Amazing Island Rentals to Book for a Summer Getaway

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Want to spend the summer in Nantucket or Martha’s Vineyard? Better start planning a trip now to one of these island homes.


Summer may seem a long way off when you look at the calendar (wasn’t it snowing a few weeks ago?), but mentally people are already in sunny July and booking their vacations. So if you want to enjoy a week on one of the beautiful local islands, you better act now, because all the good spots are getting ripped off. Lucky for you, we’ve compiled some of the best places you can rent for a week or two (or dream of living there all summer).

Photo by Michael Rynes

3 Wingspread Lane, Shawkemo, Nantucket
5 bedrooms, 5.5 bathrooms, sleeps up to 14, from $30,000 per week

“Why rent a house with a pool on a beach vacation?” some might wonder. These people have never seen this house with an infinity pool so magnificent that it rivals the view of the harbor from this house. Should 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 might want to stay in this rental all year round.

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Photo courtesy of Douglas Elliman

33.5 Vesper Way, Brant Point, Nantucket
7 bedrooms, 5 full bathrooms and 2 half baths, sleeps up to 14 people, from $25,000 per week

Family vacations are great, but a trip with the brood where everyone has their space? Even better. La Grande et la Petite Ourse (a five-bedroom main house and its accompanying two-bedroom guesthouse) offer just that in an updated, well-designed setting. The main house has a spacious, open kitchen/dining room and a lovely outdoor patio for group dining, while the living room fireplace provides a great place to relax if you have a rainy day in the middle of the day. your getaway. Alternatively, enjoy time at nearby Cisco and Surfside beaches. Yes, you are close to both, which means even more space for everyone to enjoy summer fun.

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Photo by Fisher Real Estate

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

This neighborhood on the west side of the island is known for its pristine beaches, gourmet restaurants, walking trails and beautiful sunsets. You can enjoy those stunning views and the warmth of the summer sun from the back patio of this beach cottage. Inside, a well-equipped kitchen open to the living room allows you to meet while preparing meals, perfect for a group of friends spending the week together.

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Photo by Bob Gothard

24 Jennie Lane, Edgartown, Martha’s Vineyard
3 bedroom, 2.5 bath, sleeps up to 8, from $9,500 per week

Situated on three acres of land on a quiet street, this newly remodeled coastal home offers a peaceful respite from everyday life. Enjoy a laid-back evening of grilling on the outdoor patio, ending with a night under the stars or a cool post-beach soak in the outdoor shower. While this home offers a taste of coastal seclusion, it’s also close enough to vineyard shops and restaurants that you can still enjoy local flavors during your visit.

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Photo by Michael Rynes

14 Wood Hollow Road, Tom Nevers, Nantucket
5 bedrooms, 5 full bathrooms and 2 partial bathrooms, sleeps up to 10 people, from $25,000 per 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 porch, decks and patios of this abode. And you don’t have to keep those views to yourself: with an expansive main house and accompanying guest cottage, this property can accommodate the whole family for a week of summer fun.

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Photo by Bob Gothard

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

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

rental 2 overview

Photo courtesy of Fisher Real Estate

89 Squam Road, Squam, Nantucket
4 bedrooms, 4.5 bathrooms, sleeps up to 8, $38,000 per 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 down to the shore, reminding you why you opted for a week here rather than battling the crowds in Cape Town. An outside deck and porch provide additional outdoor space to enjoy the views and the perfect summer weather you will hopefully have while vacationing here.

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Photo by Cassie Bradley

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

One of the best things about working remotely is that it can be done just about anywhere, which means you can turn a week’s vacation into a fully-fledged summer getaway. This brand new three bedroom home offers the perfect opportunity to do just that, with an open plan living area that can accommodate an office area. If that doesn’t work out, you can sit in one of the three bedrooms (each with its own bathroom) or on the patio veranda. And with nearby cafes, shops, the beach, and hiking trails, you can still enjoy your unique remote workplace, even after the busiest days..

rental 4 overview

Photo courtesy of Fisher Real Estate

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

OK, generally people choose vacation spots based on what there is to do there, not where they are staying. But no one would blame you if you booked a stay in this house because of its beauty. Committed home cooks can take advantage of brand new kitchen appliances under a charming wood-beamed ceiling. In the master suite, you’ll rest on a king-size bed with a glass-enclosed shower and bathtub for ultimate relaxation. And the hustle and bustle of downtown Nantucket is right outside your door.

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Photo courtesy of Douglas Elliman

30 Madequecham Valley Road, Madequecham, Nantucket
5 bedrooms, 6 full bathrooms and 1 powder room, can accommodate up to 10 people, from $45,000

Minutes from the airport and the ocean, you can spend the most of your surf vacation at this private resort. Located right on the water, you can relax after a day on the beach with a dip in your own private hot tub or heated pool. A big-screen TV and in-home gym, plus multiple lounge areas provide additional ways to unwind, so you can return from your trip feeling totally relaxed.

About Michael B. Billingsley

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