A beach with people, umbrellas, and surfboards.

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

Nantucket - edge of town

Nantucket - edge of town
West of Town
9.8 out of 10, Exceptional, (92 reviews)
"Host was very responsive and helpful. Great location. "
United States
Barbara Z.
The price is CA $1,060
CA $1,684 total
includes taxes & fees
Jul 27 - Jul 28
Nantucket - edge of town

Private Modern Bedroom In a Central Location

Private Modern Bedroom In a Central Location
Nantucket Town
9.0 out of 10, Wonderful, (37 reviews)
"Super clean and modern room. Good location. Hosts were very nice and very available. Amazing spot, we would stay again"
United States
Christina R.
The price is CA $551
CA $820 total
includes taxes & fees
Aug 3 - Aug 4
Private Modern Bedroom In a Central Location

Brand new modern 2 bedroom apartment

Brand new modern 2 bedroom apartment
Nantucket
9.4 out of 10, Exceptional, (33 reviews)
"Clean and nice host the beds didn’t have enough blankets and there weren’t blankets in closets. Also had soap needed in the bathrooms. Great location Bike rentals were next door and a cafe"
United States
Krista
The price is CA $828
CA $1,435 total
includes taxes & fees
Jul 19 - Jul 20
Brand new modern 2 bedroom apartment

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 $955
CA $1,987 total
includes taxes & fees
Jul 19 - Jul 20
Romantic, Two Blocks to Main Street and Water. Queen bedroom and Two Bathrooms.

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, (23 reviews)
"Great location and host was very accommodating and helpful!"
United States
Doreen S.
The price is CA $984
CA $1,589 total
includes taxes & fees
Jul 26 - Jul 27
Relax on Nantucket in our Cozy, 1-bedroom condo with AMAZING views!

Private Beach Cottage in Historic Sconset!

Private Beach Cottage in Historic Sconset!
Nantucket
9.8 out of 10, Exceptional, (26 reviews)
"Perfect location for quiet beach stay!"
United States
Jim N.
The price is CA $1,414
CA $2,163 total
includes taxes & fees
Aug 10 - Aug 11
Private Beach Cottage in Historic Sconset!

Charming cottage, close to lower Main Street.

Charming cottage, close to lower Main Street.
Nantucket Town
10.0 out of 10, Exceptional, (134 reviews)
"Another great stay at a great location on Nantucket"
United States
Joe F.
The price is CA $1,052
CA $1,629 total
includes taxes & fees
Jul 28 - Jul 29
Charming cottage, close to lower Main Street.

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, (7 reviews)
"clean, easy access to downtown"
United States
william t.
The price is CA $736
CA $1,175 total
includes taxes & fees
Aug 5 - Aug 6
Noddy - Cozy & cute 1st Floor Studio close to town with everything you need.

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, (55 reviews)
"Great stay, wonderful host!"
United States
Samantha W.
The price is CA $1,585
CA $2,491 total
includes taxes & fees
Aug 5 - Aug 6
Newly renovated house in Brandt Point, right near town and Children's Beach

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, (125 reviews)
"Wonderful stay. Clean, convenient and great location. "
United States
Nicholas B.
3 bedroom 2 1/2 bath house 1 1/2 Blocks From Main Street, one block from harbor.

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
9.6 out of 10, Exceptional, (5 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 $2,429
CA $3,731 total
includes taxes & fees
Jul 22 - Jul 23
Mid island oasis with large pool and outdoor entertainment area. Pet friendly!

Three bedrooms Four Blocks to Town and Harbor with parking

Three bedrooms Four Blocks to Town and Harbor with parking
Nantucket Town
10.0 out of 10, Exceptional, (15 reviews)
"Perfect location close to town and beaches had the best time! "
United States
whitney F.
The price is CA $1,625
CA $3,015 total
includes taxes & fees
Jul 28 - Jul 29
Three bedrooms Four Blocks to Town and Harbor with parking

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, (246 reviews)
"This was the perfect place for our 4-night stay in Nantucket! The location was ideal — just about a 10-minute walk to Main Street. The layout worked especially well for two couples, and it was such a nice bonus that they allowed my parents’ dog. The home had everything we needed, and the beds were incredibly comfortable. We would absolutely stay here again!"
United States
Allison
Luxurious Harbor View “Cynthia” cottage. Walk & bike to everything!

5BR Oasis @ Tom Nevers - Heated Pool - Tennis Court

5BR Oasis @ Tom Nevers - Heated Pool - Tennis Court
Tom Nevers
5BR Oasis @ Tom Nevers - Heated Pool - Tennis Court

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, (19 reviews)
"Nice location near bus stop."
United States
Angela T.
The price is CA $2,400
CA $3,711 total
includes taxes & fees
Aug 9 - Aug 10
Mid island oasis! 3-bedroom, 4 bath in the middle of “second downtown”

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)
"The house was even better than advertised. Would book again! "
United States
Margot t.
Luxurious Harbor View “Cindy” Cottage. Walk & Bike To Everything!

Ultimate relaxation at the beach and conservation land, completely renovated.

Ultimate relaxation at the beach and conservation land, completely renovated.
Madaket
9.8 out of 10, Exceptional, (10 reviews)
"Wonderful location right by beach, yard for kiddos to play, house very clean and well equipped. Communication from house manager execellent and very helpful."
United States
Emily J.
The price is CA $3,937
CA $5,902 total
includes taxes & fees
Jul 17 - Jul 18
Ultimate relaxation at the beach and conservation land, completely renovated.

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, (301 reviews)
"Great location, cozy"
United States
John P.
The price is CA $2,241
CA $3,218 total
includes taxes & fees
Aug 7 - Aug 8
Luxurious Harbor View “Eliza” Cottage! Next To White Elephant!

Luxury Nantucket Getaway | Hot Tub

Luxury Nantucket Getaway | Hot Tub
Nantucket
4.0 out of 10, (1 review)
"Hot tub wasn’t working when we got there, the heating system in the house was not working , had to use space heaters the entire time, and unit had a lot of construction all around. Not up to standards for the price"
United States
Michael B.
The price is CA $3,047
CA $4,520 total
includes taxes & fees
Jul 21 - Jul 22
Luxury Nantucket Getaway | Hot Tub

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 $4,182
CA $6,058 total
includes taxes & fees
Jul 21 - Jul 22
Steps to the Beach and 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.
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?

Nantucket - edge of town: Visitors like this Surfside vacation home rental. It offers a fireplace, a furnished patio, and a barbecue grill to help you feel perfectly comfortable in your new surroundings. It has 3 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. Kick off your shoes and enjoy yourself with a garden and a selection of games.

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.