Surfside Vacation Rentals

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Check prices for these dates

In two weeks
Oct 31 - Nov 2
In two months
Dec 12 - Dec 14
In three months
Jan 9 - Jan 11
In four months
Feb 6 - Feb 8

Vacation Rentals in Surfside

Duplex Sunny Condo in residential neighborhood, 5min walk to bike paths!!!
Exterior
Duplex Sunny Condo in residential neighborhood, 5min walk to bike paths!!!
8.8 out of 10, Excellent, (80)
"3rd time staying at the rental and we really enjoyed as always! "
Duplex Sunny Condo in residential neighborhood, 5min walk to bike paths!!!
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, (283)
"Perfect for a couple!Everything was amazing."
Luxurious Harbor View “Eliza” Cottage! Next To White Elephant!
Renovated Cottage off Main Street- Great Location
Exterior
Renovated Cottage off Main Street- Great Location
10.0 out of 10, Exceptional, (161)
"Super cute place and close to town! Really responsive host. We enjoyed our stay. "
Renovated Cottage off Main Street- Great Location
LUXURIOUS Cottage with Breathtaking Harbor Views
Fridge, microwave, oven, stovetop
LUXURIOUS Cottage with Breathtaking Harbor Views
9.8 out of 10, Exceptional, (168)
"Beautiful house in a great location! "
LUXURIOUS Cottage with Breathtaking Harbor Views
Harborview Nantucket
View from property
Harborview Nantucket
4.0 star property
9.6 out of 10, Exceptional, (14)
"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! "
The price is ￥90,714
￥101,328 total
includes taxes & fees
Oct 19 - Oct 20
Harborview Nantucket
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, (172)
"Beautiful cottage , great location. Would love to stay again "
The price is ￥62,328
￥116,232 total
includes taxes & fees
Oct 14 - Oct 15
LUXURIOUS New Cottage! 5-min. walk to Main St. And Harbor Beaches
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, (228)
"Great house. Great location. Responsive host. "
The price is ￥43,051
￥98,415 total
includes taxes & fees
Nov 7 - Nov 8
Luxurious Harbor View "Millie" Cottage! Walk & bike to everything!
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, (43)
"The house was very clean and I loved the outdoor shower."
The price is ￥22,301
￥108,245 total
includes taxes & fees
Oct 14 - Oct 15
HIGH TIDE - Comfy Home W/Pool, High Tide
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, (83)
"We loved our stay at Literary Oasis! The apartment location was amazing for first time visitors to Nantucket or those wanting an in-town location. We had an easy walk to all the shopping, restaurants, and pier spots. The actual home was amazing. As an avid reader, I loved the book theme of the unit. We will definitely be booking this stay again ."
A Literary Oasis In The Heart Of Nantucket Town
Luxurious Harbor View “Cynthia” cottage. Walk & bike to everything!
Fridge, microwave, oven, stovetop
Luxurious Harbor View “Cynthia” cottage. Walk & bike to everything!
10.0 out of 10, Exceptional, (226)
"Such a great property! Cant wait to stay again!"
Luxurious Harbor View “Cynthia” cottage. Walk & bike to everything!
Brand New modern 2 bedroom 2nd floor apartment
Fridge, microwave, oven, stovetop
Brand New modern 2 bedroom 2nd floor apartment
9.8 out of 10, Exceptional, (21)
"Very nice space and only 10 minutes from town. Would stay again!"
The price is ￥65,994
￥124,379 total
includes taxes & fees
Oct 14 - Oct 15
Brand New modern 2 bedroom 2nd floor apartment
Newly renovated house in Brandt Point, right near town and Children's Beach
Smart TV, fireplace
Newly renovated house in Brandt Point, right near town and Children's Beach
9.8 out of 10, Exceptional, (44)
"Awesome stay. Only wish we'd found the secret room sooner!"
The price is ￥66,524
￥126,829 total
includes taxes & fees
Oct 15 - Oct 16
Newly renovated house in Brandt Point, right near town and Children's Beach
This two-bedroom cottage features one queen bed, two twin beds, and a sofa bed.
Property grounds
This two-bedroom cottage features one queen bed, two twin beds, and a sofa bed.
9.4 out of 10, Exceptional, (38)
"Lovely accommodations mid island amidst what appeared to be a blue collar neighborhood. About ten minutes from center of Nantucket and a half hour out to Madaket. Our only transportation were bicycles and we enjoyed the many bike paths on island. "
This two-bedroom cottage features one queen bed, two twin beds, and a sofa bed.
Gorgeous 10 min. walk to Downtown. Perfect for families. Large backyard.
Marina
Gorgeous 10 min. walk to Downtown. Perfect for families. Large backyard.
10.0 out of 10, Exceptional, (88)
"Great property close to town. Very clean and well equipped. Owner was very communicative and checked in with us appropriately. Would stay again!"
Gorgeous 10 min. walk to Downtown. Perfect for families. Large backyard.
Nantucket Party Pad near Cisco Brewers- 7 bedrooms, 6.5 bathrooms, Pool, Spa, AC
Property grounds
Nantucket Party Pad near Cisco Brewers- 7 bedrooms, 6.5 bathrooms, Pool, Spa, AC
10.0 out of 10, Exceptional, (42)
"We had the best time at this property! It was clean, spacious, and really lent itself to a large group weekend away! The pool really makes this stay 10/10! "
Nantucket Party Pad near Cisco Brewers- 7 bedrooms, 6.5 bathrooms, Pool, Spa, AC
Private Modern Bedroom In a Central Location
Property grounds
Private Modern Bedroom In a Central Location
9.4 out of 10, Exceptional, (27)
"Super clean and modern room. Good location. Hosts were very nice and very available. Amazing spot, we would stay again"
Private Modern Bedroom In a Central Location
Cozy 4 bedroom cottage in town, with parking
Terrace/patio
Cozy 4 bedroom cottage in town, with parking
2.0 star property
9.0 out of 10, Wonderful, (21)
"Fantastic house in a great location for our group! Would gladly book again!"
Cozy 4 bedroom cottage in town, with parking
Nantucket - edge of town
Exterior
Nantucket - edge of town
9.6 out of 10, Exceptional, (87)
"We used this home as a base for a visit to Nantucket. It was nicely located, comfortable, and great for our family."
The price is ￥35,832
￥84,102 total
includes taxes & fees
Oct 14 - Oct 15
Nantucket - edge of town
Luxurious Harbor View "Lizzie" Cottage! Walk & bike to everything!
Beach nearby, sun loungers, beach towels
Luxurious Harbor View "Lizzie" Cottage! Walk & bike to everything!
10.0 out of 10, Exceptional, (122)
"Very cute place a short walk to town. House came equipped with everything we needed. "
Luxurious Harbor View "Lizzie" Cottage! Walk & bike to everything!
Free 3rd Night!* New house! Walk to bars/restaurants/harbor, Nantucket in Town!
Exterior
Free 3rd Night!* New house! Walk to bars/restaurants/harbor, Nantucket in Town!
9.4 out of 10, Exceptional, (41)
"We stayed at 8 Atlantic Avenue for the Daffodil Festival weekend. The home is impeccable and beautiful - spacious with gorgeous hardwood floors and a kitchen meant for entertaining. Close to town for shopping and restaurants. Owners were a pleasure to work with and I would highly recommend this property! We loved every aspect of our stay and will definitely rent there again."
Free 3rd Night!* New house! Walk to bars/restaurants/harbor, Nantucket in Town!
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

Jared Coffin House

Jared Coffin House

10/10 Excellent
"Lovely breakfast"
Patrice 1-night trip
Posted 2 days ago
Jared Coffin House

Find out more about Surfside

Search for holiday rentals in Surfside on Expedia! You can easily find your home rentals, villas, holiday apartments in Surfside using one of the methods below:

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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: You might want to consider this vacation home rental near Surfside, which 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 22 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 The Old Mill and Nantucket Historical Association.

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.