Villa holiday rentals in Brookhaven

Just renovated Southampton retreat w/ heated pool

JUST RENOVATED! INQUIRE ABOUT MONTHLY RENTALS! Come and enjoy with family and friends your own beautiful house in Southampton. 5-minute drive to Cooper’s Beach and to Southampton Village. Enjoy beautiful ocean beaches, have brunch in the Village, swim in your 32’ heated salt water pool, enjoy a BBQ on your patio under the shadow of a Japanese Maple, indulge in a quiet evening with a book by the fireplace, or take advantage of the home office while your family & friends enjoy the property.

Incredible 9+ Bed Watermill Home Wellness Retreat

Luxury 9000 SF Southampton villa with a heated gunite pool, hot tub, steam shower & sauna, 9-bedroom, 8.5-bathroom, nestled on a quiet cul-de-sac in Watermill. Bright with large windows, e-shades in bedrooms, indoor/outdoor sound system, W/D on every floor (3 sets). Formal dining/living area, chefs' kitchen, TV room, movie room, gym, outdoor kitchen, arcade, pool table, air hockey and foosball. Please read our disclosures & house manual. Not a party house and no events permitted.

Hamptons WaterLiving-Dock, Kayak, Beach, EV charge

[FOLLOW US on INSTA @29watersedge] 1-mile from the beach, this child-friendly waterfront Southampton home is a perfect family getaway. Ready for watersports: kayak, paddleboard, boat, or jet ski. Walk down to the beach for a swim in the bay. At home, the backyard has it all: large dock, fire pit, swing/playset, hammock, grill, & oversized deck to take in the views. Surrounded by nature and water, you are just minutes from restaurants and shopping in Southampton Village &Sag Harbor.

Gorgeous stately room with fireplace

Experience refined living at this distinguished 1897 Victorian Mansion, nestled in the historic enclave of Oyster Bay and Oyster Bay Cove. Set on a half-acre of landscaped grounds, the residence preserves its original character while offering timeless elegance. Your private room provides both comfort and charm, just steps from Main Street’s shops, Roosevelt Beach, and Park. Ez train access to New York City Additional rooms available upon request—perfect for families, or groups

Farm reserve sunset views

Beautiful villa in beginning part of the Hamptons for a more convenient commute. A private hideaway surrounded by nature where you can relax. It’s perfect for families and friends who love nature, horses and beautiful sunsets. Since our property is spread out over an acre (and surrounded by greater than acre properties), we have the space to allow our guests the ability to maintain a safe distance while still being able to relax comfortably during their stay.

Theodore Roosevelt, Victorian Private room

This 1897 Mansion in the Historical Town Of Oyster Bay and Oyster Bay Cove has been one of Long Islands' most seclusive yet fun spots to stay in. Your Private room in a Classic Vintage Victorian House Set on Half an Acre of land. This Home Has Preserved the original character. Blocks away from the main street, Roosevelt Beach, Theodore Roosevelt Park, LIRR Train Station to New York City (20) to Penn Station. More rooms available. Just ask

First Floor Bedroom

Big bedroom "BR" w/ private bath and shared use o f beautiful New kitchen, Dining Room, LR, finished Basement w "Total Gym", Sports Room, & Bar, rear patio & yard to use. Front yard covered outdoor bench too. Near, NYC, Hofstra, NCC, Nassau Medical Center, parks, Vinyards , beaches, JFK, LIRR & Buses, bike trails, Brooklyn, Queens & Manhattan.

The Arena House

Escape to a modern and stylish home just a short drive from New York City. Nestled in a peaceful neighborhood, this upscale villa features a ping pong table, an arcade game, a spacious yard with a basketball court, and all the comforts you need for an unforgettable stay. Perfect for relaxing, recharging, or enjoying time with friends!!

Southampton Private Retreat with Ocean Views

Escape to the Hamptons at this peaceful and ideally located home, just minutes from South Hampton Village, Historic Shinnecock Hills Golf Club, world class beaches & fine dining.

Lindenhurst Home/ Ryder Cup spot

This unique place has a style all its own. A perfect spot close to the 2025 Ryder Cup being held at Bethpage course at Bethpage State Park in Farmingdale, Long Island.