How to Find the Perfect Luxury Rental on Nantucket 2019

Looking for the perfect rental home on Nantucket this summer? Have a look at our 7-step guide to finding the perfect luxury rental. Then check out the fun facts and good-to-knows that we’ve 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.

Nantucket 101

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.

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.

Nantucket Reds

How to Find the Perfect Luxury Rental on Nantucket 2019

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. Located just a short walk from the center of town is this beautifully updated 6-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 cheery and modern 2-bedroom cottage is well-suited for a small family, tucked away on a quiet lane.

Hotels.  Union Street InnWhite Elephant Village76 MainNantucket Hotel & ResortGreydon House; Hotel Pippa

Restaurants.  AfterhouseLo La 41⁰CruNautilusMillie’sGalley BeachBlack 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.  Check out this contemporary 7-bedroom family compound complete with in-home movie theater, pool and ample outdoor living space. This one-of-kind 6-bedroom estate is the epitome of luxury and set up for outdoor living with an infinity pool, par-three golf course, kitchen and landscaped gardens. For something a little more simple, this classic 4-bedroom cottage is located right on the beach with its own private stairs down to the sand.

Restaurants. 45 Surfside, Surfside Beach Shack

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. 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? This 2-bedroom cottage is comfy and tastefully decorated with harbor and beach access.

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.


Available Rentals. Bright and cheery, this impeccably maintained 3-bedroom property has water views and expansive outdoor living space. Recently renovated in a contemporary style, this 4-bedroom house set 100 feet from the Bluff is a serene spot for summer living. We love this stunning and eclectic 5-bedroom cottage with soaring ceilings and chef’s kitchen for a glamorous girlfriends getaway.

Hotels. The Summer House

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

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

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Crediting her training as a cultural anthropologist at Wellesley College, Julie has immersed herself in various industries in the last 15 years including fashion design, event planning, fitness and even investigating police misconduct. Julie lives in NYC where she loves trying every ramen and dumpling restaurant with her husband and three children. She finds joy in bold prints, biographies of fierce women, kickboxing and spending way too long finding the perfect polish color to express her mood.

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