Villa vacation rentals in Long Island

Find and book unique villas on Airbnb

Top-rated villa rentals in Long Island

Guests agree: these villas are highly rated for location, cleanliness, and more.

0 of 0 items showing

1 of 3 pages

Guest favorite

Villa in Southampton

5 out of 5 average rating, 93 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.

Superhost

Villa in Greenport

4.86 out of 5 average rating, 50 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 in Killingworth

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 in Guilford

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".

Superhost

Villa in Chester

4.86 out of 5 average rating, 98 reviews

Mansion, Heated Pool, HotTub, FirePit, Huge B'yard

Treat yourself and entire family in this huge, magnificent villa located in the best of Orange County. -> Only 45 min. drive from GWB -> 10 min. to Legoland park -> 15 min. to Woodbury commons outlet mall -> 30 min. to West Point -> 15 min. to Mount Peter Ski Area -> 30 min. to Mountain Creek Ski Area -> And close to many Wineries and Breweries. An Ideal Retreat for: -> Family Vacation or Reunion. -> Company Workshop or Retreat. -> Group Holiday getaway -> Birthday Celebration -> And More!

Guest favorite

Villa in Water Mill

4.96 out of 5 average rating, 25 reviews

Incredible 9+ Bedroom Watermill Home w Heated Pool

Luxury 9000 SF Southampton villa with a heated gunite pool & hot tub, steam shower, 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, fire pit, outdoor kitchen, sauna, arcade, pool table, air hockey and foosball. Please read our disclosures & house manual. Not a party house and no events permitted.

Guest favorite

Villa in East Hampton

4.99 out of 5 average rating, 78 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 in Deer Park

4.88 out of 5 average rating, 66 reviews

A Modern Getaway Perfect for Families & Business

Discover the perfect blend of style and functionality in this modern two-story home, ideal for both family retreats and business gatherings. It boasts 4 bedrooms, 3 bathrooms, 2 fully-equipped kitchens, and 3 spacious living rooms. With 6 comfortable beds, an authentic wood-burning fireplace, and 4 smart TVs, you’ll find all the comforts of home. Enjoy the private balcony, 2 outdoor furnished patios, BBQ grill for entertaining, 3 bicycles and 6 private parking spots for you and your guests.

Superhost

Villa in Chester

4.98 out of 5 average rating, 40 reviews

Harmony Hambletonian-A Luxury Retreat Back in Time

Pamper yourself in our beautiful Victorian estate. Built in 1850 and home to one of the most famous racehorses in history, Harmony Hambletonian is kept in pristine condition & updated w/ modern comforts. Designated a Historic home but running on Solar energy our country-style home offers 7 bedrooms, 4.5 baths, large living spaces & dining areas, chefs kitchen, fireplaces, pool, pool house, patio, grill, lawns & gardens. Walking distance to cafes & shops in Chester & only 50 miles to NYC!

Guest favorite

Villa in New Haven

4.98 out of 5 average rating, 112 reviews

Dove Haven | Find Your Peace

Best & most beautiful Airbnb in New Haven. No expense has been spared in our well-appointed architectural gem just minutes from downtown New Haven. Luxurious amenities and curated design elements await you. Take lunch in the light-filled sun porch, unwind in the 8-person hot tub, move your body in the equipped home gym, or entertain in the private Zenscape garden. Endless possibilities exist at Dove Haven. You will leave feeling relaxed, inspired, and rejuvenated.

Superhost

Villa in Ossining

4.81 out of 5 average rating, 101 reviews

Castle - Winter Wonderland - Cross Country Skiing

Fall - Autumn Paradise at Westchester Castle: Your Sunny Group Getaway! 7 Bedrooms, 4 Bathrooms: Sleeps 13 with varied bed types for comfort. Entertainment Galore: Smart TV, pool table, board games. Gourmet Kitchen: Fully equipped for all culinary needs. Relaxation: In-ground pool and indoor tub. Convenience: Free 100 Mbps WiFi, self-check-in/check-out, washer & dryer. Nearby Attractions: Close to parks, family spots, dining, and more!

Guest favorite

Villa in Southampton

4.96 out of 5 average rating, 28 reviews

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.