Nantucket Rentals Perfect for a Group Getaway
12/22/2025
Planning a getaway with a big group, whether it’s an extended family vacation, a milestone celebration, or a friends’ retreat, means finding a home with enough space for everyone to spread out and settle in. Luckily, Nantucket has no shortage of roomy, well-designed rentals that make traveling with a crowd feel effortless. Below, we’ve rounded up some excellent large-capacity Nantucket rentals, perfect for long summer days spent together.
89 Vestal Street
7 bedrooms, 7.1 bathrooms – sleeps: 14
This expansive, newly renovated rental is ideal for large groups seeking privacy, space, and great shared amenities. Located down a quiet country road with elevated pastoral views, the home features an infinity pool, spacious stone patio, and multiple outdoor seating areas that are perfect for relaxing together or enjoying sunset cocktails.
Inside, the open layout offers multiple living spaces, including several lounge areas, a sunroom overlooking the pool, and a large dining room with seating for ten, plus additional island seating. The gourmet kitchen is built to handle group cooking with high-end appliances, dual built-in refrigerators, and a hidden pantry.
With king bedrooms spread across all three levels, the home makes group travel easy by giving every guest plenty of privacy. The lower level adds even more room to gather, offering two large lounge areas with sectional sofas, a wet bar, a dining space, and extra laundry.
To read more about this rental, click here.
18 Parson Lane
7 bedrooms, 7.2 bathrooms – sleeps: 14
This spacious retreat offers 7 bedrooms, multiple living areas, and extensive amenities designed for gathering. The property includes a new 1,000 sq. ft. pool and guest house with its own king bedroom, full kitchen, and 1.5 baths.
Outside, groups will love the 20' x 50' heated pool, hot tub, fire pit, and outdoor dining area. Inside, there’s plenty of room to spread out with a large open living/dining/kitchen area featuring seating for ten, a chef’s kitchen with island seating for four, and several lounge spaces throughout the home.
Multiple king bedrooms, a bunk-style queen room, and ensuite baths make group sleeping arrangements easy. For entertainment, the lower level offers a game room (ping pong, pool, foosball), a family room, and an exercise room.
With two laundry rooms and abundant space indoors and out, this home is perfectly equipped for group vacations, reunions, and extended stays.
To read more about this rental, click here.
59 South Shore Road
9 bedrooms, 8.1 bathrooms – sleeps: 20
This well-sized Nantucket rental is built for large groups, offering exceptional indoor and outdoor spaces designed for gathering and entertaining. The property features multiple outdoor living areas, including a large courtyard with dining and lounge spaces, a fire pit, pergola, and manicured lawns, plus a separate pool area with a pool, hot tub, grill, and additional seating. Close to South Shore beaches yet very private, it’s ideal for group getaways.
Inside, the open main living area includes a spacious kitchen with island seating, a dining area for large groups, and a comfortable lounge that opens directly to the outdoor spaces. What really sets this home apart for big groups is the dedicated entertainment wing, complete with a full bar, billiards, shuffleboard, live-band setup, and a commercial-grade catering kitchen perfect for hosting events or feeding a crowd.
Sleeping arrangements are spread across multiple levels, making it easy for groups to spread out. Every bedroom throughout the house features either a king or queen bed, except for the bunk room on the lower level that has two sets of twin-over-queen beds - ideal for kids or mixed-aged groups. Additional amenities include a media room, gym, and a separate pool house with its own bathroom.
To read more about this rental, click here.
10 Medouie Creek Road
6 bedrooms, 5.1 bathrooms – sleeps: 14
Set on 2.75 private acres overlooking Polpis Harbor and protected conservation land, “Deer Run” is an exceptional Nantucket estate ideal for large groups seeking privacy, views, and access to the water. A short path from the property leads directly to Polpis Harbor, offering easy access to boating, kayaking, paddle boarding, and fishing.
Designed for both refined living and group enjoyment, the estate includes a main house and guest cottage with expansive gathering spaces throughout. Highlights include multiple living and dining areas, a spacious kitchen, dedicated entertainment spaces, and sweeping harbor views from many rooms and decks.
Resort-style amenities complete the experience, featuring an 18x36 swimming pool with integrated spa, a custom outdoor fireplace, home theater, billiard room, gym, wine-tasting room, and a separate guest cottage with harbor views, making this a premier setting for memorable group vacations and retreats.
To read more about this rental, click here.
37 Cato Lane
6 bedrooms, 6 bathrooms – sleeps: 14
“Cato Beach” is a fully renovated Nantucket retreat designed for groups who love to entertain and enjoy seamless indoor-outdoor living. Located one mile from town and abutting conservation land, the home sits on nearly an acre and offers privacy, while still remaining close to bike paths and island attractions.
The property is built for outdoor fun, featuring an oversized 20’x40’ sports pool with automatic cover, outdoor movie setup, professional grill, and expansive landscaped yard. Multiple decks, patios, and lounge areas create the perfect setting for daytime relaxation and evening entertaining.
Inside, the home offers generous shared spaces and modern amenities, including a chef’s kitchen, multiple living and media rooms, and ample bedroom accommodations across three levels. An optional five-bedroom guest cottage is also available, making this an ideal choice for large group vacations, reunions, or extended family stays.
To read more about this rental, click here.
37 Cato Ln.
21 Woodbine Street
7 bedrooms, 7.3 bathrooms – sleeps: 14
Just minutes from two of Nantucket’s most beautiful beaches, this modern custom-designed home exemplifies luxury, space, and exceptional outdoor living. With an open floor plan, high-end finishes, and multiple living spaces (including a main house, pool cabana, and newly renovated cottage), this property offers both comfort and flexibility for group stays.
Designed for entertaining, the home seamlessly blends indoor and outdoor living, opening to an oversized deck, a stunning 20’ x 50’ pool and spa, and a fully equipped outdoor living area. Highlights that create a true resort-style experience include a large cabana with a bar and half bath, outdoor fireplace, custom grill, and multiple outdoor showers.
Inside, there are generous shared spaces and entertainment amenities, including a lower-level game and media room with home theater and full bar. With ample sleeping accommodations across the main house and cottage, this property is perfectly suited for a memorable group getaway.
To read more about this rental, click here.
5 Eel Point Road
6 bedrooms, 4 bathrooms – sleeps: 14
Privately situated in the highly desirable Dionis Beach area, this property provides convenient access to Town, beaches, bike paths, and walking trails. The estate includes a four-bedroom main house and a two-bedroom cottage, offering flexible accommodations ideal for families or groups traveling together.
Designed for relaxed group living, the home features open-concept gathering spaces and multiple indoor and outdoor lounging areas, including a covered porch and pool area. Updated furnishings and poolside amenities enhance comfort throughout the property.
The separate cottage offers additional perks, including its own living space, kitchen, and deck with water views, making it perfect for extended family, multiple households, or guests seeking additional privacy while still enjoying a shared pool and grounds.
To read more about this rental, click here.
19 Medouie Creek Road
6 bedrooms, 5.1 bathrooms – sleeps: 17
Set on over five acres at one of the highest elevations in the area, this Nantucket retreat is ideal for a group seeking privacy and scenic views. With expansive grounds and multiple outdoor gathering areas - including a spectacular porch overlooking the property - this home is perfectly suited for group getaways.
The interior is designed for gathering and comfort, featuring three levels of generous living space with a dramatic great room. The layout allows groups to come together while still offering cozy, private areas across multiple bedroom wings.
Additional highlights include a large walkout lower-level entertainment space with wet bar, ample sleeping accommodations, and a roof walk with panoramic views of the harbor.
To read more about this rental, click here.
Renting a Vacation Home with Great Point Properties
Renting a vacation home with Great Point Properties makes finding the perfect rental for a large group simple and stress-free. With access to spacious homes and expert guidance every step of the way, Great Point Properties helps you secure a place where everyone can live comfortably - without the compromise.