Holiday rentals with a fire pit in Jamesport

Fair Harbor, Fire Island sunny 3 bedroom

Newly renovated home steps from the beach, the bay and the ferry. Extra high ceilings with sunlight streaming into every room. After a day at the beach, enjoy the large outdoor shower, grill and lounge area. Take a glass of wine and portable speakers to the clawfoot tub or indulge in the rain shower. Get some exercise with four new bikes and beach games or ping pong, foosball, air hockey and darts under the house. Two extra twin mattresses for guests with crisp white linens. Fast Wifi.

Modern Farmhouse Oasis in GP Village

Newly renovated modern farmhouse with the perfect blend of style & comfort. Bask in the serenity of our fully equipped 600 sq ft deck and outdoor oasis. Charming Greenport Village is a 10 min walk with its vibrant mix of restaurants, bars, & shops. Walk to Claudio’s, Jitney, train, & ferry to Shelter Island. 5 min drive: beaches, winery, golf. Embrace the coastal, farm, and winery allure by unwinding in our thoughtfully designed home, where every detail is tailored for a memorable stay.

Beautiful home with Game Room

Beautiful home with modern farmhouse decor located near the beach, the vineyards and the Hamptons! We have board games, a ping pong table, a poker table and a tv with Hulu! Hangout by the firepit on chilly nights or stay in the Central A/C on those hot days. Play outside with the kids or watch them play from the hammock. Grill some burgers and hang on the back patio. Everything you need for a fantastic stay. Come check it out! We promise you won’t be disappointed :) *No Parties*

Explore the Water & Woods at a Relaxing Retreat

Flick through records under soaring ceilings and hang out in the year-round hot tub at this East Hampton open-plan retreat. Unwind in the wooded backyard, take a dip in the pool or spa, detox in the sauna, grill on BBQ, relax in the movie-theatre seats to watch a film, then snuggle up to fireplace or firepit before drifting to sleep in super comfy beds. Minutes to village, beaches and hiking trails. Terrific for families & friends looking for a relaxing getaway.

North Fork Farmhouse with Saltwater Pool

Enjoy spectacular sunsets from the great room and deck overviewing your secluded hedged yard and saltwater pool. Located in the heart of the North Fork this 1820s farmhouse with modern amenities is nestled amongst vineyards and farmland with dramatic views in every direction. Quaint villages, premier restaurants, wineries, farms and beaches surround you. A truly magical, peaceful paradise for you and your group. Note pool is open May through mid October.

There's a Beach Getaway!

Welcome to our family-friendly oasis just two blocks from beautiful beaches! Our house offers an open space living area, an expansive yard, fire pits, and a basement with a playroom and workout area. Enjoy our quiet neighborhood. We provide kid-friendly toys, beach gear, bicycles, and more. Sleeps six, with additional options available for larger parties. Cleaning fees for winter stays are 0$.

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.

Mid-Century Modern House - Ciela Haus

IG: @cielahaus A mid-century modern home with cathedral ceilings, carefully curated interiors and a warming indoor charcoal BBQ. It is the perfect getaway for a group of friends or family to explore the outdoors, farms, wineries or to simply enjoy tranquility. I hope you enjoy staying here as much as I loved renovating, curating and styling it!

Greenport Village walking distance to all

Large spacious home in the heart of wine country. Roomy den for relaxing after the wineries. Screened in patio for al fresco dining and enjoying the spacious yard. Hot tub operational year round! Strong, fast wifi with multiple extenders. Message me with any questions or for special offers on 4/5 day stays or midweek 2/3 night specials.