A beach with people, umbrellas, and surfboards.

Surfside Vacation Rentals

Check prices for these dates

In two weeks
Sep 18 - Sep 20
In two months
Oct 30 - Nov 1
In three months
Nov 27 - Nov 29
In four months
Dec 25 - Dec 27

Our top choices for Surfside vacation rentals

A spacious kitchen with a central island, a dining area with a wooden table and chairs, and a spiral staircase leading to an upper level.

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

New to VRBO! 2/1 Mid Island Apartment, Sleeps 5
Nantucket Town
9.2 out of 10, Wonderful, (23 reviews)
"Loved our time here! Perfect location and the host was so friendly and communicative during our trip! Would absolutely stay here again! "
United States
Kylie C.
$437 nightly
The price is $488
Sep 13 - Sep 14
Total with taxes and fees
New to VRBO! 2/1 Mid Island Apartment, Sleeps 5
A large, multi-story hotel with a wooden exterior and multiple balconies. A wooden boardwalk leads to the entrance.

2. Harborview Nantucket

Harborview Nantucket
4.0 star property
Nantucket Town
9.4 out of 10, Exceptional, (18 reviews)
"Very nice location, easy walk to town. Right next to the bus depot. Excellent rooms , plenty of space. Could do with some instructions for the coffee machine, and what to do with rubbish once the bin is full. Would happily stay again."
United Kingdom
Richard
$630 nightly
The price is $704
Oct 4 - Oct 5
Total with taxes and fees
Harborview Nantucket
A small cabin with a deck, a large window, and a staircase leading to the entrance.

3. 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, (26 reviews)
"Great spot, great host!"
United States
Jill I.
$629 nightly
The price is $703
Oct 6 - Oct 7
Total with taxes and fees
Relax on Nantucket in our Cozy, 1-bedroom condo with AMAZING views!
A residential street with houses, a sidewalk, and a fire hydrant.

4. 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.
$1,057 nightly
The price is $1,181
Sep 15 - Sep 16
Total with taxes and fees
Romantic, Two Blocks to Main Street and Water. Queen bedroom and Two Bathrooms.
A wooden mailbox with a number plate, surrounded by a wooden fence and a wooden archway covered with pink roses.

5. Charming cottage, close to lower Main Street.

Charming cottage, close to lower Main Street.
Nantucket Town
10.0 out of 10, Exceptional, (139 reviews)
"Another great stay at a great location on Nantucket"
United States
Joe F.
$631 nightly
The price is $705
Sep 8 - Sep 9
Total with taxes and fees
Charming cottage, close to lower Main Street.
A wooden deck with a staircase leading to a covered area.

6. 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, (12 reviews)
"clean, easy access to downtown"
United States
william t.
$533 nightly
The price is $595
Sep 13 - Sep 14
Total with taxes and fees
Noddy - Cozy & cute 1st Floor Studio close to town with everything you need.
A single-story house with a brick chimney, white trim, and a small porch.

7. Nantucket - edge of town

Nantucket - edge of town
West of Town
9.6 out of 10, Exceptional, (96 reviews)
"Mary is such a great host and such a sweet person."
United States
Pathfinder Tree S.
$762 nightly
The price is $851
Sep 7 - Sep 8
Total with taxes and fees
Nantucket - edge of town
A modern open-plan living and dining area with a round glass table, a sofa, and a kitchen in the background.

8. 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
9.8 out of 10, Exceptional, (7 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.
$1,758 nightly
The price is $1,964
Oct 7 - Oct 8
Total with taxes and fees
Mid island oasis with large pool and outdoor entertainment area. Pet friendly!
A beach with clear blue water and a sandy shore.

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

Luxurious Harbor View "Lizzie" Cottage! Walk & bike to everything!
Nantucket Town
10.0 out of 10, Exceptional, (130 reviews)
"Great little spot. Looking forward to coming back!"
United States
Anonymous traveler
$897 nightly
The price is $1,002
Sep 7 - Sep 8
Total with taxes and fees
Luxurious Harbor View "Lizzie" Cottage! Walk & bike to everything!
A two-story house with a grey siding exterior, a front porch with a wooden railing, and a small staircase leading to the entrance.

10. 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, (127 reviews)
"House is adorable and so comfortable. Location could not be better. We loved our stay."
United States
Julie
$825 nightly
The price is $922
Sep 14 - Sep 15
Total with taxes and fees
3 bedroom 2 1/2 bath house 1 1/2 Blocks From Main Street, one block from harbor.
A residential area with a house featuring a front porch, a wooden fence, and a well-maintained hedge.

11. Cozy upper studio- fully equipped & close to town, harbor, shops & restaurants!

Cozy upper studio- fully equipped & close to town, harbor, shops & restaurants!
Nantucket Town
9.8 out of 10, Exceptional, (28 reviews)
"It’s was perfect for our family. Very close to everything."
United States
Patrick&Suzi S.
$629 nightly
The price is $703
Sep 20 - Sep 21
Total with taxes and fees
Cozy upper studio- fully equipped & close to town, harbor, shops & restaurants!
A modern room with a wooden bench, clear chairs, a staircase, and a view of boats through a window.

12. Beachy right near “Children’s” Beach, near town and walking distance from Ferry.

Beachy right near “Children’s” Beach, near town and walking distance from Ferry.
Nantucket Town
10.0 out of 10, Exceptional, (119 reviews)
"Comfortable stay for a family of 4 (2 adults, 2 kids) could fit a third family member if needed. The host was very communicative and responded within the day for most messages if not sooner."
United States
Stanford
$768 nightly
The price is $858
Sep 15 - Sep 16
Total with taxes and fees
Beachy right near “Children’s” Beach, near town and walking distance from Ferry.
An aerial view of a marina with numerous boats docked, surrounded by residential buildings and greenery.

13. 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, (248 reviews)
"Beautiful and comfortable place to stay right in town with our infant and dog. Would definitely stay here again."
United States
Laura U.
$1,131 nightly
The price is $1,263
Sep 7 - Sep 8
Total with taxes and fees
Luxurious Harbor View “Cynthia” cottage. Walk & bike to everything!
An aerial view of a marina with numerous boats docked, surrounded by residential buildings and greenery.

14. Luxurious Harbor View "Lilly" Cottage! Walk & Bike To Everything!

Luxurious Harbor View "Lilly" Cottage! Walk & Bike To Everything!
Nantucket Town
9.8 out of 10, Exceptional, (64 reviews)
"Great location!"
United States
Doris O.
$1,308 nightly
The price is $1,461
Sep 8 - Sep 9
Total with taxes and fees
Luxurious Harbor View "Lilly" Cottage! Walk & Bike To Everything!
A white building with a black door, a sign reading 'Union Suits,' and a number '36' above the door.

15. Three bedrooms Four Blocks to Town and Harbor with parking

Three bedrooms Four Blocks to Town and Harbor with parking
Nantucket Town
9.8 out of 10, Exceptional, (18 reviews)
"Perfect location close to town and beaches had the best time! "
United States
whitney F.
$1,570 nightly
The price is $1,754
Oct 7 - Oct 8
Total with taxes and fees
Three bedrooms Four Blocks to Town and Harbor with parking
A residential area with houses, green lawns, and a body of water in the background.

16. Historic 2BR Nantucket Cottage | Walk to Downtown

Historic 2BR Nantucket Cottage | Walk to Downtown
Nantucket Town
8.0 out of 10, Very Good, (3 reviews)
"Great location and comfortable for a family of 4."
United States
Christy C.
$1,021 nightly
The price is $1,111
Sep 24 - Sep 25
Total with taxes and fees
Historic 2BR Nantucket Cottage | Walk to Downtown
An aerial view of a marina with numerous boats docked, surrounded by residential buildings and greenery.

17. 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)
"We thoroughly enjoyed our stay. The check in process was seamless. Communication with our host was great and always prompt. Cottage was spotless. Thoughtfully appointed with excellent attention to detail. Location was a convenient walk to restaurants and shops. Also centrally located for bike rides to all of the island. An instantly welcoming feel when we walked in. Would strongly recommend without hesitation and definitely hope to return again!"
United States
Seth R.
$1,308 nightly
The price is $1,461
Sep 7 - Sep 8
Total with taxes and fees
Luxurious Harbor View “Cindy” Cottage. Walk & Bike To Everything!
A rectangular swimming pool with a wooden deck and stone tiles, surrounded by a wooden fence and a brick house.

18. Historic Island Home | Heated Pool

Historic Island Home | Heated Pool
Nantucket Town
$3,044 nightly
The price is $3,400
Sep 17 - Sep 18
Total with taxes and fees
Historic Island Home | Heated Pool
A spacious kitchen with wooden beams, white cabinetry, and pendant lighting.

19. 6 BDR, Pet-friendly, newly remodeled whaling captain’s house downtown Nantucket!

6 BDR, Pet-friendly, newly remodeled whaling captain’s house downtown Nantucket!
Nantucket Town
10.0 out of 10, Exceptional, (57 reviews)
"Great house in a great location. Walkable to most everything"
United States
Michael P.
$2,407 nightly
The price is $2,689
Sep 8 - Sep 9
Total with taxes and fees
6 BDR, Pet-friendly, newly remodeled whaling captain’s house downtown Nantucket!
A bright, well-lit room with a white sofa, a small round table, and a television mounted on the wall.

20. 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
Nantucket Town
10.0 out of 10, Exceptional, (83 reviews)
"Convenient location, sweet property, well cared for."
United States
Barbara W.
$1,344 nightly
The price is $1,501
Sep 21 - Sep 22
Total with taxes and fees
Swedish Blue and Yellow house new 2021! Just over a block to harbor and Main St
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

Cliff Lodge

Cliff Lodge

10/10 Excellent
"Great place to stay over the holiday weekend. A bit of a walk but more quiet than in town. Will stay again."
Matthew 1-night trip
Posted 4 hours ago
Cliff Lodge

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 $488 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.

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: Visitors like this Surfside vacation home rental. It 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.

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.