Surfside Vacation Rentals

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    Upfront pricing

    We are not like the others - we include taxes and fees

Check prices for these dates

In two weeks
Sep 26 - Sep 28
In one month
Oct 10 - Oct 12
In two months
Nov 7 - Nov 9
In three months
Dec 5 - Dec 7

Vacation Rentals in Surfside

Our top choices for Surfside vacation rentals

Harborview Nantucket
View from property

Harborview Nantucket

4.0 star property
9.6 out of 10, Exceptional, (13)
"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 5 - Oct 6
Total with taxes and fees
Harborview Nantucket
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, (78)
"Had a great time during our weekend trip to Nantucket. Property was in a great area and close to bus stop to get into town easily. Host was very responsive and easy to get a hold of. Only downsides were that the bathroom floors would get soaked during a shower even with the shower curtain and the basement felt slightly humid/moist. No tv in main living area. Other than those minor things would definitely recommend this property as an affordable option to stay in Nantucket "
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, (165)
"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
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, (222)
"Absolutely loved staying here. Great location and Theresa was super responsive! The property was well stocked and had everything we needed for a peaceful couple weeks. Our dogs loved being so close to the beach! "
$908 nightly
The price is $1,014
Oct 2 - Oct 3
Total with taxes and fees
Luxurious Harbor View "Millie" Cottage! Walk & bike to everything!
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, (152)
"Adorable cottage just a short walk to town and ferry! "
$897 nightly
The price is $1,001
Oct 3 - Oct 4
Total with taxes and fees
Luxurious Harbor View “Elizabeth” Cottage! Walk & bike to everything
Private Modern Bedroom In a Central Location
Property grounds

Private Modern Bedroom In a Central Location

9.4 out of 10, Exceptional, (27)
"Very nice hosts.Very clean."
Private Modern Bedroom In a Central Location
LUXURIOUS Cottage with Breathtaking Harbor Views
Fridge, microwave, oven, stovetop

LUXURIOUS Cottage with Breathtaking Harbor Views

9.8 out of 10, Exceptional, (164)
"We loved this property and all talked about the next time we can book! The location is perfect and the interior is beautiful. Also super comfy beds!"
$908 nightly
The price is $1,014
Sep 28 - Sep 29
Total with taxes and fees
LUXURIOUS Cottage with Breathtaking Harbor Views
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!

8.4 out of 10, Very Good, (26)
"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!
Renovated Cottage off Main Street- Great Location
Exterior

Renovated Cottage off Main Street- Great Location

10.0 out of 10, Exceptional, (158)
"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, (223)
"Great location and beautiful house! "
$908 nightly
The price is $1,014
Oct 6 - Oct 7
Total with taxes and fees
Luxurious Harbor View “Cynthia” cottage. Walk & bike to everything!
Love Sand, Madaket on the Beach, Lovely Seaside Home
Exterior

Love Sand, Madaket on the Beach, Lovely Seaside Home

10.0 out of 10, Exceptional, (52)
"We thoroughly enjoyed our two nights and are sad to leave. The property is iconically Nantucket. Its location - and the views- is spectacular. It is well equipped for a relaxing family or couples vacation. Hope we can make it back. "
$976 nightly
The price is $1,052
Sep 15 - Sep 16
Total with taxes and fees
Love Sand, Madaket on the Beach, Lovely Seaside Home
Cozy 4 bedroom cottage in town, with parking
Terrace/patio

Cozy 4 bedroom cottage in town, with parking

2.0 star property
9.2 out of 10, Wonderful, (19)
"Great stay, would stay 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, (79)
"We loved our stay at this property. We appreciated how spacious the apartment was and all of the design elements were thoughtful and beautiful. The best part was the location - right in town. I would not hesitate to stay here again. "
A Literary Oasis In The Heart Of Nantucket Town
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, (280)
"Perfect for a couple!Everything was amazing."
$1,249 nightly
The price is $1,395
Sep 16 - Sep 17
Total with taxes and fees
Luxurious Harbor View “Eliza” Cottage! Next To White Elephant!
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

9.6 out of 10, Exceptional, (4)
$722 nightly
The price is $806
Sep 16 - Sep 17
Total with taxes and fees
Enjoy Autumn On Nantucket in our Cozy, 1-bedroom condo with WiFi
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!"
$803 nightly
The price is $897
Oct 13 - Oct 14
Total with taxes and fees
Newly renovated house in Brandt Point, right near town and Children's Beach
L0W TIDE, with Private Pool, Low Tide
Pool

L0W TIDE, with Private Pool, Low Tide

10.0 out of 10, Exceptional, (45)
"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."
$976 nightly
The price is $1,052
Sep 15 - Sep 16
Total with taxes and fees
L0W TIDE, with Private Pool, Low Tide
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, (41)
"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
Luxurious Harbor View "Lizzie" Cottage! Walk & bike to everything!
Beach nearby, sun loungers, beach towels

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

10.0 out of 10, Exceptional, (119)
"Very cute place a short walk to town. House came equipped with everything we needed. "
$705 nightly
The price is $787
Oct 3 - Oct 4
Total with taxes and fees
Luxurious Harbor View "Lizzie" Cottage! Walk & bike to everything!
Gorgeous 10 min. walk to Downtown. Perfect for families. Large backyard.
Marina

Gorgeous 10 min. walk to Downtown. Perfect for families. Large backyard.

10.0 out of 10, Exceptional, (87)
"Great property close to town. Very clean and well equipped. Owner was very communicative and checked in with us appropriately. Would stay again!"
Gorgeous 10 min. walk to Downtown. Perfect for families. Large backyard.
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

Hotel Pippa

Hotel Pippa

10/10 Excellent
"Very comfortable and cl"
Kathleen 2-night trip
Posted 2 days ago
Hotel Pippa

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 Miacomet Golf Course 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.