Holiday rentals with a kayak in Napeague

Modern Cabin near the Beach

Kick back and relax in this sweet cozy cabin near some favorite local spots in the area. Quick access (under 5 minutes) to Maidstone beach, Rita’s Cantina, Bostwicks on the Harbor, S&S Coffee Shop, Springs Tavern…to name a few. In 10-12 minute drive you can be in East Hampton village or Amagansett Village. The home is set on a half acre in a serene setting in the Lions Head beach association. Walk to private access bay beach from the property. The cabin was renovated top to bottom in 2025.

Amagansett Beach Cottage - Short Walk to the Ocean

Escape to our charming, contemporary beach cottage nestled in the Napeague Dunes. South of the highway with a semi-private ocean beach only two short blocks away. Our well-appointed home, also cherished by us, the owners, is thoughtfully stocked to ensure a comfortable stay. Grille, dine on the back porch, surrounded by tree-lined privacy, or cook in the nicely equipped kitchen. The Lobster Roll, and Goldberg's Bagels are a walk or bike away. Located 8-minutes between Amagansett and Montauk.

Breathtaking Panoramic Waterfront

Relax to sweeping views from every room in this unique, 4600 sq foot direct-waterfront home with large pool, hot-tub, bar, kayaks, and fire pit. 2 floors of wraparound patio/deck, plus 3rd floor loft and roof patio. Open floor plan, 5 bedrooms (bedroom 5 has separate entrance by pool and is summer only) plus loft, 3.5 bath plus half bath and outdoor shower by pool. (Note: pool not heated and open mid-may to mid-Oct only; hot tub closed after new year until March; parking for 6 cars max)

Serene East Hampton Escape - Warm Pool til Nov

A luxuriously curated woodland escape with massive pool (heated and open May through 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.

Steps to Beach • Hot Tub • Game Room • Water Views

Beautiful coastal beach house directly across from a private beach and tennis club with complimentary guest access. Backing up to a serene marsh with stunning views, this home offers a peaceful, upscale setting perfect for families and groups. Relax in the hot tub with outdoor TV, fire pit, and kayaks. Inside features 4 bedrooms, a workspace, and a new game room with a 100” TV, pool table, shuffleboard, and darts. Minutes from Branford’s town center, dining, and waterfront attractions.

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.

Mermaid Oasis - 5bd, Pool, Walk to Beach

Wake up in the trees and stroll to the beach! Mermaid Oasis is reminiscent of a tree house with all the amenities of a modern beach home. 4 bedrooms (1 king, 3 queen, 1 full) 2 futons, 3 full baths, outdoor pool and shower, two spacious decks with grill, fully equipped chef’s kitchen, laundry, pool table, smart TVs. Desirable, quiet Hither Woods neighborhood. Short walk to beach. Great for small groups and families with kids. Quiet place to work from home or truly check out!

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.

Private Beach Community with exceptional light

Kick back and relax in this calm, light filled home in Lionshead’s Private Beach Community. Paddle right out off your backyard. Enjoy organic garden vegetables, feed the swans. Kayac into the sunsets or sit by a gorgeous fireplace.This is a NO SMOKING , no vaping and no party home. If you are intending to travel with your dog please let us know prior to your arrival and ask for permission. We are very dog friendly but would love to know what kind of dog and will decide ASAP

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.

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.

Sag Harbor Village Waterfront Cottage

Relax with the whole family at this peaceful place to stay. This waterfront Sag Harbor cottage is on a quiet street but walking distance to downtown. It's filled with beach life charm and offers the best sunsets in town sitting on the screened in porch, or on the dock benches. Enjoy paddle boarding, the big outdoor shower, expansive yard and private beach.