A beach with people, umbrellas, and surfboards.

Surfside Vacation Rentals

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Check prices for these dates

In two weeks
Sep 25 - Sep 27
In two months
Nov 6 - Nov 8
In three months
Dec 4 - Dec 6
In four months
Jan 1 - Jan 3

Our top choices for Surfside vacation rentals

Exterior

1. Nantucket - edge of town

Nantucket - edge of town
West of Town
9.6 out of 10, Exceptional, (96 reviews)
"Mary is such a great host and such a sweet person."
United States
Pathfinder Tree S.
The price is ￥57,911
￥111,529 total
includes taxes & fees
Oct 4 - Oct 5
Nantucket - edge of town
Interior

2. Mid island oasis! 3-bedroom, 4 bath in the middle of “second downtown”

Mid island oasis! 3-bedroom, 4 bath in the middle of “second downtown”
Nantucket Town
9.8 out of 10, Exceptional, (22 reviews)
"Home is wonderful, well maintained and had all that we needed. Host was very responsive to the few questions we had and it is in a great location for getting around the island. "
United States
steven c.
Mid island oasis! 3-bedroom, 4 bath in the middle of “second downtown”
Property grounds

3. Cozy upper studio- fully equipped & close to town, harbor, shops & restaurants!

Cozy upper studio- fully equipped & close to town, harbor, shops & restaurants!
Nantucket Town
9.8 out of 10, Exceptional, (28 reviews)
"It’s was perfect for our family. Very close to everything."
United States
Patrick&Suzi S.
The price is ￥59,908
￥101,920 total
includes taxes & fees
Oct 11 - Oct 12
Cozy upper studio- fully equipped & close to town, harbor, shops & restaurants!
Exterior

4. 3 bedroom 2 1/2 bath house 1 1/2 Blocks From Main Street, one block from harbor.

3 bedroom 2 1/2 bath house 1 1/2 Blocks From Main Street, one block from harbor.
Nantucket Town
10.0 out of 10, Exceptional, (127 reviews)
"House is adorable and so comfortable. Location could not be better. We loved our stay."
United States
Julie
The price is ￥73,733
￥135,893 total
includes taxes & fees
Sep 17 - Sep 18
3 bedroom 2 1/2 bath house 1 1/2 Blocks From Main Street, one block from harbor.
Beach nearby, sun loungers, beach towels

5. Luxurious Harbor View "Lizzie" Cottage! Walk & bike to everything!

Luxurious Harbor View "Lizzie" Cottage! Walk & bike to everything!
Nantucket Town
10.0 out of 10, Exceptional, (131 reviews)
"Great little spot. Looking forward to coming back!"
United States
Anonymous traveler
The price is ￥89,862
￥147,046 total
includes taxes & fees
Sep 21 - Sep 22
Luxurious Harbor View "Lizzie" Cottage! Walk & bike to everything!
Smart TV, fireplace

6. Mid island oasis with large pool and outdoor entertainment area. Pet friendly!

Mid island oasis with large pool and outdoor entertainment area. Pet friendly!
Nantucket Town
9.8 out of 10, Exceptional, (7 reviews)
"Fantastic house, nice easy walk to restaurants and shopping. The pool was perfect for warm summer days, and there was plenty of room for our group throughout the house."
United States
Chris M.
The price is ￥184,332
￥298,211 total
includes taxes & fees
Oct 7 - Oct 8
Mid island oasis with large pool and outdoor entertainment area. Pet friendly!
Property grounds

7. Romantic, Two Blocks to Main Street and Water. Queen bedroom and Two Bathrooms.

Romantic, Two Blocks to Main Street and Water. Queen bedroom and Two Bathrooms.
Nantucket Town
10.0 out of 10, Exceptional, (2 reviews)
"Could not be happier with the place and location. The apartment was adorable, clean, as advertised. No complaints at all. Would definitely stay again! "
United States
Keira O.
The price is ￥76,805
￥181,363 total
includes taxes & fees
Sep 15 - Sep 16
Romantic, Two Blocks to Main Street and Water. Queen bedroom and Two Bathrooms.
Property grounds

8. Charming cottage, close to lower Main Street.

Charming cottage, close to lower Main Street.
Nantucket Town
10.0 out of 10, Exceptional, (140 reviews)
"Another great stay at a great location on Nantucket"
United States
Joe F.
The price is ￥73,733
￥125,427 total
includes taxes & fees
Oct 4 - Oct 5
Charming cottage, close to lower Main Street.
Terrace/patio

9. Beautiful Cottage, Historic Home

Beautiful Cottage, Historic Home
Nantucket Town
The price is ￥80,799
￥176,559 total
includes taxes & fees
Oct 12 - Oct 13
Beautiful Cottage, Historic Home
View from property

10. Harborview Nantucket

Harborview Nantucket
4.0 star property
Nantucket Town
9.4 out of 10, Exceptional, (18 reviews)
"Very nice location, easy walk to town. Right next to the bus depot. Excellent rooms , plenty of space. Could do with some instructions for the coffee machine, and what to do with rubbish once the bin is full. Would happily stay again."
United Kingdom
Richard
The price is ￥96,774
￥108,097 total
includes taxes & fees
Oct 4 - Oct 5
Harborview Nantucket
Interior

11. Noddy - Cozy & cute 1st Floor Studio close to town with everything you need.

Noddy - Cozy & cute 1st Floor Studio close to town with everything you need.
Nantucket Town
10.0 out of 10, Exceptional, (12 reviews)
"clean, easy access to downtown"
United States
william t.
The price is ￥47,926
￥86,648 total
includes taxes & fees
Sep 20 - Sep 21
Noddy - Cozy & cute 1st Floor Studio close to town with everything you need.
Interior

12. Beachy right near “Children’s” Beach, near town and walking distance from Ferry.

Beachy right near “Children’s” Beach, near town and walking distance from Ferry.
Nantucket Town
10.0 out of 10, Exceptional, (119 reviews)
"Comfortable stay for a family of 4 (2 adults, 2 kids) could fit a third family member if needed. The host was very communicative and responded within the day for most messages if not sooner."
United States
Stanford
The price is ￥65,284
￥123,197 total
includes taxes & fees
Sep 15 - Sep 16
Beachy right near “Children’s” Beach, near town and walking distance from Ferry.
Property grounds

13. Cisco Surf Penthouse: Lux 3 Bed 3 Bath, Brand New Construction, right in town!

Cisco Surf Penthouse: Lux 3 Bed 3 Bath, Brand New Construction, right in town!
Nantucket Town
10.0 out of 10, Exceptional, (4 reviews)
"Great place right in town with simple check in and out"
United States
Matt L.
Cisco Surf Penthouse: Lux 3 Bed 3 Bath, Brand New Construction, right in town!
Smart TV, fireplace, stereo, offices

14. Swedish Blue and Yellow house new 2021! Just over a block to harbor and Main St

Swedish Blue and Yellow house new 2021! Just over a block to harbor and Main St
Nantucket Town
10.0 out of 10, Exceptional, (83 reviews)
"Convenient location, sweet property, well cared for."
United States
Barbara W.
The price is ￥116,744
￥190,971 total
includes taxes & fees
Sep 21 - Sep 22
Swedish Blue and Yellow house new 2021! Just over a block to harbor and Main St
Marina

15. Luxurious Harbor View "Lilly" Cottage! Walk & Bike To Everything!

Luxurious Harbor View "Lilly" Cottage! Walk & Bike To Everything!
Nantucket Town
9.8 out of 10, Exceptional, (64 reviews)
"Great location!"
United States
Doris O.
The price is ￥145,161
￥224,258 total
includes taxes & fees
Sep 23 - Sep 24
Luxurious Harbor View "Lilly" Cottage! Walk & Bike To Everything!
Marina

16. Cisco Surf Suite: Brand New 3 bed 2 bath Condo, Ideally located IN town!

Cisco Surf Suite: Brand New 3 bed 2 bath Condo, Ideally located IN town!
Nantucket Town
10.0 out of 10, Exceptional, (7 reviews)
"We loved our stay at Cisco Surf suites! What a hidden gem! We fortunately found this brand new gorgeous upscale three bedroom unit! Centrally located to everything near the Nantucket harbor, just the right size place for our group of 3 guests, the beds were super comfy, each bathroom was made for guests, I loved the shampoo and conditioner! The host was very communicative, check in was easy! We will definitely be back!"
United States
Suzanne N.
Cisco Surf Suite: Brand New 3 bed 2 bath Condo, Ideally located IN town!
Coffee/tea maker, fridge, microwave, oven

17. Steps to the Beach and Town!

Steps to the Beach and Town!
Nantucket Town
9.6 out of 10, Exceptional, (17 reviews)
"Great location, great host"
United States
Stefan J.
The price is ￥185,100
￥309,879 total
includes taxes & fees
Oct 12 - Oct 13
Steps to the Beach and Town!
Exterior detail

18. Three bedrooms Four Blocks to Town and Harbor with parking

Three bedrooms Four Blocks to Town and Harbor with parking
Nantucket Town
9.8 out of 10, Exceptional, (18 reviews)
"Perfect location close to town and beaches had the best time! "
United States
whitney F.
The price is ￥120,891
￥257,201 total
includes taxes & fees
Oct 8 - Oct 9
Three bedrooms Four Blocks to Town and Harbor with parking
Exterior

19. Historic 2BR Nantucket Cottage | Walk to Downtown

Historic 2BR Nantucket Cottage | Walk to Downtown
Nantucket Town
8.0 out of 10, Very Good, (3 reviews)
"Great location and comfortable for a family of 4."
United States
Christy C.
Historic 2BR Nantucket Cottage | Walk to Downtown
Property grounds

20. Gorgeous home in town 3Bed 3 bath. screened porch- 3 levels of living & parking

Gorgeous home in town 3Bed 3 bath. screened porch- 3 levels of living & parking
Nantucket Town
10.0 out of 10, Exceptional, (43 reviews)
"This property exceeded all of our expectations. The house was spotlessly clean, beautifully decorated, and equipped with everything we needed for a comfortable stay. The location was fantastic—close to local attractions but still quiet and peaceful. Our host was incredibly responsive, welcoming, and made the check-in process completely seamless. We would love to stay here again and highly recommend it to anyone looking for a perfect getaway!"
United States
Marcee S.
The price is ￥152,074
￥270,243 total
includes taxes & fees
Oct 8 - Oct 9
Gorgeous home in town 3Bed 3 bath. screened porch- 3 levels of living & parking
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

The Beachside

The Beachside

10/10 Excellent
"Great place that was needed in Nantucket"
Quintin 3-night trip
Posted 2 hours ago
The Beachside

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:

  • View our selection of featured holiday rentals in Surfside
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Look no further and take a look at our great range of rental properties in Surfside!

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.

How many vacation rentals are there in Surfside?

With 10 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.