Family-friendly holiday rentals in Bellport

Guest suite in Fire Island Pines

The cabin's entrance is framed by lush greenery and flowering plants. A wooden walkway leads to the door, and a small set of steps offers access. The rustic exterior features dark wood siding and a window for natural light.

4.96 out of 5 average rating, 103 reviews

Fire Island Pines: Studio Cabin

Studio cabin (approx. 13.5 x 15 ft.) Functional, basic, rustic, atmospheric—It's just a little cabin in the woods. The shack can accommodate only 2 people max. Queen bed (sheets, blankets) Bathroom (shower/towels) Kitchenette (fridge, microwave, sink, dishwasher, dishes, cutlery, glasses) A/C (window unit) Fan Basic tv Internet Beach chairs/umbrellas, Outside shower The Pines is primarily a gay community, but welcoming to all. We love our wild deer and squirrels but no pets in the cabin

Superhost

A spacious living area features large glass windows that frame a stunning sunset over the water. The open design enhances natural light, illuminating the room's elegant furnishings and wooden accents. A dining table is positioned near the windows, inviting relaxed meals with a view.

Cabin in Shirley

4.83 out of 5 average rating, 195 reviews

A-Frame cabin with private beach & epic sunsets

Just a 1.5 hour drive from NYC, this home is the perfect beach getaway spot, with a few steps from the deck to the private beach with its beautiful view across the Great South Bay. Remote work with stunning water views through the wall of windows & in cold weather light a fire while sunlight floods the living space. Two queen bedrooms & bunk bed room sleeps 6 guests, great for families or a small gathering of friends. 5 min drive to ocean beach with great swimming & surfing at Smith Point.

4.96 out of 5 average rating, 197 reviews

A modern living area features a dark sectional sofa accented by cushions and a stylish area rug. In the background, a dining space with four chairs and a kitchen area is visible. Natural light enters through multiple windows, creating a bright, inviting environment.

Apartment in Patchogue

Charming 2 Bedroom apartment

Enjoy our charming 2 Bedroom apartment that is in a quiet and friendly neighborhood in a cul-de-sac. Private entrance on first floor of our house with 2 Bedrooms, 1 Bathroom, Living room, Dining area, and a Kitchen. Close to: Main highways (Sunrise HWY/Long Island Expressway), Grocery stores, Winery & Vineyards, Davis park ferry, Downtown Patchogue village (Restaurants, bars, breweries, shopping), Beaches, Top Golf, MacArthur airport, Long Island Community Hospital, St Joseph’s College.

4.94 out of 5 average rating, 133 reviews

A calm waterfront scene features a vibrant sailboat gliding across the bay, surrounded by green marshland. A wooden dock leads into the water, with several colorful chairs positioned for relaxation. Soft hills and houses line the distant shore under a gentle mist.

Home in Mastic Beach

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.

4.93 out of 5 average rating, 153 reviews

A neatly made bed is positioned in a softly lit room, featuring a light blue bedspread and decorative pillows. Two bedside lamps provide warm lighting on either side, creating a calm and restful environment.

Apartment in Bayport

Private Studio in Lovely South Bayport

Studio offers a private, sequestered nook in quiet Bayport. The 350 sq ft. space offers: Queen bed (Drexel Heritage pillow-top mattress) with cotton bedding, 2 king pillows. Large bathroom with roomy shower, good towels. We use natural cleaners. Wifi, Roku television as well as contactless check-in/ out. Easy access. Close to ferries to FI beaches. Close to main street. Walk to two parks. Dedicated off-street parking. NO SMOKING. NO ANIMALS. Violations result in eviction/ fines imposed.

4.96 out of 5 average rating, 169 reviews

Home in Mastic

Family Retreat with Heated Pool, Hot Tub, Sauna.

🛏 6 Bedrooms, 9 beds & 3 Full Baths 🏊‍♂️ Heated Pool & Relaxing Hot Tub 4-person Sauna 🏀 Half Basketball Court & 🏐 Volleyball Area 🏌️‍♂️ Private Golf Putting Green 🔥 Cozy Firepit & Outdoor Lounge Area 🛝 Swing Set & Kid-Friendly Yard 🍽 Fully Stocked Kitchen & Spacious Dining 🌐 High-Speed Wi-Fi & Smart TVs 10 min to Smith Point Beach & Boardwalk 15–20 min to Long Island Wine Country Nearby hiking at Wertheim Wildlife Refuge Short drive to Tanger Outlets & restaurants

4.89 out of 5 average rating, 165 reviews

An outdoor deck is seen featuring a spacious octagonal hot tub. It overlooks a calm canal bordered by green grass and trees. Nearby boats are docked, and the tranquil water reflects the clear sky, creating a peaceful atmosphere.

Home in Oakdale

Waterfront Round House View

A unique little beach house on the south shore of long island with the most beautiful view. The house is located on a canal. Dock is available! **We have Paddle Boards, Surf Boards and 3- 2 person Kayaks onsite for you to use during your stay** You can get to the Great South Bay by paddling to the mouth of the canal. And you can get to Fire Island by hiring a Water Taxi to pick you up! The octagon house was built in the 1970s. It's recently been refreshed with all new beds & linens.

4.93 out of 5 average rating, 145 reviews

A patio is shown with a wooden table and a dark wicker chair overlooking a scenic view. A clear sky with scattered clouds is visible in the background, along with open fields and distant structures. Utility poles line the road, adding context to the setting.

Home in Patchogue

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.

4.94 out of 5 average rating, 141 reviews

A cozy living space features exposed wooden beams and natural light streaming through the windows. A small kitchenette with modern appliances is visible, alongside a comfortable sofa and a rustic wooden coffee table. Decorative shelves and a unique tree branch accent add character to the room.

Tiny home in Mastic

Cozy craftsman style home close to beaches

Feel refreshed when you stay in this rustic gem. 10 minutes from the fire island beaches this newly renovated home will take your breath away. 20 minutes from local wineries theres no shortage of things to do. This is a single dwelling home. There is a basement apartment with a separate entrance. The tenant does not have access to the house. Everything pictured is yours to use! Kick your feet up and enjoy the details of this handcrafted home. Tree house inside and out!

4.99 out of 5 average rating, 101 reviews

The exterior of a charming cottage displays a white facade with dark blue trim and a welcoming front door. A well-manicured lawn featuring stepping stones leads up to the porch, surrounded by colorful flower beds and greenery.

Home in Patchogue

Hamptons Style Cottage close to everything!

Hamptons style cottage home is family friendly with a wonderful, fully equipped, kitchen to cook-in and spa inspired marble bathroom with huge shower and soaking tub to relax in. Rear patio with nicely landscaped yard shaded or unshaded by a large retractable awing. Located in Patchogue on a quiet block just a short walk to the fire island ocean ferries, restaurants, town's bustling main street, local bay beaches, and parks. Perfect for a weekend getaway or an extended stay!

4.89 out of 5 average rating, 125 reviews

A living room is highlighted by a cozy sofa draped with a light throw. A glass coffee table sits atop a soft rug. A fireplace is set within a white mantel, complemented by plants and framed art that add a touch of character.

Home in Bellport

The Stella ~ A 1920s Beach Bungalow

Welcome to The Stella, a thoughtful 1920's home set in the heart of Bellport Village. This is the place for a summer romance, a family gathering, or a creative re-centering. Inspired by the subtle palette and refined geometry of the American artist Frank Stella—who often spent time on Long Island—The Stella enjoys close proximity to many beaches and wetlands. ~ ask about our monthly winter rates for 2025-2026 ~

4.95 out of 5 average rating, 265 reviews

A spacious living area displays rustic log walls and a mix of wooden and upholstered furniture. A comfortable leather sofa is positioned near a stone wood stove, while a colorful armchair adds charm. Natural light fills the room through windows adorned with patterned curtains.

Cottage in Patchogue

Quaint Cottage on Long Island's South Shore.

The Cottage is a lovely space enclosed in hedges for privacy on a one acre property. I do have 3 dogs, they are kept in a separate gated area on the property. The cottage is located 3 miles from downtown Patchogue which is enjoying a renaissance. There are many restaurants and cultural activities as well as ferry access to Fire Island (Davis Park) in the warmer weather. We are also the "Gateway" to The Hamptons.

Popular amenities for Bellport family-friendly rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

4.93 out of 5 average rating, 135 reviews

The home theater features a large screen and 15 electric recliner seats arranged in a semi-circle. Dark blue walls and patterned carpeting create a cozy movie-watching environment. Subtle lighting enhances the overall ambiance without overwhelming brightness.

Guest suite in Northport

Coastal Villa Suite pool•sauna•gym•theater•beach

4.97 out of 5 average rating, 212 reviews

A serene outdoor area showcases a saltwater pool with a spa, surrounded by well-maintained landscaping featuring vibrant yellow flowers. Lush green fields extend into the distance, framed by a clear sky with scattered clouds.

Home in North Fork

Private Oasis W/Stunning Vinyard and Pool Views

4.99 out of 5 average rating, 203 reviews

A screened-in patio features a wooden ceiling and overhead fans, providing a comfortable space for relaxation. A navy blue sofa pairs with a coffee table, while tall chairs surround a dining table. Views of a spacious yard and trees are visible through the screens.

Home in North Fork

Greenport Village walking distance to all

4.81 out of 5 average rating, 391 reviews

A charming red cottage is set among lush greenery, showcasing a manicured lawn leading to the porch. The house features a rustic stone chimney and a welcoming front porch adorned with white railings. Nearby, a small structure complements the main home with a rounded window.

Home in Port Jefferson

The Hilltop Harborview

Apartment in Fire Island Pines

An outdoor deck is viewed, featuring a swimming pool surrounded by lounge chairs and shaded by red umbrellas. A dining table with ample seating is situated on one side, enhancing the open-air space with lush greenery in the background.

4.98 out of 5 average rating, 121 reviews

"SOUTH APT." Renovated 1 Br Apt. In Great Location

Superhost

The open living area features a custom slate pool table with a vibrant arrangement of billiard balls. A modern kitchen is visible in the background, including sleek cabinetry and a refrigerator. A tasteful seating area includes a fireplace and a large wall-mounted television.

Home in Shirley

4.94 out of 5 average rating, 264 reviews

By NYC & Hamptons - Hot Tub, Pool Table, Speakeasy

5 out of 5 average rating, 10 reviews

The living room features a combination of light blue walls and warm wooden floors. A gray sectional sofa is accompanied by a matching armchair and an ottoman. Natural light filters through multiple windows, and a staircase is visible in the background. A wall-mounted television and decorative plant add to the space.

Home in Patchogue

Cozy Village Home with Hot Tub

A spacious saltwater pool is surrounded by a well-manicured yard, featuring lounge chairs and large umbrellas. Water features create gentle splashes, enhancing the serene environment. The area is framed by trees, providing a natural backdrop for relaxation.

4.98 out of 5 average rating, 100 reviews

Brand new house with an all year round hot tub.

Family- and pet-friendly home rentals

Superhost

A light-filled living area features a comfortable sofa adorned with nautical-themed pillows. A wooden coffee table rests on a woven rug, while a stylish floor lamp and wooden chair enhance the space. The ceiling showcases exposed beams, adding character to the room.

Home in Huntington

4.86 out of 5 average rating, 306 reviews

Nautical Farm House on Working Farm with Animals

4.93 out of 5 average rating, 137 reviews

Beach Barn w/ Heated Pool & Sauna - Dog Friendly

4.91 out of 5 average rating, 127 reviews

A spacious living area features a red sofa and a cozy armchair, situated around a wooden coffee table. Natural light floods the room, highlighting a framed painting above the sofa. The open kitchen is visible in the background, equipped with dark cabinetry and modern appliances.

Guest suite in Patchogue

Charming Garden Hideaway near downtown Patchogue

4.98 out of 5 average rating, 120 reviews

A bright living area is present, featuring a comfortable white sofa with blue accent pillows and a natural woven rug. A modern coffee table is placed in front, while large windows allow ample natural light. A fireplace adds a cozy focal point, complemented by a TV mounted above.

Home in East Norwalk

Family Cottage with 4 King Beds and Fire Pit

4.88 out of 5 average rating, 563 reviews

A serene beach scene illustrates a vast stretch of shoreline, with gentle waves lapping at the sand. The water is a mix of blue and green hues under a clear sky, providing a calming seaside atmosphere.

Cabin in Rocky Point

Little, cozy place near beach for a couple.

4.93 out of 5 average rating, 179 reviews

An aerial view captures the serene neighborhood, showcasing small homes interspersed with trees and greenery. The bay can be seen in the distance, along with the nearby beach access. The well-maintained grounds of the property highlight a clean, welcoming environment.

Home in Shirley

Waterview Beach House: 3 Kings + Putting Green

4.96 out of 5 average rating, 112 reviews

A comfortable sleeping area features a spacious bed with a blue quilt and decorative pillows. Two side tables with lamps are placed beside the bed. A small arrangement of flowers adds a touch of color. Blinds cover the window, allowing for adjustable natural light.

Guesthouse in Shirley

La casita J place

4.97 out of 5 average rating, 185 reviews

A cozy bedroom featuring a spacious bed dressed in soft linens is positioned against a light-colored wall. Natural light filters through two windows, casting gentle shadows on the warm wooden floor. A ceiling fan hangs overhead, and a mirror and chair add functional elements to the space.

Home in North Fork

Secluded Farmhouse - Studio Apartment Style Unit

Family-friendly home rentals with a pool

5 out of 5 average rating, 18 reviews

Home in Centereach

Summer Retreat: Private Jacuzzi, Game room & more

An open living area is presented with a large gray sofa and a rustic wooden dining table. A television and a contemporary fireplace are visible, surrounded by stacked firewood. Natural light floods in through large windows, illuminating the space and creating a welcoming atmosphere.

5 out of 5 average rating, 15 reviews

Beautiful Hampton’s beach house

5 out of 5 average rating, 35 reviews

The image captures a spacious outdoor area featuring a large, heated swimming pool surrounded by lounge chairs. A well-maintained lawn is visible, along with a charming cottage that includes an inviting porch. Lush greenery and trees form a serene backdrop.

Cottage in The Hamptons

Newly built cottage near the bay and hamptons

A sparkling pool reflects the clear blue sky, surrounded by a sleek stone patio. Lounge chairs are positioned nearby, inviting relaxation. Lush greenery and vibrant gardens frame the space, enhancing the private outdoor setting.

5 out of 5 average rating, 51 reviews

Luxury Hamptons Poolside Paradise w/ Outdoor Sauna

4.94 out of 5 average rating, 79 reviews

The outdoor patio features a hot tub surrounded by lounge chairs and umbrellas. A dining table is positioned near a barbecue, offering ample space for relaxation and dining. Lush greenery lines the perimeter, enhancing the tranquil outdoor setting.

Home in Bellport

Bellport Home: Pool, Hot Tub & Ping-Pong Oasis

5 out of 5 average rating, 40 reviews

Home in Center Moriches

40x20 Heated Salt Pool · Sun Deck · Sleeps 6

4.94 out of 5 average rating, 72 reviews

An aerial view showcases a spacious outdoor area featuring a heated pool, hot tub, and multiple seating arrangements. A patio dining table accommodates ten, while lounge chairs surround a fire pit. String lights illuminate the space, enhancing the inviting atmosphere for relaxation and entertainment.

Home in Shirley

Beach Getaway w/ Heated Pool & Hot tub