Beach house vacation rentals in Montauk

A landscaped yard features a lush green lawn framed by mature trees and bushes. The expansive bay and ocean views are visible in the background. A colorful sunset paints the sky, creating a serene and tranquil setting.

4.98 out of 5 average rating, 52 reviews

Best View + Putting Green + Private Beach

Perched high atop the Shinnecock Hills, our home boasts panoramic bay and ocean views unlike any other in the Hamptons! Located just 5 minutes from Shinnecock Hills Golf Club + your own private putting green, our property will create an awesome guest experience for the upcoming 2026 US Open! Tranquil, sanctuary like setting with manicured landscaping, mature privacy trees, waterfalls, like your own arboretum! Private beach, local favorite restaurants and hang outs are within walking distance!

A charming cottage is set against a backdrop of lush greenery, featuring a welcoming front porch with a white railing. Natural light illuminates the exterior, showcasing the textured shingle siding and a gabled roof. The grassy area extends toward the tree line, creating a serene atmosphere.

4.95 out of 5 average rating, 248 reviews

Private beach, fully updated house, on 2 acres.

Each the special magic that only the Hamptons offer—historic charm, a rural atmosphere, white sandy beaches and a relaxed lifestyle—while staying in this light-filled three-story cottage. Tucked away on a beautiful 2.2-acre wooded lot, this bayside oasis offers a tranquil retreat, with deer sightings, private beach access, stunning view and picture-perfect sunsets. A short drive to the beaches and town, quick trips to nearby shops, market stands, restaurants, museums and Jackson Pollack house.

A spacious heated in-ground pool is surrounded by a stone patio and vibrant landscaping. Lounge chairs are arranged along the poolside, accompanied by a large umbrella for shade. Lush greenery and blooming flowers frame the area, creating a serene outdoor retreat.

4.97 out of 5 average rating, 68 reviews

4 BR Hamptons Oasis w/ Pool,Jacuzzi & Beach Access

Your dream Hamptons vacation! Located on the border of Southampton and Hampton Bays, this stunning home is nestled at the end of a private cul de sac, just steps away from the gorgeous Peconic Bay Beach. Below are amazing features you can look forward to during your stay: • In-ground Heated Pool w/lounge chairs • Outdoor Shower • 3-Burner Weber Grill • 1 Acre Yard fully fenced in that is child-friendly • Beach Bicycles • Bay Beach Access • Minutes from the ocean beach (Ponquogue Beach)

4.98 out of 5 average rating, 220 reviews

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

4.89 out of 5 average rating, 237 reviews

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

Beautiful 1920's beach cottage with beach access just across the street. Enjoy the sea breeze, ocean views, and sound of the waves lapping in this quaint home with unique architecture. Ten minutes to downtown New Haven and Yale for great places to eat, museums, and nightlife. Public beach and playground nearby. Warm and welcoming community. Master bedroom has vaulted ceilings and deck with views of the sea. Central Air, Cable TV, outdoor grill, plenty of parking. Enjoy this lovely home!

4.92 out of 5 average rating, 100 reviews

The main living area features large windows offering sweeping views of Long Island Sound. A cozy seating area with throw pillows is positioned beside a dining table that comfortably seats six, illuminated by natural light. Light-colored hardwood flooring enhances the inviting space.

Home in East Haven

Luxury Beachfront Retreat - Modern Shoreline Villa

Welcome to luxury living and the peaceful beach vibes on Cosey Beach! Jutting out into Long Island Sound, guests will enjoy unparalleled waterfront living as waves break directly under your luxury vacation villa. Breathtaking sunrises and sunsets abound from the main living spaces and multiple decks. Descend to your private beach to use one of the provided kayaks or paddle boards, or wander down the street to family friendly fun, including splash pad, casual restaurants, and ice cream counter.

A wooden deck area features a dining table with six chairs, accompanied by a grill. A large umbrella provides shade, while the picturesque view of the water and distant marina is visible beyond the railing, set against a clear blue sky.

5 out of 5 average rating, 137 reviews

Hamptons Waterfront- Great Location- On the bay

Amazing Beachfront vacation home located directly on a private sandy beach on Shinnecock Bay. Stunning waterfront views- sunrises/sunsets. Have a bbq and relax right on the back deck and watch the boats pass by or take a quick walk or shuttle boat to some of the Hamptons best restaurants. No worries about having a drink and getting home. You’ll love my place because of the location and the ambiance. My place is good for couples, solo adventurers, business travelers, and families (with kids).

An open living space is highlighted by large glass doors that offer views of the lake. A cozy seating area is complemented by a stone fireplace and contemporary decor. Natural light fills the room, enhancing the inviting atmosphere amidst greenery just outside.

4.96 out of 5 average rating, 78 reviews

Waterfront Home with Private Beach

Note: From mid-June through Labor Day: our rentals are 7-day periods from Saturday-Saturday. in May and the first part of June, we have a 3-night minimum. Enjoy your own private beach, fireplace, large deck with amazing sunset views, Kayaks, SUPs, bikes and long summer days on Lake Montauk. Our beach front midcentury house has views from every angle. Swim in the lake or take a short bike ride to Gin Beach. Make fabulous feasts in our chef's kitchen and eat at the large outdoor table.

4.98 out of 5 average rating, 103 reviews

Breezy Waterfront Home With private Dock

This charming waterfront home is the ideal getaway for the active family with the Hamptons' largest natural 'saline pool' (the Peconic Bay) just footsteps away. This home easily sleeps 7 - with 3 bedrooms and 3 separate kids' sleeping cabins. You can jump on our standup paddle board right off our private dock, jog along wide stretches of pebble beach, have a swim race to our floating swim platform or simply relax in the hammock. 2 bathrooms indoors and 1 private outdoor shower,

5 out of 5 average rating, 14 reviews

A spacious living area features a white sectional sofa and leather armchairs, arranged to face large glass doors that provide views of the beach. Natural light fills the room, highlighting warm wood paneling and a cozy, inviting atmosphere. A dining table is visible in the background.

Home in North Fork

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

★ "Beautiful hidden home on the water… enjoy the North Fork summer in style." Private beachfront property with 2 homes & views of Gardiner’s bay. ☞ Bikes + kayaks + paddle boards ☞ Wrap around balcony w/ seating ☞ Fully equipped + stocked kitchen ☞ Deck w/ lounging + water views ☞ Dedicated workspace + printer ☞ Master w/ king + bathroom ☞ 55” Smart TV + Xbox ☞ Indoor gas fireplace 6 mins → DT Greenport (cafes, dining, shopping) 13 mins → Orient Beach State Park ⛱

4.98 out of 5 average rating, 100 reviews

Sea Roost

This private, two-cottage property contains a few of the last remaining original fisherman cottages at Hither Hills built in the 1940s. Set on a lush, private knoll - South of the Highway - Sea Roost boasts mature landscaping and is located steps to Montauk's quiet and secluded Hither Hills Beach. The property consists of a 2 bed/2 bath cottage with separate artist studio (Qn bed, kitchenette & full bath). Dogs negotiable with pet fee. IG @searoosts