Holiday rentals with a pool in Westhampton

The Hideout, Westhampton Beach Coastal Getaway

Welcome to the Hideout! This beautiful Hamptons getaway is the perfect escape for a staycation or vacation. The Hideout is a calm coastal design that will bring peace and serenity to anyone. This property features a gym, pool, hot tub, laundry room, and tennis court. There is also a desk with a printer, in case you have some work to do. It is about a 10 minute drive to Westhampton Main St. with food and shopping spots. It is about 8 min driving to Quogue Village beach (2.6 miles from the house)

Location · Family · Bathroom

Mamma Mia Getaway

Escape this holiday season to Eastport, NY, and indulge in a memorable stay at this spacious 4-bedroom, 2-bathroom vacation rental house. With a dreamy yard, and a deck, this home has everything needed for a relaxing getaway. Explore nearby attractions such as the captivating wineries and breweries, apple picking, the vibrant Montauk Point Lighthouse, and the unspoiled beauty of the Hamptons. After a day of adventure, return home to unwind by the deck or in the cozy bar room. Eastport awaits!

Family · Location · Comfort

Hamptons Getaway/ Backyard OASIS/EV charger

Resort Style Backyard just 15 minutes from Southampton Village and close to Restaurants and Shopping. Home is completely Renovated just 2 years ago. Heated salt water/chlorine combo pool. 1 year old. Perfect for families looking to get away from the Hustle and Bustle of the city. Great for Families- 2 Bedroom/ 1 Bath. No Pets Allowed. Barbecue Grill set up in the Backyard. Stone fire pit for cooking smores at night with the kids or simply to enjoy a glass of wine. Great for the Fall time.

Family · Location · Barbecue

1940’s Westhampton renovated bungalow

Come stay at this centrally located hamptons chic property. The whole group will enjoy easy access to many beaches, downtown Westhampton Beach and many NoFo wineries. Westhampton Beach is 6 minutes from the house and filled with many amazing restaurants and shops to explore. Explore all of the Hamptons and Northfork from this beautiful 4 bed and 3.5 bath home with inground pool. Pool open MDW- LDW *** No smoking or drugs on property. ***No pets Please note there is no fence around the pool.

Family · Value · Condition

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.

Location · Family · Indoor spaces

Joyful Beach House, viewing The Great South Bay

Amazing Great South Bay view with access to Shorefront and Rider Parks. This Ranch has an unobstructed view of the Shorefront Band Shell. Watch concerts and sunsets from the comfort of your patio. Walk down to the Patchogue Beach Club and enjoy the pool and beach. This open-concept home has 2 bedrooms, one bath, a remodeled bathroom, and a kitchen. The kitchen has stainless steel appliances, a farm sink, and a butcher block countertop with natural lighting that will brighten the home.

Value · Family · Heating

Charming & Bright Pool Cottage

Take a deep breath when you enter this very bright, well appointed pool cottage. Lush backyard with the main residence and use of the salt water, unheated pool and outdoor shower. Property is on a tree lined street that ends at the bay. A 5 minute walk to the quaint village of East Quogue. Want to hit the fabulous Hampton beaches, they are a 10 minute drive away. Closest downtown Hamptons are Hampton Bays (5 min), Westhampton (our favorite ...10 min) and Southampton (15 min).

Location · Hospitality · Outdoor spaces

Chic Hamptons Gateway | Pool, Hot Tub, Beach

Stylish & airy Hamptons retreat on over an acre, 5 min 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.

Location · Family · Accuracy

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

Value · Family · Decor

Beach House Feel - Newly renovated Backyard Oasis

You will love this sunny, completely renovated three bedroom ranch. It's beautifully decorated with beach and nautical themes throughout the house. You can cook or barbeque at home on your private deck or go out and enjoy the many award winning restaurants in the area. Come home from the beach or shopping and lounge by the pool. At night, gather around the fire pit while making smores or just admiring the stars. This house is perfect for families, couples, or a girls/guys getaway.

Location · Value · Nearby

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.

Location · Family · Checkout

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.

Value · Family · Nearby