Surfside Vacation Rentals

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Vacation Rentals in Surfside

Two-bedroom cottage with one Queen-size bed, two twin beds, and a sofa bed.
9.0 out of 10, Wonderful, 8 reviews
"We enjoyed our stay!"
Two-bedroom cottage with one Queen-size bed, two twin beds, and a sofa bed.
2 Bedrooms plus Loft - sleeps 6 in beds - 5 Blocks to Center of Town
10.0 out of 10, Exceptional, 74 reviews
"5 Honeysuckle Ln. is an absolutely perfect little cottage that is welcoming and has everything you need for your stay on Nantucket. It had all the comfort of home and I loved sleeping in the loft. It was like a little piece of heaven, looking out the window up there. Our dear friends, enjoyed the master bedroom which had a wonderful king bed, and so much room to sort themselves out during our vacation. We didn’t require the twin bedroom so we used it as a dressing room and that worked...
2 Bedrooms plus Loft - sleeps 6 in beds - 5 Blocks to Center of Town
Beautifully Renovated Main Street Cottage- Great Location
10.0 out of 10, Exceptional, 95 reviews
"My family of four plus a dog were very comfortable in this cottage. The cottage is beautiful and well stocked. Beds were comfy. Kitchen is also well stocked. Location was great. We walked easily into town or rode bikes to various beaches. All in all this is a great rental property."
Beautifully Renovated Main Street Cottage- Great Location
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LUXURIOUS Cottage with Breathtaking Harbor Views
9.8 out of 10, Exceptional, 125 reviews
"Theresa’s property is perfect for a small group trip. My family and I stayed for the week and couldn’t have been happier with the location, cleanliness, and comfort of the home. Truly felt like we were in our own little paradise! We will definitely be back."
The price is CA $1,509
CA $2,276 total
includes taxes & fees
Jun 20 - Jun 21
LUXURIOUS Cottage with Breathtaking Harbor Views
Luxurious Harbor View “Elizabeth” Cottage! Walk & bike to everything
9.8 out of 10, Exceptional, 133 reviews
"Cute and cozy for a small family."
The price is CA $1,201
CA $1,856 total
includes taxes & fees
Jun 23 - Jun 24
Luxurious Harbor View “Elizabeth” Cottage! Walk & bike to everything
Quiet getaway for two
9.6 out of 10, Exceptional, 52 reviews
"perfect little place for the perfect weekend! had everything you need and allowed dogs which is always more than appreciated. Great little private patio and suite."
Quiet getaway for two
Rustic, sunny cottage w/ deck & W/D - walk to the beach & town!
8.0 out of 10, Very good, 12 reviews
"We loved this house. Sure, it is rustic (as the title says), but we loved the vibe. The architecture, exposed wood, and white floors felt like a 60s surf bungalow. The house is interesting and there are some quirks, but nothing that had any impact on our stay. It was clean and well appointed where it mattered- the linens were clean and fresh, the kitchen and bathroom were clean, the mattresses on the twin beds seemed new. It was walking distance to the little town, beach, playground, Sconset...
Rustic, sunny cottage w/ deck & W/D - walk to the beach & town!
Private Modern Bedroom In a Central Location
9.4 out of 10, Exceptional, 8 reviews
"It was great"
The price is CA $465
CA $699 total
includes taxes & fees
Jul 2 - Jul 3
Private Modern Bedroom In a Central Location
Luxurious Harbor View "Lizzie" Cottage! Walk & bike to everything!
10.0 out of 10, Exceptional, 101 reviews
"Wonderful place to spend a getaway on Nantucket :)"
The price is CA $1,029
CA $1,601 total
includes taxes & fees
Jun 23 - Jun 24
Luxurious Harbor View "Lizzie" Cottage! Walk & bike to everything!
Tranquilty
10.0 out of 10, Exceptional, 29 reviews
"The hosts were very nice accommodating and welcoming. The property exceeding our expectations and would love to stay there again in the future."
Tranquilty
Nantucket - edge of town
9.8 out of 10, Exceptional, 67 reviews
"Nice rental,Stayed only one night but will definitely be back"
The price is CA $1,148
CA $1,816 total
includes taxes & fees
Jul 8 - Jul 9
Nantucket - edge of town
Ireland Time | House in Nantucket with deck, full kitchen, & W/D
8.0 out of 10, Very good, 1 review
Ireland Time | House in Nantucket with deck, full kitchen, & W/D
Luxurious Harbor View “Cynthia” cottage. Walk & bike to everything!
10.0 out of 10, Exceptional, 193 reviews
"Our first visit to Nantucket was all we hoped for. The Cynthia Cottage is a lovely property; well appointed & true to the online pix. Theresa was very responsive & helpful. We’re very happy we chose this home for our visit."
The price is CA $1,201
CA $1,882 total
includes taxes & fees
Jun 19 - Jun 20
Luxurious Harbor View “Cynthia” cottage. Walk & bike to everything!
Renovated Cottage off Main Street- Great Location
10.0 out of 10, Exceptional, 138 reviews
"This was our first time visiting Nantucket and we could not have had a better time! The cottage was great and the centralized location could not have been better."
Renovated Cottage off Main Street- Great Location
LUXURIOUS New Cottage! 5-min. walk to Main St. And Harbor Beaches
10.0 out of 10, Exceptional, 114 reviews
"When everyone gives this place a 5 star review they’re not exaggerating!"
LUXURIOUS New Cottage! 5-min. walk to Main St. And Harbor Beaches
Private Beach Cottage in Historic Sconset!
9.8 out of 10, Exceptional, 14 reviews
"Nick and Kristi were such wonderful hosts. I had an amazing four nights stay at the cottage in March. It was nice to enjoy the quiet time of ‘Sconset off season. Walking into the cottage, I immediately noticed how clean it was and how nice it smelled. The use of the small space is clever and feels so much bigger than you’d think. There was everything you’d need and more for a stay. When I had a couple of questions Kristi was so quick to respond and so kind. I would love to come back and stay...
The price is CA $822
CA $1,308 total
includes taxes & fees
Jun 26 - Jun 27
Private Beach Cottage in Historic Sconset!
Luxurious Harbor View "Millie" Cottage! Walk & bike to everything!
10.0 out of 10, Exceptional, 197 reviews
"We loved our time in the Millie Cottage. The distance to town was perfect and Theresa was so easy to communicate with. If we make it back to Nantucket we will stay here again!"
The price is CA $1,201
CA $1,882 total
includes taxes & fees
Jun 23 - Jun 24
Luxurious Harbor View "Millie" Cottage! Walk & bike to everything!
Duplex Sunny Condo in residential neighborhood, 5min walk to bike paths!!!
8.8 out of 10, Excellent, 62 reviews
"Accommodations were as expected. Communication with the host was great."
Duplex Sunny Condo in residential neighborhood, 5min walk to bike paths!!!
FREE 3rd Night!* (See description) Nantucket in Town 3 Bedroom 1 Bath Cute House
9.6 out of 10, Exceptional, 41 reviews
"Our time in Nantucket was spectacular! This property was not! Borders on false advertising! Cigarette butts all over front yard, dog feces left in bag in yard, broken coffee maker, no shades or ripped shades on windows, filthy windows and sills, rug horrible condition. Mouse ran over sister while sleeping. It was insane! No window leading to cellar. Filthy coolers, and hammock. Exuberant amount of money for cleaning fees and rental. It was shocking and disgraceful! "
FREE 3rd Night!* (See description) Nantucket in Town 3 Bedroom 1 Bath Cute House
Spacious Beach Cottage with Grill, Patio, Outdoor Shower & High-Speed WiFi
6.8 out of 10, 11 reviews
"I was here on business. But would be a great stay for a family. Plenty of room."
Spacious Beach Cottage with Grill, Patio, Outdoor Shower & High-Speed WiFi
Don't see what you're looking for?
See all available properties in Surfside
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Other types of properties in Surfside you may be interested in

Jared Coffin House
4.0 star property
9.2 out of 10, Wonderful, 582 reviews
"A most welcoming staff awaits you and takes good care of you. The one snafu was my initially trying to procure a ride from the ferry to the hotel, calling earlier days: whomever answered calls or emails did not, but at the last minute came through and throughout our stay communication was excellent, caring kind staff, conditions beautiful, great location. Great first visit to Nantucket and Jared Coffin House."
The price is CA $617
CA $690 total
includes taxes & fees
Jun 24 - Jun 25
Jared Coffin House
Faraway Nantucket
3.5 star property
8.8 out of 10, Excellent, 226 reviews
"Quaint, cozy, and great location!"
The price is CA $694
CA $814 total
includes taxes & fees
Jun 24 - Jun 25
Faraway Nantucket
Nantucket Inn
3.5 star property
8.6 out of 10, Excellent, 299 reviews
"Excellent place. Beautiful rooms and cabin w fireplace. Transport was excellent along with the staff. We loved our stay ❤️"
The price is CA $778
CA $869 total
includes taxes & fees
Jul 18 - Jul 19
Nantucket Inn
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with Surfside. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.

It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.

Frequently asked questions

Can I find a vacation rental in Surfside?

Yes, we offer vacation rentals close to well known local attractions in Surfside, or you can select a more remote option if you'd like a relaxing place to stay.

What are some of the best vacation rentals that Surfside has to offer?

Rustic, sunny cottage w/ deck & W/D - walk to the beach & town!: You might want to consider this vacation home rental near Surfside, which has air-conditioning and laundry facilities to help you feel perfectly comfortable in your new surroundings.

How many vacation rentals are there in Surfside?

With 26 Expedia vacation rentals, you're sure to find just the right place for your Surfside stay.

What’s there to see and do in Surfside?

Surfside Beach and Nobadeer Beach are a couple of lovely local spots to get outside and enjoy nature. In the larger area, you’ll find Nantucket Historical Association and Nantucket Atheneum.

What’s a vacation rental in Surfside like?

Vacation rentals are private properties you can stay in for several days or longer in Surfside. Vacation rentals feature amenities such as hot tubs, fire pits, and patios so you'll have all the comforts of home. If you're concerned about a sanitized environment, a vacation rental can offer a sense of seclusion away from shared hotel elevators and lobbies bustling with people while still allowing you the experience of travel. You'll also have more space in a vacation rental than in a hotel, which makes a vacation rental an attractive option for a family trip or a small group gathering.

Recent reviews of Surfside properties
Expedia verified reviews