Amagansett vacation rentals

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Top-rated vacation rentals in Amagansett

Guests agree: these vacation rentals are highly rated for location, cleanliness, and more.

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Guest favorite

Cabin in Montauk

4.96 out of 5 average rating, 424 reviews

Montauk | Tiny Cottage in Private Hither Woods

A little cabin on our property in Hither Woods. A cozy hideaway conveniently located 12 minutes walk from Gurney's Beach Resort, 16 minute walk from public path to beach, and 6 minutes drive from Montauk town for restaurants and nightlife. Good for couples and solo adventurers, the space is private and homey, with outdoor shower and Chimenea fire pit. The main house is 65ft away, but we honor your privacy. The cottage comes with WiFi, window A/C and complimentary coffee or tea. Parking for 1 car

Oct 22 – 29

ﺩ.ﺇ1,193 per night

Guest favorite

Home in East Hampton

4.94 out of 5 average rating, 202 reviews

Private beach Historical House with large property

Entire three-story house. 3 large bedrooms and 3 FULL BATHROOMS on a very private, 2+acre wood lot on the bay in Historical East Hampton with private beach access. Fully renovated in 2018 with modern amenities while preserving the original charm. A/C and heating. Private upper floor with bedroom + sitting area for office and extra sleeping. Modern kitchen with island that opens to living room with fireplace. Walk through the secluded backyard to enjoy the amazing sunsets. Ideal for fishing.

Jan 29 – Feb 5

ﺩ.ﺇ3,005 per night

Guest favorite

Apartment in Sag Harbor

4.96 out of 5 average rating, 132 reviews

Hamptons Hills Escape

Located in a quiet and safe neighborhood tucked into the woods of Sag Harbor, yet just a 10-minute drive from Sag Harbor town. Down the road is "Morton's Wildlife Refuge" with a beautiful walk to a beach and where birds eat seed directly from your hand. The lovely Long Beach is 5 minutes away - day passes are available. You only have one entrance/exit to deal with, the white door at the top of the wooden stairs that are pictured. Perfect for a couple looking to cook, relax, and spin records.

Aug 28 – Sep 4

ﺩ.ﺇ1,396 per night

Guest favorite

Condo in Montauk

4.99 out of 5 average rating, 181 reviews

Montauk Waterfront Condo w/ Sunset Views

Modern 1 Bedroom Condo in gated community (Rough Riders) with sunset views from beautiful deck. The community has multiple tennis courts, pool, jacuzzi, and sauna (pool area only open Late May - early October). The property is great for walks along the boardwalk and many guests enjoy fishing and swimming off the pier. The unit is less than a 5 minute car / Uber ride to town and a short 5-10 minute walk to Navy Beach and Duryea's. Strong wifi in unit, Smart TV ( Netflix, etc, - no cable)

Mar 4 – 11

ﺩ.ﺇ1,404 per night

Guest favorite

Home in East Hampton

4.97 out of 5 average rating, 120 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.

Oct 15 – 22

ﺩ.ﺇ2,582 per night

Guest favorite

Home in Montauk

4.87 out of 5 average rating, 180 reviews

Laid-Back Bungalow. 10 min Walk to Beach & Town!

Discounts available for longer stays. Find us @studiomtk to inquire about best pricing. Historic Montauk fisherman's cottage tastefully re-made into a stylish 2-bd beach getaway located within walking distance of the beach & downtown. Plywood accents, handmade furniture & eclectic finishes create a cool, laid-back vibe. Westward views across Fort Pond provide sunlight all day & beautiful sunsets. Designed by Studio MTK, this is Montauk at its best! EH Rental Registry: 22-1360

Jan 5 – 12

ﺩ.ﺇ1,897 per night

Guest favorite

Home in East Hampton

4.97 out of 5 average rating, 116 reviews

Explore the Water & Woods at a Relaxing Retreat

Flick through records under soaring ceilings and hang out in the year-round hot tub at this East Hampton open-plan retreat. Unwind in the wooded backyard, take a dip in the pool or spa, detox in the sauna, grill on BBQ, relax in the movie-theatre seats to watch a film, then snuggle up to fireplace or firepit before drifting to sleep in super comfy beds. Minutes to village, beaches and hiking trails. Terrific for families & friends looking for a relaxing getaway.

Dec 19 – 26

ﺩ.ﺇ3,349 per night

Guest favorite

Apartment in Sag Harbor

4.98 out of 5 average rating, 117 reviews

Sag Harbor Retreat

Experience the many wonderful things the Hamptons has to offer in the Summer in centrally-located Sag Harbor. Our place is a professionally-decorated luxury apartment with its own entrance, yard and two parking spaces. This home-away-from-home is an immaculate and well-appointed retreat located in Sag Harbor. Great for couples and solo adventurers. Close to Sag Harbor's Main Street with abundant recreational activities, shopping and restaurants.

May 17 – 24

ﺩ.ﺇ2,982 per night

Guest favorite

Guest suite in East Hampton

4.89 out of 5 average rating, 222 reviews

Private Cozy Cottage with Pool / Private Beach

**POOL CLOSES SEPTEMBER 30TH** **POOL opens last week of May** This is a guest house for 1 or 2 adults. Its separate from the main house. Kids are allowed but must bring own sleeping arrangements. You do NOT have to do any chores before checking out. **PETS NOT ALLOWED** I hate to do this but someone ruined it for everyone. Max Occupancy: 4 Guests can only bring 1 vehicle since there is not enough room in the driveway

May 16 – 23

ﺩ.ﺇ984 per night

Guest favorite

Home in Sag Harbor

4.85 out of 5 average rating, 250 reviews

Exclusive Sag Harbor Compound

A private country compound in heart of Sag Harbor. House just gut renovated with all top of line (all Wolf and Subzero appliances). The main house is 3 bedrooms, 3.5 bath main house PLUS separate large guest cottage (with a King bed, bar fridge, and full bathroom). Gunite pool (i.e., salt chlorinated which makes it feels like clean freshwater). Walk to town, bay beach, public tennis courts, 1000 acre nature preserve.

Dec 5 – 12

ﺩ.ﺇ1,924 per night

Guest favorite

Home in Montauk

4.91 out of 5 average rating, 418 reviews

DITCH PLAINS SURF HOUSE

Beach house on quiet street, 200 yards to Montauk's best surfing beach, Ditch Plains. The house is a simple all white home with 2 decks, BBQ, bikes, kayak, and easy open floorplan. You can hear the ocean all day long on this hidden Montauk street. Easily walk or bike to the beach, where you find waves, food trucks in the summer & miles of sand and ocean heading west to Montauk.

Mar 21 – 28

ﺩ.ﺇ822 per night

Guest favorite

Guest suite in Cutchogue

4.88 out of 5 average rating, 586 reviews

Walk to Vineyards, Beaches, Farms & Town

Private bungalow with a separate entrance in a historical tudor home. Spacious bedroom with king-sized bed, kitchenette and bathroom. Two bikes, cable TV, internet, AC, beach towels, parking, snacks, coffee and water all provided. Walking distance to the beach, restaurants, shops, vineyards, grocery, farms and fish market. Jitney stop is one block away!

Oct 15 – 22

ﺩ.ﺇ626 per night

Vacation rentals for every style

Get the amount of space that is right for you

Popular amenities for Amagansett vacation rentals

Laptop-friendly workspace

Stay near Amagansett's top sights

Indian Wells Beach61 locals recommend

La Fondita63 locals recommend

The Stephen Talkhouse136 locals recommend

Indian Wells Tavern20 locals recommend

Cirillos Markets Amagansett IGA51 locals recommend

Hampton Chutney Co.69 locals recommend

Other great vacation rentals in Amagansett

Guest favorite

Home in Greenport

4.92 out of 5 average rating, 423 reviews

Blue Bay Dream

Jan 14 – 21

ﺩ.ﺇ447 per night

Guest favorite

Home in East Hampton

4.92 out of 5 average rating, 128 reviews

Heated pool, games room, near beach, kid-friendly

Oct 23 – 30

ﺩ.ﺇ2,537 per night

Guest favorite

Home in East Hampton

4.91 out of 5 average rating, 142 reviews

Charming Quiet Cottage

Nov 19 – 26

ﺩ.ﺇ1,265 per night

Guest favorite

Home in Sag Harbor

4.95 out of 5 average rating, 129 reviews

Luxury Private King Suite + 2 Floor Living Space

Dec 23 – 30

ﺩ.ﺇ1,553 per night

Guest favorite

Home in East Hampton

4.87 out of 5 average rating, 188 reviews

Heated Saltwater Pool, Walk to Beach, Dog Friendly

Sep 19 – 26

ﺩ.ﺇ2,083 per night

Guest favorite

Home in Sag Harbor

4.97 out of 5 average rating, 260 reviews

Sag Harbor Cottage, Walk to the Beach!

Sep 1 – 8

ﺩ.ﺇ3,031 per night

Guest favorite

Home in Southampton

4.9 out of 5 average rating, 215 reviews

PICTURE PERFECT SOUTHAMPTON HOME-

Sep 14 – 21

ﺩ.ﺇ2,114 per night

Guest favorite

Home in Sag Harbor

4.97 out of 5 average rating, 123 reviews

Relax into Coastal Life at a Sun-Drenched Sag Harbor Home

Nov 24 – Dec 1

ﺩ.ﺇ1,910 per night

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Amagansett beach vacation rentals

Guest favorite

Guest suite in East Hampton

4.96 out of 5 average rating, 142 reviews

Be our guest!Near to beaches, shops,eats+ Pvt pool

Jun 4 – 11

ﺩ.ﺇ2,180 per night

Guest favorite

Cottage in Montauk

4.87 out of 5 average rating, 217 reviews

Waterfront Cottage, Fort Pond MTK

Jan 31 – Feb 7

ﺩ.ﺇ3,359 per night

Guest favorite

Guest suite in Sag Harbor

4.88 out of 5 average rating, 310 reviews

Artists Sag Harbor Village Retreat

Dec 4 – 11

ﺩ.ﺇ895 per night

Superhost

Vacation home in East Hampton

4.79 out of 5 average rating, 102 reviews

Unit 15- New beautiful East Hampton Private Apt!

Aug 4 – 11

ﺩ.ﺇ1,558 per night

Guest favorite

Cottage in Montauk

4.91 out of 5 average rating, 139 reviews

Montauk Cottage Escape

Oct 12 – 19

ﺩ.ﺇ1,390 per night

Superhost

Apartment in Montauk

4.83 out of 5 average rating, 132 reviews

MONTAUK OCEAN FRONT!

Oct 20 – 27

ﺩ.ﺇ1,648 per night

Guest favorite

Cottage in Riverhead

4.98 out of 5 average rating, 126 reviews

Savor Blazing Ocean Sunsets at a Soothing Beachfront Haven

Jan 9 – 16

ﺩ.ﺇ2,735 per night

Guest favorite

Guesthouse in Southampton

4.95 out of 5 average rating, 411 reviews

Tiny Home in Prime Spot in Southampton Village

Sep 21 – 28

ﺩ.ﺇ1,312 per night

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Beach house rentals in Amagansett

Guest favorite

Home in Greenport

4.97 out of 5 average rating, 221 reviews

The Greenport Bungalow

Aug 18 – 25

ﺩ.ﺇ2,106 per night

Guest favorite

Home in Greenport

4.98 out of 5 average rating, 164 reviews

Nofo Bungalow-In The Heart of Greenport Village

Sep 4 – 11

ﺩ.ﺇ2,102 per night

Superhost

Home in Sag Harbor

4.81 out of 5 average rating, 108 reviews

Sag Harbor Gem, private, 4 Bedrooms, Pool w Summer

Jun 6 – 13

ﺩ.ﺇ3,156 per night

Guest favorite

Home in Montauk

4.99 out of 5 average rating, 81 reviews

Sea Roost

Nov 5 – 12

ﺩ.ﺇ2,514 per night

Guest favorite

Home in Amagansett

4.9 out of 5 average rating, 21 reviews

Classic Hamptons Cottage - Heart of Amagansett

Apr 4 – 11

ﺩ.ﺇ2,619 per night

Guest favorite

Home in East Hampton

5.0 out of 5 average rating, 7 reviews

Springs Retreat Renovated Home, New Pool, Bay Walk

Dec 8 – 15

ﺩ.ﺇ2,298 per night

Guest favorite

Home in East Hampton

4.89 out of 5 average rating, 19 reviews

Springs Bungalow Retreat

May 25 – Jun 1

ﺩ.ﺇ2,325 per night

Guest favorite

Home in East Hampton

4.94 out of 5 average rating, 49 reviews

Hampton Springs by Summer | Open Breezy Bungalow

Feb 21 – 28

ﺩ.ﺇ2,626 per night

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Quick stats about vacation rentals in Amagansett

Total rentals
280 properties
Rentals with a pool
180 properties have a pool
Pet-friendly rentals
110 properties allow pets
Family-friendly rentals
230 properties are a good fit for families
Total number of reviews
3.4K reviews
Nightly prices starting at
ﺩ.ﺇ551 before taxes and fees

Frequently Asked Questions

Are there vacation rentals with a dedicated workspace in Amagansett?
Yes! Work meets play with ease at over 150 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 110 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 $150 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 50 house rentals with a gym in Amagansett. Enjoy a tailored experience with all the comforts you desire.
Are there Amagansett hotel rentals on Airbnb with pools?
Yes! Dive into the perfect getaway at one of over 10 hotel 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 50 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.

Amagansett vacation rentals

Top-rated vacation rentals in Amagansett

Vacation rentals for every style

Cottages

Houses

Hotels

Popular amenities for Amagansett vacation rentals

Stay near Amagansett's top sights

Other great vacation rentals in Amagansett

Home in Greenport

Home in East Hampton

Home in East Hampton

Home in Sag Harbor

Home in East Hampton

Home in Sag Harbor

Home in Southampton

Home in Sag Harbor

Amagansett beach vacation rentals

Guest suite in East Hampton

Cottage in Montauk

Guest suite in Sag Harbor

Vacation home in East Hampton

Cottage in Montauk

Apartment in Montauk

Cottage in Riverhead

Guesthouse in Southampton

Beach house rentals in Amagansett

Home in Greenport

Home in Greenport

Home in Sag Harbor

Home in Montauk

Home in Amagansett

Home in East Hampton

Home in East Hampton

Home in East Hampton

Quick stats about vacation rentals in Amagansett

Total rentals

Rentals with a pool

Pet-friendly rentals

Family-friendly rentals

Total number of reviews

Nightly prices starting at

Frequently Asked Questions

Are there vacation rentals with a dedicated workspace in Amagansett?

Are there pet-friendly vacation rentals in Amagansett?

How much does it cost to stay in house rentals in Amagansett?

Do cottage rentals in Amagansett have a bbq area?

Do house rentals in Amagansett have a gym?

Are there Amagansett hotel rentals on Airbnb with pools?

Do house rentals in Amagansett have self check-in?

Are there family-friendly cottage rentals in Amagansett?

Destinations to explore