Cherry Grove Vacation Rentals

Exclusive New Rental Opportunity... Step through the gates to the lush gardens of 54 Bay Walk. This stylish vacation home boasts high ceilings with lots of natural light Master en suite with views of the pool and gardens...newly renovated with attention to every detail. Close to town and [...]

$1,685,000

Brand new custom built construction & fully winterized home. This home offers 3 private deck spaces with a dipping pool, redwood cabinetry, open concept chefs kitchen, 2 entry way atrium & spectacular bay views from the roof top deck with a the potential for a large rental return.

This stunning Pines home is the perfect getaway to enjoy your summer on Fire Island. Step into this very private home and you are greeted with Large Windows that open the space up and also overlooks the pool, 4 bedrooms and an open concept floor plan that is ideal for entertaining. Now offerin [...]

This spacious 7 bedroom 8 bath home is perfect for all your needs RENT & STAY Whether looking for a quarter-share this summer or a limited stay, the house is a perfect place to unwind and enjoy The Pines. FUNDRAISERS & EVENTS The traditional host of The Fire Island Dance Festival, [...]

$3,500

Check out this wonderful 2 bedroom, 1 bath home in Cherry Grove! Very spacious layout with an amazing outdoor space.

$11,000

Welcome to your Fire Island Pines dream vacation! Step into this 4 bedroom, 3 bathroom Pines masterpiece just minutes from the ferry. This home has been transformed to provide all the luxuries you'd want and expect from a vacation rental, while keeping the character of the Pines aesthetic. The [...]

This beautiful bay front oasis boasts 5 spacious bedrooms, 4 en suite private baths and 1 shared bathroom. Keep warm by the wood burning fireplace or enjoy the full house air conditioning. The kitchen is fit for entertaining complete with 2 dishwashers and an ice maker. Hot Tub is O [...]

Welcome to Sugar Hill! Ocean and Great South Bay views greet you in this beautiful 2 bedroom, 2 bath home. Cozy up by the wood burning fireplace...Catch our stunning winter sunsets from the panoramic roof deck...Stroll our beautiful shoreline with some of mother natures furry friends. Di [...]

Completely renovated 3 Bedroom, 3 Bath Bay Front house has every amenity that you could want in your Pines rental. Sliding glass doors span the entire bayside. Electric blinds in the bayside bedrooms, wake up to sunrise or go to sleep to the sunset or close for privacy while “resting” on [...]