
Vacation rentals with a pool in Westhampton
Find and book unique homes with a pool on Airbnb
Top-rated rentals with a pool in Westhampton
Guests agree: these homes with a pool are highly rated for location, cleanliness, and more.

Amazing Home close to Everything -
Elegantly designed home featuring modern appliances, a seasonal heated pool, and situated just moments away from ocean beaches, Wolffer Vineyard, and the vibrant Bridgehampton/Sag Harbor villages. Set within meticulously curated landscaping, this property embodies perfection and meticulous attention to detail. Familiarize yourself with our disclosures, guidelines, and house rules. We maintain a strict no events, no parties, and no smoking policy — our home and property grouds are smoke-free.

Stylish+Cozy Hamptons Winter Getaway-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.

East Hampton Village Fringe, Renovated with Pool
This remarkable East Hampton home, nestled along a quiet cul-de-sac, is just moments from shopping, restaurants, and ocean beaches. The residence features an abundance of natural light, crisp neutral color tones, and tall, pitched ceilings that enhance the sense of space. The calming, heated pool provides a perfect retreat for relaxation. Please review our disclosures and house manual to ensure this home meets your needs and expectations. We want to make sure it’s the perfect fit for you.

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.

Stunning Hamptons Waterfront Escape w/ Sunset View
Experience an unforgettable trip in the Hamptons at our waterfront haven! Savor the views 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! Note our pool and dock are closed and will open Memorial Day Weekend (late May 2026).

Stunning Farmhouse in NoFo I Heated Pool, Wineries
Chic & Luxurious North Fork Farmhouse Retreat Set on a private 1-acre lot, this stylish farmhouse offers a pool, lounge areas, and refreshing ocean breezes. Just 1.5 hours from NYC, you’ll be minutes from beaches, wineries, farm stands, hiking, and golf. Inside, enjoy modern interiors, a full kitchen, and fast Wi-Fi. Perfect for families, couples, or friends, this retreat is ideal for a peaceful escape, remote work, or exploring wine country near the Hamptons and North Fork.

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.

Luxury modern farmhouse with heated pool & hot tub
*pool closes end of October This beautiful modern farmhouse is located on a one-acre lot and features a custom designed open-concept living space with vaulted ceilings that opens directly into a pool area. Hidden behind a bookshelf, you'll find a gorgeous game room with a piano and a pool table that can be easily converted into a ping pong table or working space. Please note that we do not allow weddings and events at this time.

Peaceful Retreat in Immaculate Architect’s House
This "like new" contemporary home features 4 bedrooms, 3.5 baths, open living spaces, soaring ceilings, abundant natural light, and a modern kitchen. Nestled in tranquil West Tiana Shores, minutes from bay & ocean beaches, and charming Hampton villages (Southampton, Westhampton, Quogue). The living room directly faces your private pool, cedar deck, and lush garden—a perfect getaway for vibrant summers and relaxing winters

Greenport Beach house Mini Resort Spa & Catering
Nestled steps from the beach, and all that Greenport and the North Fork has to offer, this exquisitely charming 3 bedroom 2 bathroom waterfront home is absolutely delightful.. You’ll love my place because of the views, the location, the people, the ambiance, the outdoors space, and the Saltwater pool.. My place is good for couples, solo adventurers, business travelers, families (with kids), groups, and furry friends (pets).

Exclusive Sag Harbor Compound
A private country compound in heart of Sag Harbor. House just gut renovated with all top of line (all Wolf and Subzero appliances). The main house is 3 bedrooms, 3.5 bath main house PLUS separate large guest cottage (with a King bed, bar fridge, and full bathroom). Gunite pool (i.e., salt chlorinated which makes it feels like clean freshwater). Walk to town, bay beach, public tennis courts, 1000 acre nature preserve.
Popular amenities for Westhampton rentals with a pool
House rentals with a pool

Southampton Hideaway

Splendid private cottage

Year-Round Private Jacuzzi | Peaceful Fenced Yard

Joyful Beach House, viewing The Great South Bay

Cozy w/ Heated Pool/Spa (OPEN NOW!) & Fireplace

Hampton Bays 6 bed/5 bath large secluded property

Beach House Feel - newly renovated backyard Oasis

Gorgeous Waterfront and Indoor Pool Family Oasis!
Condo rentals with a pool

Beautiful condo on Long Islands Northfork

2 BR Waterfront Autumn Escape in Wine Country

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

Waterfront Autumn Escape in Wine Country: 2BR

A Unique Piece of Paradise, Water Front pool
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

Southampton Quiet Private Home/Pool 6min to Villag
Perfect Getaway at Sunny Modern Shampton LakeHouse
Saltbox with Separate Poolhouse in Northwest Woods
When is the best time to visit Westhampton?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $1,141 CAD | $1,051 CAD | $1,015 CAD | $1,029 CAD | $1,402 CAD | $1,486 CAD | $1,542 CAD | $1,634 CAD | $1,255 CAD | $1,191 CAD | $974 CAD | $981 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

Total vacation rentals
Explore 140 vacation rentals in Westhampton

Nightly prices starting at
Westhampton vacation rentals start at $210 CAD per night before taxes and fees

Verified guest reviews
Over 1,620 verified reviews to help you choose

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

Pet-friendly vacation rentals
Find 70 rentals that welcome pets

Rentals with dedicated workspaces
80 properties have a dedicated workspace

Wifi availability
140 of Westhampton vacation rentals include wifi access

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

4.9 Average rating
Westhampton stays are highly rated by guests—averaging 4.9 out of 5!
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- Yale University
- Jones Beach
- Fairfield Beach
- Southampton Beach
- Cooper's Beach, Southampton
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- Robert Moses State Park
- Ocean Beach Park
- Walnut Public Beach
- Rowayton Community Beach
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