Villa vacation rentals in Long Island

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Top-rated villa rentals in Long Island

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Guest favorite

Villa

5 out of 5 average rating, 92 reviews

Hamptons WaterLiving-Dock, Kayak, Beach, EV charge

*Follow Us: 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. Return home to a backyard that has it all: a large dock, fire pit, swing/playset, hammock, grill, and oversized deck to take in the views. Surrounded by nature and water, you are just minutes from restaurants and shopping in Southampton Village and Sag Harbor.

Guest favorite

Villa

4.93 out of 5 average rating, 92 reviews

Great Villa Comfy&Private NYC, EWR, JFK, Outlets

Escape to a secluded, spacious, very comfortable, private & quiet oasis. Away from the hustle and bustle, yet very near to all the comforts you might crave. Your Cozy Villa features lots of air and light, windows all around, private sunny garden sitting areas and swimming pool . Near 3 train stations with NYC service, as well as being close to all major highways and all modes of public transportation. 7 minutes from Newark Liberty International airport. 45 minutes away from JFK or LGA.

Guest favorite

Villa

5 out of 5 average rating, 5 reviews

The Pelham Oasis / 15 Min to NYC

Enjoy & Relax at This Chic & Contemporary Retreat Across the Water. Discover the ultimate getaway at our stylish and modern oasis, perfectly situated across the street from the Pelham waterfront. This upscale villa boasts a sleek granite kitchen, luxurious marble baths, and spacious bedrooms for the utmost comfort. Includes a game room ft a pool table & arcade games, ensuring hours of fun for everyone. The Backyard Oasis complete with a BBQ grill & outdoor seating for an enjoyable experience.

Guest favorite

Villa

4.95 out of 5 average rating, 22 reviews

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

Superhost

Villa

4.86 out of 5 average rating, 49 reviews

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.

Guest favorite

Villa

5 out of 5 average rating, 14 reviews

1-of-a-kind Estate w/ Pool, Spa, Tennis & Pond

Nestled in nature, this luxurious property is situated on 3.5 park-like acres with two streams that wrap around the house. This one-of-a-kind estate has breathtaking views, deluxe amenities, & comes fully stocked for all your vacation needs. Relax in the comforts of the home or enjoy the blue stone patios, heated gunite pool & spa, private tennis court, or kayaking on the pond. Secluded yet conveniently located, the property is a mere 15 minutes away from shops, restaurants, and the shoreline.

Guest favorite

Villa

5 out of 5 average rating, 25 reviews

TREETOPS! An upscale, unique 5 bdrm home with POOL

TREETOPS is a 4850 square ft 5 bedroom Mid century Modern perched on an outcropping of granite cliffs, surrounded by 2 acres of beautiful forest. *Property not suitable for children under 8 years old* Stroll along the loop trail in our woods, sit in the garden, have a fire in the fire pit, or relax and get some sun by the marine-blue, stone-decked pool! Birdwatching, breakfast, and evening cocktails are best on the spacious wrap-around deck. Hiking is just steps away at "Westwoods Trailhead".

Guest favorite

Villa

4.95 out of 5 average rating, 55 reviews

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.

Guest favorite

Villa

4.99 out of 5 average rating, 76 reviews

East Hampton Village Fringe, Renovated with Pool

This remarkable East Hampton home, nestled along a quiet cul-de-sac, is just moments from shopping, restaurants, and ocean beaches. The residence features an abundance of natural light, crisp neutral color tones, and tall, pitched ceilings that enhance the sense of space. The calming, heated pool provides a perfect retreat for relaxation. Please review our disclosures and house manual to ensure this home meets your needs and expectations. We want to make sure it’s the perfect fit for you.

Guest favorite

Villa

5 out of 5 average rating, 18 reviews

Bird Haven Farmhouse: Luxury Villa Living w/ Pool.

Escape the city and step into luxury living at Bird Haven Farmhouse, a stylish retreat with all the amenities of a luxury hotel at your fingertips, while in a totally private villa setting. Designer details thru out this 3-Bedroom home: perfect for a summer or winter holiday, while having all the elements needed for a work-from-home set up. The former home of an artist and photographer, Bird Haven's manicured gardens and pool are the perfect setting for your retreat, or as a film location.

Superhost

Villa

4.85 out of 5 average rating, 20 reviews

Mediterranean Villa

Whether you’re looking for a relaxing getaway or a family trip filled with adventure, you’ll love staying at the ‘Mediterranean Villa’ in the scenic Hudson Valley. Tucked away in Monroe, NY this Villa offers 5-bedrooms, 4-bathrooms, a wood-burning fireplace & enough space for your family to come together and make new memories. Location provides easy access to local attractions: take a day trip to the Catskills, shop locally at the Woodbury Commons or check out the local wineries.

Guest favorite

Villa

4.94 out of 5 average rating, 18 reviews

Great 4 bed 4.5 bath home w hot tub & heated pool

One of a kind modern 4-bedroom plus office 4.5 bath home is perfectly outfitted for your valuable r & r. This mid-century modern home comes with a hot tub (year round) and heated in ground pool with outdoor heated shower (seasonal). The home has extensive southern exposure and ton of windows; hence it gets great light. House sits on a 2-acre leveled lot. And is professionally furnished with designer furniture and accessories. TVs (75 & 65 inch) and propane BBQ grill.