A beach with people, umbrellas, and surfboards.

Surfside Vacation Rentals

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Our top choices for Surfside vacation rentals

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

New to VRBO! 2/1 Mid Island Apartment, Sleeps 5
Nantucket Town
9.2 out of 10, Wonderful, (23 reviews)
"Loved our time here! Perfect location and the host was so friendly and communicative during our trip! Would absolutely stay here again! "
United States
Kylie C.
The price is CA $331
CA $687 total
includes taxes & fees
Sep 13 - Sep 14
New to VRBO! 2/1 Mid Island Apartment, Sleeps 5

2. 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 CA $872
CA $974 total
includes taxes & fees
Oct 4 - Oct 5
Harborview Nantucket

3. Relax on Nantucket in our Cozy, 1-bedroom condo with AMAZING views!

Relax on Nantucket in our Cozy, 1-bedroom condo with AMAZING views!
Nantucket Town
10.0 out of 10, Exceptional, (26 reviews)
"Great spot, great host!"
United States
Jill I.
The price is CA $484
CA $958 total
includes taxes & fees
Oct 6 - Oct 7
Relax on Nantucket in our Cozy, 1-bedroom condo with AMAZING views!

4. 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 CA $692
CA $1,604 total
includes taxes & fees
Sep 15 - Sep 16
Romantic, Two Blocks to Main Street and Water. Queen bedroom and Two Bathrooms.

5. Charming cottage, close to lower Main Street.

Charming cottage, close to lower Main Street.
Nantucket Town
10.0 out of 10, Exceptional, (139 reviews)
"Another great stay at a great location on Nantucket"
United States
Joe F.
The price is CA $542
CA $975 total
includes taxes & fees
Sep 8 - Sep 9
Charming cottage, close to lower Main Street.

6. 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 CA $465
CA $824 total
includes taxes & fees
Sep 13 - Sep 14
Noddy - Cozy & cute 1st Floor Studio close to town with everything you need.

7. 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 CA $646
CA $1,178 total
includes taxes & fees
Sep 7 - Sep 8
Nantucket - edge of town

8. 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 CA $1,660
CA $2,737 total
includes taxes & fees
Oct 7 - Oct 8
Mid island oasis with large pool and outdoor entertainment area. Pet friendly!

9. 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, (130 reviews)
"Great little spot. Looking forward to coming back!"
United States
Anonymous traveller
The price is CA $809
CA $1,386 total
includes taxes & fees
Sep 7 - Sep 8
Luxurious Harbor View "Lizzie" Cottage! Walk & bike to everything!

10. 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 CA $706
CA $1,269 total
includes taxes & fees
Sep 14 - Sep 15
3 bedroom 2 1/2 bath house 1 1/2 Blocks From Main Street, one block from harbor.

11. 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 CA $581
CA $972 total
includes taxes & fees
Sep 20 - Sep 21
Cozy upper studio- fully equipped & close to town, harbor, shops & restaurants!

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 CA $635
CA $1,181 total
includes taxes & fees
Sep 15 - Sep 16
Beachy right near “Children’s” Beach, near town and walking distance from Ferry.

13. Luxurious Harbor View “Cynthia” cottage. Walk & bike to everything!

Luxurious Harbor View “Cynthia” cottage. Walk & bike to everything!
Nantucket Town
10.0 out of 10, Exceptional, (248 reviews)
"Beautiful and comfortable place to stay right in town with our infant and dog. Would definitely stay here again."
United States
Laura U.
The price is CA $1,059
CA $1,748 total
includes taxes & fees
Sep 7 - Sep 8
Luxurious Harbor View “Cynthia” cottage. Walk & bike to everything!

14. 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 CA $1,308
CA $2,022 total
includes taxes & fees
Sep 8 - Sep 9
Luxurious Harbor View "Lilly" Cottage! Walk & Bike To Everything!

15. 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 CA $1,175
CA $2,427 total
includes taxes & fees
Oct 7 - Oct 8
Three bedrooms Four Blocks to Town and Harbor with parking

16. 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.
The price is CA $891
CA $1,538 total
includes taxes & fees
Sep 24 - Sep 25
Historic 2BR Nantucket Cottage | Walk to Downtown

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

Luxurious Harbor View “Cindy” Cottage. Walk & Bike To Everything!
Nantucket Town
9.8 out of 10, Exceptional, (65 reviews)
"We thoroughly enjoyed our stay. The check in process was seamless. Communication with our host was great and always prompt. Cottage was spotless. Thoughtfully appointed with excellent attention to detail. Location was a convenient walk to restaurants and shops. Also centrally located for bike rides to all of the island. An instantly welcoming feel when we walked in. Would strongly recommend without hesitation and definitely hope to return again!"
United States
Seth R.
The price is CA $1,308
CA $2,022 total
includes taxes & fees
Sep 7 - Sep 8
Luxurious Harbor View “Cindy” Cottage. Walk & Bike To Everything!

18. Historic Island Home | Heated Pool

Historic Island Home | Heated Pool
Nantucket Town
The price is CA $2,788
CA $4,705 total
includes taxes & fees
Sep 17 - Sep 18
Historic Island Home | Heated Pool

19. 6 BDR, Pet-friendly, newly remodeled whaling captain’s house downtown Nantucket!

6 BDR, Pet-friendly, newly remodeled whaling captain’s house downtown Nantucket!
Nantucket Town
10.0 out of 10, Exceptional, (57 reviews)
"Great house in a great location. Walkable to most everything"
United States
Michael P.
The price is CA $2,491
CA $3,884 total
includes taxes & fees
Sep 8 - Sep 9
6 BDR, Pet-friendly, newly remodeled whaling captain’s house downtown Nantucket!

20. 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 CA $1,273
CA $2,037 total
includes taxes & fees
Sep 21 - Sep 22
Swedish Blue and Yellow house new 2021! Just over a block to harbor and Main St
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

Find out more about Surfside

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?

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 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.