
Holiday rentals with a kayak in Shelter Island
Find and book unique kayak rentals on Airbnb
Quick stats about holiday rentals with a kayak in Shelter Island

Total holiday rentals
Explore 10 holiday rentals in Shelter Island

Nightly prices starting at
Shelter Island holiday rentals start at $350 AUD per night before taxes and fees

Verified guest reviews
Over 400 verified reviews to help you choose

Family-friendly holiday rentals
10 properties offer extra space and kid-friendly amenities

Pet-friendly accommodation
Find 10 rentals that welcome pets

Rentals with dedicated workspaces
10 properties have a dedicated workspace

Wi-Fi availability
10 of Shelter Island holiday rentals include Wi-Fi access

Popular amenities for guests
Guests love Kitchen, Wifi and Pool across Shelter Island rentals

4.9 Average rating
Shelter Island stays are highly rated by guests—averaging 4.9 out of 5!
Top-rated Accommodation with a Kayak in Shelter Island
Guests agree: these holiday homes with a kayak are highly rated for location, cleanliness and more.

Sprawling Hamptons Estate with Hot Tub & Amenities
Spacious & private Hamptons Oasis. High speed WiFi. Family friendly. Massive home on 1.4 acres hosts 15 guests across 6 bedrooms, 8 beds, 4 full baths plus crib & pack 'n play. Gorgeously decorated by Judy Posey Large heated gunite pool (42 x 20 feet) hot tub and sundeck. Fireplace, over-sized kitchen w/ 3 fridges, electric wood-fired grill, huge yard, firepit, bar/lounge, Golden Tee arcade™, bikes & kayaks. Just 2 miles from towns of East Hampton and Amagansett and several white sand beaches
Outdoor spacesValueBarbecue
4.78 out of 5 average rating, 145 reviews
The North Star: Greenport Waterview Beach Getaway
Welcome to our charming home in Greenport, NY. Right across the street from the private community beach! We are neighbors to the most famous wineries on the North Fork. 3 bedrooms, 2 baths, & a den that has a pull-out queen sleeper sofa. Private beach. Outdoor shower. Comes fully equipped with towels & linens. 2 miles from the town of Greenport. Perfect house for families/groups. DOG(s) FRIENDLY (w/ a pet fee) with fenced front yard & deck- sorry no cats! Looking for adults aged 30 or over.
ValueLocationComfort
4.96 out of 5 average rating, 69 reviews
The Sandy Shack - Coastal Escape
Escape to your own private oasis at this charming beach house in Greenport. This beachfront home offers views of the ocean in every room. Inside, the living space gives plenty of natural light and sitting areas. The kitchen has everything you need to cook for family & friends. There are 4 beds to choose from, which can sleep 6 total. Outside, enjoy your own private beach as well as kayaks to use at your leisure. Located next to Greenport's best restaurants and wineries, book your stay today!
LocationOutdoor spacesAccuracy
4.9 out of 5 average rating, 31 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.
Outdoor spacesValueLaundry
5.0 out of 5 average rating, 113 reviews
Stunning Hamptons Waterfront Escape w/ Sunset View
Experience an unforgettable trip in the Hamptons at our waterfront haven! Savor the views and sunset 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! Our pool will close on September 15th, 2026 and will reopen May 29, 2027.
ValueOutdoor spacesBarbecue
4.87 out of 5 average rating, 137 reviews
The Saltbox: Outdoor Dining, Fire Pit, Soaking Tub
𓇼Walk to the Beach! ༄Location: quiet oasis by nature preserve, vineyards, breweries, farm stands, restaurants + attractions, 5 min to Greenport Village + Southold 𓇼Firepit, outdoor dining with string lights, grill, beverage cooler ༄Equipped kitchen w/blender, coffee, waffle maker + more! 𓇼Bathrooms w/heated floors + a clawfoot soaking tub (Please note there is only 1 shower) ☼Family Friendly: Board games, packNplay, high chair, beach chairs + toys ༄Kayak + bikes 𓇼Smart TVs
Outdoor spacesLocationWi-Fi
4.97 out of 5 average rating, 59 reviews
North Fork Sound Front Home with Pool
This Long Island Sound front property on nearly three acres of land with an inground, custom designed, gunite pool is the perfect vacation home. Walk down the ramp to your private beach for a kayak, paddle board or swim in the summer and enjoy a luxurious outdoor shower afterwards. In the fall and winter months, enjoy the extensive book collection and stay cozy by the fireplaces. Spacious and bright, this home has a unique aesthetic and can accommodate 8 guests comfortably.
Outdoor spacesValueAccuracy
4.89 out of 5 average rating, 44 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.
LocationValueBarbecue
4.87 out of 5 average rating, 124 reviews
Southamp Waterview, DogsFREE! Kayaks, Ping-Pong
Beachy casual feel-good home easily located at the entrance to The Hamptons. Lovely views of Bay, Nightly Sunsets & birds! Launch our Kayaks at street's tiny beach flowing from Cold Spring Pond into Bay. Or cuddle by the fireplace and play our many available games. We provide soft sheets & towels for the showers and & beach...priding ourselves on your comfort! Our Private-Pool is heatable & plant-surrounded with Outdoor Shower.
LocationOutdoor spacesHospitality
4.95 out of 5 average rating, 204 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.
Outdoor spacesLocationIndoor spaces
4.88 out of 5 average rating, 291 reviews
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.
Outdoor spacesLocationCondition
4.92 out of 5 average rating, 116 reviews
Laid Back Relaxation
Kick back and relax in this calm, stylish space. Nice newly updated home on a quiet street within walking distance to beaches, restaurants and a golf course. Great location near Shelter Island heights town, Crescent beach and Sunset beach. The location provides both privacy and relaxation at home with just a short walk or ride to popular Shelter Island spots.
LocationOutdoor spacesComfort
5.0 out of 5 average rating, 22 reviewsPopular amenities for Shelter Island kayak rentals
Holiday House Rentals with a Kayak

Cozy home. Comfy living
ValueLocationAccuracy
4.87 out of 5 average rating, 150 reviews
Heart of the Hamptons
ValueLocationAccuracy
4.85 out of 5 average rating, 115 reviews
Coastal Cottage on the Water
Outdoor spacesLocationDecor
4.9 out of 5 average rating, 41 reviews
Luxe Beach Cottage-Steps to Water-Firepit
LocationOutdoor spacesView
4.96 out of 5 average rating, 48 reviews
Wake up to Stunning Views at a Serene Waterfront Haven
ValueOutdoor spacesAccuracy
4.92 out of 5 average rating, 48 reviews
Lakehouse Getaway North Fork
ValueLocationAccuracy
4.98 out of 5 average rating, 51 reviews
Private Beach Community with exceptional light
Outdoor spacesLocationCheck-in
4.87 out of 5 average rating, 23 reviews
Hang by the (Chel)SEA
Outdoor spacesLocationFamily
5.0 out of 5 average rating, 44 reviewsCottages with a kayak

Renovated 2-Bedroom Cottage on the North Fork
Outdoor spacesValueNearby
5.0 out of 5 average rating, 56 reviews
Stunning waterfront modern farmhouse with dock.
ValueOutdoor spacesParking
4.98 out of 5 average rating, 62 reviews
Bayside bliss - Charming 2bdrm on the water w dock
Outdoor spacesLocationHospitality
4.95 out of 5 average rating, 73 reviews
The Bay Breeze
Outdoor spacesLocationHospitality
5.0 out of 5 average rating, 29 reviews
Amagansett Beach Cottage - Short Walk to the Ocean
LocationOutdoor spacesPets
5.0 out of 5 average rating, 33 reviews
Lovely North Fork Beach Cottage (2 BR/2 bath)!
Outdoor spacesValueIndoor spaces
4.94 out of 5 average rating, 33 reviews
Westhampton Beach cozy cottage, walk to all
ValueLocationBarbecue
4.98 out of 5 average rating, 55 reviews
Shelter Island Waterfront Getaway
Outdoor spacesValueBreakfast
4.97 out of 5 average rating, 115 reviewsOther holiday rentals with a kayak

Modern Cabin near the Beach
LocationHospitalityAmenities
5.0 out of 5 average rating, 6 reviews
Spacious apartment in Sag Harbor
LocationOutdoor spacesGetting around
5.0 out of 5 average rating, 68 reviews
Southampton Modern Barn, Private Pool and Hot Tub
Outdoor spacesLocationCondition
4.99 out of 5 average rating, 78 reviews
The Captain's Crib
Outdoor spacesLocationWalkability
4.96 out of 5 average rating, 56 reviews
“The Cool House” Waterfront Oasis, 3 Bedrm 2 bath
ValueOutdoor spacesSleep quality
4.91 out of 5 average rating, 95 reviews
New listing | 50ft Pool on 1.6 Private Acres
Check-inHospitalityNearby
5.0 out of 5 average rating, 3 reviews
Relaxing Water views
Outdoor spacesLocationSleep quality
5.0 out of 5 average rating, 39 reviews
Stunning sunset charming waterfront home 4 seasons
Outdoor spacesLocationView
4.97 out of 5 average rating, 100 reviewsDestinations to explore
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- Yale University
- Mohegan Sun
- Foxwoods Resort Casino
- Cooper's Beach, Southampton
- East Matunuck State Beach
- Fairfield Beach
- Ocean Beach Park
- Charlestown Beach
- Mystic Seaport Museum
- Mystic Aquarium
- Southampton Beach
- Sunken Meadow State Park
- Soundview Beach
- Hammonasset Beach State Park
- Powder Ridge Mountain Park & Resort
- Wölffer Estate Vineyard
- Ocean Beach
- Sleeping Giant State Park
- Orient Beach State Park
- Meschutt Beach
- Ditch Plains Beach
- Wesleyan University
- Long Island Aquarium
- Splish Splash Water Park





