Surfside Vacation Rentals

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Vacation Rentals in Surfside

Duplex Sunny Condo in residential neighborhood, 5min walk to bike paths!!!
Exterior

Duplex Sunny Condo in residential neighborhood, 5min walk to bike paths!!!

8.8 out of 10, Excellent, (80)
"3rd time staying at the rental and we really enjoyed as always! "
Duplex Sunny Condo in residential neighborhood, 5min walk to bike paths!!!
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, (170)
"Beautiful cottage , great location. Would love to stay again "
$691 nightly
The price is $772
Oct 12 - Oct 13
Total with taxes and fees
LUXURIOUS New Cottage! 5-min. walk to Main St. And Harbor Beaches
Harborview Nantucket
View from property

Harborview Nantucket

4.0 star property
9.6 out of 10, Exceptional, (14)
"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! "
$600 nightly
The price is $670
Oct 19 - Oct 20
Total with taxes and fees
Harborview Nantucket
Renovated Cottage off Main Street- Great Location
Exterior

Renovated Cottage off Main Street- Great Location

10.0 out of 10, Exceptional, (161)
"Super cute place and close to town! Really responsive host. We enjoyed our stay. "
Renovated Cottage off Main Street- Great Location
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, (225)
"Such a great property! Cant wait to stay again!"
Luxurious Harbor View “Cynthia” cottage. Walk & bike to everything!
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, (227)
"Great house. Great location. Responsive host. "
$640 nightly
The price is $715
Nov 7 - Nov 8
Total with taxes and fees
Luxurious Harbor View "Millie" Cottage! Walk & bike to everything!
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, (282)
"Perfect for a couple!Everything was amazing."
Luxurious Harbor View “Eliza” Cottage! Next To White Elephant!
HIGH TIDE - Comfy Home W/Pool, High Tide
Fridge, microwave, oven, stovetop

HIGH TIDE - Comfy Home W/Pool, High Tide

9.6 out of 10, Exceptional, (43)
"The house was very clean and I loved the outdoor shower."
$714 nightly
The price is $755
Oct 14 - Oct 15
Total with taxes and fees
HIGH TIDE - Comfy Home W/Pool, High Tide
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, (44)
"Awesome stay. Only wish we'd found the secret room sooner!"
$754 nightly
The price is $842
Oct 15 - Oct 16
Total with taxes and fees
Newly renovated house in Brandt Point, right near town and Children's Beach
Private Modern Bedroom In a Central Location
Property grounds

Private Modern Bedroom In a Central Location

9.4 out of 10, Exceptional, (27)
"Super clean and modern room. Good location. Hosts were very nice and very available. Amazing spot, we would stay again"
Private Modern Bedroom In a Central Location
Rustic, sunny cottage w/ deck & W/D - walk to the beach & town!
2 bedrooms, free WiFi, bed sheets

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

8.6 out of 10, Excellent, (32)
"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!"
Rustic, sunny cottage w/ deck & W/D - walk to the beach & town!
Luxurious Harbor View “Elizabeth” Cottage! Walk & bike to everything
Beach nearby, sun loungers, beach towels

Luxurious Harbor View “Elizabeth” Cottage! Walk & bike to everything

9.8 out of 10, Exceptional, (153)
"Adorable cottage just a short walk to town and ferry! "
$897 nightly
The price is $1,001
Oct 12 - Oct 13
Total with taxes and fees
Luxurious Harbor View “Elizabeth” Cottage! Walk & bike to everything
LUXURIOUS Cottage with Breathtaking Harbor Views
Fridge, microwave, oven, stovetop

LUXURIOUS Cottage with Breathtaking Harbor Views

9.8 out of 10, Exceptional, (167)
"Beautiful house in a great location! "
LUXURIOUS Cottage with Breathtaking Harbor Views
Enjoy Autumn On Nantucket in our Cozy, 1-bedroom condo with WiFi
Fridge, oven, stovetop, dishwasher

Enjoy Autumn On Nantucket in our Cozy, 1-bedroom condo with WiFi

9.8 out of 10, Exceptional, (10)
Enjoy Autumn On Nantucket in our Cozy, 1-bedroom condo with WiFi
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, (38)
"Lovely accommodations mid island amidst what appeared to be a blue collar neighborhood. About ten minutes from center of Nantucket and a half hour out to Madaket. Our only transportation were bicycles and we enjoyed the many bike paths on island. "
This two-bedroom cottage features one queen bed, two twin beds, and a sofa bed.
New Home with Pool, Bocce court & 2 basement game rooms close to Surfside Beach
Outdoor pool, a heated pool

New Home with Pool, Bocce court & 2 basement game rooms close to Surfside Beach

10.0 out of 10, Exceptional, (42)
"Beautiful home, great for families! Joao is helpful and communicates with guests well. Fabulous kitchen and outdoor areas. Would love to return!"
New Home with Pool, Bocce court & 2 basement game rooms close to Surfside Beach
Cozy 4 bedroom cottage in town, with parking
Terrace/patio

Cozy 4 bedroom cottage in town, with parking

2.0 star property
9.0 out of 10, Wonderful, (21)
"Fantastic house in a great location for our group! Would gladly book again!"
Cozy 4 bedroom cottage in town, with parking
A Literary Oasis In The Heart Of Nantucket Town
Fridge, microwave, oven, stovetop

A Literary Oasis In The Heart Of Nantucket Town

10.0 out of 10, Exceptional, (83)
"Great central location right downtown. Beautiful accommodations, well appointed. Easy walk to all Harborside hot spots."
A Literary Oasis In The Heart Of Nantucket Town
Brand New modern 2 bedroom 2nd floor apartment
Fridge, microwave, oven, stovetop

Brand New modern 2 bedroom 2nd floor apartment

9.8 out of 10, Exceptional, (21)
"Very nice space and only 10 minutes from town. Would stay again!"
$735 nightly
The price is $820
Oct 8 - Oct 9
Total with taxes and fees
Brand New modern 2 bedroom 2nd floor apartment
Charming one bedroom cottage, close to lower Main Street and Handlebar Cafe.
Fridge, microwave, oven, stovetop

Charming one bedroom cottage, close to lower Main Street and Handlebar Cafe.

10.0 out of 10, Exceptional, (117)
"Thank you for another great getaway! We enjoyed our time at Samtucket! "
Charming one bedroom cottage, close to lower Main Street and Handlebar Cafe.
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

White Elephant Hotel

White Elephant Hotel

10/10 Excellent
"Great staff. Easy access to restaurants, shopping, walking."
Hilda 1-night trip
Posted 16 hours ago
White Elephant Hotel

Find out more about Surfside

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, condos, resorts, cabins, villas, motels. 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 low season months. For more hustle and bustle, you may prefer to visit Surfside in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $670 per night. Rates vary depending on your travel dates, location, and amenities so make a search and 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.

Explore a world of travel with Expedia

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?

LUXURIOUS New Cottage! 5-min. walk to Main St. And Harbor Beaches: You might want to consider this vacation home rental near Surfside, which is located in the city center and has a patio, a garden, and a barbecue grill to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge, and a stovetop. You and your friends and family can relax into your vacation with amenities like a hot tub.

How many vacation rentals are there in Surfside?

With 24 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.