Looking for the perfect rental home on Nantucket this summer? Have a look at our 9-step guide to finding the perfect luxury rental. Then check out the fun facts and good-to-knows that our correspndent Julie Chang Murphy has uncovered, and view some specific properties that are currently for rent on the island that caught our eye. We’ve profiled five Nantucket neighborhoods, along with the hotels and eateries that get strong reviews, in case you decide to visit during your house hunt. We feel you coming, summer. And we are so ready. Here’s how to find the best luxury summer rental home on Nantucket 2023 for you, your family and friends among homes currently on the market.

How to Find the Best Luxury Summer Rental Home on Nantucket 2023

Nantucket retains the bygone glory of a 19th-century New England seaport town. This 14-mile long island was once the capital of the whaling industry. Its inhabitants prospered, and ultimately the island became one of the wealthiest communities in America.

It is still home to over 800 lovingly restored pre-Civil War homes, flanked by cobblestone streets and the distinctive widow’s walks overlooking the Nantucket Sound. The beaches are a haven of pristine natural beauty. And over 45% of the island’s rolling grasslands, bogs, forests and wildlife refuges are now protected by conservation land trusts.

Here’s how to find the best luxury summer rental home on Nantucket 2023 for you, your family and friends among homes currently on the market. Nantucket Marshes.

The vibe is classic preppy New England — surely you’ve heard of Nantucket Reds. In the summer, the population balloons to 50,000 from its 10,000 year-round residents. It skews toward Fortune 500 CEOs, financiers and their broods.

Despite its small size, Nantucket offers plenty of sophisticated luxury options. Think lavish homes, boutique hotels, high-end shopping and creative restaurants. It’s home to 24 distinct neighborhoods, and for the purpose of this piece we’ve chosen to highlight five of the standouts.

How to Find the Perfect Luxury Rental on Nantucket 2023

If you’re thinking of renting with a long-term eye toward buying on the island, be aware that the Nantucket Historic District Commission requires that all houses be shingled, and restricts the number of paint colors that homeowners can use. The consistency is part of the island’s charm, but you have to be prepared to comply.

1. Nantucket Town 

Nantucket’s downtown features world-class dining, charming boutiques, art galleries, inns, museums, and historic sites. Historic homes on cobblestone streets hearken back to the whaling era. Most destinations can be reached by foot, making Town the most convenient part of the island in which to live or rent.

Available Rentals. Though this 4-bedroom house is new it is reminiscent of a 200-year-old Shaker setting. They used only antique materials including hand-hewn barnwood beams, 200 year-old soft pine flooring, antique wainscot, salvaged hardware, and doors. You are only two blocks from town center but have lots or privacy as it is set on-the historic Nantucket Lily Pond preserve. Located just 2-blocks from the center of town is this beautifully updated 7-bedroom home, with multiple cozy areas for lounging and gathering. If you’re looking for a pool, check out this 4-bedroom beauty on an exceptionally large private lot. This fully restored 2- bedroom fishing cottage on the wharf is well-suited for a couple or small family.

Hotels.  Union Street Inn, White Elephant Village; 76 Main; Nantucket Hotel & Resort; Greydon House; Hotel Pippa

And be sure to check Greydon House’s recently launched sister property, 52 Union. Designed by Boston-based Lianne Leventhal, the three bedroom Craftsman-style property offers water views and hotel service within walking distance to downtown. Originally built in 1930, the property is an outlier of mid-century design, and as Nantucket’s newest destination for small groups and secluded getaways, 52 Union provides the luxury service that neighboring property, Greydon House, has become known for in a private residential setting.

Restaurants.  Afterhouse; Lo La 41⁰; Cru; Millie’s; Galley Beach; Black Eyed Susan’s

2. Monomoy

Monomoy is a high-end residential area in a quiet corner just off Nantucket Harbor. Only 2.5 miles from town, residents enjoy a private beach and views across the harbor of Coatue’s barrier beach and wildlife refuge, Great Point, Nantucket Town and the Yacht Club.

Available Rentals.  If you’re planning for a family retreat, look no further than this spacious, sun-filled 6-bedroom property with a pool and accompanying guest cottage for those surly teenagers. Located just a 1/4 of a mile to the beach, this elegant 6-bedroom home offers all the bells and whistles: chef’s kitchen, pool, hot tub, steam room and gym. This newly constructed 4-bedroom is gorgeously designed and decorated, overlooking Nantucket Harbor.

3. Surfside

The close proximity to town and to one of the most admired beaches on Nantucket makes Surfside an attractive location. During the summer, regular shuttle service drops you off right at the edge of the beach, where you can visit the snack bar and hang out on a beautiful wide beach with lifeguards and great waves.

Available Rentals.  This bright and sunny 5-bedroom house is perfect for a large group or two families or if you just want a lot of space! With a pool and a grand yard, this is the ultimate vacation spot plus new furnishings provided in the last year.  Or perhaps this elegant 6-bedroom estate with a house and cottage with swimming pool and built-in spa? Or want some history as part of your Nantucket vacation. This 5-bedroom home, located on Orange Street, is just a few blocks away from Main Street and will make you feel like went back in time. 

Restaurants. 45 Surfside, Fusaro’s Homemade Italian, Keeper’s Restaurant

4. Wauwinet

Wauwinet is the furthest-east section of the island. Overlooking Coatue and leading to Great Point, this is a secluded plot of land that mirrors the beauty and simplicity of nature. Here, you can enjoy access to incredible fishing and bird watching.

Available Rentals. Perfect for a large group (it sleeps 7 comfortably) this elegant house provides an easy walk to restaurants, shops, and in-town attractions. It’s on the bike path; a short cycle to beaches, Bartlett’s Farm, and other points of interest. We love this cozy 2-bedroom spot with its own private beach for a family getaway. The kids will love the built-in bunks. Classic charm and no frills unless you count a private path straight to the beach, this 6-bedroom retreat is a great base for your Nantucket summer. Looking for a quiet spot to write your New England based tome? 

Hotels.  Wauwinet

Restaurants.  Topper’s

5. Siasconset

Siasconset aka ‘Sconset, located on the island’s southwestern side is a popular place for a bike ride and stroll along Bluff Walk, a deeded public path that runs between private backyards and the Atlantic Ocean. There are adorable, squat bungalows- some more than two centuries old and the bluff views are otherwordly. The beach has light surf and no steep inclines, making it a sought-after spot for children and mature beachgoers.

Perfect for a small to medium-sized family that loves the beach! This fresh, light and bright 4-bedroom cottage is immaculate and comfortable plus just steps from the beach. Available Rentals. This classic 3-bedroom Sconset home has panoramic views of the Atlantic Ocean from every room. Another beauty is this 4-bedroom house just minutes away from the beach. It is available starting Daffodil weekend Memorial Day all of July and August is negotiable.

Hotels. The Summer House

Restaurants. Claudette’s Sandwich Shop, Chanticleer Restaurant and Gardens, Sconset Cafe

How to Find the Best Luxury Summer Rental Home on Nantucket 2023

There you have it: a few leads to get you started in the hunt for your summer dream house. Good luck!