Villa holiday rentals in Montauk

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.

Picturesque 5-bedroom Hamptons villa with pool

Relax with the whole family at this peaceful place to stay. Go for a swim in the 20’ x 40’ heated pool or enjoy the scenic garden and woods while lounging in the outdoor living room. Grill some burgers or make s’mores over the fire pit. Centrally located. 6 min. drive to LIRR and Hampton Jitney and minutes to I-495. 2 mins. to bay beaches and 10 mins. to ocean beaches. 10 mins. to Southampton Village. 20 mins. to the wineries. Explore all the Hamptons have to offer and more!

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.

Oasis Event Venue

Located in a prime spot, this venue is perfect for events like baby showers, gender reveals, milestone celebrations, corporate gatherings, and creative retreats. Featuring modern design, expansive spaces, and a cozy atmosphere, it’s ideal for any occasion. Enjoy personalized service, seamless planning, and access to a first-floor guest bedroom for overnight stays. Exclusively available for events, it offers a unique escape to create lasting memories.

Heavenly SH Village Escape W Heated Pool

Nestled in the core of Southampton Village, this fully revamped 3 bed/2.5 bath residence is a stone's throw from Main St and renowned ocean beaches. The home boasts contemporary upgrades, including central heat/AC and a newly installed 20 x 40-foot heated gunite pool set on spacious grounds. Beaches and Town are easily accessible by bike, and car. Experience luxury with top-tier furnishings, elegant décor, and marble-finished bathrooms.

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.