Surfside Vacation Rentals

  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
In two months
In three months
In four months

Our top choices for Surfside vacation rentals

Save now for Stroll and winter! Charming cottage, close to lower Main Street.

Save now for Stroll and winter! Charming cottage, close to lower Main Street.
Nantucket Town
10.0 out of 10, Exceptional, (124 reviews)
"Terrific cottage filled with great light and decorated with quaint Nantucket Charm!Comfortable sleigh bed with a large TV in the room, with an attached spacious bathroom with washer and dryer!Ideal location in town and a spacious parking spot! "
United States
kristin v.
The price is CA $128
CA $423 total
includes taxes & fees
Mar 8 - Mar 9
Save now for Stroll and winter! Charming cottage, close to lower Main Street.

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, (76 reviews)
"Great location, very accommodating hosts. The house was updated, well furnished, and perfect fkr a family."
United States
Daniel H.
The price is CA $177
CA $605 total
includes taxes & fees
Feb 18 - Feb 19
Swedish Blue and Yellow house new 2021! Just over a block to harbor and Main St

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, (47 reviews)
"Great location , very clean easy check in and out "
United States
Kathleen E.
The price is CA $159
CA $584 total
includes taxes & fees
Feb 18 - Feb 19
Newly renovated house in Brandt Point, right near town and Children's Beach

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, (21 reviews)
"Great place and very convenient to everything in town. Bed was extremely comfortable ."
United States
Rick V.
The price is CA $136
CA $380 total
includes taxes & fees
Mar 12 - Mar 13
Cozy upper studio- fully equipped & close to town, harbor, shops & restaurants!

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, (112 reviews)
"We had a great stay! The home had everything we needed and was in walking distance to everything. We loved it. We would definitely stay again and recommend it to anyone. "
United States
Mary S.
The price is CA $177
CA $605 total
includes taxes & fees
Feb 18 - Feb 19
Beachy right near “Children’s” Beach, near town and walking distance from Ferry.

The best location Downtown Nantucket Condo minutes from Ferries.

The best location Downtown Nantucket Condo minutes from Ferries.
Nantucket Town
The price is CA $477
CA $786 total
includes taxes & fees
Feb 18 - Feb 19
The best location Downtown Nantucket Condo minutes from Ferries.

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, (121 reviews)
"Great location! Great home base to explore Nantucket! The hosts were super responsive and check-in/check out was very easy. "
United States
Charlene R.
The price is CA $142
CA $562 total
includes taxes & fees
Mar 1 - Mar 2
3 bedroom 2 1/2 bath house 1 1/2 Blocks From Main Street, one block from harbor.

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, (6 reviews)
"clean, easy access to downtown"
United States
william t.
The price is CA $123
CA $399 total
includes taxes & fees
Mar 15 - Mar 16
Noddy - Cozy & cute 1st Floor Studio close to town with everything you need.

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, (40 reviews)
"We really enjoyed our stay, beautiful house close to town"
United States
Golie S.
The price is CA $1,021
CA $1,994 total
includes taxes & fees
Feb 18 - Feb 19
Gorgeous home in town 3Bed 3 bath. screened porch- 3 levels of living & parking

Steps to the Beach and Town!

Steps to the Beach and Town!
Nantucket Town
10.0 out of 10, Exceptional, (15 reviews)
"Great location, great host"
United States
Stefan J.
The price is CA $1,069
CA $2,055 total
includes taxes & fees
Feb 18 - Feb 19
Steps to the Beach and Town!

Beautiful 5BR with Pool. 3 Renovated Levels of Luxury. Walk to Town or Beach.

Beautiful 5BR with Pool. 3 Renovated Levels of Luxury. Walk to Town or Beach.
Nantucket
10.0 out of 10, Exceptional, (1 review)
"Wonderful house, plenty of space, gorgeous peaceful view out back. Very responsive host!"
United States
Leslie B.
The price is CA $2,043
CA $3,454 total
includes taxes & fees
Feb 18 - Feb 19
Beautiful 5BR with Pool. 3 Renovated Levels of Luxury. Walk to Town or Beach.

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, (2 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.
The price is CA $912
CA $2,115 total
includes taxes & fees
Feb 18 - Feb 19
Cisco Surf Suite: Brand New 3 bed 2 bath Condo, Ideally located IN town!

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, (2 reviews)
"No detail has been missed in terms of outfitting this apartment. As everything was brand new, there were a few hiccups, but the property manager was really responsive. Two of the bedrooms were quite small, but it was nevertheless very comfortable. What wasn’t that clear from the description is that this is above the Brotherhood of Thieves tavern, which came with early morning garbage pickup, which was a little annoying. But the flip side is that it was so well located in town, near so many...
United States
Nancy S.
The price is CA $912
CA $2,115 total
includes taxes & fees
Feb 18 - Feb 19
Cisco Surf Penthouse: Lux 3 Bed 3 Bath, Brand New Construction, right in town!

Love Sand, Madaket on the Beach, Lovely Seaside Home

Love Sand, Madaket on the Beach, Lovely Seaside Home
Nantucket
9.8 out of 10, Exceptional, (56 reviews)
"Great location and overall experience. "
United States
Michael S.
The price is CA $201
CA $1,058 total
includes taxes & fees
Mar 1 - Mar 2
Love Sand, Madaket on the Beach, Lovely Seaside Home
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.

The Annual Vacation Sale

Members save up to 40% on hotels and homes. Plan this year’s big trip and save.
Save an average of 15% on thousands of hotels when you're signed in

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?

Newly renovated house in Brandt Point, right near town and Children's Beach: Visitors like this Surfside vacation home rental. It is located in the city center and has a fireplace, a patio, and a barbecue grill to put you at ease in your new surroundings. It has 4 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family.

How many vacation rentals are there in Surfside?

With 28 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 Cisco Brewers.

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.