
Holiday rentals with a pool in Westhampton Beach
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Top-rated rentals with a pool in Westhampton Beach
Guests agree: these homes with a pool are highly rated for location, cleanliness and more.

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 a variety of 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.

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!

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.

The Quail’s Nest
A beautifully landscaped tranquil oasis. Newly constructed private two bedroom, one bathroom guest extension to owner occupied house. Guests share large yard and pool with owner, and have private deck and seating area. Private entry and parking. Guest's may enjoy outdoor shower and BBQ. Please note there is no kitchen, however a small fridge, Keurig coffeemaker and microwave, plates/utensils are provided. Conveniently located to beaches, shopping and local restaurants in East Hampton.

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.

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.

Private Oasis W/Stunning Vinyard and Pool Views
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.

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

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 (seasonal) 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!

Luxury modern farmhouse with heated pool & hot tub
*pool closed November to end of April 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.

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 Beach rentals with a pool
House rentals with a pool

Hamptons 3/2 - New Gunite Pool &Bluestone Patio

Stylish Southampton Getaway

Beautiful Hampton’s beach house

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

Hamptons oasis~1 block to water, 8 mins to Main St

Amazing Home close to Everything -

Relax Villa ,Hot tub /New pool,7min from the beach

Exclusive Sag Harbor Compound
Apartment rentals with a pool

Greenport Getaway at Cliffside Condos

Water front, sunsets, sail boats, Wi-fi, birds

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

1856 Trading House close to water

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

5br / 5ba; Bike to town and beach; Heated Pool
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 | $828 SGD | $804 SGD | $866 SGD | $828 SGD | $1,189 SGD | $1,350 SGD | $1,709 SGD | $1,521 SGD | $1,178 SGD | $1,141 SGD | $1,140 SGD | $1,141 SGD |
| 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 holiday rentals with a pool in Westhampton Beach

Total holiday rentals
Explore 140 holiday rentals in Westhampton Beach

Nightly prices starting at
Westhampton Beach holiday rentals start at $204 SGD per night before taxes and fees

Verified guest reviews
Over 1,670 verified reviews to help you choose

Family-friendly holiday rentals
120 properties offer extra space & child-friendly amenities

Pet-friendly holiday rentals
Find 60 rentals that welcome pets

Rentals with dedicated workspaces
80 properties have a dedicated workspace

Wifi availability
140 of Westhampton Beach holiday 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!
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