Villa holiday rentals in Long Island

Westchester Winter - Fireplace Pet Friendly Events

Winter retreat at The Westchester Manor, cozy 5BR, 4BA villa for 13 guests in Ossining. Unwind by the in-house bar, pool table, relax with Arcade Games, Smart TVs, and fast WiFi. Fully equipped kitchen and pet-friendly. Nearby winter highlights include Sleepy Hollow, Rockefeller State Park Preserve snowy trails, Croton Gorge Park frozen waterfalls, Hudson RiverWalk views, and Bear Mountain Snowy Trails. Perfect for family or group stays. Events are welcome, contact us in Airbnb for more details!

New! Sweet home near NYC

This is a brand new construction furnished home which can comfortably accommodate corporate travelers and families. Walking distance to local shops, stores What's Nearby: *12mins to Newport mall-Jersey City, NJ *12mins to Hoboken, NJ *25mins to World Trade Center, NYC *25 mins to Empire State Building, NYC *40 mins bus ride to Manhattan, NJ (Bus station in Time Square) *45 mins to Williamsburg-Brooklyn,NY *14 mins to Newark Airport,NJ *45 mins to Laguardia Airport,NY *55 mins to JFK Airport,NY

Waterfront Holiday Vacation Villa New England

Have fun with the whole family at this stylish VILLA with water (kayak) access to Ocean State Beach Park and a 4 minute drive to the quaint Waterford Beach. This idyllic leisure home has everything you need to enjoy your gateway. SECLUDED setting with 300 ft of waterfront access for kayaking , fishing. Sauna, bicycles, waterfront gazebo with fire pit , basketball hoop and hammocks. All spaces are newly renovated and tastefully decorated. New fully stocked kitchen . Close to Mystic - Foxwoods

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.

Spacious Waterfront Getaway

Relax on the water and experience the outdoors with your family and friends. Enjoy expansive views of the Niantic estuary, kayak from the private beach. BBQ and enjoy a relaxing day on your chaise, overlooking the water. Enjoy time together in comfortable living areas with everything you need. Whether you're planning a weekend getaway or a longer vacation, enjoy charming coastal towns, pristine beaches, natural beauty, and culinary delights less than 15 minutes away from your comfortable home.

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.

Indulge in Prime Luxury 3BR 3-7 Guest

Experience luxury and convenience at our stunning villa! Whether you're planning a group retreat or a family escape, our exquisite property is your ideal haven. Located just moments away from major hospitals, universities, and transportation hubs, our villa provides unmatched accessibility to all your needs. Note: lower level unit listing it might be someone staying/living on the lower unit. They will not be able to disturb or enter the listing separately entrance

Mediterranean villa •pool•hot tub•fire place

Discover the Mediterranean Villa, a stunning 5-bedroom, 4-bath luxury retreat nestled in the scenic Hudson Valley. This Monroe, NY escape offers elegant interiors, a cozy wood-burning fireplace, outdoor fire pit ,Smart TVs, a private hot tub, spacious living areas designed for comfort and style. Perfect for families or groups, it’s minutes from Catskills trails, Woodbury Commons shopping, and Legoland. Unwind, explore, and indulge in upscale relaxation year-round.

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.

Luxe|Pool|Game Rm|Outdoor Movie|HotTub|Firepit

SERENITY AT SHOREWOOD Luxurious Newly Renovated Mid Century Modern Home in East Hampton with Beach Car! Peaceful and stylish with three bedrooms, 3 1/2 baths, spectacular great room, huge deck, heated pool and more, less than four miles to the heart of East Hampton Village, world renowned for its restaurants, shopping and ocean beaches. A designer-curated architectural gem! Kick back and relax in this calm, stylish space.

Tuxedo Hilltop Retreat with a Large Hot Tub

Welcome to our peaceful getaway home set in the stunning Sterling Forest Park in the Hudson Valley, only an hour from New York City. Enjoy the tranquil outdoors, the oversized hot tub, the wrap-around balcony, and the spacious deck. Relax in a great room overlooking the forest and unique natural rock formations. And for the ski enthusiasts our home is only 10mi or an easy 20 min drive to Mt. Peter Ski Area.

Spacious 5BR Near Yale | Ideal for Groups & Family

Welcome to Dove Haven — a peaceful and stylish retreat in the heart of Westville. Relax in the private hot tub, enjoy cozy sun-filled spaces, and walk to charming cafés, top restaurants, and beautiful Edgewood Park. Just minutes from Yale and downtown, this spacious home offers warmth, comfort, and good vibes — perfect for families, groups, and work trips seeking a relaxing escape.