Surfside Vacation Rentals from CA $465: Short-Term Rentals for 2025

Check prices for these dates

Tonight

Tomorrow

This weekend

Next weekend

Vacation Rentals in Surfside

Enjoy outdoor activities on the deck with a railing, surrounded by a well-maintained lawn and garden.

"He property was beautiful. Very private, clean and plenty of space. The hosts are also super friendly. The property is close to a stop on the Miacomet line of The Wave. It’s about 1.5 miles from the middle of town and 2.5 miles from Surfside."

CA $708 total

includes taxes & fees

Aug 4 - Aug 5

Relax in this serene bedroom with a large bed, bedside table, and window offering a view of the outdoors.

"The property was perfect for our family. It’s in a great location. We rented bikes and enjoyed being able to walk and bike to the beach and market. Thanks for letting us stay!"

Relax on the porch with a bench and table, surrounded by a well-maintained lawn and string lights.

"We had an excellent stay at harbor view cottages! The property is beautiful and close to everything. it is clear that the owners paid attention to all the little details when furnishing the cottage, which I always appreciate. I will definitely be returning! "

Stunning home with a gabled roof and white picket fence, featuring a central entryway and symmetrical facade.

"What a perfect vacation spot. The home was perfect for two and well-appointed. Close to town and dining. Wonderful treasures to find on a walk. Would certainly book for our next trip to Nantucket. "

CA $1,761 total

includes taxes & fees

Aug 10 - Aug 11

Relax in a serene outdoor space surrounded by tall trees, featuring a lounge chair, table, and lush greenery.

"Great place to stay for a couple , quiet , beautiful, clean. Great outdoor space and conveniently located on the island for all our adventures. Highly recommended. "

Relax in a shaded seating area surrounded by lush greenery, complete with a barbecue grill for outdoor cooking.

"Beautiful cottage , great location. Would love to stay again "

Enjoy cooking in this well-equipped kitchen with a central island, Whirlpool dishwasher, gas stove, and sink with a stainless steel faucet.

"We loved our stay and the location. Lots of charm, beach vibes and decor, plenty of space and everything you need. Just bring a hair dryer. We would stay here again."

Relax in a serene outdoor space with a sofa, armchairs, and coffee table, surrounded by lush greenery.

"Great stay, would stay again "

Efficient kitchen and living space with central island, dining area, and spiral staircase.

"Our in laws had a wonderful stay in Jais’s place! It was clean and comfortable, had ample parking and was in a great location. Communication was terrific!!! We highly recommend!"

Traditional home with a gabled roof, front porch, and chimney, surrounded by a charming garden.

"Cute spot and great location!"

Cozy living room with a sofa, coffee table, and dining area, featuring a large window and modern kitchen.

"The property was perfect. Great location, well Thought out for its guests. Amazing kitchen, hot tub and clean rooms. We had an excellent stay and would highly recommend to others. "

Prepare meals in a spacious kitchen with oven and stovetop, plus a large island with seating.

"Great location and perfect for family. "

CA $2,449 total

includes taxes & fees

Aug 16 - Aug 17

Enjoy cooking in this well-equipped kitchen with a stainless steel refrigerator, oven, and gas stove.

"Cindy's Cottage was perfect for our weekend stay. We wish we could have stayed longer to enjoy all the comforts of this beautiful home. "

CA $2,579 total

includes taxes & fees

Aug 13 - Aug 14

Relax in this stylish living space with a large sofa and armchair, perfect for unwinding.

"Friendly and accommodating! Perfect place for Our family!"

Enjoy meals around the central dining table surrounded by comfortable chairs.

"We were thrilled to arrive at our property with everything as pictured but actually more charming in person. It is easily walkable to town and restaurants. Communication with the owner was easy and I can recommend it to anyone who wants to stay on Nantucket. "

Traditional home with a brick chimney, shingled roof, and a cozy front porch.

"The house was adorable - we loved it. "

CA $1,323 total

includes taxes & fees

Jul 18 - Jul 19

Enjoy cooking in this well-lit kitchen with a large island, white cabinetry, and an oven and dishwasher.

"We greatly enjoyed our stay at this warm and welcoming home. The house was perfectly equipped with everything we needed for our stay and the location was so easy to get to so many great spots on the island. We can’t wait to go back. "

Relax by the pool surrounded by a deck and lounge chairs.

"We enjoyed our stay at the Low Tide. It is as pictured, easy to find and check-in. Host is lovely, good communication. If visiting Nantucket again, we would look to stay here again. Highly recommend."

CA $1,870 total

includes taxes & fees

Jul 20 - Jul 21

Enjoy waterfront views and serene surroundings from this coastal retreat.

"We take a golf trip to Nantucket every year and this house was perfect for us. Will be staying again next year if possible. "

Cozy retreat with a large bed, kitchenette, and dining area.

"We thoroughly enjoyed this little bungalow "

CA $5,102 total

includes taxes & fees

Aug 2 - Aug 3

Save an average of 15% on thousands of hotels when you're signed in

Sign in

Sign up, it's free

Find out more about Surfside

Everything you need to know about Surfside vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Surfside vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Surfside vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Surfside vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Surfside. If you’re looking for a little peace, consider booking during the quieter months, such as . For more hustle and bustle, you may prefer to visit in .

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Surfside vacation rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a vacation rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Surfside vacation rentals we have selected for you start as low as CA $465 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Surfside rentals

At Expedia, we put the best Surfside vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Surfside rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Surfside vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Surfside. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Recent reviews of Surfside properties

5/5 Excellent

"The Beachside Hotel is a 10 out of 10 and I think it is the best lodging option on Nantucket. 1. Beautiful pool area, excellent service while at pool, plenty of towels etc 2. Food at pool is delicious 3. Arcade is adorable and genius idea 4. The room is perfectly decorated 5. The landscaping is stunning and beautifully maintained 6. The gym has all you need 7. The lobby is unique with cool bar 8. Coffee and donuts in the morning are a nice touch only thing there is maybe to have muffins too 9. Plentiful nice staff 10. Walk to beach and town in no time "

A verified traveller from milton stayed at The Beachside

Posted 1 day ago

5/5 Excellent

"My wife and I enjoyed our 3 night stay at Nantucket inn. The room was spacious and very clean. The property was well maintained . We enjoyed a few hours at the outdoor pool one afternoon which was very nice. We took advantage of the free shuttle to town as well as to surf side beach. The shuttle service was very prompt despite the heavy traffic much of the time. We will definitely be back and would recommend the Nantucket Inn. "

A verified traveller stayed at Nantucket Inn

Posted 1 day ago

5/5 Excellent

"Wonderful boutique inn in a fantastic location downtown. Staff were were terrific. We arrived early and they invited us to hold our luggage and enjoy breakfast. It was nice having breakfast included: coffee, tea, juice, croissants and muffins, fresh fruit, hard boiled egg and yogurt and overnight oats with fruit. A nice inside seating area and Avery nice outdoor area as well. You can have a glass a wine and relax there. Fire pits which we didn’t get a chance to use. We were in Room 6. It was clean and had comfortable and attractive bedding, but it was very small. So small we didn’t have a place for our two carry-on bags so we swapped out a chair for a second luggage stand. The bathroom, shower, towels and amenities were good. I would definitely stay here again. Aside from the size of the room, everything was perfect and again, the people who worked there made it feel special. Thank you. "

A verified traveller stayed at Hotel Pippa

Posted 9 days ago

Explore a world of travel with Expedia

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?

Rustic, sunny cottage w/ deck & W/D - walk to the beach & town!: Visitors like this Surfside vacation home rental. It offers a patio, a barbecue grill, and air-conditioning to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a fridge, a stovetop, and a microwave.

How many vacation rentals are there in Surfside?

With 26 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 Community Sailing.

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.

Members save 10% or more on over 100,000 hotels worldwide when you’re signed in

Surfside Vacation Rentals

Change your mind

Treat yourself

Be picky

Check prices for these dates

Vacation Rentals in Surfside

Private Modern Bedroom In a Central Location

Private Modern Bedroom In a Central Location

Rustic, sunny cottage w/ deck & W/D - walk to the beach & town!

Rustic, sunny cottage w/ deck & W/D - walk to the beach & town!

Harborview Nantucket

Harborview Nantucket

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

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

Quiet getaway for two

Quiet getaway for two

LUXURIOUS New Cottage! 5-min. walk to Main St. And Harbor Beaches

LUXURIOUS New Cottage! 5-min. walk to Main St. And Harbor Beaches

Spacious Beach Cottage with Grill, Patio, Outdoor Shower & High-Speed WiFi

Spacious Beach Cottage with Grill, Patio, Outdoor Shower & High-Speed WiFi

Cozy 4 bedroom cottage in town, with parking

Cozy 4 bedroom cottage in town, with parking

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

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

Renovated Cottage off Main Street- Great Location

Renovated Cottage off Main Street- Great Location

LUXURIOUS NEW Harbor View Home with Hinckley Yacht!

LUXURIOUS NEW Harbor View Home with Hinckley Yacht!

Luxurious Harbor View "Millie" Cottage! Walk & bike to everything!

Luxurious Harbor View "Millie" Cottage! Walk & bike to everything!

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

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

Tranquilty

Tranquilty

Beautifully Renovated Main Street Cottage- Great Location

Beautifully Renovated Main Street Cottage- Great Location

Nantucket - edge of town

Nantucket - edge of town

Newly constructed 3 BR house . Walk to town, harbor and restaurants

Newly constructed 3 BR house . Walk to town, harbor and restaurants

L0W TIDE, with Private Pool, Low Tide

L0W TIDE, with Private Pool, Low Tide

10 min. walk to Downtown. July 5-12 still available. Perfect for families.

10 min. walk to Downtown. July 5-12 still available. Perfect for families.

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

Find out more about Surfside

Find out more about Surfside

Recent reviews of Surfside properties

Recent reviews of Surfside properties

The Beachside

Explore a world of travel with Expedia

Explore a world of travel with Expedia

Trending destinations on Expedia.ca

Frequently asked questions