
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.

Stylish+Modern Cape w/Saltwater Pool-5min to Beach
Stylish+Modern Cape Beach House nestled in Hampton Bays South of the highway, 5 min drive to beaches. Heated Saltwater Pool. 4 Bedrooms+Crib room & Office. 2 Bathrooms. Outdoor deck w/family dining+BBQ. Fully-fenced, tree-lined back yard w/ beautiful sunsets. Upstairs King bedroom w/ensuite bthrm + Twin bedroom directly off master. Main floor has another King bedroom+Twin bedroom, master bath, lounge+kitchen w/huge sit-around island. TV Den. Central AC. 15 min walk/ 2 min drive to shops+train.

Hamptons Oasis: pool, grill, lush landscape
Kick back and relax in this calm, stylish, contemporary masterpiece. 4 beds, 3 baths, eco pool, and expansive outdoor living space. Architecturally impressive structure surrounded by lush landscape and tastefully decorated. The outdoor space includes a pool, a new outdoor grill, a fire pit, pool lounge chairs, a dining table under a wisteria pergola and an outdoor sofa area big enough to fit your entire party. Fully equipped kitchen. Short drive to the beach, walkable to downtown Westhampton.

Beachside Waterview 2Br Condo w/ Pool in Greenport
Relax in a pristine 2Br condo with ocean & pool views. Our remodeled apartment is part of high-end development nestled on LI Sound, just minutes from downtown Greenport. Sip a glass of wine while watching sunset, catch some rays on the beach or deep in the pool. 2 bedroom condo with ocean view, beach, and pool (seasonal) Comfortably sleeps 6 Private beach access year-around Pool (seasonal) Functional kitchenette 2 bathrooms, all toiletries Linens and towels are provided Smart TV AC/Heat

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.

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.

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

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.

Stunning Farmhouse in NoFo I Heated Pool, Wineries
Modern Farmhouse Oasis | Private Pool | Near Hamptons & North Fork Escape to a stylish sanctuary where modern design meets pastoral charm. Set on a private, one-acre land, this farmhouse is a masterclass in coastal living. Enjoy sun-drenched lounge areas, a sparkling pool, and the constant, cooling luxury of Atlantic breezes. Inside, the home offers a seamless blend of contemporary interiors, and high-speed Wi-Fi—perfect for a peaceful retreat or a "work-from-anywhere" getaway.

PRIVATE BASEMENT APARTMENT WITH POOL IN SAG HARBOR
Beautiful basement apartment partially in-ground, with many windows and private entrance is located in Sag Harbor , 3 minutes from village and Heavens Bech by car or 15 minutes walking distance . The apartment has king size bed and comfortable sofa in the living room . In the kitchen you can find coffe maker , toaster , microwave, dishwasher, small fridge , hot plate for light cooking . Tv , WiFi , Airconditoining , access to pool from May till end of the September .

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!

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.

*Hamptons Oasis* 4BR Cool Getaway
Can't beat autumn in the Hamptonsl. The beaches, sun, shopping, restaurants & nightlife. Or just stay at the house. It has everything you might need for a family vacation. With a spacious deck and firepit, the backyard might be all you need. And it's walking distance from town (groceries, coffee, train station & more). The neighborhood is super quiet. 55in LG TV, WiFi, X-Box, board games. Pool closes in September. Families only please.
Popular amenities for Westhampton Beach rentals with a pool
House rentals with a pool

Bronze Rabbit-Pool, Chef kitchen, Sauna, Game Room

Hamptons Vacation Rental w/ Heated Pool & Jacuzzi!

Gorgeous Hamptons Farmhouse without the Traffic!

Luxury retreat w/ heated pool, steps to the Beach!

East Hampton Oasis - Pool and Hot Tub

NOFO Ranch Home in Wine Cntry 2 Beaches 5 Min Walk

GOOD VIBEZ HOUSE! Mini Golf+Pool+Hot Tub+Game Room

Coastal Retreat|Heated Saltwater Pool|5 MinToBeach
Condo rentals with a pool

One Bedroom Apartment Nestled in the Dunes

Greenport Getaway at Cliffside Condos

Beautiful condo on Long Islands Northfork

Waterfront Escape | Private Beach, Pool & Views

Waterfront Elevated Bungalow - Spectacular Views

Beautiful Waterview Condo on the North Fork of LI

Newly Renovated Modern Townhouse w/Pool & Tennis

1856 Trading House close to water
Home rentals with a private pool

East Hampton Ranch with Access to Clearwater Private Beach

Explore the Water & Woods at a Relaxing Retreat
Enchanting Home with Large Decks and Heated Pool
Perfect Getaway at Sunny Modern Shampton LakeHouse
Saltbox with Separate Poolhouse in Northwest Woods
When is the best time to visit Westhampton Beach?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $898 CAD | $872 CAD | $939 CAD | $898 CAD | $1,290 CAD | $1,464 CAD | $1,854 CAD | $1,649 CAD | $1,278 CAD | $1,238 CAD | $1,236 CAD | $1,238 CAD |
| Avg. temp | 0 °C | 1 °C | 4 °C | 10 °C | 15 °C | 21 °C | 24 °C | 23 °C | 19 °C | 13 °C | 8 °C | 3 °C |
Quick stats about vacation rentals with a pool in Westhampton Beach

Total vacation rentals
Explore 120 vacation rentals in Westhampton Beach

Nightly prices starting at
Westhampton Beach vacation rentals start at $221 CAD per night before taxes and fees

Verified guest reviews
Over 1,580 verified reviews to help you choose

Family-friendly vacation rentals
110 properties offer extra space and kid-friendly amenities

Pet-friendly vacation rentals
Find 60 rentals that welcome pets

Rentals with dedicated workspaces
70 properties have a dedicated workspace

Wifi availability
120 of Westhampton Beach vacation rentals include wifi access

Popular amenities for guests
Guests love Kitchen, Wifi, and Pool across Westhampton Beach rentals

4.9 Average rating
Westhampton Beach stays are highly rated by guests—averaging 4.9 out of 5!
Destinations to explore
- Plainview Vacation rentals
- New York City Vacation rentals
- Tuckahoe Vacation rentals
- Long Island Vacation rentals
- Boston Vacation rentals
- East River Vacation rentals
- Washington Vacation rentals
- Hudson Valley Vacation rentals
- Jersey Shore Vacation rentals
- Philadelphia Vacation rentals
- South Jersey Vacation rentals
- Pocono Mountains Vacation rentals
- Rentals with a firepit Westhampton Beach
- House rentals Westhampton Beach
- Pet-friendly rentals Westhampton Beach
- Rentals with a fireplace Westhampton Beach
- Family-friendly rentals Westhampton Beach
- Beach house rentals Westhampton Beach
- Rentals with a patio Westhampton Beach
- Rentals with a washer and dryer Westhampton Beach
- Rentals with a hot tub Westhampton Beach
- Beachfront rentals Westhampton Beach
- Rentals with outdoor seating Westhampton Beach
- Waterfront rentals Westhampton Beach
- Rentals with beach access Westhampton Beach
- Fitness-friendly rentals Westhampton Beach
- Rentals with pools Suffolk County
- Rentals with pools New York
- Rentals with pools United States
- Yale University
- Jones Beach
- Cooper's Beach, Southampton
- Fairfield Beach
- Southampton Beach
- Robert Moses State Park Beach
- Ocean Beach Park
- Sunken Meadow State Park
- Jones Beach State Park
- Hammonasset Beach State Park
- Powder Ridge Mountain Park & Resort
- Long Island Aquarium
- Yale University Art Gallery
- Sleeping Giant State Park
- Sherwood Island State Park
- Compo Beach
- Orient Beach State Park
- Dunewood
- Meschutt Beach
- Wölffer Estate Vineyard
- East Hampton Main Beach
- Ocean Beach
- Ditch Plains Beach
- Stony Brook University




