Villa holiday rentals in Brookhaven

Year-Round Heated Pool Villa - 3 blocks from town

Pool heated to hot tub temperatures & open year round! This brand new construction house is perfect for large groups. Gather with friends and family in the double height ceiling open concept living room/dining room/kitchen area. Soak up the sun lounging by the pool. Take a super short walk to town to enjoy the incredible local shops, restaurants, and bars. Then end with a nightcap relaxing in the heated hot tub seating section of the pool. There's no better place to stay in Greenport Village.

Magic Garden Castle -1750s (4 bedrooms)

Welcome to this originally 1750s-era built charming and romantic 3,000 SQF New England Cottage on prestigious Oenoke Ridge of New Canaan. Wake up each morning to extraordinary light, relax, rejuvenate and unplug… gaze at the stars and listen to the sounds of nature from your cozy warm bed… Camping, glamping …your choice. Feel the breeze as you sleep in this magical place. Read and nap, enjoy bike ride, long walks and explore the the garden, forest and towns. Your heart and soul finally settle.

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.

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.

Hamptons Wellness Villa with pool and spa

Relax with the whole family at this peaceful wellness-style getaway. Enjoy the 20’ x 40’ heated pool, the new 9-person hot tub, and the outdoor living room with fire pit overlooking the scenic garden and woods. Grill on the deck or unwind by the fire. Centrally located: 6 min to LIRR/Jitney, minutes to I-495, 2 min to bay beaches, 10 min to ocean beaches and Southampton Village, 20 min to wineries. Explore all the Hamptons and feel restored.

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.

Hamptons Bungalow With Pool

Escape to a contemporary, minimalist, dream in Hampton Bays! The bungalow is a 5 minute drive or a 15 minute bike ride to multiple beaches, farm stands, restaurants and village center. This slice of heaven is truly a special get away.

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.