Vacation rentals with a kayak in Fire Island

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Top-rated kayak rentals in Fire Island

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Top guest favorite

Home in Shirley

4.99 out of 5 average rating, 78 reviews

Stunning sunset charming waterfront home 4 seasons

Want to relax and enjoy the water and sunsets? This home has a very relaxed vibe, whether you are grilling outside, kayaking, going to the beach, reading a book as the sound of the waves gently wash up on shore or even enjoying a glass of your preferred beverage on the deck as you gaze into the horizon, there is a sense of comfort and tranquility. Very nice open kitchen looking out into the bay. It really is a nice getaway and an environment to take a break and recharge the senses. Enjoy!

Top guest favorite

A peaceful sunset reflects on the calm waters of the pond, surrounded by lush trees and a gently sloping landscape. The sky displays a blend of warm colors, creating a serene and tranquil atmosphere that enhances the natural beauty of the waterfront setting.

Home in Centerport

5 out of 5 average rating, 21 reviews

Waterfront Home, Heated Pool, 1 Hour from NYC

Escape to your private waterfront oasis! This serene 3-bedroom, 2.5-bath waterfront retreat offers a heated pool (May-Sept), private dock, kayaks, fire pit, pickleball and BBQ lounge. Set 200 feet off the road on a private driveway, it’s perfect for families or quiet getaways. Just 8 minutes west to Huntington’s vibrant shops and restaurants, 6 minutes east to charming Northport Village, and 1 hour by train to NYC. Relax, recharge, and create lasting memories in this peaceful Long Island haven.

Guest favorite

A charming cottage exterior is presented, featuring a light yellow facade with contrasting black shutters. A vibrant red door provides a welcoming entrance. Lush green shrubs and seasonal flowers frame the walkway, enhancing the overall appeal of the front yard.

Home in The Hamptons

4.84 out of 5 average rating, 108 reviews

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.

Guest favorite

A vibrant sunset fills the sky with hues of pink, orange, and purple, reflecting on the tranquil water. Silhouettes of two birdhouses are visible on posts in the foreground, framed by lush vegetation along the shore.

Home in Milford

4.98 out of 5 average rating, 129 reviews

3 Bedroom Beach House with Hot Tub!

Enjoy breathtaking sunset views in our spacious beach house while dining or relaxing in the hot tub. Snuggle up in front of the fireplace while watching a movie on the frame TV. Wake up in the master suite to spectacular marsh views while listening to birds from the Audubon Society. Steps to a white sand beach, heated bathroom floors, luxury bathrobes, linens, and organic mattresses. 6-bikes for exploring. A true resort-like experience with a chef's kitchen making a home away from home.

Guest favorite

A charming red cottage is set among lush greenery, showcasing a manicured lawn leading to the porch. The house features a rustic stone chimney and a welcoming front porch adorned with white railings. Nearby, a small structure complements the main home with a rounded window.

Home in Port Jefferson

4.81 out of 5 average rating, 350 reviews

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! We do allow dogs with prior notice with a $65/dog.

Top guest favorite

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, 115 reviews

Steps2Beach, Fish Pond, 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!

Superhost

A serene scene features a well-kept pool surrounded by lounge chairs, reflecting the colors of the sunset. The main house and pool house are visible, each with large windows and inviting outdoor spaces. Lush greenery outlines the property, enhancing the tranquil setting.

Home in The Hamptons

4.85 out of 5 average rating, 112 reviews

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).

Guest favorite

An oceanfront space features a kayak positioned on the floor, with sunlight illuminating the area. The backdrop showcases expansive views of the water and sky, complemented by picnic tables set outside, visible through large windows. Stairs lead to an upper level, enhancing accessibility.

Home in Milford

4.96 out of 5 average rating, 108 reviews

Oceanfront Retreat: Modern Beach House

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.

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, 125 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

Home in Shirley

4.94 out of 5 average rating, 50 reviews

Waterfront Designer Stay *Sunsets•Fire Pit•Beach*

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.

Guest favorite

A spacious lawn is surrounded by mature trees, providing shade and greenery. A vintage home is visible, with outdoor seating and a grill setup nearby. Gravel paths lead through the property, inviting exploration of the shared outdoor space.

Home in Rocky Point

4.88 out of 5 average rating, 250 reviews

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.

Top guest favorite

A spacious wooden dock extends alongside the water, bordered by lush green plants. The exterior of the white house features large windows and patio seating, inviting relaxation while enjoying the waterfront views. Recreational equipment is visible, complementing the serene outdoor space.

Home in Bay Shore

4.98 out of 5 average rating, 62 reviews

Bay Shore Boat House

Waterfront retreat with stunning views, a designer kitchen, serene interiors, and outdoor amenities including a fire pit, bluestone raised patio, and cabana bar. Ideal for couples and families. Walking distance to downtown Bay Shore, close to Fire Island Ferries and Captain Bill's. Unwind, fish off the dock, and witness unforgettable sunsets. Your perfect escape awaits.