Vacation rentals with a pool in Bellport

NEW*Resort-Style Home w/ Pool, Bar&Outdoor Kitchen

NEW*Welcome to your private Bellport retreat, perfect for families or friends. This comfortable 3-bedroom home features a cozy living area with an enclosed stove and a unique bar room for entertaining. Step outside to a resort-style fully private backyard with a private pool and waterfall, outdoor shower, and full outdoor kitchen with BBQ and dining space. Located near BellportVillage,beaches,and the Fire Island ferry perfect for winter and summer getaways and peaceful weekend away from the city

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.

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.

Chic Retreat: Hot Tub, Heated Pool, Sunroom

Escape the city at our newly renovated @BrookhavenChicRetreat Tucked in a quiet cul-de-sac w/ a fully fenced yard, this home is private and safe for families. Relax or entertain w two living areas thanks to our new sunroom. Summer: Private Pool, outdoor living space Year-Round: Outdoor Hot Tub Work: Fast Wi-Fi & desks in every room Laundry: Washer/dryer Minutes from Deer Run Farm, Post-Morrow Trails, and Bellport Village. The Hamptons are just 25 mins away. Book your coastal 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.

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.

*NEW* Reno Bellport Village Home + Saltwater Pool

This newly renovated 3-bedroom home features a chef's kitchen with an induction range and espresso machine. Heated floors are found throughout the kitchen and bathrooms. Outside, discover a fully fenced backyard with a new saltwater pool, deck sofas, and chaises. Please note: we open the pool from Memorial Day to Labor Day in the summer only. It is a saltwater pool, and they come to clean it each week on a Friday. It is heated, but it is not a hot tub.

Luxury modern farmhouse with heated pool & hot tub

*Pool is now open until late 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.

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.

Southamp Waterview, DogsFREE! Kayaks, Ping-Pong

Beachy casual feel-good home easily located at the entrance to The Hamptons. Lovely views of Bay, Nightly Sunsets & birds! Launch our Kayaks at street's tiny beach flowing from Cold Spring Pond into Bay. Or cuddle by the fireplace and play our many available games. We provide soft sheets & towels for the showers and & beach...priding ourselves on your comfort! Our Private-Pool is heatable & plant-surrounded with Outdoor Shower.

Private oasis with pool steps away from the bay

Recently renovated, this charming house has all the comforts of home with the feel of a private country getaway. The long, winding driveway leads you to a charming two story house and large garage. Once inside the house, you will find a large chef's kitchen, a comfortable living room with working fireplace, 3 large bedrooms and two bathrooms. Outside, you will find a beautiful gunite pool and a deck with a Weber grill.

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!