Incredible Island Rentals to Book for a Getaway This Summer

Guides

Summer might seem far away when you look at the calendar (wasn’t it just snowing a few weeks ago?), but mentally, people are already in the July sunshine and booking their vacations. So if you want to enjoy a week on any of the gorgeous local islands, you’d better act now, because all the good places are getting snatched up. Luckily for you, we’ve compiled some of the best spots you can rent for a week or two (or dream about living in all summer long).

Photo by Michael Rynes

3 Wingspread Lane, Shawkemo, Nantucket
5 bedrooms, 5.5 bathrooms, accommodates up to 14 guests, from $30,000 a week

“Why rent a house with a pool when vacationing on the beach?” some might ask. Those people have never seen this house with an infinity pool so gorgeous it rivals the harbor views from this home. If you decide to rent this renovated abode later in the season, a hot tub and fire pit on this three-acre property will serve you well, as will the pool cabana with its own wood burning fireplace. Between that and all the space, you may want to stay in this rental all year long.

Photo courtesy of Douglas Elliman

33.5 Vesper Lane, Brant Point, Nantucket
7 bedrooms, 5 full bathrooms and 2 half baths, accommodates up to 14 guests, from $25,000 a week

Vacationing with family is nice, but a trip with the brood where everyone has their own space? Even better. The Big and Little Dipper (a five-bedroom main house and its accompanying tw0-bedroom guest cottage) offer just that in an updated and well-designed setting. The main house has a spacious and open kitchen/dining area and a lovely outdoor patio for group meals, while the living room fireplace offers a great spot to relax if you get a rainy day in the midst of your getaway. Otherwise, enjoy the time at nearby Cisco and Surfside beaches. Yes, you’re close to both, which means even more space for everyone to enjoy some summer fun.

Photo by Fisher Real Estate

49 Warrens Landing Road, Madaket, Nantucket
3 bedrooms, 2 full bathrooms,  accommodates up to 8 guests, from $6,500 a week

This neighborhood on the western side of the island is known for its pristine beaches, indulgent restaurants, walking trails, and beautiful sunsets. You can take in these stunning views and the warmth of the summer sun from the back deck of this beach cottage. Inside, a well-equipped kitchen opening up to the living room allows for mingling during meal prep, perfect for a group of friends spending the week together.

Photo by Bob Gothard

24 Jennie Lane, Edgartown, Martha’s Vineyard
3 bedrooms, 2.5 bathrooms, accommodates up to 8 guests, from $9,500 a week

Set on three acres of land off a quiet street, this recently done coastal home offers a peaceful reprieve from everyday life. Enjoy a relaxed evening of grilling on the outdoor patio, finished up by a night under the stars or a cool post-beach rinse in the outdoor shower. While this home offers a taste of coastal seclusion, it’s also close enough to the Vineyard’s shops and restaurants that you can still enjoy some local flavor while you’re visiting.

Photo by Michael Rynes

14 Wood Hollow Road, Tom Nevers, Nantucket
5 bedrooms, 5 full and 2 partial bathrooms, accommodates up to 10 guests, from $25,000 a week

Nantucket boasts abundant natural beauty, which is channeled into the grounds of this stunning rental in the form of its terraced gardens around a pond-like pool centerpiece. Enjoy this landscaping from the screened-in porch, decks, and patios of this abode. And you don’t have to keep these views to yourself: With an expansive main house and accompanying guest cottage, this property can fit the whole family in for a week of summertime delight.

SPhoto by Bob Gothard

68 North Water Street, Edgartown, Martha’s Vineyard
6 bedrooms, 5.5 bathrooms, accommodates up to 12 guests, from $30,000 a week

Enjoy your summer stay from the lap of luxury in this home. With a balcony, a guest house, and multiple bedrooms with their own bathrooms and king or queen sized beds, you’ll feel like you’re vacationing in a coastal palace. Outside, a grill and a heated pool make this rental a desirable spot even when summer turns to fall.

Photo courtesy of Fisher Real Estate

89 Squam Road, Squam, Nantucket
4 bedrooms, 4.5 bathrooms, accommodates up to 8 guests, $38,000 a week

What’s better than a beach vacation? Try one where you have your own private access to the water. This updated property in the Nantucket neighborhood of Squam has private steps leading right down to the shore, reminding you why you opted for a week here as opposed to fighting crowds on the Cape. A deck and porch outside offer additional outdoor space to enjoy the views and perfect summer weather you’ll hopefully get when vacationing here.

Photo by Cassie Bradley

10 Littlefield Lane, West Tisbury, Martha’s Vineyard
3 bedrooms, 4 bathrooms, accommodates up to 6 guests, from $9,000 a week

One of the best things about remote work is that it can be done just about anywhere, which means you can turn a weeklong vacation into a full-blown summer getaway. This brand new three-bedroom home offers the perfect opportunity to do that, with an open living space that can fit an office nook. If that doesn’t work, you can set up shop in one of three bedrooms (each with their own bathroom) or in the sunroom off the patio. And with coffee shops, stores, the beach, and hiking trails nearby, you can still take advantage of your unique remote work location, even after the busiest of days.

Photo courtesy of Fisher Real Estate

107 Main St., Downtown, Nantucket
6 bedrooms, 5 full bathrooms, accommodates up to 12 guests, from $10,500 a week

OK, usually, people pick vacation spots based on what there is to do there, not the place they’re staying. But no one would blame you if you booked a stay at this home because of how darn cute it is. Committed home cooks can enjoy the brand new kitchen appliances under a charming beamed ceiling. In the primary suite, you’ll rest on a king-sized bed with a glass encased shower and soaking tub for the ultimate relaxation. And the bustle of downtown Nantucket is right outside your door.

Photo courtesy of Douglas Elliman

30 Madequecham Valley Road, Madequecham, Nantucket
5 bedrooms, 6 full bathrooms and 1 half bath, accommodates up to 10 guests, from $45,000

Minutes from the airport and the ocean, you’ll be able to spend maximum vacation time in the surf in this private compound. Set right on the water, you can unwind after a day on the beach with a dip in your own private hot tub or heated pool. A big screen TV and home gym, plus multiple living room spaces offer additional ways to unwind, so you can come back from your trip feeling totally relaxed.