Surfside Vacation Rentals

    calendar shield illustration
    Change your mind
    Book hotels with free cancellation
    deals illustration
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    Sign in
    bed illustration
    Be picky
    Search almost a million properties worldwide

Check prices for these dates

Tonight
Jun 24 - Jun 25
Tomorrow
Jun 25 - Jun 26
This weekend
Jun 27 - Jun 29
Next weekend
Jul 4 - Jul 6

Vacation Rentals in Surfside

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

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

10.0 out of 10, Exceptional, (266)
"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. "
The price is ￥138,615
￥214,158 total
includes taxes & fees
Jul 25 - Jul 26
Luxurious Harbor View “Eliza” Cottage! Next To White Elephant!
Newly renovated house in Brandt Point, right near town and Children's Beach
Smart TV, fireplace

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

9.8 out of 10, Exceptional, (40)
"Awesome stay. Only wish we'd found the secret room sooner!"
Newly renovated house in Brandt Point, right near town and Children's Beach
Quiet getaway for two
Terrace/patio

Quiet getaway for two

9.6 out of 10, Exceptional, (66)
"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. "
Quiet getaway for two
Harborview Nantucket
View from property

Harborview Nantucket

4.0 star property
9.6 out of 10, Exceptional, (11)
"Amazing stay!!! We stayed in the Hermit Crab and it was perfect for me and my wife. Plenty big enough with a nice size shower. We will definitely be back!"
Harborview Nantucket
Nantucket - edge of town
Exterior

Nantucket - edge of town

9.8 out of 10, Exceptional, (77)
"The house was adorable - we loved it. "
The price is ￥55,076
￥107,537 total
includes taxes & fees
Jun 29 - Jun 30
Nantucket - edge of town
New to VRBO! 2/1 Mid Island Apartment, Sleeps 5
Fridge, microwave, oven, stovetop

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

9.6 out of 10, Exceptional, (11)
"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!"
New to VRBO! 2/1 Mid Island Apartment, Sleeps 5
Renovated Cottage off Main Street- Great Location
Exterior

Renovated Cottage off Main Street- Great Location

10.0 out of 10, Exceptional, (151)
"Cute spot and great location!"
Renovated Cottage off Main Street- Great Location
Private Modern Bedroom In a Central Location
Property grounds

Private Modern Bedroom In a Central Location

9.4 out of 10, Exceptional, (19)
"Great spot on free bus line"
The price is ￥44,572
￥66,759 total
includes taxes & fees
Jun 30 - Jul 1
Private Modern Bedroom In a Central Location
Free 3rd Night!* New house! Walk to bars/restaurants/harbor, Nantucket in Town!
Exterior

Free 3rd Night!* New house! Walk to bars/restaurants/harbor, Nantucket in Town!

9.4 out of 10, Exceptional, (40)
"We stayed at 8 Atlantic Avenue for the Daffodil Festival weekend. The home is impeccable and beautiful - spacious with gorgeous hardwood floors and a kitchen meant for entertaining. Close to town for shopping and restaurants. Owners were a pleasure to work with and I would highly recommend this property! We loved every aspect of our stay and will definitely rent there again."
Free 3rd Night!* New house! Walk to bars/restaurants/harbor, Nantucket in Town!
Walk to Town! Bike or Bus to Beach! Charming Cottage- Leeward- on Private Lane
Exterior

Walk to Town! Bike or Bus to Beach! Charming Cottage- Leeward- on Private Lane

10.0 out of 10, Exceptional, (71)
"We loved the apartment. It had everything we needed and was only a 15 minute walk from the downtown area."
Walk to Town! Bike or Bus to Beach! Charming Cottage- Leeward- on Private Lane
Adorable guest house with saltwater pool and spa with views close to beach
Outdoor dining

Adorable guest house with saltwater pool and spa with views close to beach

10.0 out of 10, Exceptional, (3)
"My husband, dog and I loved our stay at Alesia’s property! The location was great, Alesia was very responsive and professional, and the space was clean and welcoming. We had a lovely time and highly recommend this spot to anyone looking for somewhere to stay on Nantucket. "
Adorable guest house with saltwater pool and spa with views close to beach
LUXURIOUS New Cottage! 5-min. walk to Main St. And Harbor Beaches
Outdoor dining

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

10.0 out of 10, Exceptional, (155)
"It was a quick stay unfortunately!! My husband and I loved this place. It had everything we needed and then some. Super easy walk to town. The outdoor space was amazing. It was very quiet and private. Hope to stay in this beautiful house again soon! "
The price is ￥114,722
￥181,441 total
includes taxes & fees
Jul 8 - Jul 9
LUXURIOUS New Cottage! 5-min. walk to Main St. And Harbor Beaches
Luxurious Harbor View “Cynthia” cottage. Walk & bike to everything!
Fridge, microwave, oven, stovetop

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

10.0 out of 10, Exceptional, (216)
"This was the perfect place for the Christmas Stroll! Everything was perfect with the house and Theresa was perfect as a host. We will be returning!"
The price is ￥186,035
￥276,579 total
includes taxes & fees
Jul 6 - Jul 7
Luxurious Harbor View “Cynthia” cottage. Walk & bike to everything!
Cozy 4 bedroom cottage in town, with parking
Terrace/patio

Cozy 4 bedroom cottage in town, with parking

2.0 star property
9.8 out of 10, Exceptional, (7)
"Great stay, would stay again "
Cozy 4 bedroom cottage in town, with parking
Private Beach Cottage in Historic Sconset!
On the beach

Private Beach Cottage in Historic Sconset!

9.8 out of 10, Exceptional, (21)
"Very peaceful "
The price is ￥145,944
￥219,849 total
includes taxes & fees
Jun 28 - Jun 29
Private Beach Cottage in Historic Sconset!
2 Bedrooms + Loft - sleeps 6 in beds but max 4 adults- 5 Blocks to Town
Property grounds

2 Bedrooms + Loft - sleeps 6 in beds but max 4 adults- 5 Blocks to Town

10.0 out of 10, Exceptional, (86)
"Perfect set up for families traveling together. "
2 Bedrooms + Loft - sleeps 6 in beds but max 4 adults- 5 Blocks to Town
Located right on the edge of town, the perfect Nantucket getaway!
Fridge, microwave, oven, stovetop

Located right on the edge of town, the perfect Nantucket getaway!

10.0 out of 10, Exceptional, (2)
"We really enjoyed our stay at this property and were very appreciative of the quick and thorough communication from the host. This unit is located right near the edge of town and close to one of the major grocery stores on the island. The guest parking and private entry were great amenities to have in addition to the large open living space. Would highly recommend for your visit to ACK. "
Located right on the edge of town, the perfect Nantucket getaway!
HIGH TIDE - Comfy Home, High Tide
Fridge, microwave, oven, stovetop

HIGH TIDE - Comfy Home, High Tide

9.6 out of 10, Exceptional, (39)
"Great house for 2 couples. Clean, good living space, nice deck, quiet-wonderful to have 2 king-sized beds! "
HIGH TIDE - Comfy Home, High Tide
This two-bedroom cottage features one queen bed, two twin beds, and a sofa bed.
Property grounds

This two-bedroom cottage features one queen bed, two twin beds, and a sofa bed.

9.4 out of 10, Exceptional, (28)
"This property has a wonderful location and is set up just right for comfort and convenience. I would definitely stay here again."
This two-bedroom cottage features one queen bed, two twin beds, and a sofa bed.
Luxurious Harbor View "Millie" Cottage! Walk & bike to everything!
Fridge, microwave, oven, stovetop

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

10.0 out of 10, Exceptional, (217)
"Great location and perfect for family. "
The price is ￥111,759
￥184,560 total
includes taxes & fees
Jun 29 - Jun 30
Luxurious Harbor View "Millie" Cottage! Walk & bike to everything!
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
Sign in
Sign up, it's free

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 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 Miacomet Pond and Miacomet Golf Course.

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.