House holiday rentals in Westhampton

4.85 out of 5 average rating, 151 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!

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

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.

Superhost

4.96 out of 5 average rating, 113 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 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, 136 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.

4.87 out of 5 average rating, 134 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.

4.94 out of 5 average rating, 111 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!

Home in Remsenburg - Speonk

5.0 out of 5 average rating, 17 reviews

Westhampton Retreat to the Woods

Newly renovated 3-bedroom, 2-bath home on 1.5 private acres just minutes from the beach. Features an open kitchen, two new bathrooms, and modern finishes. Outdoors, enjoy a hammock lounge, al fresco dining, outdoor shower, and expansive grounds. The highlight: a heated saltwater pool kept at 80°. Perfect for family, friends, or a romantic Hamptons getaway. Pool is open from Memorial Day until late September, d pending on weather conditions.

A charming cottage exterior features wood shingles and white trim. An American flag hangs proudly from the front, while window boxes with greenery add a touch of color. The light blue front door complements the natural elements, inviting guests inside.

4.98 out of 5 average rating, 170 reviews

Luxury Hamptons Home with Heated Saltwater Pool

Get away from it all in this meticulously renovated Westhampton Beach home. Pull up to the cottage in the heart of Westhampton Beach, a place that delivers all the Hamptons have to offer, all while being within a two hour drive of NYC. No detail was overlooked in the renovation of this cottage… the beauty is only matched by the comfort and function. With the open floor plan, sunny kitchen, furnished open air patio, you won’t want to leave.

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, 137 reviews

Charming House close to 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.

4.95 out of 5 average rating, 201 reviews

A serene view of calm water featuring kayakers enjoying a sunny day. The distant shoreline is dotted with houses, creating a relaxed coastal atmosphere. Clear blue skies reflect on the water, enhancing the peaceful scene.

Home in Shinnecock Hills

Southamp Waterview, DogsFREE! Kayaks, Ping-Pong

Beachy casual feel-good home easily located at the entrance to The Hamptons. Lovely views of Bay, Nightly Sunsets & birds! Launch our Kayaks at street's tiny beach flowing from Cold Spring Pond into Bay. Or cuddle by the fireplace and play our many available games. We provide soft sheets & towels for the showers and & beach...priding ourselves on your comfort! Our Private-Pool is heatable & plant-surrounded with Outdoor Shower.

Popular amenities for Westhampton house rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

A heated saltwater pool is surrounded by a spacious green lawn and lounge chairs, with a tree-lined white fence in the background. The house features a charming design with large windows and a wide patio area, suitable for outdoor dining and relaxation.

4.97 out of 5 average rating, 149 reviews

Stylish+Modern Cape w/Saltwater Pool-5min to Beach

4.99 out of 5 average rating, 148 reviews

A landscaped outdoor area features a stone fire pit surrounded by bright blue chairs on a gravel surface. Lush greenery and tall trees provide privacy, while a spacious pool bordered by lounge chairs is situated in the background.

Home in East Quogue

Beach House Feel - Newly renovated Backyard Oasis

4.96 out of 5 average rating, 220 reviews

A solar-heated pool is surrounded by a spacious bluestone patio, offering various lounge chairs and shaded areas. A brick fireplace is visible alongside a dining space, all framed by mature landscaping and trees, enhancing the outdoor relaxation experience.

Home in Shinnecock Hills

Dream Home with a wonderful heated pool in SH

Luxe

A charming cottage is surrounded by lush greenery, featuring a spacious lawn edged with neatly arranged flower beds. Large windows invite natural light, and a covered porch adds to the welcoming ambiance of the home.

Home in Amagansett

4.99 out of 5 average rating, 264 reviews

Historic Designer Farmhouse - Saltwater Pool

An aerial view captures a backyard featuring a heated pool surrounded by comfortable seating and a dining area. A deck is adorned with lounge chairs and a patterned rug, while manicured grass enhances the outdoor space. Sunlight reflects off the crystal-clear pool water.

4.86 out of 5 average rating, 102 reviews

Hampton Bays village summer home!

4.96 out of 5 average rating, 206 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

4.97 out of 5 average rating, 217 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

4.93 out of 5 average rating, 139 reviews

A modern farmhouse is set on a spacious lot. The architecture features a blend of dark and light siding with a white chimney. A well-maintained path leads to a front porch, surrounded by landscaped greenery, enhancing the inviting curb appeal.

Home in Sound Beach

Luxury modern farmhouse with heated pool & hot tub

Weekly house rentals

4.94 out of 5 average rating, 18 reviews

Home in Southampton

Brand New Sun Filled Home

5.0 out of 5 average rating, 16 reviews

Hamptons Retreat • Hot Tub • Minutes to Beaches

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, 92 reviews

Splendid private cottage

4.78 out of 5 average rating, 45 reviews

Home in Quogue

Luxurious Hamptons Beach Heated Pool Wineries

4.95 out of 5 average rating, 22 reviews

A serene backyard showcases a sparkling swimming pool surrounded by lush greenery. Comfortable seating is arranged near the poolside, and a large umbrella provides shade. The inviting space is designed for relaxation and enjoyment.

Home in Eastport

Mamma Mia Getaway

5.0 out of 5 average rating, 39 reviews

3Bed/2 Bath - Hamptons Getaway w/ Heated Pool!

4.98 out of 5 average rating, 65 reviews

A spacious two-story home with a light exterior sits on a well-maintained lawn, featuring a gravel driveway that leads to a double garage. An American flag is displayed prominently, and lush greenery surrounds the property, creating a welcoming entrance.

Home in Westhampton

NEW DECK! Private, Heated Pool, Home Office & Gym

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.

5.0 out of 5 average rating, 80 reviews

The Hamptons Surf Cottage!

Private house rentals

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.

4.97 out of 5 average rating, 63 reviews

Sophisticated and Sweet

An open kitchen and dining area feature modern cabinetry and a large central island with seating. Natural light pours in through a skylight, highlighting the contrast between dark wood flooring and light-colored furniture. A dining table is set for four, accented by decorative elements.

4.93 out of 5 average rating, 30 reviews

Modern Oasis in Hampton Bays

A modern kitchen features white cabinetry and sleek countertops, accompanied by stainless steel appliances. A central island with seating for six is centrally positioned, while expansive glass doors allow natural light to fill the space. Warm wood flooring complements the overall design.

5.0 out of 5 average rating, 25 reviews

Classic Hampton Bays Cottage, Newly Renovated

4.98 out of 5 average rating, 55 reviews

A sparkling pool reflects the clear blue sky, surrounded by a sleek stone patio. Lounge chairs are positioned nearby, inviting relaxation. Lush greenery and vibrant gardens frame the space, enhancing the private outdoor setting.

Home in Shinnecock Hills

Luxury Hamptons Poolside Paradise w/ Outdoor Sauna

4.98 out of 5 average rating, 44 reviews

A comfortable living room features a cozy sofa adorned with plaid pillows. A fireplace is positioned beneath a wall-mounted television. Natural light enters through well-dressed windows, illuminating the space and providing a view of the green yard outside.

Home in East Quogue

Cozy Home with Pool - Near Beach and Restaurants

A modern kitchen features sleek white cabinetry and stainless steel appliances. A large island with a wooden base is surrounded by four white bar stools. Skylights provide natural light, illuminating the airy space, which is complemented by a subtle woven runner along the floor.

5.0 out of 5 average rating, 20 reviews

Beautiful modern only 3.8 miles to Shinnecock

4.98 out of 5 average rating, 64 reviews

Home in Mastic

Home & Near the Hamptons

A landscaped yard features a lush green lawn framed by mature trees and bushes. The expansive bay and ocean views are visible in the background. A colorful sunset paints the sky, creating a serene and tranquil setting.