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House vacation rentals in Amagansett

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Top-rated house rentals in Amagansett

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

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Top guest favorite

A charming single-story house features a classic shingle exterior with a brick chimney. A spacious front deck is bordered by white railings and overlooks a manicured lawn surrounded by trees. Soft sunlight filters through the leaves, enhancing the serene setting.

Home in East Hampton

4.95 out of 5 average rating, 230 reviews

Private beach, fully updated cottage, on 2 acres.

Each the special magic that only the Hamptons offer—historic charm, a rural atmosphere, white sandy beaches and a relaxed lifestyle—while staying in this light-filled three-story cottage. Tucked away on a beautiful 2.2-acre wooded lot, this bayside oasis offers a tranquil retreat, with deer sightings, private beach access, stunning view and picture-perfect sunsets. A short drive to the beaches and town, quick trips to nearby shops, market stands, restaurants, museums and Jackson Pollack house.

Top guest favorite

A stylish dining area is highlighted by a round table paired with modern chairs beneath a vibrant artwork. Natural light filters through large windows, providing a view of the outdoors. A cabinet with decorative items adds character to the inviting space.

Home in North Fork

5 out of 5 average rating, 9 reviews

Stylish Beach Getaway: pool & walking location

Perfectly located within walking distance to shops, beaches, and restaurants, our designer home offers comfort, luxury amenities, and privacy. Interested in a long term rental? Message us! Enjoy a beautifully landscaped backyard with pool, chefs kitchen for hosting, and nearby beach farms & wineries. Bedrooms boast organic linens and bathrooms offer Bathing Culture products. Kitchen is stocked with local organic pantry staples and stainless steel appliances to cook or grill on the patio.

The entrance of the home is framed by white, picket fencing and vibrant floral landscaping. A covered porch with classic columns supports a welcoming entrance. The door features decorative glass elements, providing an inviting touch to the exterior.

Home in North Fork

4.98 out of 5 average rating, 100 reviews

Designer's Dream - Charming Boathouse

An architect's and interior decorator's dream home! This home is a historic boathouse built in the late 1890's, and recently & lovingly fully renovated and restored. In the middle of Greenport Village - walking distance to train station, Jitney stop, and Shelter Island Ferry as well as the best North Fork restaurants, vineyards, bars, and beaches. Two bedroom home with ground floor fireplace, outdoor shower (not enclosed), and beautifully landscaped outside patio w/grilling & dining areas.

An open floor plan showcases a stylish living area with a comfortable seating arrangement and a large area rug featuring subtle blue tones. Natural light fills the space, highlighting the decorative elements and providing a cozy yet modern atmosphere. A smart TV is mounted on the wall.

Home in Hampton Bays

4.92 out of 5 average rating, 119 reviews

Hamptons "Get Away" Near Beach/Wineries/Golf

Located in Hampton Bays-the heart of The Hamptons surrounded by water! Close to beaches, waterfront restaurants, wineries, golf & wedding venues. Open floor plan w/ modern flair. 4 bedrooms, 2 full baths, eat-in kitchen, spacious living room and lower level recreation area/ foosball. Enjoy amenities including smart TVs/appliances, EV Charger, 2 fireplaces, 1Gb WiFi, large deck w/ string lites, BBQ, firepit, & outdoor shower. Great for families, couples, coworkers and friends!

The front exterior of the home is framed by lush greenery and a flower-lined pathway made of stone. Two trees add natural shade, while a charming yellow door welcomes guests. A fenced yard and gravel accents enhance the inviting entrance.

Home in North Fork

4.93 out of 5 average rating, 107 reviews

Maritime Village Getaway with Backyard

Well located Greenport 3 bedroom, 2 bath home. Historic renovated private home with modern furnishings and updated appliances and finishings. Patio and yard with outdoor shower, fire pit, and yard. Central AC and heat. Properly licensed as a rental with Greenport Village and Suffolk County. I now add the airbnb fees and local and state taxes onto the listing. If you have questions about this please reach out. Not sure how transparent the fee structure is for guests.

A spacious living room features a large sectional sofa adorned with colorful cushions, offering comfort and relaxation. A sleek television is mounted on the wall, while natural light streams through wide windows, illuminating a wooden coffee table and a decorative fireplace in the corner.

4.88 out of 5 average rating, 102 reviews

Cozy home. Comfy living

The whole group will enjoy access to everything from this centrally located home. three comfy bedroom, two bathrooms, large living room, dining and kitchen. close to the beach, nature reserved, kayaking, sky diving and Tanger outlet mall, restaurant and all the fast food located nearby. long island vast array of winery and farms stand etc. Guest is expected to follow house rules. 15 mins after check out time is given after that fees will incur at nightly rate

A living area features a comfortable dark leather sofa and a light upholstered armchair, arranged around a glass coffee table. A contemporary bookshelf stands nearby. A modern kitchen is visible in the background, alongside a fireplace and large windows that allow natural light to enter.

Home in Westhampton Beach

5 out of 5 average rating, 4 reviews

Summer Main Home plus cottage close to Main Street

Come relax and enjoy! Beautifully updated Main home with separate cottage. Perfect for in-laws and guests. Each home has its own kitchen, living space, washer/dryer, and outdoor seating. Main house: 4 Br, 3 ba Cottage: 2 Br, 1 ba Outdoor shower for an after beach rinse, 2 patios, pergola, hammock, bbq. A two person kayak available for use; beach passes included. Games, internet, tv... Walk to coffee shops, restaurants, worship, and marina. Bike to beach.

A bright living area is illuminated by natural light through large windows. A decorative black wall with a welcome message adds character. A comfortable seating arrangement and dining space is featured. Art pieces are displayed, enhancing the creative ambiance of the space.

Home in Montauk

4.99 out of 5 average rating, 101 reviews

6 minute walk to Ditch Plains Beach

IMPORTANT: From Memorial Day 2024 - Labor Day 2024: weekly (1 week/2 week/3 week rentals must start and end on Saturdays. Monthly rentals can start on the first of the month regardless of the day of the week. Great beach house close to Ditch Plains beach with 3 bedrooms and 2 bathrooms. 2 queen beds and 2 bunk beds, deck, barbecue, outside shower, huge yard, recreation room. Spend your days at the beach and grill at night. Wifi, tv, and outdoor fire pit.

An airy living area features vaulted ceilings with exposed wooden beams. Large windows allow natural light to illuminate the space, while a comfortable seating arrangement includes a white sofa and stylish armchairs. A modern fireplace serves as a focal point, and decorative lamps add a touch of charm.

Home in Montauk

5 out of 5 average rating, 6 reviews

Hilltop Bright Home w/New Pool Summer 2024

Home is professionally managed by Montauk Rental Management Group. Your family will be close to everything when you stay at this centrally-located Montauk home. Short drive to Town and Beaches. This home was recently painted and updated, it's clean, bright and the perfect family rental! -4 bedrooms -3 bathrooms -Spacious deck with water views -Outdoor dining & seating -Grill -Peaceful, quiet location perched on a hill Rental Registry 23-780

A contemporary living room features a sleek gray sofa paired with a vibrant orange chair. Natural light flows through large windows, illuminating the polished wooden floor and highlighting a decorative lamp. An abstract painting adds a touch of color to the light walls.

Home in Southampton

4.94 out of 5 average rating, 270 reviews

Southampton Village Classic, Walk to Downtown!

Beautiful Southampton Village property, walk to shops, restaurants, train & jitney, no car needed! The main house includes 4 bedrooms, 3 beautiful baths, a well-stocked high-end kitchen (Viking, Bosch, Cherry Cabinets...), accommodating 8. Large deck for lounging, a seasonal heated pool and beach nearby. Quintessential Hamptons experience. Bonus cottage accommodating 3 more, bringing total to 11.

A rocky shoreline is framed by a silhouetted tree against a colorful sunset. Clouds display shades of pink and orange as the sun sets over the water, creating a serene atmosphere. The beach area offers a peaceful view of nature.

Home in Shelter Island

4.9 out of 5 average rating, 115 reviews

There's a Beach Getaway!

Welcome to our family-friendly oasis just two blocks from beautiful beaches! Our house offers an open space living area, an expansive yard, fire pits, and a basement with a playroom and workout area. Enjoy our quiet neighborhood. We provide kid-friendly toys, beach gear, bicycles, and more. Sleeps six, with additional options available for larger parties. Cleaning fees for winter stays are 0$.

Top guest favorite

An open-concept living space is highlighted by a wooden dining table set with neutral décor. A comfortable seating area features a dark couch and large windows allowing natural light. Ceiling fans provide airflow in this bright and airy environment.

Home in North Fork

4.98 out of 5 average rating, 179 reviews

Greenport Village walking distance to all

Large spacious home in the heart of wine country. Roomy den for relaxing after the wineries. Screened in patio for al fresco dining and enjoying the spacious yard. Hot tub operational year round! Strong, fast wifi with multiple extenders. Message me with any questions or for special offers on 4/5 day stays or midweek 2/3 night specials.

Vacation rentals for every style

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Cottages

Quaint homes, peaceful surroundings

Hotels

Stylish accommodations and amenities

Unique stays

Spaces that are more than just a place to sleep

Popular amenities for Amagansett house rentals

Free parking on premises

Air conditioning

House rentals with a pool

A light-filled dining area features a round wooden table surrounded by four white chairs. French doors open to a lush outdoor space, and the wood-beamed ceiling adds a rustic touch. The adjacent kitchen with white cabinetry is partially visible, enhancing the open feel.

Home in East Hampton

4.88 out of 5 average rating, 106 reviews

4 BD w/ Heated Pool in E Hampton, Fully Furnished

A modern home is showcased with a unique angular design, featuring a combination of wood and glass. The surrounding lawn is spacious and well-maintained, with natural landscaping, including grasses and a small tree, contributing to the serene outdoor setting.

Home in East Hampton

4.88 out of 5 average rating, 109 reviews

Modern East Hampton Home w/ Heated Saltwater Pool

Home in Southampton

4.93 out of 5 average rating, 14 reviews

Southampton Escape, Heated Pool, hot tub, 3 bed,

Top guest favorite

A welcoming living area showcases a light grey sofa and two upholstered chairs flanking a coffee table. Natural light floods the space through large windows, highlighting a collection of framed artwork on the wall. A modern chandelier adds a stylish touch overhead.

Home in East Hampton

5 out of 5 average rating, 36 reviews

Stunning Central E. Hampton Home w/ gunite pool.

A serene outdoor pool is surrounded by greenery, with lounge chairs positioned along the patio. A stone border frames the pool, and sunlight reflects off the clear water, creating a calm and inviting setting within a peaceful landscape.

Home in East Hampton

5 out of 5 average rating, 5 reviews

The Hideaway

A calm waterfront scene features a vibrant sailboat gliding across the bay, surrounded by green marshland. A wooden dock leads into the water, with several colorful chairs positioned for relaxation. Soft hills and houses line the distant shore under a gentle mist.

Home in Mastic Beach

4.93 out of 5 average rating, 120 reviews

Gorgeous Waterfront and Indoor Pool Family Oasis!

A smooth gravel driveway leads to a two-story house, surrounded by lush greenery and mature trees. An adjacent lawn is neatly maintained, while a wooden fence borders the property, enhancing the natural setting.

Home in East Hampton

4.84 out of 5 average rating, 31 reviews

Private East Hampton Estate

Home in Southampton

4.91 out of 5 average rating, 45 reviews

New Southampton mega home with heated gunite pool!

Weekly house rentals

A black lounge chair is positioned beside large glass doors, offering views of Napeague Harbor. Natural light fills the space, highlighting the warm wooden floors and nearby outdoor seating. A shading sail is visible outside, along with a pop of red from an umbrella.

Home in Amagansett

4.93 out of 5 average rating, 14 reviews

Amagansett, Waterfront retreat

A charming historic bungalow is presented with a shingle exterior and turquoise accents. The entrance is framed by flower boxes, and brick paving extends to the driveway. Lush greenery surrounds the property, while clear blue skies complement the inviting facade.

Home in North Fork

4.98 out of 5 average rating, 186 reviews

Nofo Bungalow-In The Heart of Greenport Village

Home in North Fork

4.97 out of 5 average rating, 254 reviews

The Greenport Bungalow

Top guest favorite

A blue bungalow exterior is shown, featuring a spacious deck with black railings and multiple glass doors. A picnic table is situated on the lawn, alongside a children's toy. Lush greenery surrounds the property, enhancing the setting.

Home in Montauk

5 out of 5 average rating, 20 reviews

Montauk beach house!

Top guest favorite

Home in Shelter Island

5 out of 5 average rating, 29 reviews

Family Friendly Oasis Steps to Water - Heated Pool

A two-story home is set back from the road, framed by lush greenery and gravel landscaping. A red umbrella provides shade on the upper deck, and large windows offer glimpses of the interior. The house is light-colored, blending well with the coastal surroundings.

Home in Southampton

4.96 out of 5 average rating, 166 reviews

POOL in APRIL! Waterview, Free For Dogs! Kayaks

A bright living area features a comfortable white sofa, accentuated by dark blue chairs. A modern television is mounted above a cozy fireplace. The double-height ceiling adds an airy feel, while large windows invite natural light from the outdoors, enhancing the spacious environment.

Home in Bridgehampton

4.76 out of 5 average rating, 38 reviews

Cheerful 3 bed-3bath beach cottage home with pool

A sandy beach stretches into the distance, meeting the calm ocean waves under a clear blue sky. The shoreline is marked by gentle tire tracks, leading towards the water’s edge. The serene landscape suggests a peaceful coastal environment.

Home in Montauk

4.89 out of 5 average rating, 63 reviews

Twin Pond Ocean View White Cottage

Private house rentals

The exterior of a single-story home is set among lush greenery, featuring a varied facade with shingle and clapboard elements. Symmetrical landscaping includes neatly trimmed shrubs and a spacious lawn. A pathway leads to the front door, framed by tall trees providing natural shade.

Home in Shelter Island

4.88 out of 5 average rating, 26 reviews

Peaceful and Private 3 bedroom home in the woods

Top guest favorite

The exterior of a charming farmhouse is shown, surrounded by a lush, green landscape. A gravel driveway leads to the entrance, while a wooden fence and two bicycles are visible in the foreground. The home features a blend of natural wood and modern elements against a clear blue sky.

Home in East Hampton

5 out of 5 average rating, 14 reviews

Restored farmhouse, walk to Carissa's, beach, town

Top guest favorite

A light-filled living area features a neutral-colored sofa alongside a blue couch, with decorative pillows adding subtle color. A wooden coffee table rests in front, and large windows with bamboo shades allow natural light to brighten the space.

Home in North Fork

4.88 out of 5 average rating, 123 reviews

The Perfect North Fork Escape

A spacious backyard features a large swimming pool surrounded by a brick patio. The two-story home, with a screened-in porch and an upper deck, is complemented by lush greenery. A pool house and lounge chairs provide additional relaxation areas.

Home in East Hampton

4.88 out of 5 average rating, 110 reviews

Gorgeous East Hampton Getaway

A two-story home features a welcoming front porch with steps leading up to it. A gravel driveway is visible, bordered by lush greenery and flowering bushes. Bicycles can be seen propped against the house, surrounded by a peaceful, natural setting.

Home in East Hampton

4.74 out of 5 average rating, 89 reviews

Clean Home Pool Cent-Loc. Quiet Reserve Pet Friend

A wooden walkway leads down to a calm beach, with gentle waves lapping at the shore. The water reflects a clear sky and distant land. A floating object is seen in the water, enhancing the serene coastal scene.

Home in North Fork

4.92 out of 5 average rating, 12 reviews

Private Beach access along the Wine Trail

A private country compound is showcased, featuring a main house with a classic white exterior and black shutters. A blossoming tree stands prominently in the foreground, surrounded by a well-maintained lawn and neatly trimmed hedges.

Home in Sag Harbor

4.85 out of 5 average rating, 262 reviews

Exclusive Sag Harbor Compound

Two wooden chairs are positioned on a well-manicured lawn, facing a stylish beach house with large windows. Lush greenery surrounds the area, providing a sense of privacy. The sky is partly cloudy, enhancing the tranquil ambiance of the outdoor space.

Home in Montauk

4.71 out of 5 average rating, 21 reviews

The Raffle Beach House

Quick stats about house rentals in Amagansett

Total rentals
300 properties
Nightly prices starting at
$120 before taxes and fees
Total number of reviews
3.4K reviews
Family-friendly rentals
270 properties are a good fit for families
Pet-friendly rentals
130 properties allow pets
Rentals with a pool
190 properties have a pool

Destinations to explore