Vacation rentals in Westhampton

4.98 out of 5 average rating, 65 reviews

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

BRAND NEW DECK! Relax, dine, and take in the view. POOL is open EARLY MAY to END OF SEPT! Ideal for family getaways Privacy and tranquility can be appreciated on this 1 acre land that is surrounded by tall trees and lush landscaping. Plenty of space indoors for working at home or gathering together and outdoors for bbq and sun. House is centrally located near famed Dune Road beaches, Downtown Main Street shops and restaurants, and just a quick drive away from the best winery, golf and farms!

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.

4.91 out of 5 average rating, 34 reviews

Luxe Westhampton Beach Home w/ Pool & Hot Tub

Finally get around to planning that luxury Hamptons getaway you've been dreaming of at this beautifully furnished home in Westhampton Beach! Designed for a couple's getaway, this vacation rental boasts 4 beds, 3 baths, and on-site entertainment, including a pool table and theater system. Begin your days with a gentle flow in the yoga room, then relax by the heated pool with a good book. Come evening, walk to Main St. for a night on the town, or enjoy a soak in the private hot tub. Bella Group

4.98 out of 5 average rating, 184 reviews

A light-filled living space is highlighted by a wall of glass, providing expansive views of the water and a natural landscape. The space includes a round coffee table on a light floor, with comfortable seating arranged to enjoy the serene outdoor scenery.

Cottage in Riverhead

Savor Ocean Sunsets at a Soothing Beachfront Haven

Newly renovated and featured as a top Airbnb by New York Magazine, The Beach Cottage has been designed and decorated in a modern organic style, with a palette of whites and neutrals to create a serene and peaceful escape. Relax in the airy, light and open living room, which features a wall of glass for indoor/outdoor living with expansive, uninterrupted water views. Stay on the property for swimming, beach walks, sunsets and BBQs - or venture out to enjoy all the North Fork has to offer.

5.0 out of 5 average rating, 23 reviews

Chic Hamptons Gateway | Pool, Hot Tub, Beach

Stylish & airy Hamptons retreat on over an acre, minutes to ocean beaches and Westhampton Village. Thoughtfully designed, this home features 4 bedrooms, 3 full baths, and a modern open layout across 2 floors. Outside, a heated pool, hot tub and fully fenced yard offer space to unwind in privacy. Clean design, abundant natural light, seamless indoor-outdoor flow, and a calm vibe make this home ideal for an escape. Enjoy peaceful mornings, beach walks, and cozy nights by the fireplace.

4.97 out of 5 average rating, 58 reviews

Home in East Quogue

Cozy Home with Pool - Near Beach and Restaurants

Bright, modern, and designed for easy beachside living, this home is the perfect retreat. Enjoy an open layout with a cozy fireplace and updated kitchen, ideal for relaxed mornings or entertaining. The professionally landscaped, fenced yard is perfect for outdoor fun, BBQs, and features a private gunite, saltwater, heated pool. Minutes to beaches, parks, restaurants, shops, and the gym. EV charger on-site. Ideal as a year-round home or summer escape. Your Hamptons getaway awaits!

4.87 out of 5 average rating, 144 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

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 close on September 15th, 2026 and will reopen May 29, 2027.

Cottage in Westhampton Beach

A bright and airy living space features a light-colored sofa adorned with a decorative pillow. Two woven poufs are situated in front of the couch on a neutral rug. Sunlight enters through a large window, illuminating the room and providing a welcoming atmosphere.

Westhampton Beach cozy cottage, walk to all

Stay for a wedding, concert/show, wineries, vacation or work? “The Cottage,” is cozy & located in a prime village location. WALK to coffee shops, Sunset Theater, Sushi Kaydon, Main Street for cafés & boutiques, Westhampton Beach Performing Arts Center, Farmers Market, grocery, liquor store, CVS. Bike or drive to Rogers village beach (1.5 miles), passes provided or walk the bridges. Enjoy Kayaking rent at Stephens Marina, 25 minutes from Shinnecock Hills, wineries/Southampton.

4.98 out of 5 average rating, 55 reviews

4.82 out of 5 average rating, 50 reviews

Expansive green lawn extends towards the horizon, bordered by white fencing and mature trees. A serene landscape is visible with grazing horses in the background. Bright blue sky complements the lush surroundings, creating a peaceful outdoor environment.

Villa in East Quogue

Farm reserve sunset views

Beautiful villa in beginning part of the Hamptons for a more convenient commute. A private hideaway surrounded by nature where you can relax. It’s perfect for families and friends who love nature, horses and beautiful sunsets. Since our property is spread out over an acre (and surrounded by greater than acre properties), we have the space to allow our guests the ability to maintain a safe distance while still being able to relax comfortably during their stay.

4.94 out of 5 average rating, 119 reviews

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.

Home in Hampton Bays

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, 167 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!

4.8 out of 5 average rating, 69 reviews

Tennis & Sea Escape - Hydrangeas in the Hamptons

Escape the city and enjoy a Tennis & Sea Escape at our charming cabana. The private har-tru (green clay) tennis court is perfect for tennis enthusiasts, while the spacious patio and landscaped backyard offer relaxation after a day out. Access the beach and town within minutes, and plug in your EV car before rinsing off in the outdoor shower. Enjoy a perfect blend of comfort, luxury, and convenience with coffee, TV, WiFi, and towels provided.

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, 179 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.

Popular amenities for Westhampton vacation rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Other great vacation rentals in Westhampton

Home in Remsenburg - Speonk

Westhampton Retreat to the Woods

5.0 out of 5 average rating, 21 reviews

4.99 out of 5 average rating, 96 reviews

Home in East Quogue

Hamptons Oasis | Saltwater Pool, Hot Tub & Games

Cottage in Remsenburg - Speonk

The image captures a spacious outdoor area featuring a large, heated swimming pool surrounded by lounge chairs. A well-maintained lawn is visible, along with a charming cottage that includes an inviting porch. Lush greenery and trees form a serene backdrop.

Newly built cottage near the bay and hamptons

4.98 out of 5 average rating, 40 reviews

5.0 out of 5 average rating, 97 reviews

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.

Home in Hampton Bays

The Hamptons Surf Cottage!

A spacious living area features a billiards table at its center, with natural light flooding in through a skylight above. Large glass doors open to the outdoor space, while a dining area is positioned to the side. Warm hardwood flooring enhances the inviting atmosphere.

4.87 out of 5 average rating, 112 reviews

Pool, tennis, basketball, walk from train station

Apartment in Westhampton Beach

A cozy living area is presented with a light-colored futon and two wooden chairs. A television is mounted above a low white console, while two windows allow natural light to fill the space, adorned with soft fabric treatments.

NEW, steps to the village 1 mile to Dune Road

4.94 out of 5 average rating, 106 reviews

The exterior of a charming two-story carriage house is shown, featuring a light blue façade. A red awning covers a section of the porch, which is framed by large windows. An outdoor dining area with a dark wicker table and chairs is placed on the patio, surrounded by well-maintained grass.

4.95 out of 5 average rating, 81 reviews

In-Town Charming Westhampton Village Beach House

A serene outdoor space is highlighted, featuring a heated saltwater pool surrounded by lounge chairs and shaded with large umbrellas. Lush green grass extends around the pool area, with trees and outdoor seating visible in the background.