Surfside Vacation Rentals

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Check prices for these dates

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Aug 9 - Aug 10
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Aug 10 - Aug 11
Next weekend
Aug 15 - Aug 17
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Aug 22 - Aug 24

Vacation Rentals in Surfside

Cozy, 1-bedroom condo with WiFi, AC in charming Nantucket
Private kitchen

Cozy, 1-bedroom condo with WiFi, AC in charming Nantucket

10.0 out of 10, Exceptional, (3)
"Cozy apartment in a great location. Host was very responsive. Would definitely stay here again! "
Cozy, 1-bedroom condo with WiFi, AC in charming Nantucket
A Literary Oasis In The Heart Of Nantucket Town
Fridge, microwave, oven, stovetop

A Literary Oasis In The Heart Of Nantucket Town

10.0 out of 10, Exceptional, (76)
"We loved our stay at this property. We appreciated how spacious the apartment was and all of the design elements were thoughtful and beautiful. The best part was the location - right in town. I would not hesitate to stay here again. "
A Literary Oasis In The Heart Of Nantucket Town
LUXURIOUS New Cottage! 5-min. walk to Main St. And Harbor Beaches
Outdoor dining

LUXURIOUS New Cottage! 5-min. walk to Main St. And Harbor Beaches

10.0 out of 10, Exceptional, (159)
"Beautiful cottage , great location. Would love to stay again "
LUXURIOUS New Cottage! 5-min. walk to Main St. And Harbor Beaches
Renovated Cottage off Main Street- Great Location
Exterior

Renovated Cottage off Main Street- Great Location

10.0 out of 10, Exceptional, (156)
"The cabin was perfect. It was on more of a busy road than we anticipated, but everything else was wonderful. We enjoyed ourselves so much!!"
Renovated Cottage off Main Street- Great Location
Beautifully Renovated Main Street Cottage- Great Location
Dining

Beautifully Renovated Main Street Cottage- Great Location

10.0 out of 10, Exceptional, (117)
"We were thrilled to arrive at our property with everything as pictured but actually more charming in person. It is easily walkable to town and restaurants. Communication with the owner was easy and I can recommend it to anyone who wants to stay on Nantucket. "
Beautifully Renovated Main Street Cottage- Great Location
Rustic, sunny cottage w/ deck & W/D - walk to the beach & town!
2 bedrooms, free WiFi, bed sheets

Rustic, sunny cottage w/ deck & W/D - walk to the beach & town!

8.2 out of 10, Very Good, (23)
"The property was perfect for our family. It’s in a great location. We rented bikes and enjoyed being able to walk and bike to the beach and market. Thanks for letting us stay!"
Rustic, sunny cottage w/ deck & W/D - walk to the beach & town!
Private Modern Bedroom In a Central Location
Property grounds

Private Modern Bedroom In a Central Location

9.6 out of 10, Exceptional, (23)
"He property was beautiful. Very private, clean and plenty of space. The hosts are also super friendly. The property is close to a stop on the Miacomet line of The Wave. It’s about 1.5 miles from the middle of town and 2.5 miles from Surfside."
The price is ￥45,075
￥69,823 total
includes taxes & fees
Aug 21 - Aug 22
Private Modern Bedroom In a Central Location
Harborview Nantucket
View from property

Harborview Nantucket

4.0 star property
9.6 out of 10, Exceptional, (13)
"We had an excellent stay at harbor view cottages! The property is beautiful and close to everything. it is clear that the owners paid attention to all the little details when furnishing the cottage, which I always appreciate. I will definitely be returning! "
Harborview Nantucket
Luxurious Harbor View "Millie" Cottage! Walk & bike to everything!
Fridge, microwave, oven, stovetop

Luxurious Harbor View "Millie" Cottage! Walk & bike to everything!

10.0 out of 10, Exceptional, (220)
"Absolutely loved staying here. Great location and Theresa was super responsive! The property was well stocked and had everything we needed for a peaceful couple weeks. Our dogs loved being so close to the beach! "
The price is ￥135,625
￥215,523 total
includes taxes & fees
Sep 7 - Sep 8
Luxurious Harbor View "Millie" Cottage! Walk & bike to everything!
Quiet getaway for two
Terrace/patio

Quiet getaway for two

9.6 out of 10, Exceptional, (70)
"Great location mid island, outdoor space was a really nice perk to the quaint room and bathroom was a good size. Loved having a fridge, microwave and TV for unwinding at the end of the day and the complimentary beach chairs were so great. Patricia is responsive and super helpful, we’ll definitely be back!! "
Quiet getaway for two
Beautiful House Minutes from Town, on Bike Path
Exterior

Beautiful House Minutes from Town, on Bike Path

10.0 out of 10, Exceptional, (44)
"Beautiful home in a convenient location just outside of Main Street. We were able to walk from the ferry to the house with suitcases in tow. The beds were comfortable, kitchen was well stocked. Would definitely stay there again."
Beautiful House Minutes from Town, on Bike Path
HIGH TIDE - Comfy Home W/Pool, High Tide
Fridge, microwave, oven, stovetop

HIGH TIDE - Comfy Home W/Pool, High Tide

9.6 out of 10, Exceptional, (41)
"The house was very clean and I loved the outdoor shower."
The price is ￥125,520
￥243,941 total
includes taxes & fees
Sep 1 - Sep 2
HIGH TIDE - Comfy Home W/Pool, High Tide
Escape to Nantucket's charm, just a 6-min drive from Surfside Beach
Outdoor dining

Escape to Nantucket's charm, just a 6-min drive from Surfside Beach

10.0 out of 10, Exceptional, (7)
"Beautiful property that is well maintained. Close to beaches and close to town. Also some amazing trails nearby. Owners of the home were very kind and warm people. We had an amazing vacation and can’t wait to rebook again."
Escape to Nantucket's charm, just a 6-min drive from Surfside Beach
Nantucket - edge of town
Exterior

Nantucket - edge of town

9.8 out of 10, Exceptional, (79)
"The house was adorable - we loved it. "
Nantucket - edge of town
New to VRBO! 2/1 Mid Island Apartment, Sleeps 5
Fridge, microwave, oven, stovetop

New to VRBO! 2/1 Mid Island Apartment, Sleeps 5

9.6 out of 10, Exceptional, (14)
"Our in laws had a wonderful stay in Jais’s place! It was clean and comfortable, had ample parking and was in a great location. Communication was terrific!!! We highly recommend!"
New to VRBO! 2/1 Mid Island Apartment, Sleeps 5
Nantucket Beach House Oasis. 4 Beds, 3 baths, with spectacular views
Fridge, microwave, oven, stovetop

Nantucket Beach House Oasis. 4 Beds, 3 baths, with spectacular views

10.0 out of 10, Exceptional, (1)
"Sea Lion is a beautiful property and we very much enjoyed all aspects of our stay there. "
Nantucket Beach House Oasis. 4 Beds, 3 baths, with spectacular views
Luxurious Harbor View “Cindy” Cottage. Walk & Bike To Everything!
Fridge, microwave, oven, stovetop

Luxurious Harbor View “Cindy” Cottage. Walk & Bike To Everything!

9.8 out of 10, Exceptional, (59)
"Cindy's Cottage was perfect for our weekend stay. We wish we could have stayed longer to enjoy all the comforts of this beautiful home. "
The price is ￥109,287
￥174,268 total
includes taxes & fees
Sep 1 - Sep 2
Luxurious Harbor View “Cindy” Cottage. Walk & Bike To Everything!
Charming one bedroom cottage, close to lower Main Street and Handlebar Cafe.
Fridge, microwave, oven, stovetop

Charming one bedroom cottage, close to lower Main Street and Handlebar Cafe.

10.0 out of 10, Exceptional, (114)
"Clean, easy to find, location was great"
Charming one bedroom cottage, close to lower Main Street and Handlebar Cafe.
Luxurious Harbor View “Eliza” Cottage! Next To White Elephant!
Exterior

Luxurious Harbor View “Eliza” Cottage! Next To White Elephant!

10.0 out of 10, Exceptional, (272)
"What a perfect vacation spot. The home was perfect for two and well-appointed. Close to town and dining. Wonderful treasures to find on a walk. Would certainly book for our next trip to Nantucket. "
The price is ￥118,654
￥188,999 total
includes taxes & fees
Aug 10 - Aug 11
Luxurious Harbor View “Eliza” Cottage! Next To White Elephant!
Newly constructed 3 BR house . Walk to town, harbor and restaurants
Fridge, microwave, oven, stovetop

Newly constructed 3 BR house . Walk to town, harbor and restaurants

10.0 out of 10, Exceptional, (33)
"We greatly enjoyed our stay at this warm and welcoming home. The house was perfectly equipped with everything we needed for our stay and the location was so easy to get to so many great spots on the island. We can’t wait to go back. "
Newly constructed 3 BR house . Walk to town, harbor and restaurants
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.
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Top Surfside Hotel Reviews

Faraway Nantucket

Faraway Nantucket

10/10 Excellent
"I really appreciated the staff - some amenities need to be updated in the rooms"
Deivi 3-night trip
Posted 3 days ago
Faraway Nantucket

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?

LUXURIOUS New Cottage! 5-min. walk to Main St. And Harbor Beaches: Visitors like this Surfside vacation home rental. It is located in the city center and has a patio, a garden, and a barbecue grill to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge, and a stovetop. You and your friends and family can relax into your vacation with amenities like a hot tub.

How many vacation rentals are there in Surfside?

With 24 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.