House holiday rentals in Remsenburg - Speonk

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.

4.94 out of 5 average rating, 204 reviews

Waterview Beach House: 3 Kings + Putting Green

Unwind at this 3-story waterview beach home in Shirley, NY. Bellport Bay is right across the street with easy beach access. 0.4 mi to Shirley Beach 1.8 mi to Smith Point Beach — perfect for ocean days or Fire Island trips. Featuring: • 3 king beds + 1 full + 3 sofa beds • 70” living room TV + 3x 50” bedroom TVs • Fully equipped kitchen • BBQ grill, fire pit & putting green on premium turf • 6 beach chairs + 2 umbrellas included • High-speed WiFi & keyless entry Your Long Island beach escape!

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An expansive deck offers a view of the Great South Bay, with a mix of comfortable seating options, including lounge chairs and a sectional sofa. The area is complemented by manicured green grass and a wooden railing, providing a serene backdrop for outdoor relaxation.

4.98 out of 5 average rating, 243 reviews

Luxurious Waterfront Beach House On The Bay

Relax and enjoy your time at this beautiful east end waterfront getaway. This house is located right on the relaxing and exclusive Great South Bay with private beach... The experience will bring you the feel of tranquility everyone desires with vacationing out east. While offering all the enjoyments the island has at your fingertips. Centrally located to all island destinations. 90 minutes from Manhattan - 15 minutes to West Hampton - 15 minutes to Fire Island Ferrys. Visit top winery’s WiFi

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A heated saltwater pool is surrounded by a spacious green lawn and lounge chairs, with a tree-lined white fence in the background. The house features a charming design with large windows and a wide patio area, suitable for outdoor dining and relaxation.

4.97 out of 5 average rating, 155 reviews

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.

ValueFamilyPets

4.93 out of 5 average rating, 135 reviews

A serene landscape features a heated saltwater pool bordered by lush greenery. Sun loungers are positioned around the pool under umbrellas, while a wooden fence with trees creates a peaceful backdrop, enhancing the outdoor relaxation space.

Home in Mattituck

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.

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4.88 out of 5 average rating, 152 reviews

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. Our original 1920's Cape Cod style home is full of old and new finds that appeal to curious journeyers and creative weekenders.

LocationFamilyComfort

4.96 out of 5 average rating, 184 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

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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.

4.93 out of 5 average rating, 271 reviews

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

Welcome to Coast to Coast - the perfect getaway from NYC! You may have heard about our new little secret - but you’ll have to come see it for yourself to believe it! Step back into prohibition era Long Island in our hidden speakeasy! Right by Smith Point Beach, we provide accommodations that go above and beyond- this is not your average AirBnB! Soak up the sun at one of LI's top beaches, then enjoy complimentary Netflix, Hulu, cable and more while you shoot pool or play games.

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A charming entrance features a white gate framed by decorative stonework. American flags adorn the front of the house, which is surrounded by lush greenery. The pathway is lined with manicured grass, creating a welcoming approach to the front door.

4.87 out of 5 average rating, 109 reviews

House of peace.

Welcome to my families heart. This house may be old but it is filled with so much love its truly the heart of our family. For many generations we have gathered here. Lovely 3 bedroom house with large property on quiet road. Dining room, kitchen, living room, laundry room. Small sitting room off the master bedroom . There are puzzles and some games for children. Please feel free to use what you want. Close to shopping, beach, casino, ferry, LIRR, LIE, sunrise and The Hamptons.

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A serene scene features a well-kept pool surrounded by lounge chairs, reflecting the colors of the sunset. The main house and pool house are visible, each with large windows and inviting outdoor spaces. Lush greenery outlines the property, enhancing the tranquil setting.

4.87 out of 5 average rating, 138 reviews

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 close on September 15th, 2026 and will reopen May 29, 2027.

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4.87 out of 5 average rating, 150 reviews

A spacious living room features a large sectional sofa adorned with colorful cushions, offering comfort and relaxation. A sleek television is mounted on the wall, while natural light streams through wide windows, illuminating a wooden coffee table and a decorative fireplace in the corner.

Home in Mastic

Cozy home. Comfy living

The whole group will enjoy access to everything from this centrally located home. three comfy bedroom, two bathrooms, large living room, dining and kitchen. close to the beach, nature reserved, kayaking, sky diving and Tanger outlet mall, restaurant and all the fast food located nearby. long island vast array of winery and farms stand etc. Guest is expected to follow house rules. 15 mins after check out time is given after that fees will incur at nightly rate

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A contemporary ranch-style home is surrounded by lush greenery. The custom-shaped heated pool features a waterfall and is bordered by a stone patio with lounge chairs and umbrellas. A state-of-the-art hot tub is positioned nearby, enhancing the outdoor relaxation space.

4.93 out of 5 average rating, 165 reviews

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!

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A charming cottage exterior features wood shingles and white trim. An American flag hangs proudly from the front, while window boxes with greenery add a touch of color. The light blue front door complements the natural elements, inviting guests inside.

4.98 out of 5 average rating, 174 reviews

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.

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Popular amenities for Remsenburg - Speonk house rentals

Kitchen

Wi-Fi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

4.92 out of 5 average rating, 145 reviews

A modern farmhouse is set on a spacious lot. The architecture features a blend of dark and light siding with a white chimney. A well-maintained path leads to a front porch, surrounded by landscaped greenery, enhancing the inviting curb appeal.

Home in Sound Beach

Luxury modern farmhouse with heated pool & hot tub

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A landscaped outdoor area features a stone fire pit surrounded by bright blue chairs on a gravel surface. Lush greenery and tall trees provide privacy, while a spacious pool bordered by lounge chairs is situated in the background.

4.99 out of 5 average rating, 151 reviews

Beach House Feel - Newly renovated Backyard Oasis

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The living area features high ceilings and large windows that fill the space with natural light. A neutral-colored sofa and loveseat provide comfortable seating, complemented by a simple coffee table. A ceiling fan enhances air circulation, while a welcoming rug adds warmth to the wooden floor.

4.89 out of 5 average rating, 114 reviews

*Hamptons Oasis* 4BR Cool Getaway

ValueFamilyBathroom

4.94 out of 5 average rating, 334 reviews

An enclosed outdoor living space features a wooden deck overlooking a heated pool. Furnished with a large round table and comfortable seating, natural light floods through the screens, creating an airy atmosphere. Elegant trees and lounge chairs visible outside enhance the serene environment.

Home in Bridgehampton

Amazing Home close to Everything -

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4.99 out of 5 average rating, 186 reviews

Home in Commack

GOOD VIBEZ HOUSE! Mini Golf+Pool+Hot Tub+Game Room

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4.93 out of 5 average rating, 158 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

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4.97 out of 5 average rating, 218 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

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An aerial view captures a backyard featuring a heated pool surrounded by comfortable seating and a dining area. A deck is adorned with lounge chairs and a patterned rug, while manicured grass enhances the outdoor space. Sunlight reflects off the crystal-clear pool water.

4.86 out of 5 average rating, 108 reviews

Hampton Bays village summer home!

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Weekly house rentals

Home in Remsenburg - Speonk

A serene waterfront scene is presented, featuring a small boat docked alongside a gently flowing waterway. Wooden Adirondack chairs are positioned on sandy ground, surrounded by lush green grass and coastal plants, enhancing the connection to nature.

4.96 out of 5 average rating, 25 reviews

Peaceful Hamptons Waterfront 3 bedroom, 2 bath

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A bright kitchen features sleek white cabinetry and stainless steel appliances. A circular table sits centrally, complemented by a small potted plant. Natural light filters through the patterned window treatment, enhancing the modern atmosphere of the space.

5.0 out of 5 average rating, 31 reviews

Charming Home in WestHampton Beach

LocationFamilyBeach

A bright and airy living space features a cozy beige sofa facing large windows with water views. A staircase leads to the upper level, and natural light illuminates the open layout. Light-colored furniture and decorative accents create a relaxing coastal ambiance.

4.97 out of 5 average rating, 38 reviews

Magnificent Bayfront Retreat

LocationFamilyAccuracy

4.92 out of 5 average rating, 52 reviews

A two-story blue house is set in a well-maintained yard with green grass and neatly trimmed hedges. A double garage doors are visible on the left, and a front porch with steps leads to the main entrance, framed by decorative shrubs.

Home in Center Moriches

Peaceful and Bright 4 Bedroom Getaway Home

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4.92 out of 5 average rating, 63 reviews

A serene waterfront scene is presented, showcasing calm blue waters extending towards the horizon under a clear sky sprinkled with a few clouds. The sandy shoreline gently curves along the edge, bordered by sparse greenery for a peaceful coastal ambiance.

Home in Mastic Beach

Mastic Beach Surf House

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Superhost

Home in Westhampton

5.0 out of 5 average rating, 4 reviews

Westhampton Summer Retreat!

LocationConditionAccess

4.98 out of 5 average rating, 65 reviews

Home in Westhampton

NEW DECK! Private, Heated Pool, Home Office & Gym

ValueFamilyWalkability

4.99 out of 5 average rating, 67 reviews

Home in Mastic

Modern Hamptons Home

ValueFamilyDecor

Private house rentals

4.98 out of 5 average rating, 54 reviews

Cozy Home with Pool - Near Beach and Restaurants

LocationFamilyBackyard

5.0 out of 5 average rating, 23 reviews

A modern kitchen features sleek white cabinetry and a large island with bar seating for four. Two woven pendant lights hang above, illuminating the space. Large windows allow natural light to fill the room, enhancing the open and airy atmosphere.

Home in Westhampton

1940’s Westhampton renovated bungalow

LocationValueLayout

4.99 out of 5 average rating, 93 reviews

Hamptons Oasis | Saltwater Pool, Hot Tub & Games

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An outdoor space featuring a saltwater pool with a jacuzzi positioned nearby. A patio area includes an umbrella and ample seating options. Lush green grass surrounds the pool, while two white decorative swan floats are visible on the water, enhancing the inviting atmosphere.

4.91 out of 5 average rating, 65 reviews

Hamptons Vacation Rental w/ Heated Pool & Jacuzzi!

LocationFamilyOutdoor spaces

5.0 out of 5 average rating, 44 reviews

An outdoor deck features a large dining table surrounded by multiple chairs, shaded by a sun umbrella. In the background, beach chairs and an umbrella are set on the sand, with calm waters extending toward the horizon.

Home in North Fork

Hang by the (Chel)SEA

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Luxe

A modern living area is displayed with light-colored furniture, including two patterned armchairs, a round leather ottoman, and a cozy seating arrangement. A fireplace is framed by built-in shelves showcasing decorative items and a large framed photograph hangs above, complementing the bright ambiance.

5.0 out of 5 average rating, 21 reviews

Charming, Beautiful, Close-to-All Hamptons Gem

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A charming two-story home is surrounded by lush greenery, featuring a well-maintained lawn and a small ornamental tree in the foreground. The front porch is designed with steps leading to a welcoming entrance, complemented by large windows that enhance natural light.

4.98 out of 5 average rating, 59 reviews

Vacation home in the Hamptons.

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