Vacation rentals with a kayak in Long Island

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Top-rated kayak rentals in Long Island

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Top guest favorite
An open concept living area features vaulted wooden ceilings and large windows offering natural light and forest views. A cozy sofa is positioned in front of a modern coffee table. An adjacent dining area and fully equipped kitchen complete the layout, promoting a spacious atmosphere.
Cabin in Greenwood Lake
4.99 out of 5 average rating, 117 reviews

Modern Nordic Designed Cabin

Newly designed Modern Nordic Cabin. Escape to the tranquility of the mountains and lakes. The Nordic cabin is modern with high-end finishes throughout. The open concept living area features a fireplace, waterfall shower, vaulted ceilings, and large windows that offer stunning views of the surrounding forest and lake. Getting to and from NYC is easy. There is a bus stop down the street and a train station 15 minutes away. Perfect for a convenient getaway from the city Warwick town Permit 34469

Superhost
An aerial view captures the coastal neighborhood, with a sandy beach and clear blue water. The vibrant homes line the shore, featuring varied architectural styles. Lush greenery borders the area, enhancing the sense of tranquility and charm typical of beachside living.
Home in Milford
5 out of 5 average rating, 116 reviews

Walnut Beach Escape Fenced Oasis Yard

🌊 Steps from Walnut Beach & Silver Sands State Park, this guest-favorite coastal escape blends beach access, privacy & relaxed luxury. Enjoy a tropical-inspired backyard oasis with a cascading fish pond, multiple lounge areas & a seasonal palm tree—perfect after a day by the shore. Inside, unwind in a beautifully designed home with a gourmet kitchen & modern comforts. Just 90 minutes from NYC & 15 from New Haven, it’s an ideal retreat for beach days, nature lovers & laid-back coastal living.

Top guest favorite
A hammock is suspended between two trees, providing a relaxing spot beside the lake. Vibrant autumn leaves in shades of orange and yellow frame the serene water view, while a wooden dock is visible in the background, inviting guests to enjoy the tranquil setting.
Home in Putnam Valley
4.99 out of 5 average rating, 147 reviews

Luxury Lake House Sauna 1h From NYC

Enjoy the lakefront from my charming home! Fish or Kayak from the private dock or relax on the large deck overlooking the water tucked away on the lake. Boats are included for all guests! Heated bathroom floors, massive TV (86in) + ample lake views. We also have a free Tesla Charger (with an adaptor you can use for other EVs). This is a relaxing retreat tucked away in one of New York's most convenient lakefronts from the city. 20 min to Bear Mountain 35 min to West Point 1 hour to NYC

Top guest favorite
A serene view of Walton Lake captures a wooden dock extending into calm waters. The setting sun casts a warm glow over the landscape, reflected in the lake. Lush greenery frames the scene, enhancing the tranquil atmosphere.
Cottage in Monroe
4.98 out of 5 average rating, 184 reviews

Cozy Winter Lake Cabin

Make wonderful memories on pristine Walton Lake. 1 hr from NYC . This ALL INCLUSIVE Waterfront Cabin is like a mini resort! Rustic, rugged, off grid feel yet 2 miles from town. It has 2 docks, over water hammock & fire pit🔥. Enjoy sunsets on the covered porch & deck. Fish, & look for bald eagles🦅 Hungry? Paddle🛶 across the lake for tacos🌮 & drinks🍸. Inside has retro & antique decor, modern appliances, fireplace♨️, & strong WIFI. Includes COMPLIMENTARY Firewood, NO CLEANING/PET FEES🐕

Top guest favorite
A six-person Jacuzzi hot tub is positioned on a patio, overlooking a serene lake surrounded by trees. The bubbling water reflects the greenery, creating a peaceful atmosphere for relaxation.
Home in Greenwood Lake
4.96 out of 5 average rating, 300 reviews

Stylish Lakeside Chalet with Hot Tub

Welcome to Greenwood Lakeside Chalet, an all-season waterfront retreat on beautiful Greenwood Lake (just over an hour from NYC) surrounded by the Sterling Forest and the Appalachian Trail Corridor. No car? No problem! Conveniently located just steps away from an express bus stop with regular service to/from Port Authority. Boating, Hiking, Fishing, Skiing, Breweries, Wineries, Apple Picking, Waterfront Restaurants, Shopping, Historical Sites, Golf - all nearby (or right in the backyard).

Top guest favorite
A lush backyard features a children's playset alongside a hammock. Adirondack chairs are arranged around a fire-pit, framed by trees and greenery. A serene waterfront view is visible, with a dock extending into the calm waters, enhancing the natural landscape.
Villa in Southampton
5 out of 5 average rating, 106 reviews

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.

Top guest favorite
An aerial view captures a cozy cottage surrounded by lush greenery, featuring large windows that glow warmly in the evening light. A stone patio is visible, with outdoor seating and a fire pit. Nearby, a well-maintained lawn and a parking area with vehicles can be seen.
Cottage in Guilford
4.99 out of 5 average rating, 107 reviews

Waterfront Joshua Cove Cottage with private beach.

Beautiful architecturally designed 1 Bedroom + loft Cottage on Joshua Cove in Guilford. The sunsets are spectacular from your own private beach. Enjoy Fall Foliage, swimming, fishing, and some of the best Kayaking from this perfect setting. Minutes from the Guilford train station, restaurants, shopping, and historic town green. The property is just 15 minutes from New Haven, and the Yale campus. The Thimble Island cruise, and the Ct. river steam train/cruise are nearby as well.

Guest favorite
The exterior features a charming facade with wooden shingles and a welcoming front porch. Two vibrant blue doors highlight the entrance, surrounded by blooming flower pots and neatly arranged greenery. White columns support the porch roof, enhancing the spacious feel of the entryway.
Home in Port Jefferson
4.9 out of 5 average rating, 183 reviews

Harborfront Star

Hang up your car keys and your worries and come visit this beautiful, stylish, coastal gem. Everything that Port Jefferson Village has to offer -- the marina, Harborfront Park, restaurants, clubs, shops, galleries, skating rink, green market, Danfords -- is all within easy walking distance. So come enjoy being in the middle of the action -- and the cool breezes off Long Island Sound -- at the Harborfront Star. We are dog friendly and have a pet fee of $65 per dog (max of 3 dogs).

Guest favorite
Home in Milford
4.95 out of 5 average rating, 127 reviews

Oceanfront Beach House w/ Private Hot Tub

Escape to this luxurious 4-bedroom, 2.5-bath oceanfront home on the stunning Long Island Sound. Enjoy direct beach access, a private hot tub, and a fully equipped patio with a gas grill and dining area. Perfect for families or groups, this retreat offers breathtaking views, a full kitchen, arcade games, and modern amenities. Located minutes from restaurants and shops, it’s ideal for relaxation or adventure. Book now for a perfect blend of comfort and coastal charm.

Guest favorite
A spacious living area features exposed wooden beams and a cozy brick fireplace. Comfortable seating includes a brown sofa and recliner, with decorative pillows adding warmth. A glass coffee table stands on a colorful area rug, while large windows overlook the greenery outside.
Cabin in Riverhead
4.87 out of 5 average rating, 113 reviews

Beach & Woods: Cozy Cabin, Hot tub, Peloton, Oh My

Welcome to nature's retreat, our secluded North Fork haven where 2+ acres of wild beauty and private beach access promise unparalleled relaxation. Delight in our hot tub's warmth under the stars, unwind on swings, or glide on bay waters with our kayak. With enchanting porch views, an invigorating outdoor shower, and nearby organic farms, our cabin is an idyllic escape. Experience the local charm with vineyard tours and return to a haven of comfort and adventure.

Superhost
A spacious living room features a large sectional sofa adorned with colorful cushions, offering comfort and relaxation. A sleek television is mounted on the wall, while natural light streams through wide windows, illuminating a wooden coffee table and a decorative fireplace in the corner.
Home in Mastic
4.86 out of 5 average rating, 132 reviews

Cozy home. Comfy living

The whole group will enjoy access to everything from this centrally located home. three comfy bedroom, two bathrooms, large living room, dining and kitchen. close to the beach, nature reserved, kayaking, sky diving and Tanger outlet mall, restaurant and all the fast food located nearby. long island vast array of winery and farms stand etc. Guest is expected to follow house rules. 15 mins after check out time is given after that fees will incur at nightly rate

Guest favorite
Tiny home in East Lyme
4.95 out of 5 average rating, 144 reviews

Lakefront Retreat Tiny House

Discover a tranquil lakeside escape in our cozy tiny house, nestled within a boutique RV Park in East Lyme, CT, just 15 minutes from Mystic. Perfect for couples seeking a romantic getaway or individuals looking for a serene retreat. Compact in size but loaded with all the comforts you need: a comfy queen bed, smart TV and fast WiFi, a fully-equipped kitchen, a bathroom with full sized shower and flushing toilet, inviting decor and an unbeatable lake view!

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