Holiday rentals with a kayak in Springs

Heart of the Hamptons

Peaceful 3 bedroom cottage in a quaint section of the Hamptons. Located on the south shore, closest to the ocean beaches you can get. Bay water at end of lane, ocean beach just over the Ponquogue bridge. Large backyard for games & BBQ grilling. Enclosed patio for morning coffee & evening dinners. The house is best suited for families & friends needing space & looking for simple, low key relaxation. Please click "Contact Host" if you have specific booking requests & I will look to accommodate.

Family-friendly with pool, beach car, new hot tub

Huge, gunite pool with heater. Perfect spot for families or large groups. 5 bedrooms + 4 full baths. 2004 Land Rover included with parking permit—the only way to park at many exclusive Hamptons beaches! Outdoor shower, deck with BBQ & dining. 2 firepits. Kids' playscape. Fast Wi-Fi. Located in historic Springs area. Minutes from secluded beaches on Gerard point and private bay beaches and amenities at Clearwater Beach. Kayak and paddleboard available. No "share houses”. Rental number 17-522.

Chic & Spacious Designer Home, Heated Pool/Spa

RowHouse_EH, Ideally located just down the block from East Hampton's best waterfront restaurants, this chic beach house is designed as a year-round getaway. This 3 bedroom & 2.5 bath home combines sunny interiors & dreamy outdoor living spaces with thoughtful amenities & privacy on a 1-acre lot. Heated saltwater pool & spa, designer chef’s kitchen with Viking appliances. Walk to dinner on the water, take the four bikes out for a spin, then relax in a stylishly modern, luxurious setting.

Hamptons WaterLiving-Dock, Kayak, Beach, EV charge

[FOLLOW US on INSTA @29watersedge] 1-mile from the beach, this child-friendly waterfront Southampton home is a perfect family getaway. Ready for watersports: kayak, paddleboard, boat, or jet ski. Walk down to the beach for a swim in the bay. At home, the backyard has it all: large dock, fire pit, swing/playset, hammock, grill, & oversized deck to take in the views. Surrounded by nature and water, you are just minutes from restaurants and shopping in Southampton Village &Sag Harbor.

Waterfront NoFo Cottage w/ public beach access

Enjoy this waterfront cottage overlooking Marion Lake surrounded by lush landscape and wildlife. Experience 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 #1060

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,

Stunning Hamptons Waterfront Escape w/ Sunset View

Experience an unforgettable trip in the Hamptons at our waterfront haven! Savor the views 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! Note our pool and dock are closed and will open Memorial Day Weekend (late May 2026).

Serene East Hampton Escape - New Outdoor Sauna

A luxurious woodland escape with massive pool, outdoor dining living and play areas, fully fenced and just minutes from EH Village & Ocean Beaches. This impeccably renovated four-bedroom, four-and-a-half-bath home offers refined comfort in a serene, private setting. Sunlight floods the expansive interiors, featuring rich luxurious finishes, a separate office, a freestanding soaking tub, and a designer chef’s kitchen with a custom dining table for ten or more.

Cedar Hot Tub, Suana, Heated Pool walk to water

Heated pool through April 25-November 1st. Sauna & hot tub open year round. Kayak, swim, fish 3 mile harbor, 5 min walk to water, 1 mile to Sammy's Beach, 9min to EH village and 13min to Sag Harbor. organic bedding, best cookware, decorated with ligne roset, Roche Bobois etc. 3 bikes , 2-single sea kayaks. New HUUM Sauna, 1200 sq ft ipe deck w/ cedar hot tub. *POOL HOUSE with additional queen bed, full bath and steam shower available May 1st.

Captains Quarters | Off Season avail. ask for deal

Charming traditional & at the same modern cottage with hot tub and sauna, and a fireplace inside create a peaceful and private ambiance in close proximity to the waters of Three Mile Harbor. Located on a tranquil country lane this house lets you enjoy the serene and picturesque Springs neighborhood year-round. Child friendly with fun playhouse structure and Zip line. The landscaped garden is fully fenced in and pet friendly.

Walk to Breakwater Beach in Heart of Wine Country

Private and peaceful cottage walking distance to Breakwater Beach and Old Mill Inn Restaurant on the water opening Spring 2025. There are two large decks to relax by the firepit and drink your wine from the local wineries. Bikes, kayak, and paddle board are stored in the barn for guests use. Easy access to the marina, fishing, fine dining, vineyards, and farm stands.

Waterfront House on Fort Pond, MTK

Spacious house right on Fort Pond with relaxed bohemian vibe. Enjoy the open kitchen, reclaimed wood beams, and hand crafted furniture. Access directly to the water from the back yard. There are two other cottages that are two bedrooms each on property as well. We do live on the property full time and enjoy making our space a safe and clean environment.