Vacation rentals with a kayak in Springs

Hamptons Waterfront Escape/ Hot Tub/ Resort Style

Waterfront apartment in Flanders, a Southampton Hamlet – perfect for a couple’s retreat. Resort Style: large saltwater hot tub yr round, private dock with 2-person kayak, fire pit, lounge chairs, and beach towels. Features include self-check-in, private entrance, porch, central air, 55" smart TV, electric fireplace, and outdoor shower. Take in the waterfront beautiful sunrise and sunset views. Just 19 minutes to Southampton Village for restaurants and shopping. Adults only. No pets or children.

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.

Wake up to Stunning Views at a Serene Waterfront Haven

This is a simple but lovely house with spectacular views of the water. Enjoy the sunset from the back patio or take kayaks out right off the dock. The comfortable living room has full length windows. There is also a guest cottage on the property that is ideal for extra space and privacy. Please know that there is a full size bedroom connected to the queen bedroom, there is a door but It is not entirely private since you have to walk through the queen bedroom to access the full bedroom.

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

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).

BeachCottage|Steps To Water|Firepit|Top10%

Kick back and relax in this calm, stylish beach cottage in Sag Harbor. It is the perfect spot for a single or couple to enjoy the Hamptons beachy lifestyle. Fully appointed for your stay, just bring your bathing suit. Outside is your own patio with sitting area, dining table with umbrella, BBQ and my own tiny cottage “Bouy Cottage” is across the lawn so I (or other guests may be there in August/September/October stays). Firepit area is shared with Bouy Cottage.

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 ⛱

House on Napeague Harbor, Amagansett

This family-friendly, rustic beach house was designed around the position of the setting sun and weather co-operating, most evenings guests are not disappointed. The shallow water of the Harbor is a mere 50' from the house - enjoy breakfast on the patio while cormorants and egrets cruise the harbor. Windsurfers, kite-surfers are active when the wind is up; kayakers and SUPers love the calmness of the bay.

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.

Garden Studio with private entrance

Take it easy at this unique and tranquil getaway a short walk to bay beach, wineries and marina. 3 miles to the Sound beaches for amazing sunsets. Or walk down to the bay beach for amazing sunrises. Wheelchair accessible. Beach fun starts here! Beach chairs, coolers, Kayaks, floats, skim boards and boogie boards are available for use.