A beach with people, umbrellas, and surfboards.

Surfside Holiday Rentals

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Check prices for these dates

In two weeks
16 Oct - 18 Oct
In two months
27 Nov - 29 Nov
In three months
25 Dec - 27 Dec
In four months
22 Jan - 24 Jan

Our top choices for Surfside holiday rentals

A spacious kitchen with a central island, a dining area with a wooden table and chairs, and a spiral staircase leading to an upper level.

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)
"Close to town and supermarket. Charles and Honey were exceptional. Would definetly stay again"
United States
Colin
New to VRBO! 2/1 Mid Island Apartment, Sleeps 5
Property grounds

2. Historical Rose Covered Cottage with Ocean View

Historical Rose Covered Cottage with Ocean View
Siasconset
The price is HK$10,985
HK$19,518 total
includes taxes & fees
2 Oct - 3 Oct
Historical Rose Covered Cottage with Ocean View
A large, multi-story hotel with a wooden exterior and multiple balconies. A wooden boardwalk leads to the entrance.

3. Harborview Nantucket

Harborview Nantucket
4.0 star property
Nantucket Town
9.4 out of 10, Exceptional, (19 reviews)
"Everything was even better than we'd hoped. The cottage was absolutely beautiful and extremely clean, and we couldn't have been in a better location! The view of the harbor, proximity to shopping and dining, and ease of check-in/out made for the perfect vacation. The bed was super comfy and the kitchen was outfitted with everything you could need. I highly recommend this beautiful property for your stay on Nantucket!"
United States
Kim
The price is HK$4,943
HK$5,521 total
includes taxes & fees
7 Oct - 8 Oct
Harborview Nantucket
A wooden deck with a staircase leading to a covered area.

4. 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 HK$1,883
HK$3,690 total
includes taxes & fees
4 Oct - 5 Oct
Noddy - Cozy & cute 1st Floor Studio close to town with everything you need.
A residential area with a house featuring a front porch, a wooden fence, and a well-maintained hedge.

5. 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, (32 reviews)
"It’s was perfect for our family. Very close to everything."
United States
Patrick&Suzi S.
The price is HK$2,432
HK$4,382 total
includes taxes & fees
4 Oct - 5 Oct
Cozy upper studio- fully equipped & close to town, harbor, shops & restaurants!
A single-story house with a brick chimney, white trim, and a small porch.

6. Nantucket - edge of town

Nantucket - edge of town
West of Town
9.6 out of 10, Exceptional, (98 reviews)
"Mary is such a great host and such a sweet person."
United States
Pathfinder Tree S.
The price is HK$2,958
HK$5,776 total
includes taxes & fees
13 Oct - 14 Oct
Nantucket - edge of town
A wooden mailbox with a number plate, surrounded by a wooden fence and a wooden archway covered with pink roses.

7. Charming cottage, close to lower Main Street.

Charming cottage, close to lower Main Street.
Nantucket Town
10.0 out of 10, Exceptional, (141 reviews)
"Another great stay at a great location on Nantucket"
United States
Joe F.
The price is HK$2,636
HK$4,934 total
includes taxes & fees
4 Oct - 5 Oct
Charming cottage, close to lower Main Street.
A beach with clear blue water and a sandy shore.

8. 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, (132 reviews)
"Great little spot. Looking forward to coming back!"
United States
Anonymous traveller
The price is HK$3,001
HK$5,833 total
includes taxes & fees
19 Oct - 20 Oct
Luxurious Harbor View "Lizzie" Cottage! Walk & bike to everything!
A two-story house with a white picket fence, a well-maintained lawn, and a clear blue sky.

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

Luxurious Harbor View “Eliza” Cottage! Next To White Elephant!
Nantucket Town
10.0 out of 10, Exceptional, (311 reviews)
"Great location and very clean and well decorated. This was the perfect place for my wife and I while staying in Nantucket."
United States
John K.
Luxurious Harbor View “Eliza” Cottage! Next To White Elephant!
A two-story house with a grey siding exterior, a front porch with a wooden railing, and a small staircase leading to the entrance.

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, (128 reviews)
"House is adorable and so comfortable. Location could not be better. We loved our stay."
United States
Julie
The price is HK$3,390
HK$6,529 total
includes taxes & fees
6 Oct - 7 Oct
3 bedroom 2 1/2 bath house 1 1/2 Blocks From Main Street, one block from harbor.
A hot tub in front of a house with a wooden deck, a barbecue grill, and a table with candles.

11. Beautiful Cottage, Historic Home

Beautiful Cottage, Historic Home
Nantucket Town
10.0 out of 10, Exceptional, (1 review)
"Lovely little place! Good location. Would stay again!"
United States
Lauren N.
The price is HK$3,735
HK$8,519 total
includes taxes & fees
12 Oct - 13 Oct
Beautiful Cottage, Historic Home
An aerial view of a marina with numerous boats docked, surrounded by residential buildings and greenery.

12. 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, (253 reviews)
"Beautiful and comfortable place to stay right in town with our infant and dog. Would definitely stay here again."
United States
Laura U.
Luxurious Harbor View “Cynthia” cottage. Walk & bike to everything!
A staircase with a white railing leading to a landing with a bench and a shelf with books.

13. 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 HK$4,237
HK$7,608 total
includes taxes & fees
1 Nov - 2 Nov
Beachy right near “Children’s” Beach, near town and walking distance from Ferry.
A modern kitchen with white cabinetry, a central island, and a staircase with wooden steps.

14. 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
9.4 out of 10, Exceptional, (26 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.
The price is HK$6,277
HK$11,613 total
includes taxes & fees
5 Oct - 6 Oct
Mid island oasis! 3-bedroom, 4 bath in the middle of “second downtown”
A modern open-plan living and dining area with a round glass table, a sofa, and a kitchen in the background.

15. 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 HK$9,416
HK$15,522 total
includes taxes & fees
7 Oct - 8 Oct
Mid island oasis with large pool and outdoor entertainment area. Pet friendly!
A white building with a black door, a sign reading 'Union Suits,' and a number '36' above the door.

16. 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, (20 reviews)
"Perfect location close to town and beaches had the best time! "
United States
whitney F.
The price is HK$5,438
HK$12,156 total
includes taxes & fees
1 Nov - 2 Nov
Three bedrooms Four Blocks to Town and Harbor with parking
A sandy path leading to the beach, surrounded by tall grass.

17. Renovated 2024, Blocks From the Inner Harbor/ Downtown - King, Twins, Pull out.

Renovated 2024, Blocks From the Inner Harbor/ Downtown - King, Twins, Pull out.
Nantucket Town
9.8 out of 10, Exceptional, (17 reviews)
"House was amazing and Kate was so responsive!!!"
United States
Jennifer M.
Renovated 2024, Blocks From the Inner Harbor/ Downtown - King, Twins, Pull out.
A bright, well-lit room with a white sofa, a small round table, and a television mounted on the wall.

18. 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, (84 reviews)
"Convenient location, sweet property, well cared for."
United States
Barbara W.
Swedish Blue and Yellow house new 2021! Just over a block to harbor and Main St
A dining area with a wooden table and chairs, a television, and a bookshelf with various items.

19. Historic Nantucket Home | Hot Tub & Downtown Steps

Historic Nantucket Home | Hot Tub & Downtown Steps
Nantucket Town
8.0 out of 10, Very good, (3 reviews)
"Authentic and charming home. Well equipped with beach towels, coolers, lots of bathroom and great outdoor space."
United States
Mary M.
Historic Nantucket Home | Hot Tub & Downtown Steps
A modern kitchen with a central island, clear chairs, and a white sofa with green cushions.

20. Newly renovated house in Brandt Point, right near town and Children's Beach

Newly renovated house in Brandt Point, right near town and Children's Beach
Nantucket Town
9.8 out of 10, Exceptional, (62 reviews)
"Great stay, wonderful host!"
United States
Samantha W.
The price is HK$4,541
HK$8,350 total
includes taxes & fees
18 Oct - 19 Oct
Newly renovated house in Brandt Point, right near town and Children's Beach
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

Nantucket Inn

Nantucket Inn

10/10 Excellent
"Nantucket Inn is clean, modern, friendly, and well maintained. The pool is well kept, and comfortable. I highly recommend."
Gary 7-night trip
Posted less than an hour ago
Nantucket Inn

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
  • Use the map to find apartments and other holiday homes in the Surfside neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Surfside while they last

Look no further and take a look at our great range of rental properties in Surfside!

Frequently asked questions

Can I find a holiday rental in Surfside?

Yes, there are holiday rentals close to the most popular sights in Surfside, or you can select a more secluded option if you're looking for a relaxing stay.

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

Beautiful House Minutes from Town, on Bike Path : This holiday home rental outside of Surfside offers a patio, a selection of games and a BBQ to help you feel perfectly comfortable in your new surroundings. It has 4 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family.

How many holiday rentals are there in Surfside?

With 11 Expedia holiday rentals, you're guaranteed 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 wider area, you’ll find The Old Mill and Nantucket Historical Association.

What’s a holiday rental in Surfside like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Surfside. Holiday rentals feature extras such as laundry facilities and kitchens so your stay will be comfortable. If you're concerned about a sanitised environment, a holiday rental can provide a sense of security away from shared hotel lifts and busy front desks while still allowing you the enjoyment of travel. You'll also get more space in a holiday rental than in a traditional hotel, which makes a holiday rental a popular option for small groups.