Holiday rentals with outdoor seating in Amagansett

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, 253 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.

4.91 out of 5 average rating, 128 reviews

Serene, private, Hamptons oasis; 1 block to dining

Experience the calm and stillness of this serene home. Enjoy the privacy of your own space. Designed to be a zen oasis for you! Relax poolside with nature surrounding you; you may spot a deer or bunny on the property! Spark up the BBQ + firepit under the starry sky; sip your morning coffee on the porch, enjoy 80' streaming TV. You will be in an ideal location; you can walk just 1 block to waterfront cafe + dining w/ the best sunsets. Drive 3-10 minutes to Main Street, beaches + so much more!

4.96 out of 5 average rating, 103 reviews

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.

Home in Amagansett

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.

5 out of 5 average rating, 109 reviews

A well-maintained outdoor space features a large swimming pool surrounded by a wooden deck. Lounge chairs are placed around the pool, with red umbrellas providing shade. Adjacently, a patio area includes a dining table. Lush greenery frames the area, contributing to a serene ambiance.

Guest house in Springs

The Quail’s Nest

A beautifully landscaped tranquil oasis. Newly constructed private two bedroom, one bathroom guest extension to owner occupied house. Guests share large yard and pool with owner, and have private deck and seating area. Private entry and parking. Guest's may enjoy outdoor shower and BBQ. Please note there is no kitchen, however a small fridge, Keurig coffeemaker and microwave, plates/utensils are provided. Conveniently located to beaches, shopping and local restaurants in East Hampton.

Guest suite in East Hampton

A spacious living area is presented with a cozy blue sofa and an accent chair, complemented by a decorative rug. A dining table for four is positioned nearby, and a large TV center is visible. The room is well-lit with natural light streaming through skylights.

4.98 out of 5 average rating, 146 reviews

Hamptons Dream Suite

Hampton's Dream Suite- Is a guest suite in East Hampton, NY. From relaxing by the pool, to taking a day trip to Montauk, or visiting some of the best beaches in the Hamptons, the opportunities here are endless! It offers a bedroom with a Queen size Select Comfort bed, living room has two queen sofa beds and a full bathroom. It has a Kitchenette, Central AC/Heat with a 65" smart TV with surround sound and DVD, Blue ray and Xbox Games . There is also a TV and blue Ray player in the bedroom.

4.95 out of 5 average rating, 123 reviews

An open living area features a comfortable sectional sofa and a large area rug, with natural light streaming through multiple windows. A dining table is visible, accompanied by stools, and the kitchen area includes modern appliances and a view into the outdoor patio space.

Flat in Montauk

Modern Montauk retreat with wood stove by Harbor

Scandinavia meets Montauk in this sophisticated, comfy, all-season getaway with open-plan interior & large, private fenced yard. • 950 sq ft, 2 BRs (compact but comfy), 1 Ba, full high-end kitchen, W/D, A/C • Wood stove, Solo stove, patio, outdoor shower, high-end linens & furnishings/decor • Steps to LI Sound & Harbor. 3 mi to ocean/Town • Owner is in a private studio w/ own entrance in the house. No shared spaces! • Ask about dogs & flexible rental periods CLICK MORE for IMPORTANT INFO!

4.97 out of 5 average rating, 160 reviews

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.

Home in East Hampton

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.

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.

4.92 out of 5 average rating, 127 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.

An outdoor area features a rectangular pool surrounded by a wooden deck. Lounge chairs are positioned along the pool's edge, and a shaded seating area is located nearby under an umbrella. Lush trees provide privacy and a natural backdrop.

4.83 out of 5 average rating, 127 reviews

East Hampton Oasis - Pool and Hot Tub

Nestled at the end of a private road in the Springs section of East Hampton, this classic Hamptons home will keep you and your friends/family entertained. Living room with sonos sound system, kitchen, 3 bedrooms, 2 bathrooms, outdoor living area with lounge chairs, a bbq, bar, pool and hot tub. All 3 bedrooms have AC. Towels and linens provided. Washer/dryer available. CLOSE TO BEACH AND EH VILLAGE. The pool is open May 5 through October 5. The hot tub remains open year round.

4.99 out of 5 average rating, 114 reviews

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.

Home in Montauk

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.

4.98 out of 5 average rating, 123 reviews

An inviting living area is presented, featuring a white brick fireplace as a focal point. Comfortable seating includes light-colored sofas adorned with varying throw pillows. Large windows allow natural light to fill the space, and double doors lead to the outdoor area.

Holiday home in Montauk

2 BR apartment near ocean in Hither Hills

Relax and enjoy a peaceful stay that is a 3 block walk to one of the most beautiful ocean beaches in the Hamptons! This apartment is located in a beautiful, wooded, quiet neighborhood. Town is 1.5 miles away. This apartment has an open concept living space with a fully equipped kitchen. There are 2 cozy bedrooms and one bath with a walk in shower. We prefer families and mature adults. We supply beach towels, chairs, umbrella and beach wagon.

4.88 out of 5 average rating, 130 reviews

Flat in Montauk

Recharge at our Renovated ocean front unit

Looking for a relaxing weekend to recharge on the beach? Then this newly renovated, bohemian-chic, apartment is perfect for you. Imagine waking up every morning to beautiful unobstructed ocean views and ending your night with a drink in hand watching the sunset. If you’re lucky, you might see some whales or dolphins breaching in the water right off our private beach. We would love to host you for your Montauk beach getaway.

Popular amenities for outdoor seating rentals in Amagansett

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with outdoor seating

The kitchen and dining area feature modern cabinetry in muted tones against light wood flooring. A vintage-inspired Smeg fridge stands opposite a sleek kitchen layout with a black stove. Eye-catching circular wall art accents the space, complemented by a wooden dining table surrounded by six chairs.

4.96 out of 5 average rating, 25 reviews

Secluded Oasis salt water pool near beach

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, 116 reviews

Modern East Hampton Home w/ Heated Saltwater Pool

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.

4.75 out of 5 average rating, 102 reviews

Clean Home Pool Cent-Loc. Quiet Reserve Pet Friend

4.99 out of 5 average rating, 74 reviews

A bright kitchen features a large island with wooden countertop and seating for three. Stainless steel appliances and open shelving provide ample storage, while large windows allow natural light to fill the space. French doors open to a deck area with views of the outdoors.

Home in Montauk

Renovated Montauk Home

4.89 out of 5 average rating, 55 reviews

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.

Home in East Hampton

East Hampton Secluded Escape with Gunite Pool

4.95 out of 5 average rating, 317 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!

5 out of 5 average rating, 32 reviews

The exterior of a charming cottage is framed by lush greenery, with high hedges providing privacy. A well-maintained lawn features a seating arrangement with Adirondack chairs. Sunlight filters through the trees, creating a dappled effect on the ground.

Home in Amagansett

Ocelot Cottage

5 out of 5 average rating, 5 reviews

Home in Sag Harbor

Sag Harbor Village 3 Bedroom Gem

Apartment rentals with outdoor seating

4.96 out of 5 average rating, 163 reviews

A charming two-story house is nestled among lush greenery, with large windows reflecting sunlight. The wooden exterior features shingle siding, and a gentle slope of grass leads up to the entrance. Surrounding trees create a serene, private atmosphere.

Flat in Sag Harbor

Hamptons Hills Escape

4.96 out of 5 average rating, 168 reviews

A bright and airy great room combines kitchen, dining, and living areas. Light wood cabinetry and stainless steel appliances complement the open layout. Soft white sofas with navy pillows are arranged around a wooden coffee table, and a round mirror enhances the natural light from multiple windows.

Flat in Greenport

Upscale Newly Constructed Apartment

Flat in Shelter Island Heights

A round wooden dining table is surrounded by four metal chairs. Natural light enters through two large windows, with framed black-and-white photographs arranged on the wall beside them. A decorative centerpiece is placed on the table, offering a rustic touch to the space.

4.9 out of 5 average rating, 261 reviews

Squire Chase House

4.84 out of 5 average rating, 142 reviews

A well-lit living area is highlighted by a cream-colored sofa with nautical-themed pillows. A wooden coffee table features shells and a vase of flowers. Display shelves in the background hold decorative items, with natural light streaming through large windows.

Flat in Hampton Bays

Vacation at the Beach: Entire Home

4.94 out of 5 average rating, 227 reviews

An open layout features a cozy living area with a patterned rug and a glass coffee table. A small dining space with two stools is positioned near a kitchenette, which includes a refrigerator. A private sleeping area with a bed is visible in the background.

Flat in Montauk

Private paradise 3 min from town ice skating pond!

4.82 out of 5 average rating, 114 reviews

An open studio space features a spacious bed with a light duvet and decorative pillows. A leather couch complements the area, while large windows provide natural light, framed by white blinds. A bedside table and warm lighting create a cozy ambiance.

Flat in Center Moriches

Cozy Studio 15 Min From Hampton Beaches

4.94 out of 5 average rating, 141 reviews

A serene beach scene captures a golden sunset reflecting on calm waters. The sandy shore leads to gentle ripples, while distant land silhouettes frame the horizon. A tranquil ambiance is created as the sun descends, providing a peaceful setting for evening strolls.

Flat in Southold

Bright, Southold Studio Apt near beach & town

4.98 out of 5 average rating, 130 reviews

A sandy path leads through beach grass, flanked by wooden fencing, toward a tranquil ocean beyond. Clear blue skies complement the scene, where gentle waves are visible on the horizon.

Flat in Hampton Bays

Walk to Bay and Ocean-Newly Renovated

Apartment rentals with outdoor seating

An expansive hallway features arched doorways and rustic wooden beams overhead. Potted plants add greenery, while large windows dressed with floral curtains allow natural light to illuminate the stone floor. Comfy seating arrangements are positioned along the walls, creating inviting spaces for relaxation.

4.93 out of 5 average rating, 41 reviews

1 BR Loft Apt- Montauk Manor- Pools, Tennis & Gym!

A living area features shiplap walls and ample natural light from large windows. A dark sectional sofa is positioned next to a glass coffee table with a small plant. An open kitchen area is visible, along with access to a screened porch through sliding doors.

4.86 out of 5 average rating, 130 reviews

Beautiful condo on Long Islands Northfork

A view from the balcony overlooks the pool area, featuring a clear blue pool surrounded by lounge chairs. Colorful umbrellas provide shade for several tables, while the surrounding buildings reflect a simple, two-story design.

4.8 out of 5 average rating, 242 reviews

Montauk Royal Atlantic Beach Resort North

A light-filled living area features a cozy neutral sofa, accompanied by a matching armchair. A decorative coffee table sits in the center, and a Smart TV is mounted on the wall. Sliders lead to a private waterfront deck with seating, enhancing the space's openness.

4.84 out of 5 average rating, 160 reviews

Waterfront Escape | Private Beach, Pool & Views

Two wooden Adirondack chairs are positioned on a spacious sun deck, overlooking expansive views of lush greenery and the waterfront. The bright blue sky complements the serene atmosphere, creating an inviting space for relaxation and enjoyment of the natural surroundings.

5 out of 5 average rating, 253 reviews

Montauk Waterfront Condo w/ Sunset Views

The living area features a spacious dark gray couch, a light wooden coffee table, and a white dining table with woven chairs. Natural light filters through the window with plantation shutters, while decorative elements like a round mirror and wall art create a welcoming ambiance.

4.9 out of 5 average rating, 181 reviews

Beautiful Waterview Condo on the North Fork of LI

Two blue Adirondack chairs are positioned on a manicured lawn, facing a vibrant sunset over the ocean. The sky displays pink and orange hues as the sun sets on the horizon, creating a serene outdoor setting.

4.89 out of 5 average rating, 150 reviews

Beachside Waterview 2Br Condo w/ Pool in Greenport

A spacious private deck overlooks the ocean, featuring wooden railings and loungers positioned for relaxation. The sea and sandy beach are visible beyond the deck, with light clouds scattered across a bright blue sky.