Vacation rentals with a pool in Westhampton Beach

Serene w/ large pool ~1 block to waterfront dining

Serene, chic Hamptons oasis! Located 1 block from waterfront dining + 8 mins to beaches + Main St. Enjoy your large private home nestled in nature, perched back on a quiet tree lined street. Swim in your pool, spark up the BBQ + firepit under the starry sky! Cook in your Chef's kitchen + stream on the 80' TV. Walk 1 block to waterfront dinner + cocktails watching the best sunsets. Enjoy morning coffee on the sea. Walk back home in 4 minutes. You'll be 8 minutes to Main St., beaches + more!

Hampton Bays village summer home!

2 min away from Hampton Bays town. Heated pool, newly furnished, brand new wood floors, freshly painted living room with a classic gray look for a clean refreshing atmosphere !. This 1 story home offers 3 bedrooms, 2 full baths, lovely living room with high ceilings, windows for your perfect summer rental in the Hamptons! This house also offers 2 car garage for visitors! H.B has a verity of restaurants, bars, & beautiful beach etc!! NOTE: there is NO inside cameras / only outside to secure.

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.

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.

Designer Home w/ Heated, Salt-Water Pool

Welcome to your charming and modern Hamptons retreat, the perfect escape for a weekend getaway, family vacation, business trip, or cozy staycation. Whether you’re relaxing poolside, working remotely, or exploring nearby beaches, this home blends luxury comfort with laid-back Hamptons living. Enjoy a private yard with an 18x36 salt-water heated pool, alfresco dining area, grill, outdoor shower, lounge seating, and fire pit, just five minutes from the ocean beaches in beautiful Hampton Bays.

Newly built cottage near the bay and hamptons

Kick back and relax by the amazing pool in this calm, newly built stylish space hosted by a super host! In the estate area of Remsenburg ten minutes from Westhampton Beach Main Street and fifteen minutes from several beaches. At the end of a private road across from the Moriches bay. Wonderful area to bike and walk. Tour options available and include sunset cruising, fishing, etc. Inquire within! Vineyards about 40 minutes away. Exclusive access to 1300 square foot cottage. 2 bed/2 bath!

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).

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 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.

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 (Memorial Day to Labor Day) 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!

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.