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Beach house holiday rentals in Montauk

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Top-rated beach house rentals in Montauk

Guests agree: These beach houses are highly rated for location, cleanliness and more.

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Top Guest favourite
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

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!

ValueFamilyQuiet

4.94 out of 5 average rating, 208 reviews
Top Guest favourite
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.
Home in Shirley

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

LocationFamilyGetting around

4.98 out of 5 average rating, 244 reviews
Top Guest favourite
A dining table with six surrounding chairs is situated on a spacious deck. An umbrella provides shade above the table. In the background, the tranquil Shinnecock Bay can be seen, along with lush greenery and a grill nearby.
Home in Hampton Bays

Hamptons Beach House- Sun, Sand & Relax-Beachfront

This beautiful Hamptons beachfront home is right on Shinnecock bay with your own sandy beach right in the backyard! Relax with your toes in the sand or go for a swim. Located just 4 min. by car from the main town for all your shopping needs. My place is also within walking distance to one of the Hamptons best waterfront Caribbean restaurants- so no worries about having a drink and getting home. The location and ambiance is what makes my place stand out from the rest. You’re gonna love it here!

FamilyLocationCleanliness

4.97 out of 5 average rating, 69 reviews
Top Guest favourite
A vibrant sunset reflects on calm waters, with shades of orange and purple illuminating the sky. Silhouettes of small boats are visible along the sandy shoreline, while gentle waves create a serene atmosphere. The scene offers a tranquil view of Long Island Sound at dusk.
Home in New Haven

Beach Haven - waterfront, near Yale, sunsets

Everything you need for an amazing vacation, year-round, in our comfortable home right on the beach! Walk out the back door and dip your toes in the sand and in Long Island Sound. Enjoy spectacular views from the back patio, sun room, and most rooms in the house. Watch the sunset while soaking in the hot tub. Sit by the gas fireplace with a book. Stroll along the lovely nearby sea wall. 10-minute drive to Yale and all downtown New Haven has to offer. 5-minute drive to Lighthouse Point Park.

ValueLocationGetting around

4.96 out of 5 average rating, 147 reviews
Guest favourite
A cocktail is presented in a tall glass with a vibrant green stem, garnished with red berries. Sunlight glows in the background, reflecting off the water. A white adirondack chair is visible nearby, set against a tranquil evening scene.
Home in Branford

Breathtaking Panoramic Waterfront

Relax to sweeping views from every room in this unique, 4600 sq foot direct-waterfront home with large pool, hot-tub, bar, kayaks, and fire pit. 2 floors of wraparound patio/deck, plus 3rd floor loft and roof patio. Open floor plan, 5 bedrooms (bedroom 5 has separate entrance by pool and is summer only) plus loft, 3.5 bath plus half bath and outdoor shower by pool. (Note: pool not heated and open mid-may to mid-Oct only; hot tub closed after new year until March; parking for 6 cars max)

LocationFamilyNearby

4.93 out of 5 average rating, 46 reviews
Guest favourite
Home in North Fork

Waterfront 3BR Home w/Private Beach on Peconic Bay

Enjoy a variety of activities when staying at this charming bungalow with a private beach on the Peconic Bay. Enjoy the local Vineyards, take a leisurely stroll in downtown Greenport, ferry to Shelter Island, drive to Orient, or discover local hiking trails. Savor the culinary delights at the area's great restaurants, with fresh seafood and farm-to-table dining. Nestled between Greenport and Orient Point, East Marion provides access to all the North Fork has to offer. Rental Permit # 0449

FamilyLocationView

4.89 out of 5 average rating, 44 reviews
Guest favourite
Home in Montauk

4-Minute Walk to Secluded Beach - Hither Hills Gem

Sunny, Spacious 2-story Modern House With Partial Ocean Views, Large Backyard, Two Wrap-around Decks upstairs and downstairs, 4-Minute Stroll to Secluded, Quiet Beach. 4-Minute Drive to Town Rustic Setting in Montauk’s Most Exclusive Neighborhood, Hither Hills Weber gas grill for BBQs Teakwood outdoor dining table & eight chairs for your outdoor dining pleasure Plenty of beach & patio chairs AC upstairs and downstairs Non-declaration of guests will result in termination of booking

ValueFamilyBackyard

4.81 out of 5 average rating, 54 reviews
Guest favourite
An open living area features high ceilings and large windows that bring in natural light. A sectional sofa in deep blue surrounds a vibrant orange rug, while an artwork adorns the wall. A dining area with a wooden table and chairs can be seen in the background.
Home in Baiting Hollow

North Fork True Beachfront Home

This is New York version of California's Big Sur, with direct beach access and spectacular water views, surrounded by forest. Modern, 3,000 sq feet. Walk down path from house to a fantastic sand beach with lifeguard. Large deck for lounging, BBQ, and sunset views. 4 bedrooms, 3 baths, outdoor shower, 4 person hot tub, 2 person sauna, separate den w/home theater, gym, hammocks, wood burning fireplace. Experience the Long Island Sound without neighbors and the suburbs; a naturalist's haven.

LocationValueComfort

4.88 out of 5 average rating, 48 reviews
Top Guest favourite
An open-concept kitchen and living space features modern appliances and a wood-topped island with seating for three. Light cabinets and blue walls create a bright environment, while a hallway visible in the background leads to the entrance of the cottage.
Home in Branford

The Lighthouse: Beach Cottage Getaway by the Sea!

Relax at this unique and tranquil getaway. Long Island Sound to the left, hiking trails to the right. Come kick your feet up at this quiet dead-end road. Enjoy all the modern amenities in this gem of a cottage community. Restaurants and nightlife are just a quick stroll away. Avoid roadside hotels and take a vacation for a night, week, or longer! Check in anytime and at your convenience!No keys to lose or to return! This property provides secure, keyless entry with an August Smart Lock!

FamilyLocationQuiet

4.98 out of 5 average rating, 259 reviews
Top Guest favourite
Home in Branford

Steps to Beach • Hot Tub • Game Room • Water Views

Beautiful coastal beach house directly across from a private beach and tennis club with complimentary guest access. Backing up to a serene marsh with stunning views, this home offers a peaceful, upscale setting perfect for families and groups. Relax in the hot tub with outdoor TV, fire pit, and kayaks. Inside features 4 bedrooms, a workspace, and a new game room with a 100” TV, pool table, shuffleboard, and darts. Minutes from Branford’s town center, dining, and waterfront attractions.

LocationFamilyHot tub

4.99 out of 5 average rating, 113 reviews
Guest favourite
Home in Southold

Coastal Cottage on the Water

A coastal cottage on the water surrounded by vineyards and farm stands on the North Fork. Unwind in the backyard with a private view of the Goldsmith's Inlet where you can watch the sunrise, bird watch, and admire our local swans. A quick 5-minute walk to the Long Island Sound where you can sunbathe, swim, kayak, and watch the beautiful sunset. Conveniently located near Greenport, Orient, and Southold. *IMPORTANT* Kayaks and grill are only available from May 1st to October 31st.

FamilyLocationIndoor spaces

4.88 out of 5 average rating, 43 reviews
Guest favourite
A spacious balcony extends along the side of the house, offering unobstructed views of the shimmering water. Weathered wooden benches provide seating, while the gentle waves can be observed lapping against the shore in the distance.
Home in North Fork

North Fork Sound Front Home with Pool

This Long Island Sound front property on nearly three acres of land with an inground, custom designed, gunite pool is the perfect vacation home. Walk down the ramp to your private beach for a kayak, paddle board or swim in the summer and enjoy a luxurious outdoor shower afterwards. In the fall and winter months, enjoy the extensive book collection and stay cozy by the fireplaces. Spacious and bright, this home has a unique aesthetic and can accommodate 8 guests comfortably.

LocationFamilyPool

4.87 out of 5 average rating, 46 reviews

Popular amenities for Montauk beach house rentals

KitchenWi-FiPoolFree parking on premisesAir conditioning

Beach house rentals with a pool

Superhost
A spacious beachfront home is set against a bright blue sky, with lush greenery surrounding the property. A private dock extends into the calm water, while lounge chairs are positioned on the sandy shore, inviting outdoor relaxation and enjoyment of the scenic views.
Home in Water Mill

3BR/2BA: beachfront, pool, hot tub, outdoor dining

FamilyLocationHospitality

5.0 out of 5 average rating, 3 reviews
Top Guest favourite
A two-story house is framed by lush trees and neatly trimmed shrubs. A brick pathway leads to the front door, which is flanked by potted plants. Sunlight gently illuminates the home's gray exterior and well-maintained roof.
Home in Brookhaven

Private oasis with pool steps away from the bay

FamilyLocationAmenities

5.0 out of 5 average rating, 37 reviews
Guest favourite
Home in Springs

East Hampton Beach House · Heated Pool

LocationFamilyGetting around

4.84 out of 5 average rating, 51 reviews
Top Guest favourite
Home in Hampton Bays

Breezy Bay

LocationFamilyKitchen

5.0 out of 5 average rating, 10 reviews
Home in North Fork

The View

FamilyLocationNearby

5.0 out of 5 average rating, 6 reviews
Home in Miller Place

Waterfront, Heated Pool & Private Beach

FamilyLocationBiking

4.95 out of 5 average rating, 21 reviews
Guest favourite
A serene outdoor area features a heated saltwater pool surrounded by well-manicured grass. Two lounge chairs are positioned nearby, providing a perfect spot for relaxation. The house is visible to the left, with a deck leading to the pool, framed by lush trees.
Home in Brookhaven

Beautiful 2 acres, 3 Bd /2 b, Pool, Pets Welcome

FamilyLocationHospitality

5.0 out of 5 average rating, 17 reviews
Guest favourite
A heated lap pool is set within a wooden deck, surrounded by lush greenery and a large tree with vibrant red leaves. Two sun loungers are positioned nearby, inviting relaxation under the sun, while soft deck planks create a warm and welcoming atmosphere.
Home in Brookhaven

Brookhaven Design Retreat w/ Pool

FamilyLocationBeach

4.9 out of 5 average rating, 10 reviews

Private beach house rentals

Guest favourite
A charming beachfront cottage exterior is depicted, showcasing a gabled roof and grey shingle siding. Large windows allow natural light to fill the interior, while a white table is set on the patio. Green grass surrounds the cottage, enhancing the coastal setting.
Home in Old Saybrook

Addison’s Oasis

LocationFamilyIndoor spaces

4.88 out of 5 average rating, 8 reviews
Guest favourite
A wide view of Long Island Sound is captured from a private deck, featuring tranquil water and distant boats on the horizon. A white railing frames the scene, while greenery and a flagpole are visible in the foreground, indicating a peaceful outdoor setting.
Home in Guilford

Picturesque Waterfront Villa

LocationFamilyOutdoor spaces

4.9 out of 5 average rating, 21 reviews
Guest favourite
A spacious lawn leads to a charming beachfront cottage, surrounded by lush greenery and large boulders. The structure features multiple windows and a sunroom, blending with the natural setting. A deck area is visible, inviting outdoor relaxation and enjoyment of the peaceful surroundings.
Home in Guilford

Scenic Mulberry Point Connecticut Beach House

FamilyLocationBeach

4.94 out of 5 average rating, 85 reviews
Guest favourite
A spacious living area is furnished with comfortable seating options in neutral tones. Large windows provide unobstructed views of the waterfront, letting in ample natural light. Ceiling fans enhance the air circulation, while hardwood floors add warmth to the space.
Home in West Haven

Beautiful, Spacious, Waterfront Home on the Bay

LocationValueNearby

4.98 out of 5 average rating, 44 reviews
Guest favourite
Home in West Haven

New Cape Home By The Beach Fire pit & BBQ

LocationFamilyQuiet

5.0 out of 5 average rating, 12 reviews
Top Guest favourite
The beachfront home features a wrap-around balcony and large windows that provide views of the shore. The exterior is surrounded by a stone wall and sandy beach, with a staircase leading down to the water from the deck.
Home in North Fork

Kayaks ~ Bikes ~ Boards ~ 6mins> Greenport ~ 55"TV

FamilyLocationIndoor spaces

5.0 out of 5 average rating, 29 reviews
Guest favourite
Home in Sag Harbor

Sag Harbor Waterfront & Beach, 12 min walk to town

FamilyLocationDecor

5.0 out of 5 average rating, 8 reviewsA spacious dining area features a large wooden table surrounded by white chairs. Natural light floods in from arched windows, offering views of the beach and ocean. A small television is mounted on the wall, and sliding glass doors lead to the outdoor deck.
Home in North Fork

Monthly Rentals: East End Retreat - Steps to Beach

FamilyValueAmenities

4.72 out of 5 average rating, 47 reviews

Pet-friendly beach house rentals

Guest favourite
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

ValueLocationView

4.92 out of 5 average rating, 64 reviews
Guest favourite
Home in Madison

Coastal getaway with water views in every room

FamilyLocationBathroom

4.9 out of 5 average rating, 70 reviews
Guest favourite
An expansive view of the Long Island Sound is captured at sunset, with golden reflections shimmering on the water’s surface. The coastline is lined with lush greenery, offering a serene backdrop to the peaceful water scene.
Home in Sound Beach

Beach House on LI Sound Waterfront

LocationFamilyWi-Fi

4.85 out of 5 average rating, 75 reviews
Guest favourite
Home in Guilford

Guilford Beach Cottage

ValueFamilySleep quality

4.82 out of 5 average rating, 28 reviews
Top Guest favourite
The exterior of a two-story beach cottage is visible, featuring a soft gray facade and a balcony on the upper level. Large windows illuminate the lower floor, surrounded by a well-kept lawn and garden. A decorative trellis adds character to the welcoming entryway.
Home in East Haven

Beach Cottage by the Sea

FamilyLocationShared spaces

4.9 out of 5 average rating, 258 reviews
Guest favourite
A spacious bedroom features a queen size bed with gray linens. Natural light floods the room through large glass doors that open to scenic views. A comfortable chair and side table complement the space, while a textured area rug enhances the warm wooden flooring.
Home in Mattituck

North Fork Waterfront Log Cabin

LocationFamilyOutdoor spaces

5.0 out of 5 average rating, 11 reviews
Guest favourite
A serene waterfront scene captures a vibrant sunset reflecting orange and pink hues on the calm water. Silhouettes of trees frame the view, while the silhouette of a private dock juts out into the bay, enhancing the tranquil atmosphere of the setting.
Home in Southampton

Year Round Hamptons Waterfront

LocationFamilyAmenities

5.0 out of 5 average rating, 24 reviews
Guest favourite
Home in Westhampton Beach

Hamptons Bayfront Paradise!

LocationFamilyCleanliness

5.0 out of 5 average rating, 23 reviews

Destinations to explore