Cherry Grove Vacation Rentals

$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 [...]

$8,000

QUARTERLY SHARES - WEEKLY RENTALS - PINES PARTY AVAILABLE Tucked just steps from the shoreline, this charming two-bedroom, one-bath cottage offers a cozy retreat with the sound of waves as your daily soundtrack. Weathered wood siding and a deck facing the ocean give it that classic coasta [...]

$999,999

Now for SALE! as well as available for shares & weeklies 2026! Welcome to this beautifully newly renovated charming 2-bedroom, 1-bath cottage that perfectly blends classic beach living with modern luxury. Featuring an open-concept layout with cathedral ceilings, this home showcases original [...]

$35,000

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 [...]

D Katen Exclusive Welcome to your dream oasis! This newly renovated 3-bedroom, 2-bath home offers the perfect blend of modern luxury and outdoor leisure. Nestled in a tranquil neighborhood, this property promises a lifestyle of comfort and relaxation. As you step inside, you’ll be gre [...]

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 [...]

Enjoy breathtaking ocean views from every room in this modern waterfront home. New construction in 2016, no detail left unturned. The house is 21' feet above sea level, fully winterized, has a heated “basement” with high ceilings that has plenty of room for a home gym and year-round secure [...]