Holiday rentals with a kayak in The Hamptons

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

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!

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.

Magnificent Bayfront Retreat

Welcome to the Hamptons! The view from this home, that sits right on the water, boasts the most beautiful sunsets that need to be seen to be believed. Whether you’re spending the day in the sun on the beach (a short 5 minute walk), grilling on the deck watching the sunset over the bay, soaking in the hot tub, fishing on the private dock, or lounging on the couch watching a movie on our 75 inch TV after a day of fun in the sun, this home is a perfect getaway for you, your family, and friends!

Serene East Hampton Escape - Warm Pool til Nov

A luxuriously curated woodland escape with massive pool (heated and open May- October), fully fenced and just minutes from EH Village & Ocean Beaches. This impeccably renovated four-bedroom, four-and-a-half-bath home offers refined comfort in a serene, private setting. Sunlight floods the expansive interiors, featuring rich luxurious finishes, a separate office with queen sofa bed, a freestanding soaking tub, and a designer chef’s kitchen with a custom dining table for ten or more.

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.

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.

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.

Ocean House

Rare opportunity to rent your own 100’ Private Beach Front Oasis and enjoy all four seasons! This one-of-a-kind gem on a full sandy acre is only 60 miles from NYC. Brand new chef's kitchen w. Viking appliances. Living room w. wall of glass showcasing the breathtaking views of the Sound. The home also has a hot sauna & in sauna shower. Port Jefferson ferry (5mins away) connects you to New England. Our prices are not negotiable.

Hamptons Waterfront Suite | Private Hot Tub

✔ Separate private guest suite with its own entrance ✔ Entire back property exclusively yours (not shared) ✔ Year-round saltwater hot tub ✔ Private dock + 2-person kayak ✔ Fire pit, lounge chairs & beach towels ✔ Stunning waterfront sunrise & sunset views ✔ Private porch & outdoor shower ✔ 55" Smart TV & electric fireplace ✔ Self check-in & central air ✔ 19 minutes to Southampton Village ✔ Adults only – No pets – No children

Harborfront Star Walk to Harbor & Village

** Airbnb Fees are now included in the nightly Rate* **Coastal Retreat** Perfectly located just steps from the waterfront, placing you within easy walking distance of the marina, Harborfront Park, boutique shops, cafés, restaurants, and the ferry. Whether you’re here for a relaxing getaway, visiting Stony Brook, or exploring Long Island’s North Shore, this home offers the perfect blend of comfort, style, and location.

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.