Vacation rentals with a pool in Westhampton Beach

Find and book unique homes with a pool on Airbnb

Top-rated rentals with a pool in Westhampton Beach

Guests agree: these homes with a pool are highly rated for location, cleanliness, and more.

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Guest favorite

Apartment in Deer Park

4.96 out of 5 average rating, 113 reviews

Best Studio-Private Entrance+Parking-Close To All

Make yourself at home! This Deer Park Den is your perfect suburban hideaway in the heart of Long Island, close to everything and right in the middle of all the fun. Walking distance to lots of great restaurants that give you plenty of great options for ordering in or dining out. Other local destinations include: - Tanger outlets (1 Mile) - Heartland Golf Park (1.5 Miles) - Edgewood Oak Brush Plains Preserve (0.5 Mile) - Robert Moses state park (12 Miles) - Sunken Meadow state park (12 miles)

Nov 2 – 9

G$24,592 GYD per night

Guest favorite

Home in Southampton

4.88 out of 5 average rating, 193 reviews

Secluded Southampton Luxury Estate. 286

We are only on airbnb no other sites Hot water is included . The estate is close to Ocean beaches, Downtown, Village, Shopping, Restaurants, Night life, Bars, Parks, the airport, art and culture, museum . Good for couples, solo adventurers, business travelers, families (with kids), and small groups. One of the best locations for access to north fork wineries and still be just minutes to the town of Southampton. Shampoo, soap and conditioner are not supplied so make sure to bring your own.

Oct 25 – Nov 1

G$237,409 GYD per night

Guest favorite

Home in Mastic Beach

4.93 out of 5 average rating, 107 reviews

Gorgeous Waterfront and Indoor Pool Family Oasis!

Breathtaking Waterfront home with 37 foot heated indoor pool. 3 Bedrooms plus a 800 Sq/Ft master bedroom with wood burning fireplace. WiFi, 3rd floor entertainment room with 120 inch screen movie projector, karaoke, fooseball, pool table. Wraparound terrace, sunroom, 45ft dock with launching ramp, putting green, sand trap, outdoor kitchen, bar & stone patio with tables & BBQ grills & fire pit. Ability to catch abundant fish & blue crabs right from the dock. Picture tells a thousand words.

Dec 14 – 21

G$206,232 GYD per night

Guest favorite

Home in Hampton Bays

4.98 out of 5 average rating, 112 reviews

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.

Oct 8 – 15

G$113,087 GYD per night

Guest favorite

Home in Manorville

4.98 out of 5 average rating, 199 reviews

Ultimate House with Heated Pool, Hot Tub and Sauna

Ultimate house with 4 Bds, 3 Baths, finished basement with entertainment area and gym. Minutes from the Hamptons and North Fork. Everything for your rest in any weather and season. Yamaha piano, Japanese massage chair, karaoke, drum set, electric guitars, ping pong, fossball and pool tables,board games. Fully landscaped backyard with flowering plants, outdoor lights. 2 BBQ areas, Gazebo with fireplace and projector. Easy access to beaches, restaurants, farms, vineyards and shopping.

Oct 3 – 10

G$120,357 GYD per night

Guest favorite

Home in Westhampton Beach

4.92 out of 5 average rating, 26 reviews

WestHampton Beach Village house with heated pool

Enjoy a peace of heaven in this beautifully renovated 3 Bedroom, 2 Bathroom beach home w/ Reme Halo in-duct air purifier. Salt water heated pool and outdoor sitting for 8. Located just down the road from Main street, restaurants, Rogers beach, Dune road, Southampton town beaches , wineries and all the Hamptons have to offer. Property Manager 5 minutes away available. Pool open May - September. Off season pool may also be available depending on temperatures.

Mar 6 – 13

G$134,377 GYD per night

Guest favorite

Home in Westhampton Beach

4.93 out of 5 average rating, 134 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!

Oct 30 – Nov 6

G$161,535 GYD per night

Guest favorite

Home in Cutchogue

4.96 out of 5 average rating, 190 reviews

Stunning Vinyard Views - Spring Special $475/Nt!

Enjoy spectacular wine country sunset views from the living room that extend to the gorgeous saltwater gunite pool and spa. (Please note THE POOL AND SPA (attached hot tub) are OPEN FROM MAY 1 - OCTOBER 15 only). Beautifully decorated, comfortable home with an updated chef's kitchen and fireplace. Fabulous restaurants, wineries, farms, beaches and exquisite small towns all nearby. Simply put, a magical, peaceful paradise for you and your group.

Mar 19 – 26

G$173,654 GYD per night

Guest favorite

Guesthouse in Brookhaven

4.97 out of 5 average rating, 215 reviews

The Unhampton

This Brookhaven Hamlet detached space (totally separate) is for people who love nature and preserved quiet spaces. Fire Island is a ferry ride away, Manhattan is one hour by train and the Hamptons are a 25 minute ride.15 minutes from the restaurants and coffee shops in Patchogue and just a couple of minutes from Bellport Village. Centrally located and truly peaceful!

Mar 21 – 28

G$34,176 GYD per night

Guest favorite

Guesthouse in East Quogue

5.0 out of 5 average rating, 29 reviews

Petite Central Cottage

We are centrally located giving you access to both the North and South Forks of the East End. The cottage has a 3 night minimum on Thursdays with longer stays available. If you have something in mind, please send us a message and hopefully we will be able to accommodate your special request. Be sure to read the caption on our main picture for detailed information.

Apr 12 – 19

G$97,408 GYD per night

Guest favorite

Guesthouse in Westhampton

5.0 out of 5 average rating, 18 reviews

The “Birdy” Guest house

Take it easy at this peaceful guesthouse near Westhampton Beach village, Country Club, wine country (North folk), Moriches Bay and Westhampton Beaches. An amazing location for birding and kayaking. Ideal place for a couple looking to escape the city, attend a wedding, or explore wine country for a weekend to get some fresh air and experience nature.

Sep 13 – 20

G$68,698 GYD per night

Guest favorite

Loft in Southampton

4.89 out of 5 average rating, 145 reviews

Getaway cottage privet and quiet

Cottage is on the property with the owner but it is completely separate from our own home. We are in a lovely quiet neighborhood. We are friendly with animals we have our own dog as well. 5 Minute drive to the bay and 10-minute drive to the ocean. Baby crib can be additionally installed. Pool is shared with my family on property

Nov 26 – Dec 3

G$82,678 GYD per night