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

Amagansett Vacation Rentals

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Our top choices for Amagansett vacation rentals

1. Windward Shores Ocean Resort

Windward Shores Ocean Resort
3.0 star property
Napeague
8.8 out of 10, Excellent, (331 reviews)
"Omg so peaceful and beautiful. Felt like I was in paradise. My fiancee and I enjoyed every moment except checking out because we did not want to leave. Such beauty it was worth the 3 hour car ride. Perfect getaway.💜🙏"
United States
Banessa
The price is CA $188
CA $253 total
includes taxes & fees
Oct 29 - Oct 30
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 CA $225
CA $587 total
includes taxes & fees
Oct 28 - Oct 29
Unit 1021: Studio | 2nd Floor-Pool View | Starfish

3. Unit 721: Two-Bedroom | 2nd Floor-Ocean View | Sand Dollar

Unit 721: Two-Bedroom | 2nd Floor-Ocean View | Sand Dollar
Napeague
10.0 out of 10, Exceptional, (1 review)
The price is CA $377
CA $798 total
includes taxes & fees
Oct 28 - Oct 29
Unit 721: Two-Bedroom | 2nd Floor-Ocean View | Sand Dollar

4. Unit 1311: Cottage | Garden View | Deuce

Unit 1311: Cottage | Garden View | Deuce
Napeague
8.8 out of 10, Excellent, (3 reviews)
"We only needed a one night stay but this place was clean and comfortable for what we needed! The beds are super comfortable."
United States
Sherry L.
The price is CA $423
CA $862 total
includes taxes & fees
Oct 28 - Oct 29
Unit 1311: Cottage | Garden View | Deuce

5. 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 CA $225
CA $587 total
includes taxes & fees
Oct 28 - Oct 29
Unit 1011: Studio | 1st Floor-Garden View | Starfish

6. 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 CA $225
CA $587 total
includes taxes & fees
Oct 28 - Oct 29
Unit 823: Studio | 2nd Floor-Ocean View | Osprey

7. 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 CA $263
CA $639 total
includes taxes & fees
Oct 28 - Oct 29
Unit 2014: 1-Bedroom | 1st Floor-Dune View | Court Side

8. 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 CA $263
CA $639 total
includes taxes & fees
Oct 28 - Oct 29
Unit 1912: 1-Bedroom | 1st Floor-Dune View | Dunes West

9. Unit 2021: 1-Bedroom with Loft | 2nd Floor-Bay View | Court Side

Unit 2021: 1-Bedroom with Loft | 2nd Floor-Bay View | Court Side
Napeague
10.0 out of 10, Exceptional, (3 reviews)
"Loved it! Highly recommend! Beautiful property."
United States
Lacy N.
The price is CA $332
CA $735 total
includes taxes & fees
Oct 28 - Oct 29
Unit 2021: 1-Bedroom with Loft | 2nd Floor-Bay View | Court Side

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

Unit 1012: Studio | 1st Floor-Garden View | Starfish
Napeague
The price is CA $225
CA $587 total
includes taxes & fees
Oct 28 - Oct 29
Unit 1012: Studio | 1st Floor-Garden View | Starfish

11. Unit 1827: 1-Bedroom with Loft | 2nd Floor-Partial Ocean View | Dunes East

Unit 1827: 1-Bedroom with Loft | 2nd Floor-Partial Ocean View | Dunes East
Napeague
8.0 out of 10, Very good, (2 reviews)
"Lovely community on the beach"
United States
Jordan C.
The price is CA $332
CA $735 total
includes taxes & fees
Oct 28 - Oct 29
Unit 1827: 1-Bedroom with Loft | 2nd Floor-Partial Ocean View | Dunes East

12. 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 CA $225
CA $581 total
includes taxes & fees
Oct 28 - Oct 29
Unit 1023: Studio | 2nd Floor-Pool View | Starfish

13. Unit 1911: 1-Bedroom | 1st Floor-Dune View | Dunes West

Unit 1911: 1-Bedroom | 1st Floor-Dune View | Dunes West
Napeague
10.0 out of 10, Exceptional, (2 reviews)
"We love everything about this place. This was our 2nd time staying here and plan on coming back. The kitchen was redone and is beautiful. The location is perfect. It's close to the restaurants and shops in Montauk and Amagansett. The back deck is so roomy and comfortable. Sitting out there, listening to the ocean is heaven. We highly recommend this. "
United States
DiAnn E.
The price is CA $339
CA $745 total
includes taxes & fees
Oct 28 - Oct 29
Unit 1911: 1-Bedroom | 1st Floor-Dune View | Dunes West

14. Unit 1722: 1-Bedroom with Loft | 2nd Floor-Ocean Front Ocean View | Ocean Edge

Unit 1722: 1-Bedroom with Loft | 2nd Floor-Ocean Front Ocean View | Ocean Edge
Napeague
10.0 out of 10, Exceptional, (2 reviews)
"First time in the area, and we hope to return. "
United States
Amy E.
The price is CA $363
CA $777 total
includes taxes & fees
Oct 28 - Oct 29
Unit 1722: 1-Bedroom with Loft | 2nd Floor-Ocean Front Ocean View | Ocean Edge

15. Unit 1711: 1-Bedroom | 1st Floor-Ocean Front | Ocean Edge

Unit 1711: 1-Bedroom | 1st Floor-Ocean Front | Ocean Edge
Napeague
The price is CA $309
CA $703 total
includes taxes & fees
Oct 28 - Oct 29
Unit 1711: 1-Bedroom | 1st Floor-Ocean Front | Ocean Edge

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 CA $263
CA $639 total
includes taxes & fees
Oct 28 - Oct 29
Unit 1815: 1-Bedroom | 1st Floor-Garden View | Dunes East

17. 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 CA $263
CA $633 total
includes taxes & fees
Oct 28 - Oct 29
Unit 2012: 1-Bedroom | 1st Floor-Dune View | Court Side

18. Unit 1411: 1-Bedroom | 1st Floor-Garden View | Swordfish

Unit 1411: 1-Bedroom | 1st Floor-Garden View | Swordfish
Napeague
9.0 out of 10, Wonderful, (2 reviews)
"Fantastic as always!!"
United States
robert R.
The price is CA $339
CA $737 total
includes taxes & fees
Oct 28 - Oct 29
Unit 1411: 1-Bedroom | 1st Floor-Garden View | Swordfish

19. 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 CA $225
CA $587 total
includes taxes & fees
Oct 28 - Oct 29
Unit 821: Studio | 2nd Floor-Ocean View | Osprey

20. Unit 511: Cottage | Ocean View | Nautilus

Unit 511: Cottage | Ocean View | Nautilus
Napeague
10.0 out of 10, Exceptional, (3 reviews)
"Had a great weekend. Right on beach. Beautiful."
United States
Steven B.
The price is CA $604
CA $1,097 total
includes taxes & fees
Oct 28 - Oct 29
Unit 511: Cottage | Ocean View | Nautilus
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 vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation 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 or room. 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 vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . 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 . 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 vacation rental 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 vacation 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 short-term rentals, that won’t be hard to do.

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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?

Unobstructed Ocean Views ! A Beautiful Montauk Getaway : You might want to consider this vacation home rental near Amagansett, which is located on the beach and has an outdoor pool, a fireplace, and a barbecue grill 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 vacation rentals are there in Amagansett?

With 123 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.