Mansion holiday rentals in Long Island

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Top-rated mansion rentals in Long Island

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

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Top guest favourite

An enclosed outdoor living space features a wooden deck overlooking a heated pool. Furnished with a large round table and comfortable seating, natural light floods through the screens, creating an airy atmosphere. Elegant trees and lounge chairs visible outside enhance the serene environment.

Home in Sagaponack

4.94 out of 5 average rating, 325 reviews

Amazing Home close to Everything -

Elegantly designed home featuring modern appliances, a seasonal heated pool, and situated just moments away from ocean beaches, Wolffer Vineyard, and the vibrant Bridgehampton/Sag Harbor villages. Set within meticulously curated landscaping, this property embodies perfection and meticulous attention to detail. Familiarize yourself with our disclosures, guidelines, and house rules. We maintain a strict no events, no parties, and no smoking policy — our home and property grounds are smoke-free.

Top guest favourite

A bright living area is present, featuring a comfortable white sofa with blue accent pillows and a natural woven rug. A modern coffee table is placed in front, while large windows allow ample natural light. A fireplace adds a cozy focal point, complemented by a TV mounted above.

Home in Norwalk

4.97 out of 5 average rating, 119 reviews

Family Cottage with 4 King Beds and Fire Pit

Escape to Norwalk Cottage, a beautifully designed 4-bedroom, 2-bath home perfect for 8 guests. This family-friendly getaway features a fully stocked kitchen, cozy fireplace, and a fun basement playroom. Relax in the private backyard with a deck, grill, and fire pit. Located on the quiet Norwalk/Westport border, you're just minutes from Calf Pasture Beach, great restaurants, and the vibrant SoNo district. Enjoy central air, fast WiFi, and a dedicated workspace for the perfect year-round escape.

Guest favourite

An aerial view captures the serene neighborhood, showcasing small homes interspersed with trees and greenery. The bay can be seen in the distance, along with the nearby beach access. The well-maintained grounds of the property highlight a clean, welcoming environment.

Home in Shirley

4.94 out of 5 average rating, 178 reviews

Waterview Beach House: 3 Kings + Putting Green

Unwind at this 3-story waterview beach home in Shirley, NY. Bellport Bay is right across the street with easy beach access. 0.4 mi to Shirley Beach 1.8 mi to Smith Point Beach — perfect for ocean days or Fire Island trips. Featuring: • 3 king beds + 2 fulls • 70” living room TV + 3x 50” bedroom TVs • Fully equipped kitchen • BBQ grill, fire pit & putting green on premium turf • 6 beach chairs + 2 umbrellas included • High-speed WiFi & keyless entry Your low-key Long Island beach escape!

Top guest favourite

A charming red cottage is set among lush greenery, showcasing a manicured lawn leading to the porch. The house features a rustic stone chimney and a welcoming front porch adorned with white railings. Nearby, a small structure complements the main home with a rounded window.

Home in Port Jefferson

4.81 out of 5 average rating, 389 reviews

The Hilltop Harborview

Guests will immediately walk past spacious hot tub into a comfortable sunroom where you’ll watch the most colorful, water view sunsets Long Island has to offer! This one of a kind offers a sprawling layout that has 3 queen size bedrooms and 1 king . We can also provide an air mattress for an additional guest. There is a kitchen equipped with stove, oven, dishwasher and washer and dryer! This beautiful walking Village has so much to offer! We do allow dogs with prior notice with a $65/dog.

Guest favourite

A calm waterfront scene features a vibrant sailboat gliding across the bay, surrounded by green marshland. A wooden dock leads into the water, with several colorful chairs positioned for relaxation. Soft hills and houses line the distant shore under a gentle mist.

Home in Mastic Beach

4.94 out of 5 average rating, 133 reviews

Gorgeous Waterfront and Indoor Pool Family Oasis!

Breathtaking Waterfront home with 37 foot heated indoor pool. 3 Bedrooms plus a 800 Sq/Ft master bedroom with wood burning fireplace. WiFi, 3rd floor entertainment room with 120 inch screen movie projector, karaoke, fooseball, pool table. Wraparound terrace, sunroom, 45ft dock with launching ramp, putting green, sand trap, outdoor kitchen, bar & stone patio with tables & BBQ grills & fire pit. Ability to catch abundant fish & blue crabs right from the dock. Picture tells a thousand words.

Guest favourite

Home in Mastic

4.96 out of 5 average rating, 168 reviews

Family Retreat with Heated Pool, Hot Tub, Sauna.

🛏 6 Bedrooms, 9 beds & 3 Full Baths 🏊‍♂️ Heated Pool & Relaxing Hot Tub 4-person Sauna 🏀 Half Basketball Court & 🏐 Volleyball Area 🏌️‍♂️ Private Golf Putting Green 🔥 Cozy Firepit & Outdoor Lounge Area 🛝 Swing Set & Kid-Friendly Yard 🍽 Fully Stocked Kitchen & Spacious Dining 🌐 High-Speed Wi-Fi & Smart TVs 10 min to Smith Point Beach & Boardwalk 15–20 min to Long Island Wine Country Nearby hiking at Wertheim Wildlife Refuge Short drive to Tanger Outlets & restaurants

Guest favourite

A spacious saltwater pool is surrounded by a well-manicured yard, featuring lounge chairs and large umbrellas. Water features create gentle splashes, enhancing the serene environment. The area is framed by trees, providing a natural backdrop for relaxation.

Home in Westhampton Beach

4.98 out of 5 average rating, 100 reviews

Brand new house with an all year round hot tub.

Your family will be close to everything when you stay at this centrally-located place. Very close beaches near dune road. Movie theaters, supermarkets, liquor store, farms and a bunch of local restaurants that you can visit.DJs are not allowed. Loud music and parties are strictly prohibited. It's a very quiet, relaxing, and peaceful neighborhood. No smoking inside the house.check in 3pm check out 11am extra charge. If you don't check out 11am.a minimum of 5 cars, no more than 5 cars

Top guest favourite

A dining set featuring a large wooden table with eight matching chairs is positioned under a spacious umbrella, offering shade. Lush greenery and a serene waterfront view are visible nearby, providing a peaceful outdoor setting.

Home in Southampton

4.98 out of 5 average rating, 105 reviews

Breezy Waterfront Home With private Dock

This charming waterfront home is the ideal getaway for the active family with the Hamptons' largest natural 'saline pool' (the Peconic Bay) just footsteps away. This home easily sleeps 7 - with 3 bedrooms and 3 separate kids' sleeping cabins. You can jump on our standup paddle board right off our private dock, jog along wide stretches of pebble beach, have a swim race to our floating swim platform or simply relax in the hammock. 2 bathrooms indoors and 1 private outdoor shower,

Guest favourite

An open living space features a comfortable sofa adorned with patterned cushions, complemented by a light wood coffee table. A dining area with a round table is visible, and large glass doors provide access to the backyard, bringing in natural light.

Home in Hampton Bays

4.93 out of 5 average rating, 126 reviews

Hamptons "Get Away" Near Beach/Wineries/Golf

Located in Hampton Bays-the heart of The Hamptons surrounded by water! Close to beaches, waterfront restaurants, wineries, golf & wedding venues. Open floor plan w/ modern flair. 4 bedrooms, 2 full baths, eat-in kitchen, spacious living room and lower level recreation area/ foosball. Enjoy amenities including smart TVs/appliances, EV Charger, 2 fireplaces, 1Gb WiFi, large deck w/ string lites, BBQ, firepit, & outdoor shower. Great for families, couples, coworkers and friends!

Top guest favourite

Home in Milford

4.96 out of 5 average rating, 135 reviews

Oceanfront Beach House w/ Private Hot Tub

Escape to this luxurious 4-bedroom, 2.5-bath oceanfront home on the stunning Long Island Sound. Enjoy direct beach access, a private hot tub, and a fully equipped patio with a gas grill and dining area. Perfect for families or groups, this retreat offers breathtaking views, a full kitchen, arcade games, and modern amenities. Located minutes from restaurants and shops, it’s ideal for relaxation or adventure. Book now for a perfect blend of comfort and coastal charm.

Guest favourite

A serene outdoor area showcases a saltwater pool with a spa, surrounded by well-maintained landscaping featuring vibrant yellow flowers. Lush green fields extend into the distance, framed by a clear sky with scattered clouds.

Home in Cutchogue

4.97 out of 5 average rating, 212 reviews

Private Oasis W/Stunning Vinyard and Pool Views

Enjoy spectacular wine country sunset views from the living room that extend to the gorgeous saltwater gunite pool and spa. (Please note THE POOL AND SPA (attached hot tub) are OPEN FROM MAY 1 - OCTOBER 15 only). Beautifully decorated, comfortable home with an updated chef's kitchen and fireplace. Fabulous restaurants, wineries, farms, beaches and exquisite small towns all nearby. Simply put, a magical, peaceful paradise for you and your group.

Guest favourite

A modern kitchen is showcased, featuring a large center island with four wooden bar stools. Stainless steel appliances and white cabinetry are complemented by granite countertops. Natural light filters in through a window above the sink, illuminating the inviting space.

Home in Calverton

4.95 out of 5 average rating, 147 reviews

Modern Farmhouse Retreat North Fork Wine Country

Escape to this modern farmhouse retreat in North Fork Wine Country. Enjoy a luxurious stay with a fully stocked kitchen, cozy fireplace, Spacious bedrooms, and spa-inspired bathrooms. Relax in peaceful surroundings close to farms, beaches, pumpkin & apple picking, Tanger Outlets, Splish Splash Water Park, and top wineries. Outdoor dining, private fire pit, scenic views, and nearby hiking trails make it perfect for families, couples, or friends.