Beachfront holiday rentals in Oak Beach-Captree

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

Waterfront beach house 1 hr from Brooklyn and NYC

Escape to a rare waterfront beach house, just an hour from Brooklyn and NYC! Immerse yourself in the stunning natural surroundings and enjoy breathtaking 180-degree water views from every room. With 4 bedrooms and 2.5 baths, our lovingly restored mid-century modern beach house offers an open flow and airy feel thats perfect for relaxing and reconnecting. Comfortable for 2-7 people. Not ideal for small children or guests with limited mobility as there are steep stairs inside and outside.

Chill Beachfront Cottage Amazing Bay/Sunset Views!

Charming, Classic Beach Cottage right on the BEACH! with Panoramic Views & Sunsets on the Great South Bay! Summer on Fire Island is truly paradise. The ocean is sensational, the weather is perfect, the sunrises & sunsets are spectacular, the residents are friendly & creative, & life is WONDERFUL. Our Cottage has 5 Bedrooms with 8 beds that sleep 11. Like Fair Harbor, it has a casual, laid back vibe that is comfortable & enjoyable for people of all ages. * KAYAKS are AVAILABLE! Ask Roberto

Glen Laurel on the Sound (w/private beach)

Glen Laurel on the Sound is a waterfront property located on the North Shore of Long Island. A colonial style home, surrounded by expansive grounds, consisting of lawns, trees, ornamental bushes and from the Tuscan columned porch, a view of the Long Island Sound that is picturesque. Glen Laurel is an ideal place for guests who wish to spread out. It's also great for guests who might be interested in hosting rehearsal dinner gatherings and/or are looking for a bridesmaids' weekend sanctuary.

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.

Hang by the (Chel)SEA

Enjoy a relaxing stay with family and friends at this cozy soundview beach house. Wake up to breathtaking views of the water, where you can go right into the back yard of your very own private beach! Have a morning coffee on the front balcony of the home that overlooks the beautiful marshlands and then spend the day relaxing on the beach, or kayaking in the water! End the evening with a glass of wine on the back deck, that overlooks the water with the most spectacular sunsets!

Toes in the Sand Beach Cottage

Quaint Beach Cottage , on your very private beach on the bay , put your toes in the sand and enjoy this beautiful space! The cottage sleeps 4 people comfortably. There is a queen sized bed in the bedroom and the sofa has a pull out trundle which sleeps two people. Patchogue village is 1 mile away to enjoy exceptional restarants and bars , Davis Park Ferry is close by and you can get to Davis Park in 15 minutes by ferry. Kayaking and Paddleboards are fun on this beach !

Bay Front Upper Level Cottage 47E

Beach front on the water. This paradise hosts its own private beach located on the bay. The house is close to the ferry and easily accessible to restaurants and everything Fire Island has to offer. The house boasts an outdoor shower, 2 bedrooms, kitchen, an indoor full bathroom, half bath, and a grill. Located on the 2nd floor and has views of the bay, beach, and sunset from every direction. Perfect for a family get away or a couple looking to have a romantic trip.

*Waterfront Designer Retreat* | Fire Pit & Sunsets

Welcome to The Swan House 🦢🏡 —your peaceful, designer retreat on Bellport Bay. Enjoy stunning sunsets, swans gliding by, and direct water access from the backyard. Relax on the spacious deck, fire up the grill, or take a short drive to Smith Point Beach. Inside, you’ll find an open, sun-filled layout with curated furnishings and a calming coastal vibe. This stylish escape offers serene waterfront living in any season—just 90 minutes from NYC.

Studio Apt in Cherry Grove, FI.

Studio Apartment only a few steps from the beach at Dune Point Guesthouse. Located in Cherry Grove, Fire Island. Only accessible by Ferry! Adults Only Resort! Newly renovated space with full kitchen, bathroom, one queen size bed and two twins. Great space for couples, with the option of having a friend over, cook, BBQ, enjoy the beach. Located in Fire Island's town of Cherry Grove, laid back, crazy fun place with restaurant, clubs and bars.

Amalfi Dream

Welcome to Amalfi Dream Taking 2026 summer specials now Unbelievable pricing. Send inquiries direct Inquire Below for Nightly Pricing Will entertain shorter stays PLEASE READ CAREFULLY!! ***I allow pets but they have to be included and added into the reservation (pet fees applicable)*** ***PRICING CAN BE ADJUSTED AND WORKED OUT FOR LONGER STAYS*** Weekly and Monthly stays please inquire directly

Incredible Beach House -Spectacular Ocean View!

We do have short-term rent permit from the OSE. Perfect house if you are looking to get away from the city for a few weeks, you are visiting NYC but don't want to stay in the urban chaos, or just want to treat yourself with a perfect vacation. This newly-renovated beach house IS THE NUMBER ONE LOCATION and most luxurious house in the community. RIGHT BEFORE THE WATER WITH THE MILLION DOLLAR VIEW!