Cherry Grove Vacation Rentals

Step inside a true luxury beach front home. This 3 bedroom, 3.5 bath brand new home features all en suite bathrooms and custom tile. With finishes imported from all over the world, this home is truly unique. The large open concept main living space is decked out with high end appliances, and o [...]

Super Impressive Home! This 5 bedroom, 5 bath has an open living concept that is wonderful for entertaining. The front gate leads you to the spacious deck with a sun drenched pool and hot tub. The home offers impressive furnishings and updated finishes. During the hot summer months, rela [...]

Come check out this incredible bayfront investment property in the fire island pines. Just a 90-minute trip from NYC, this amazing home offers 4 en suites and an additional half bathroom. Enjoy your beautiful pool and hot tub while overlooking the great views that the great south bay has to of [...]

$1,999,000

This Horace Gifford Home has been completely renovated and remodeled. Professionally decorated and immaculately cared for. It doesn’t get better than this! Treat yourself to this luxury vacation home and you will be back season after season. Listing courtesy VP Real Estate

$27,225

Beautifully 4 Bedroom bay front with large open living space in the Classic Gifford style, with walls of glass facing the bay, a heated pool and large hot tub and AC throughout…. Exceptional outdoor living space perfect for entertaining and watching sunsets. Mature pine trees, holly and b [...]

Stunning 3 bed, 2 bath on the ocean with every amenity you could imagine. Large open floor plan with ensuite bedrooms, 2 outdoor living spaces and outdoor dining. Contact us to plan your Fire Island Pines vacation.

Fully Renovated for 2025, new photos coming soon! This four bedroom, two bath home with fireplace and pool is a Pines classic. Large rooms with high ceiling, lots of deck space and a killer view makes this the perfect beach house. Total privacy and designed for entertaining.

$12,500

Enjoy the serenity of a Fire Island experience with the true essence of the Pines. Charming corner lot house with private pool deck and bay views from the roof! Updated kitchen appliances, AC in bedrooms, a 5-minute walk from the harbor and 2 minutes to the beach. Room 1: 3 twin beds Room [...]

Spectacular one bedroom with shared pool and hot tub. Available August 21st-28th