why share it? You deserve your own slice of paradise. Booking your holiday rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in Amagansett short-term rentals, that won’t be hard to do.

Frequently asked questions

Can I find holiday rentals in Amagansett?

Yes, there are holiday rentals close to the most popular sights in Amagansett, or you can select a more secluded 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 coffee shops during your trip.

What are some of the best holiday rentals that Amagansett has to offer?

Unobstructed Ocean Views ! A Beautiful Montauk Getaway : This holiday home rental outside of Amagansett is located on the beach, and has an outdoor pool, a fireplace and a BBQ to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop. Kick off your shoes and enjoy yourself with a patio and a garden.

How many holiday rentals are there in Amagansett?

With 123 Expedia holiday rentals, you're guaranteed 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 holiday rentals like in Amagansett?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Amagansett. Holiday rentals feature amenities such as patios, hot tubs and fire pits to help you enjoy your stay. If you're concerned about a sanitised environment, holiday rentals can provide a sense of security away from shared hotel lifts and busy concierge desks while still allowing you the enjoyment of travel. You'll also get more space in a holiday rental than in a traditional hotel, which makes a holiday rental a popular choice for a small group gathering.