Cherry Grove Vacation Rentals

$1,350,000

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 unique Horace Gifford pool home is just one house from the ocean and steps from the beach. Enjoy Spectacular ocean views from the upstairs decks and Magnificent sunset views from the west deck. This home is just five minute walk to the harbor and steps to the Whyte House. Enjoy a newly ki [...]

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, [...]

This Cherry Grove Cottage is located at the West End of Cherry Grove. This Stunning 2 bedroom, 1 bathroom home is the perfect place to spend your Summer vacation on Fire Island. This home offers an open floor plan that boasts natural light as well a large outdoor deck space, your own pool and [...]

$3,800

Escape to a charming getaway nestled in the heart of Cherry Grove, where a cozy cottage awaits with its private atmosphere and modern renovations. Featuring two bedrooms and an outdoor shower, it offers a perfect retreat for a serene vacation. Conveniently located near town, you'll have easy a [...]

Available for shares & weeklies 2025! Beautiful 2 bedroom 1 bath cottage with open concept living, cathedral ceilings - combining the charm of original woodwork with superb modern finishes. The house is freshly renovated, with a gorgeous new heated salt water pool, large exceptional outdo [...]

$15,000

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 [...]

$11,000

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 [...]