House vacation rentals in Amagansett

4.91 out of 5 average rating, 138 reviews

Serene w/ large pool ~1 block to waterfront dining

Enjoy your serene, chic Hamptons oasis! Ideally located 1 block to waterfront dining + 8 mins. to Main St. + beaches! Stay in a tranquil home surrounded by nature + privacy. Swim in the pool, spark up the firepit + BBQ under the starry sky! Stream on the 80' TV + cook in your Chef's kitchen. Take a stroll 1 block to cafe for morning coffee on the sea snd dinner/cocktails watching the sun set over the harbor. Walk home in four minutes. Enjoy the peace + calmness right here in your own home!

A serene sunset is captured over the bay, with warm hues reflecting on the water's surface. Silhouettes of wooden posts emerge from the calm waves, creating a tranquil atmosphere. The horizon showcases a mix of colors as the day transitions to evening.

4.95 out of 5 average rating, 263 reviews

Private beach, fully updated house, 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.

A bright living area features a light grey sofa paired with two black chairs, positioned around a glass coffee table. Large windows allow natural light to fill the space, while a minimalist fireplace offers visual interest. A small desk is visible against the wall.

4.95 out of 5 average rating, 515 reviews

Silver House: 3BR Home with Private Beach Access

Located on a half-acre property surrounded by tall oak trees, this three-bedroom, two-bathroom home is the perfect getaway. The house is part of the Clearwater Beach community with private beach access. The recently renovated kitchen and bathrooms are modern and minimal. Natural light floods the space throughout the entire house. Here is your perfect getaway from the chaos of city life The fireplace is NOT available for guest use. Early check-in and late check-out are NOT available in season

The image captures a spacious outdoor area featuring a large heated pool with a fountain and surrounding stone patio. Nearby, lounge chairs are arranged for relaxation, while a generous lawn stretches in the background, accompanied by a well-designed home nestled among trees.

4.78 out of 5 average rating, 143 reviews

Sprawling Hamptons Estate with Hot Tub & Amenities

Spacious & private Hamptons Oasis. High speed WiFi. Family friendly. Massive home on 1.4 acres hosts 15 guests across 6 bedrooms, 8 beds, 4 full baths plus crib & pack 'n play. Gorgeously decorated by Judy Posey Large heated gunite pool (42 x 20 feet) hot tub and sundeck. Fireplace, over-sized kitchen w/ 3 fridges, electric wood-fired grill, huge yard, firepit, bar/lounge, Golden Tee arcade™, bikes & kayaks. Just 2 miles from towns of East Hampton and Amagansett and several white sand beaches

4.84 out of 5 average rating, 106 reviews

Montauk Private Beach Bungalow

Beautiful secluded cottage tucked away at the end of cul-de-sac and surrounded by a nature preserve. Montauk’s finest waterfront dining and bars are less than a mile. The house has a large living room with a fireplace, king bed in one and a full bed with a twin in the other, a full bath, outdoor shower hot & cold, an eat-in kitchen. There is a large very private patio with a grill, dining table and lounge area. The private beach is stunning and a 3 minute walk from the house. Pets are welcome.

The living room features a cozy seating arrangement, including a spacious sofa and armchairs. A round coffee table centers the room, and large windows allow natural light to brighten the space. A textured area rug adds warmth, while a chandelier complements the high ceiling.

4.96 out of 5 average rating, 110 reviews

Casa Amagansett

*REMODELED FEB 2022* Casa Amagansett is a classic Hamptons bungalow, 3 minutes from the beach. Our 3br/2b home features a beautiful kitchen with 2 sinks, a laundry room, a truly sunny Sunroom, and gorgeous outdoor space. We are perfectly situated minutes from the beach, the Amagansett LIRR train station, grocery stores, and great shops & dining. There are four bicycles available for easy breezy access to everything nearby. Suitable for couples, families, business travelers, and friends.

A modern home is set on a spacious green lawn, featuring a combination of wood and metal siding. Large windows allow natural light to fill the interior. A stone pathway leads to the entrance, framed by lush landscaping and trees, enhancing the outdoor tranquility.

4.89 out of 5 average rating, 117 reviews

Modern East Hampton Home w/ Heated Saltwater Pool

Peace and serenity in East Hampton and minutes from the Village. This exquisite modern home features high-end finishes such as Sub-Zero and Wolf appliances, quartzite waterfall kitchen island and counters, marble tiled bathrooms, designer mid-century decor and separately zoned air conditioning. The heated saltwater pool is surrounded by a bluestone patio, Ipe deck and huge yard. The house also features two wood-burning fireplaces in the living room and den and an outdoor fire-pit. RR# 26-891

A crystal-clear swimming pool is surrounded by a landscaped garden featuring lush greenery and blooming flowers. Natural stone patio borders the pool, offering space for lounging and relaxation in a private setting nestled among trees.

4.98 out of 5 average rating, 144 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. (No AI used in these photos!)

A tranquil saltwater pool area is surrounded by lush greenery, featuring four sun loungers with colorful cushions. A large blue umbrella provides shade on the paved deck, enhancing the outdoor relaxation space.

4.88 out of 5 average rating, 233 reviews

HeatedPool, Walk2Beach, Yard4Pup, Spotless, GasBBQ

Meticulous easy home.Tranquil family neighborhood in historic artist's beach community.Lush private yard! Heated saltwater pool.Wood burning fireplace.Private fenced-in backyard.Half mile to private bay beach. Bike great trails & savor delicious meals prepared in fully equipped kitchen.Enjoy Clearwater Beach's renowned sunset.We welcome all respectful guests.East Hampton's best restaurants are nearby.Smoke free.Small dogs permitted.Cell reception booster! Ask about EVcharger.RentalR-25-705

The backyard showcases a serene oasis with a sparkling pool surrounded by lush greenery. A sunroom is visible, providing a view of the inviting outdoor space. The setting offers a sense of privacy, enhanced by the natural landscape.

4.94 out of 5 average rating, 102 reviews

Oasis backyard, Pool, Gym, and Sunroom!

Oasis pool and landscaping makes it feel like your on a private island. Sunroom with smart TV over looking oasis back yard. Decks in the back yard with lounge chairs and 2 patio dining tables. Front deck with lounge chairs. Outdoor gym located in the corner of the yard. Paddle boards, boogie boards, beach chairs, and beach towels provided. Walk to EHP Resort (SiSi Restaurant), and Harbor Bistro featured on Delicious Destinations. Paddle Diva paddle board/kayak rentals also nearby.

A spacious backyard is highlighted by a blue in-ground pool surrounded by lounge chairs. Red umbrellas provide shade, while a tall wooden fence adds privacy. Lush green grass complements the natural setting, and a rustic home is visible in the background among the trees.

4.93 out of 5 average rating, 136 reviews

Private & Pristine with Pool and Kid’s Playard

INSTANT BOOK/ dates are current. Private and Pristine 3 bed / 2 bath home in the heart of East Hampton set on 1.3 acres. Home features a chef's kitchen, in-ground gated pool, and pure privacy and relaxation. Close proximity to East Hampton Village (5 mins) and East Hampton, Amangansett and Bay Beaches (7mins), Montauk (20 mins), Sag Harbor (15 mins). Kids adore the huge playground! Entire property fenced-in to ensure the safety of kids! Heated Pool open: Memorial Day - Sept 30.

The living area features two rattan chairs facing a coffee table, surrounded by vibrant wall art. A cozy sofa and plants add life to the space. Natural light streams through large windows, creating a bright and inviting atmosphere.

4.99 out of 5 average rating, 130 reviews

3 BR/Pool. Walk to Beach & Town!

Welcome to Good Tauk – a cheerful, retro-inspired 3BR, 2BA cottage tucked in the heart of Montauk and walkable to town and the beach. Thoughtfully renovated and full of personality, it’s perfect for families or longer stays. The vibe is fun, relaxed, and unmistakably Montauk. Outside, unwind in your private backyard with a pool, grill, and dining patio—ideal for lazy afternoons and sunset dinners. Just minutes from the beach, town, and everything that makes Montauk magical.

Popular amenities for Amagansett house rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

A modern living area is highlighted by a spacious sectional sofa and large windows providing natural light. A dining space with a round chandelier and a kitchen with new appliances are visible. The room features hardwood floors and a decorative fireplace, enhancing the open layout.

4.94 out of 5 average rating, 121 reviews

Marvelous 4 Bed East Hampton home w Heated Pool

A modern kitchen is featured, equipped with sleek stainless steel appliances and an island with seating for four. Pendant lights hang above the counter, illuminating the space, while the white cabinetry provides a clean look. Large windows allow natural light to fill the room.

4.9 out of 5 average rating, 99 reviews

Contemporary East Hampton 4 Bedroom, Pool

4.93 out of 5 average rating, 134 reviews

A serene landscape features a heated saltwater pool bordered by lush greenery. Sun loungers are positioned around the pool under umbrellas, while a wooden fence with trees creates a peaceful backdrop, enhancing the outdoor relaxation space.

Home in Mattituck

Modern farmhouse w/ pool, beach, horses and winery

4.93 out of 5 average rating, 143 reviews

Home in Water Mill

Beach Barn w/ Heated Pool & Sauna - Dog Friendly

4.92 out of 5 average rating, 106 reviews

A bright living area is furnished with a leather sofa and a dark coffee table, positioned on a textured rug. Natural light filters through large windows, illuminating the space. A staircase leads to an upper level, with wooden accents enhancing the modern design.

Home in Bridgehampton

Pool Central Private Bridgehampton Home

5.0 out of 5 average rating, 14 reviews

Light-filled Retreat by the Bay

5.0 out of 5 average rating, 7 reviews

Home in Sag Harbor

Designer home in Sag Harbor : 5BR walk to beach

A spacious deck surrounds a heated pool, featuring a light blue surface reflective of the sky. Four sun lounge chairs are positioned for relaxation, and an outdoor dining area with a retractable awning is available. Lush trees provide a natural backdrop to the serene setting.

5.0 out of 5 average rating, 87 reviews

East Hampton Rental w/ Pool, Moments to Amenities

Weekly house rentals

4.85 out of 5 average rating, 155 reviews

Home in Hampton Bays

Hamptons Oceanfront Oasis

4.95 out of 5 average rating, 321 reviews

A welcoming living area is illuminated by natural light from large windows. A comfortable gray sofa is complemented by light-colored armchairs and a coffee table adorned with books and decorative items. The neutral color palette is accentuated by indoor plants and a textured rug.

Home in Sag Harbor

Sag Harbor Cottage, Walk to the Beach!

A bright and airy living space features a spacious white sofa and a wooden accent chair. Sunlight floods through large windows, illuminating a glass coffee table and light-colored area rug. A dining area with a round table and stylish chairs is visible in the background.

4.94 out of 5 average rating, 32 reviews

Chic Walk to the Beach in Amagansett

The exterior of the artist's beach cottage features a charming facade with wood shingles and well-maintained landscaping. A welcoming front porch is flanked by shrubs and flower beds, while a serene lawn leads toward a lush backyard visible in the distance.

4.92 out of 5 average rating, 66 reviews

Classic Hamptons Cottage - Heart of Amagansett

An outdoor space features a modern freestanding soaking tub surrounded by wooden decking. The area is bordered by wooden walls and adorned with a potted plant, adding a touch of nature. A bright sky and trees can be seen in the backdrop.

4.68 out of 5 average rating, 31 reviews

Amagansett walk-to-the-bay Beach House

A bright kitchenette features modern cabinetry and a stainless-steel sink. Adjacent, a dining area with two chairs faces a spacious living room, highlighted by large windows allowing natural light and showcasing a comfortable sofa and wall-mounted TV.

4.97 out of 5 average rating, 32 reviews

Dockside 2BR - Marina - Dining - Charter Access Un

An open living area showcases a modern sectional sofa in shades of gray, complemented by a circular wooden table. A brick fireplace adds a warm touch to the space, while a kitchen area is visible in the background, featuring wood cabinetry and a dining table.

5.0 out of 5 average rating, 68 reviews

Bay Access Cottage + Pilates Gym

A bright living area features a spacious sectional sofa and an armchair, arranged around a rustic coffee table. Sunlight streams through multiple skylights and large windows, providing views of the lush greenery outside. A flat-screen TV is mounted above a brick fireplace.

4.97 out of 5 average rating, 32 reviews

Enchanted Story Book Home

Private house rentals

A serene outdoor space features a newly installed heated pool surrounded by a patio. The area is complemented by comfortable lounge chairs and lush greenery, providing a tranquil setting for relaxation. A wooden fence offers privacy, while manicured shrubs frame the pool.

4.91 out of 5 average rating, 89 reviews

Bright & Modern E Hampton Getaway w/ Pool & Spa

A cozy bedroom is shown, featuring a spacious bed adorned with a floral quilt. Light streams through multiple windows, illuminating the room. A white dresser and closet are visible, while a green yard can be seen through the windows.

4.82 out of 5 average rating, 143 reviews

Sunny & Serene Private Cottage near Downtown EH

A spacious backyard features a large pool surrounded by a wooden deck. Two lounge chairs are positioned beside the pool, and an umbrella provides shade nearby. Lush greenery lines the property, creating a serene and private environment for relaxation and recreation.

4.94 out of 5 average rating, 52 reviews

Sunny, walk to beach, large pool

A charming exterior view of a home is featured, surrounded by lush greenery and colorful landscaping. A tranquil swimming pool is positioned in the foreground, with a well-maintained lawn leading up to the house, which includes multiple large windows and a spacious patio area.

4.82 out of 5 average rating, 11 reviews

Beautiful Cozy Home in East Hampton

A spacious living area features large windows dressed with natural shades, allowing ample light to filter in. Comfortable seating includes a plush sofa with blue accents, woven chairs, and a wooden coffee table. A modern kitchen area with a wine fridge is visible in the background.

5.0 out of 5 average rating, 46 reviews

Stunning Central E. Hampton Home w/ gunite pool.

5.0 out of 5 average rating, 9 reviews

Harbor View • Newly Renovated

A spacious deck surrounds a large pool, complemented by red umbrellas and lounge chairs. Lush greenery and blooming hydrangeas create a serene backdrop. A cozy seating area is visible under a shaded structure, enhancing the outdoor relaxation space.

4.96 out of 5 average rating, 91 reviews

Family Friendly Springs Beach House

A private swimming pool reflects clear blue skies, surrounded by lounge chairs and umbrellas. Lush greenery frames the scene, while a wooden deck leads to the main house, which features a modern architectural design. A swing set adds an element of leisure to the serene outdoor space.