House holiday rentals in Westhampton Beach

4.84 out of 5 average rating, 148 reviews

Hamptons Oceanfront Oasis

Escape the hustle & bustle of city life and unwind at this stunning home in the Hamptons. The oceanfront oasis is the perfect way to wake up to ocean views, beaches and nearby restaurants. Relax on our spacious deck - perfect for morning coffees & sunset cocktails. It is just a short drive to the train station & only 15 minutes from the airport for quick getaways. For your safety, the home is equipped with Ring cameras and one-use key codes. Book now and experience the ultimate Hamptons escape!

A bright and airy living space features a cozy beige sofa facing large windows with water views. A staircase leads to the upper level, and natural light illuminates the open layout. Light-colored furniture and decorative accents create a relaxing coastal ambiance.

4.97 out of 5 average rating, 38 reviews

Magnificent Bayfront Retreat

Welcome to the Hamptons! The view from this home, that sits right on the water, boasts the most beautiful sunsets that need to be seen to be believed. Whether you’re spending the day in the sun on the beach (a short 5 minute walk), grilling on the deck watching the sunset over the bay, soaking in the hot tub, fishing on the private dock, or lounging on the couch watching a movie on our 75 inch TV after a day of fun in the sun, this home is a perfect getaway for you, your family, and friends!

An outdoor patio space is shown, featuring a dining set for six with dark wicker chairs and a round table. Several lounge chairs and umbrellas provide shade, arranged over a patterned rug. A privacy fence lines the area, surrounded by greenery.

4.74 out of 5 average rating, 34 reviews

The Pearl -craftman style home & modern amenities.

This cozy craft style home has all of the amenities for you to live, work and relax. • Spacious open concept living and dining room and chef kitchen • Large 3 bedrooms, 2 full bathrooms and sleeps 6 people • Remote working with Wi-Fi access throughout the house • 1 mile to Westhampton Beach main street, • 2 miles from Dune Road with complimentary beach pass • North Shore Wineries: Jamesport, Pindar, Macari Vineyards 30 min away • 1 month rental 1 complementary Italian private dinner for 6

4.99 out of 5 average rating, 81 reviews

Hamptons Oasis | Saltwater Pool, Hot Tub & Games

Welcome to our renovated 3-bedroom retreat in the pristine East Quogue community! You're just a 10-minute drive from both ocean and bay beaches. Revel in the great outdoors with a saltwater pool, hot tub, fire pit, bocce court, and ping pong — plus a backyard grill and spacious patio and deck for seating and dining. Whether you are planning an elevated weekend getaway with friends and family, or need a change in scenery for your work-from-home lifestyle, this is the perfect home to do both.

The exterior of a charming cottage features a symmetrical façade with light-colored shingle siding. A dark blue front door is framed by large windows with black shutters. Brick steps lead to the entrance, adorned with flower pots and greenery.

4.89 out of 5 average rating, 64 reviews

3BR Westhampton Beach House

Best location in Westhampton Beach. Charming 3 BR Cottage that is fully renovated. The space features a new kitchen with quartz counter tops and new stainless steel appliances. Two queen size beds, one full size bed, and a queen sized sofa sleeper for additional guests. A two minute walk to the heart of Main Street and a short bike ride to the beaches this home is in the ideal location! Includes access to 2 brand new bicycles. This home is fully stocked to meet all of your vacation needs.

A spacious saltwater pool is surrounded by a well-manicured yard, featuring lounge chairs and large umbrellas. Water features create gentle splashes, enhancing the serene environment. The area is framed by trees, providing a natural backdrop for relaxation.

4.97 out of 5 average rating, 108 reviews

Brand new house with an all year round hot tub.

Your family will be close to everything when you stay at this centrally-located place. Very close beaches near dune road. Movie theaters, supermarkets, liquor store, farms and a bunch of local restaurants that you can visit.DJs are not allowed. Loud music and parties are strictly prohibited. It's a very quiet, relaxing, and peaceful neighborhood. No smoking inside the house.check in 3pm check out 11am extra charge. If you don't check out 11am.a minimum of 5 cars, no more than 5 cars

An outdoor space featuring a saltwater pool with a jacuzzi positioned nearby. A patio area includes an umbrella and ample seating options. Lush green grass surrounds the pool, while two white decorative swan floats are visible on the water, enhancing the inviting atmosphere.

4.9 out of 5 average rating, 59 reviews

Hamptons Vacation Rental w/ Heated Pool & Jacuzzi!

Located in Hampton Bays just a 5 min drive to beaches, waterfront restaurants, wineries & golf courses. This vacation property offers an open concept single family home w/ 4 bedrooms, 5 baths, a spacious living room, an outdoor deck and patio with a table and chairs, pool, jacuzzi and a pool house! The pool is opened mid May - second week of October and can be heated at an additional cost. Located just 5min away from Hampton Bays town and 5min drive to one of our lovely beaches.

An open living space features a comfortable sofa adorned with patterned cushions, complemented by a light wood coffee table. A dining area with a round table is visible, and large glass doors provide access to the backyard, bringing in natural light.

4.93 out of 5 average rating, 128 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!

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.

4.86 out of 5 average rating, 133 reviews

Stunning Hamptons Waterfront Escape w/ Sunset View

Experience an unforgettable trip in the Hamptons at our waterfront haven! Savor the views and sunset from our spacious deck. Vaulted ceilings and large windows flood the space with natural light. Brand new Weber Grill (2025). We have completed renovations of 3 bathrooms, 2 kitchens, and the entire pool house over the last 18 months. Our home is <10 minutes drive to the beach, groceries, and restaurants! Our pool will open May 23, 2026 and close on Labor Day.

A spacious backyard is showcased with a large saltwater pool, featuring a floating inflatable and sun loungers arranged along the edge. The house stands in the background, framed by trees and an inviting grassy area, enclosed by a black fence.

4.93 out of 5 average rating, 106 reviews

Coastal Retreat|Heated Saltwater Pool|5 MinToBeach

Unwind in Hamptons Bliss! A coastal oasis awaits at this exquisite vacation house. Immerse yourself in luxury, from the elegant interiors to the serene outdoor retreat including a massive fenced-in salt water heated pool (Memorial Day to Labor Day) that will leave you in awe. Indulge in beachside bliss, upscale shopping, and culinary delights. Create memories that will linger long after the sun sets over the horizon. Your dream Hamptons getaway starts here!

A contemporary ranch-style home is surrounded by lush greenery. The custom-shaped heated pool features a waterfall and is bordered by a stone patio with lounge chairs and umbrellas. A state-of-the-art hot tub is positioned nearby, enhancing the outdoor relaxation space.

4.93 out of 5 average rating, 164 reviews

Hampton's Haven

5 bedroom, 3.5 bath contemporary ranch style home, with custom shaped heated pool and meticulously maintained 7 seater hot tub. Expansive patio w/outdoor dining for 10 - close to beach, town and more! Our home has comfortable office space with gigabit wifi throughout! Fabulous game room with ping pong, 4 person air hockey, smart tv and board game lounge. Everything you'll need for a memorable gathering of friends or the perfect family vacation!

A sunset scene is captured over a sandy landscape, where vibrant shades of orange and pink fill the sky. Silhouettes of beach fencing and grassy dunes are visible in the foreground, complemented by a wooden structure to the right.

4.99 out of 5 average rating, 133 reviews

Charming Retreat Near Ocean Beaches

Entire House! Large fenced in yard, great for pets. Two bedrooms, one song ride away from Ponquogue Beach. Have the beach to yourself for walks and exercise! Perfect place to get away and Unwind. The house is located on a quiet residential street close to the hamlet of Hampton Bays. Enjoy the patio and fire pit (use non-windy days) on 1/4 acre property. Still plenty to do here, we are 20 minutes from Wine Country and Tanger Outlets.

Popular amenities for house rentals in Westhampton Beach

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

4.97 out of 5 average rating, 214 reviews

A serene outdoor area showcases a saltwater pool with a spa, surrounded by well-maintained landscaping featuring vibrant yellow flowers. Lush green fields extend into the distance, framed by a clear sky with scattered clouds.

Home in North Fork

Private Oasis W/Stunning Vinyard and Pool Views

5 out of 5 average rating, 15 reviews

Home in Westhampton

Chic Hamptons Gateway | Pool, Hot Tub, Beach

The outdoor area features a heated pool surrounded by wooden decking. Sun loungers are positioned neatly alongside the pool, and shaded seating areas with umbrellas are visible in the background, creating a relaxing atmosphere among the lush greenery.

4.9 out of 5 average rating, 31 reviews

Luxe Westhampton Beach Home w/ Pool & Hot Tub

4.76 out of 5 average rating, 42 reviews

Home in Quogue

Luxurious Hamptons Beach Heated Pool Wineries

Superhost

A bright living area features large windows that offer views of the nearby pond. Comfortable seating includes a white sofa, patterned chairs, and a coffee table, all arranged on a natural fiber rug. Light from the windows enhances the serene atmosphere.

Home in Sag Harbor

4.88 out of 5 average rating, 126 reviews

Sag Harbor, Designer w large Pool (3 bed/2.5 bath)

4.92 out of 5 average rating, 133 reviews

A serene pool area is surrounded by lush greenery and colorful hydrangea flowers. Lounge chairs offer relaxation under large umbrellas, while the inviting pool reflects the clear blue sky. A charming home stands in the background, adding to the peaceful setting.

Home in Southampton

Southampton Charmer, 5 bedrooms w pool - Location

5 out of 5 average rating, 21 reviews

A modern kitchen features sleek white cabinetry and a large island with bar seating for four. Two woven pendant lights hang above, illuminating the space. Large windows allow natural light to fill the room, enhancing the open and airy atmosphere.

Home in Westhampton

1940’s Westhampton renovated bungalow

4.97 out of 5 average rating, 192 reviews

A cozy bedroom featuring a spacious bed dressed in soft linens is positioned against a light-colored wall. Natural light filters through two windows, casting gentle shadows on the warm wooden floor. A ceiling fan hangs overhead, and a mirror and chair add functional elements to the space.

Home in North Fork

Secluded Farmhouse - Studio Apartment Style Unit

Weekly house rentals

A seasonal pool is framed by leafy trees, with a stone patio featuring lounge chairs for relaxation. Surrounding gardens are visible, enhancing the tranquil atmosphere of the space.

4.95 out of 5 average rating, 84 reviews

Splendid private cottage

Superhost

5 out of 5 average rating, 3 reviews

Oasis in Quogue

A bright living area features a comfortable white sofa and two accent chairs. A coffee table sits in front, accompanied by a floral centerpiece. Natural light filters through a window, and a wall-mounted TV is positioned across from the seating. Steps lead to the kitchen area.

5 out of 5 average rating, 73 reviews

The Hamptons Surf Cottage!

A serene night scene showcases a heated salt water pool, illuminated in calming blue hues. Several lounge chairs are positioned around the pool area on a paver patio, surrounded by a white privacy fence that enhances the tranquil ambiance.

5 out of 5 average rating, 51 reviews

Hamptons Getaway/ Backyard OASIS/EV charger

4.97 out of 5 average rating, 32 reviews

Brand New Modern 3 BDR Home

A cozy outdoor space is illuminated by string lights, highlighting comfortable seating arranged around a central fire pit. Soft hues from a nearby hot tub create a tranquil atmosphere among greenery, enhancing the inviting yard setting during the evening hours.

5 out of 5 average rating, 17 reviews

-:Cabin By The Sea:- -Salt Hot Tub- *Dog Friendly*

A bright living room features a light-colored sectional sofa accompanied by dark accent chairs. A glass coffee table sits in the center, showcasing various books. Natural light streams through large windows, revealing a view of the outdoors. Decorative elements include a wall-mounted TV and an ornate cabinet.

4.96 out of 5 average rating, 57 reviews

Sophisticated and Sweet

5 out of 5 average rating, 13 reviews

Hamptons Retreat • Hot Tub • Minutes to Beaches

Private house rentals

4.91 out of 5 average rating, 47 reviews

Hamptons 3/2 - New Gunite Pool &Bluestone Patio

A grassy backyard area features a circular arrangement of four wooden Adirondack chairs surrounding a fire pit. In the background, a saltwater heated pool is visible, framed by lush trees and shrubs, creating a serene outdoor space.

4.92 out of 5 average rating, 49 reviews

Designer Home w/ Heated, Salt-Water Pool

A historic farmhouse is surrounded by lush greenery and colorful landscaping. A spacious porch extends around the front, offering seating areas. A gravel driveway leads up to the house, framed by tall trees and flowering plants, adding to the serene setting.

4.96 out of 5 average rating, 50 reviews

Gorgeous Hamptons Farmhouse without the Traffic!

Superhost

A spacious outdoor area features a heated swimming pool surrounded by a wood deck. Lounge chairs are set along the perimeter, with a hot tub located at one end. Vibrant greenery is visible in the background, enhancing the private and inviting space.

5 out of 5 average rating, 3 reviews

3BR/3BA: private pool, hot tub, waterfront, tennis

Luxe

5 out of 5 average rating, 19 reviews

Charming, Beautiful, Close-to-All Hamptons Gem

A spacious deck is furnished with comfortable seating and a dining table, overlooking a marina with various boats. The water reflects clear blue skies, creating a serene atmosphere. A patterned area rug adds a touch of style to the outdoor space.

5 out of 5 average rating, 30 reviews

2.5 Miles from the 2026 U.S OPEN, Waterfront

A bright living area features wood-paneled ceilings and large windows with natural light filtering in. Two black sofas are arranged around a coffee table on a light-colored rug. A television is positioned on a wooden stand, while plants add a touch of greenery.

5 out of 5 average rating, 8 reviews

Relax & fun home