Pet-friendly holiday rentals in Amagansett

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, 524 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

4.9 out of 5 average rating, 143 reviews

Serene + chic ~ 8 mins to Main Street + beaches

Escape to your private, chic, serene Hamptons oasis! Enjoy your home surrounded by bucolic nature views + endless calming vibes. Bask in the beauty of the Hamptons + natural light all throughout the space. Curl up to the wood burning fireplace, cook in the large Chef's kitchen + stream on your 80' TV. Spark up the firepit + BBQ outside under the starry sky! You will be 8 minutes to Main St of Amagansett + East Hampton, many restaurants, farm stands, pumpkin patches, the beach + so much more!

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, 267 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 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, 118 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 lighted deck and huge yard. The house features two wood-burning fireplaces in the living room and den and an outdoor fire-pit. RR# 26-891

4.99 out of 5 average rating, 126 reviews

A spacious backyard is highlighted, featuring a well-maintained lawn and a refreshing pool. Black wooden chairs surround a fire pit in the foreground, while a small shed and lush greenery can be seen creating a serene atmosphere for relaxation.

Villa in East Hampton

East Hampton Escape | Heated Pool + Outdoor Living

Escape to a 5* rated Hamptons retreat designed for effortless summer living. Set on a quiet property surrounded by mature landscapes, this light-filled designer home offers the perfect balance of privacy, comfort, and indoor-outdoor flow. The open concept layout is filled with natural light, feat a modern kitchen, multiple living areas, and thoughtfully designed bedrooms for a relaxed, and comfortable stay. Ideal for small groups looking for elevated escape minutes from beaches and town.

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, 147 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.

4.87 out of 5 average rating, 237 reviews

Fall-Getaway, WoodFireplace, Walk2Beach, Spotless

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

4.93 out of 5 average rating, 138 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

A new, modernized farmhouse with a heated saltwater pool in the heart of North Fork. Nestled on an acre of lush, fully fenced yard, the home can easily accommodate up to 8 guests and all pets! Minutes away from Love Lane (Mattituck's charming downtown), Breakwater Beach (one of best beaches in North Fork), Mattituck train station and surrounding the award winning Bridge Lane Vineyards and picturesque Seabrook Horse Farm, this bucolic home offers the perfect setting for a North Fork getaway.

A contemporary house exterior features a combination of wood and metal finishes, set against a backdrop of lush greenery. Large glass windows provide ample natural light, and a pathway of stepping stones leads through a manicured lawn, enhancing the inviting atmosphere.

4.97 out of 5 average rating, 163 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.

4.95 out of 5 average rating, 100 reviews

A well-designed outdoor area features a pristine pool with colorful floats, bordered by a spacious deck. Lounge chairs, adorned in striped blue and white, provide comfortable seating under large umbrellas. The house is illuminated, showcasing a welcoming atmosphere amidst lush greenery.

Villa in East Hampton

Insta: @staywithhamptonsmama PINKWOOD PLAYHOUSE is the perfect spot for your Hamptons stay, offering elevated design and relaxed luxury with laid back beach vibes. Perfect for families, friends or couples. This stylish and serene home features 4 bedrooms, 2.5 bathrooms, a fully equipped kitchen, soaring ceilings, games room and movie room. Bring the outdoors in with oversized windows and over 1000 square feet of deck space overlooking the gorgeous pool (can be heated for a fee).

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, 142 reviews

5 min to EH town w/pool, playground, self check-in

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, 135 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 pet-friendly home rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Pet-friendly house rentals

4.85 out of 5 average rating, 110 reviews

Montauk Private Beach Bungalow

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.

4.86 out of 5 average rating, 108 reviews

Contemporary East Hampton 4 Bedroom, Pool

The exterior of the beach house is presented, showcasing a dark blue façade complemented by a wooden deck. A white door is visible, flanked by two large windows that allow natural light. Surrounding greenery adds to the inviting entrance.

4.9 out of 5 average rating, 503 reviews

DITCH PLAINS SURF HOUSE

4.9 out of 5 average rating, 118 reviews

A cozy living area is highlighted by a chandelier, providing soft illumination. Two stylish chairs flank a round table, while a decorative sculpture and a vintage fireplace enhance the space. Large windows allow natural light to fill the room, offering views of the surrounding greenery.

Home in Sag Harbor

The Cooper-Burke House

4.88 out of 5 average rating, 233 reviews

Laid Back Bungalow btwn Surf Lodge, Beach & Town

4.93 out of 5 average rating, 143 reviews

Home in Water Mill

Beach Barn w/ Heated Pool & Sauna - Dog Friendly

4.91 out of 5 average rating, 69 reviews

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.

Home in Amagansett

Classic Hamptons Cottage - Heart of Amagansett

An in-ground salt-water pool is surrounded by natural stone, set amidst lush greenery. Sun loungers are positioned alongside the pool, and a shaded seating area is visible to the right. A wooden structure stands in the background, blending with the tranquil landscape.

4.88 out of 5 average rating, 69 reviews

East Hampton Secluded Escape with Gunite Pool

Pet-friendly home rentals with a pool

4.9 out of 5 average rating, 671 reviews

A bright studio cottage features a spacious bed with light linens and a working fireplace. A round table with two white chairs sits on a soft area rug, while a blue accent chair is positioned in the corner. Soft light enters through large windows.

Bungalow in Montauk

Atlantic Whispers

4.87 out of 5 average rating, 142 reviews

A serene scene features a well-kept pool surrounded by lounge chairs, reflecting the colors of the sunset. The main house and pool house are visible, each with large windows and inviting outdoor spaces. Lush greenery outlines the property, enhancing the tranquil setting.

Home in Hampton Bays

Stunning Hamptons Waterfront Escape w/ Sunset View

4.94 out of 5 average rating, 156 reviews

A comfortable living room area is presented, featuring a light-colored sectional sofa arranged around a wooden coffee table. Natural light enters through a large window, illuminating a piece of artwork on the wall and adding a cozy touch to the space.

Flat in Sag Harbor

PRIVATE BASEMENT APARTMENT WITH POOL IN SAG HARBOR

4.94 out of 5 average rating, 167 reviews

A well-maintained outdoor pool area is surrounded by a wooden deck and lush greenery. Lounge chairs are positioned along the pool, with a shaded area provided by a large tree. The clear blue water of the pool reflects the sunlight, inviting relaxation.

Home in Water Mill

Astounding Watermill 5 Bedroom home with Pool

4.93 out of 5 average rating, 109 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

A serene backyard features a heated salt-water pool with stone tile surrounding it. Lounge chairs are positioned beside a shaded cabana and an umbrella. Lush greenery offers a sense of privacy, enhancing the tranquil atmosphere of the outdoor space.

4.84 out of 5 average rating, 67 reviews

Salt Pool 4BR Sanctuary w ~Private Beach Access

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.

4.94 out of 5 average rating, 52 reviews

¤¤¤ Wonderful retreat on 4 acres with pool ¤¤¤

A serene pool area features a floating swan-shaped inflatable toy, surrounded by clear water. Comfortable lounge chairs are arranged at the pool's edge, partially shaded by lush greenery. A peaceful atmosphere is created by the surrounding natural landscape.

4.94 out of 5 average rating, 54 reviews

Sparkling East Hampton Oasis 3/2, heated pool

Private, pet-friendly home rentals

5.0 out of 5 average rating, 34 reviews

A spacious outdoor deck features a dining table accompanied by seating and an umbrella. The deck is surrounded by sand and greenery, with a grill positioned nearby. A flowering tree adds a pop of color, enhancing the outdoor space's ambiance.

Cottage in Amagansett

Amagansett Beach Cottage - Short Walk to the Ocean

4.91 out of 5 average rating, 11 reviews

Montauk Surf Cabin with Deck on a Nature Preserve

4.92 out of 5 average rating, 38 reviews

A clean and inviting sleeping area is presented with a spacious bed adorned with white bedding. Two decorative pillows are arranged on the bed, adding a touch of texture. A floor-length mirror and a slender arrangement of decorative branches enhance the modern aesthetic of the space.

Flat in East Hampton

NEW Private, modern centrally located Apartment!

A spacious living area features wood-paneled walls and high ceilings with exposed beams. Large windows invite natural light, complemented by modern pendant lighting. Two comfortable sofas are arranged around a central coffee table, with a kitchen area visible in the background, showcasing wooden cabinetry.

4.94 out of 5 average rating, 77 reviews

The Getaway

4.84 out of 5 average rating, 85 reviews

Flat in East Hampton

NEW- Private Modern East Hampton Apartment!

4.71 out of 5 average rating, 34 reviews

A spacious living area is illuminated by natural light from a skylight. A white sofa, adorned with decorative pillows and a colorful throw, faces a green coffee table. The open kitchen is visible in the background, featuring modern appliances and minimalistic decor.

Home in Amagansett

Amagansett walk-to-the-bay Beach House

4.85 out of 5 average rating, 13 reviews

A serene waterfront scene captures a vibrant sunset, showcasing a blend of orange, pink, and purple hues reflected on calm water. A wooden dock extends into the water, while silhouettes of people can be seen engaging at the water's edge.

Home in Sag Harbor

Sag Harbor Village Waterfront Cottage

A spacious backyard is featured, surrounded by manicured landscaping. A fire pit made of stones and logs is centrally located on the gravel area. The cottage stands in the background, framed by lush trees and greenery, creating a serene outdoor environment.