Villa holiday rentals in Brookhaven

Hamptons Retreat | Pool, Hot Tub, Sleeps 10

Spacious Hamptons retreat with heated pool, 9-person hot tub, and ideal layout for groups—just 10 minutes to Southampton Village and Shinnecock Hills (US Open 2026). Perfect for summer getaways, long weekends, or tournament stays, this 5-bedroom home comfortably sleeps 10 and is designed for both relaxing and entertaining. Centrally located: • 6 min to LIRR/Jitney • 2 min to bay beaches • 10 min to ocean beaches & Southampton Village & Shinnecock Hills Golf Club • 20 min to wineries

Cottage in Silvermine: Norwalk New Canaan Wilton

Nestled in a leafy Norwalk neighborhood filled with historic houses, this newly remodeled charming guest cottage/Barndominum on 1 acres in opposite the Silvermine river (where New Canaan, Wilton, and Norwalk meet). The guest cottage is separate from the main house. It is a quaint, quiet and cozy. 1 bedroom 1 bathroom new kitchen including range, dishwasher, Keurig and washer and dryer. The bedroom has a queen bed and the living room has a sofa and chairs. Twin cots can be brought in.

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.

Superb Shelter Island 4 bed Designer with a Pool

This contemporary, designer-updated residence provides an idyllic Shelter Island retreat. With 4 delightful bedrooms, 3 sleek bathrooms, and a seasonal heated salt wayer pool amidst mature landscaping, you're promised a calming respite. We kindly ask that you familiarize yourself with the detailed disclosures, & guidelines. Around the corner from Sunset beach, Silver beach and Shell beach, and located on a quiet street. Easily accessible to the ferries.

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

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.