Vacation rentals with a kayak in Brookhaven

Riverfront Retreat in Oakdale

Forget your worries in this spacious and serene waterfront space. Beautiful riverfront location in historic Oakdale. Very private. Gorgeous landscaped yard, open and covered outdoor spaces, fire pit,fish pond, dock, outdoor shower, covered hot tub, 3 bedrooms and sleeping den, large living room, kitchen, close to Connetquot Park, fishing,kayaking,Bayard Arboretum, shopping, restaurants ,bars,and Fire Island ferries.owner has use of lower level apartment and garage.boat at dock not for use.

“The Cool House” Waterfront Oasis, 3 Bedrm 2 bath

Discover the “Cool House” This is the coolest waterfront getaway on the south shore of Long Island! Waking up to beautiful sunrises, dinners with a sunset every night & dancing under the stars is a lifestyle your family & friends will cherish forever. The perfect escape from NYC, minutes from the Atlantic Ocean & just a short drive to the Hamptons! This meticulously renovated oasis is the perfect living & entertaining space, a trendy retro beach vibe designed for fun or relaxation.

Steps2Beach, Fish Pond w/Tropical Backyard Oasis!

🌴Steps from Walnut Beach, Silver Sands, dining, shops & more, this guest-favorite escape offers a tropical backyard oasis with a cascading fish pond, multiple lounges, & a seasonal palm tree. Explore the scenic coastline, build sandcastles, or enjoy a day of kite flying. Inside, relax in luxury with a gourmet kitchen, elegant furnishings, & modern amenities. Just 90 minutes from NYC & 15 from New Haven, it’s the perfect retreat for beach days, nature adventures, & coastal charm!

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!

Charming Fairfield Beach 3BR Cottage By The Sea

Charming Beach Cottage – Steps from Private Beach! Welcome to our newly renovated seaside retreat—a perfect getaway for families, couples, or anyone looking to relax by the shore. Nestled just steps from a private beach (right across the street!), our charming cottage offers the ideal balance of coastal tranquility and convenient access to town. Whether you enjoy walking, biking, swimming, fishing, kayaking, or simply napping in a shady hammock, this is the place for you.

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 ⛱

"The Blue Door" House Waterfront

Forget your worries in this spacious and serene place. Newly constructed and furnished, the house is located in a quiet peaceful neighborhood, yet a short walking distance to Main street with a variety of great shops and restaurants. Private access to Creek that leads out to Moriches Bay. You can go kayaking or simply enjoy waterview and nature by the fire pit. Close to the Hamptons, amazing beaches, North Fork vineyards and a train ride away from Manhattan.

The Hilltop Harborview

Guests will immediately walk past spacious hot tub into a comfortable sunroom where you’ll watch the most colorful, water view sunsets Long Island has to offer! This one of a kind offers a sprawling layout that has 3 queen size bedrooms and 1 king . We can also provide an air mattress for an additional guest. There is a kitchen equipped with stove, oven, dishwasher and washer and dryer! This beautiful walking Village has so much to offer!

The Katalpa House -by the beach

-Our beach is private, key and beach tag provided- (in brown shed) This 1000+ sf home, features a newly renovated kitchen, outdoor shower, and many quirks that come with a 90 year old home. The furnishings are eclectic and vintage. Most of the flooring is also new. The beach and bluffs are only about a 2 minute walk. The 1/4 acre lot is shared with a secondary unit as you can see in the photos which is occupied by my sister.