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Vacation rentals with a kayak in Southold

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Top-rated kayak rentals in Southold

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Rental unit in Sag Harbor

4.83 out of 5 average rating, 183 reviews

Pet friendly Apt. Plus cabin, EV charger & sauna.

Artists apartment and cabin located on quaint cul-de-sac just outside Sag Harbor Village, minutes from Long Beach, pet friendly beaches are even closer. Centrally located for easy commutes to all towns and even ocean beaches. Free bikes, surf boards, 3 stand up paddle boards and 2 canoes. Life vests for you and pets A large tick free, shaded, shaded dog run. The cabin is a separate sleeping space from the apartment and has a 2 person SAUNA recently installed. WIFI AC and heat but No bathroom!.

Home in East Haven

4.96 out of 5 average rating, 132 reviews

The Breakaway - a waterfront gem.

Located next to historic Lighthouse Park, this Morgan Point, California-style bungalow overlooks a lighthouse and breakwater that protect New Haven Harbor. Prepare oceanfront dinners in your modern kitchen; relax to sunrises, sunsets, & the sound of waves. A quiet beach is steps from the door for swimming and kayaking. New Haven sights, restaurants, & nightlife are only minutes away. Picturesque coastline communities, local vineyards, breweries, fall foliage, & commuter rail to NYC are nearby.

Home in Old Saybrook

4.97 out of 5 average rating, 118 reviews

Year Round Beach House in Old Saybrook, CT.- Pets

Our Beautiful Home is Located in Saybrook Manor Association and only a short walk to the beach . We have 4 Bedrooms that can accomadate 8 people,pull out couch,2 bathrooms, a Dining Room,Kitchen, and Spacious Living room.Our Yard is fenced in for your privacy & pets.Our home comes with many ammenities such as movies,games,kayaks, Clamming &Crabbing tools,Bikes,Floats & Beach Chairs.We have a beautiful backyard to enjoy games,barbecue or just to relax & unwind.Enjoy our beautiful & quaint beach

Home in North Fork

5 out of 5 average rating, 22 reviews

Beautiful waterfront 3 bedroom home in Southold

Beautiful waterfront home with stunning views of Hashamomuck Pond, making it the perfect escape for a memorable family vacation. Enjoy beaches, wine country, farm stands, and excellent restaurants. Featuring 3 bedrooms and 2 full baths. 1st floor, master bedroom, a guest room, and a bonus room with a pull-out couch. The second floor offers an additional guest room with two queen beds. BBQ, paddle boards, kayaks, fire pit, and plenty of seating to enjoy the beauty that surrounds this home.

Home in Hampton Bays

4.84 out of 5 average rating, 101 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.

Home in North Fork

4.94 out of 5 average rating, 52 reviews

North Fork Wine Country Cottage Heart of Mattituck

This woodsy retreat is sure to charm your family and to generate memories through years of return visits. Relaxing, eating, drinking, playing, biking. This newly renovated home offers a living room and kitchen perfect for socialization and family times. Nature on the property, beaches, hiking, vineyards, farm stands, biking, shopping and more all a step away. Cook meals with local ingredients or eat out in the low-key foodie paradise of the North Fork. Enjoy the newly added outdoor shower!

Cottage in North Fork

5 out of 5 average rating, 30 reviews

Renovated 2-Bedroom Cottage on the North Fork

Serenity awaits as you step into this totally renovated Cottage. The property is perfectly located in the heart of Long Island's Wine Country. Centered on the North Fork this home allows you to explore all that there is to offer…. antique shops, restaurants, vineyards, breweries, farm stands and the beautiful Causeway Beach is just steps from this home. The home is newly renovated with a new kitchen, appliances, new bathroom, outdoor gas grill, fire pit and a beautiful screened in porch.

Home in North Fork

4.95 out of 5 average rating, 21 reviews

Coastal Cottage on the Water

A coastal cottage on the water surrounded by vineyards and farm stands on the North Fork. Unwind in the backyard with a private view of the Goldsmith's Inlet where you can watch the sunrise, bird watch, and admire our local swans. A quick 5-minute walk to the Long Island Sound where you can sunbathe, swim, kayak, and watch the beautiful sunset. Conveniently located near Greenport, Orient, and Southold. *IMPORTANT* Kayaks and grill are only available from May 1st to September 30th.

Cottage in North Fork

4.98 out of 5 average rating, 43 reviews

Stunning waterfront modern farmhouse with dock.

Relax with the whole family or a group of friends at this peaceful, waterfront cottage. Perfect spot to bring a group for a country retreat in the heart of stunning vineyards, spectacular restaurants and stunning waterscapes. Our home’s interior is beautifully appointed where you will be comfortable both inside and outside on our patio, or deck with a breathtaking waterfront view. Peaceful, relaxing and magical place in an idyllic spot.

Home in Southampton

4.95 out of 5 average rating, 151 reviews

Waterview, DogsStayFree! Kayaks, Ping-Pong

Beachy casual feel-good home easily located at the entrance to The Hamptons. Lovely views of the 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.

Home in Rocky Point

4.89 out of 5 average rating, 216 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.

Home in North Fork

5 out of 5 average rating, 16 reviews

Waterfront with private dock & bocce court

4 bed, 2 bath waterfront home with dock, bocce court, fire pit and BBQ. Just a 5 minute walk from Love Lane and many top vineyards and a 5 minute drive to the North Forks nicest beaches. Designed to accommodate guests with ample sleeping quarters, and places inside and out to play & relax framed by the beautiful waterfront location. The property comfortably sleeps 12.**Two week minimum based on local laws and regulations**

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Popular amenities for Southold kayak rentals

Free parking on premises

Air conditioning

House rentals with a kayak

Home in East Hampton

5 out of 5 average rating, 10 reviews

Brand New Amagansett: Heated Pool, 5-beds and more

Home in Shelter Island

5 out of 5 average rating, 29 reviews

Family Friendly Oasis Steps to Water - Heated Pool

Home in Woodmont

5 out of 5 average rating, 77 reviews

Luxurious Oceanfront Escape With Hot Tub

Home in Westhampton Beach

4.94 out of 5 average rating, 17 reviews

Magnificent Bayfront Retreat

Home in East Hampton

4.97 out of 5 average rating, 31 reviews

Chic & Spacious Designer Home, Heated Pool/Spa

Home in East Hampton

5 out of 5 average rating, 12 reviews

Cozy for the Fall- East Hampton Cottage

Home in Old Saybrook

5 out of 5 average rating, 37 reviews

Great Hammcock Getaway, Nearby beaches, Hot tub

Home in North Fork

5 out of 5 average rating, 10 reviews

Hang by the (Chel)SEA

Cottage rentals with a kayak

Cottage in North Fork

5 out of 5 average rating, 12 reviews

Lovely North Fork Beach Cottage (2 BR/2 bath)!

Cottage in North Fork

4.89 out of 5 average rating, 28 reviews

Pumpkins & Sunflowers! Cozy Cottage in the Fall!

Cottage in Guilford

4.99 out of 5 average rating, 96 reviews

Waterfront Joshua Cove Cottage with private beach.

Cottage in East Hampton

5 out of 5 average rating, 6 reviews

Charming Cottage in East Hampton

Cottage in Woodmont

4.84 out of 5 average rating, 75 reviews

Cheerful 3 Bedroom Cottage with Fire Place

Cottage in North Fork

5 out of 5 average rating, 24 reviews

The Bay Breeze

Cottage in Branford

4.95 out of 5 average rating, 43 reviews

Ret's Coastal Cottage w/ Private Association Beach

Cottage in Clinton

4.98 out of 5 average rating, 98 reviews

Guest House at the Marina

Quick stats about vacation rentals with a kayak in Southold

Total rentals
30 properties
Nightly prices starting at
$180 before taxes and fees
Total number of reviews
420 reviews
Family-friendly rentals
30 properties are a good fit for families
Pet-friendly rentals
10 properties allow pets
Rentals with dedicated workspaces
20 properties have a dedicated workspace

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