A beach with people, umbrellas, and surfboards.

Surfside Vacation Rentals

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Check prices for these dates

In two weeks
Sep 11 - Sep 13
In two months
Oct 23 - Oct 25
In three months
Nov 20 - Nov 22
In four months
Dec 18 - Dec 20

Our top choices for Surfside vacation rentals

A room with a large window, a round table, and a sofa with patterned cushions.

1. Chill beach 3-bedroom getaway on Nobadeer beach

Chill beach 3-bedroom getaway on Nobadeer beach
Nantucket
10.0 out of 10, Exceptional, (1 review)
"We had a great stay here! It is so close to the beach! Hosts were very helpful and communicative! They do have a car available to rent, though we needed a bigger one to accommodate all of us. Plenty of towels and beach chairs, a nice touch! We will come back!"
United States
karen p.
$1,289 nightly
The price is $1,440
Aug 30 - Aug 31
Total with taxes and fees
Chill beach 3-bedroom getaway on Nobadeer beach
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.

2. 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, (22 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.
$414 nightly
The price is $462
Sep 13 - Sep 14
Total with taxes and fees
New to VRBO! 2/1 Mid Island Apartment, Sleeps 5
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.
$725 nightly
The price is $810
Sep 7 - Sep 8
Total with taxes and fees
Relax on Nantucket in our Cozy, 1-bedroom condo with AMAZING views!
A spacious living room with a white sectional sofa, a fluffy white chair, and a large window offering a view of the outdoors.

4. Brand New modern 2 bedroom 2nd floor apartment

Brand New modern 2 bedroom 2nd floor apartment
Nantucket
9.6 out of 10, Exceptional, (24 reviews)
"Great place, clean and a great location!!"
United States
Brian C.
$949 nightly
The price is $1,060
Sep 3 - Sep 4
Total with taxes and fees
Brand New modern 2 bedroom 2nd floor apartment
A residential street with houses, a sidewalk, and a fire hydrant.

5. 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.
$1,055 nightly
The price is $1,178
Sep 15 - Sep 16
Total with taxes and fees
Romantic, Two Blocks to Main Street and Water. Queen bedroom and Two Bathrooms.
A single-story house with a brick chimney, white trim, and a small porch.

6. Nantucket - edge of town

Nantucket - edge of town
West of Town
9.6 out of 10, Exceptional, (94 reviews)
"10/10 stay"
United States
Patrick E.
$796 nightly
The price is $889
Aug 30 - Aug 31
Total with taxes and fees
Nantucket - edge of town
A wooden deck with a staircase leading to a covered area.

7. 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, (11 reviews)
"clean, easy access to downtown"
United States
william t.
$575 nightly
The price is $642
Sep 10 - Sep 11
Total with taxes and fees
Noddy - Cozy & cute 1st Floor Studio close to town with everything you need.
A bedroom with a large bed, a sofa, and a view of the outside.

8. Luxurious Nantucket Getaway | Heated Pool

Luxurious Nantucket Getaway | Heated Pool
Nantucket
10.0 out of 10, Exceptional, (2 reviews)
"We had a great stay at a great property, celebrating a 49th birthday with a large group of friends. The host was super responsive to asks, and it was a memorable, hassle free stay. Location also has great proximity to stores, downtown and the airport, so we were never left spending too much time traveling around the island."
United States
Salem S.
$3,434 nightly
The price is $3,836
Sep 7 - Sep 8
Total with taxes and fees
Luxurious Nantucket Getaway | Heated Pool
A modern open-plan living and dining area with a round glass table, a sofa, and a kitchen in the background.

9. 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.
$2,093 nightly
The price is $2,338
Sep 9 - Sep 10
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.

10. 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 location"
United States
Josephine S.
$896 nightly
The price is $1,001
Sep 7 - Sep 8
Total with taxes and fees
Luxurious Harbor View "Lizzie" Cottage! Walk & bike to everything!
A wooden mailbox with a number plate, surrounded by a wooden fence and a wooden archway covered with pink roses.

11. 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.
$882 nightly
The price is $985
Sep 8 - Sep 9
Total with taxes and fees
Charming cottage, close to lower Main Street.
An aerial view of a marina with numerous boats docked, surrounded by residential buildings and greenery.

12. 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.
$1,305 nightly
The price is $1,458
Sep 8 - Sep 9
Total with taxes and fees
Luxurious Harbor View "Lilly" Cottage! Walk & Bike To Everything!
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, (247 reviews)
"This was a beautiful, well-decorated home. The location was perfect and the entire experience was extremely comfortable. These properties are excellent!"
United States
Toni L.
$1,125 nightly
The price is $1,257
Sep 3 - Sep 4
Total with taxes and fees
Luxurious Harbor View “Cynthia” cottage. Walk & bike to everything!
A room with a wicker table, a blue vase, a white chair, a hanging light fixture, and a window with greenery outside.

14. Rare 8BR Nantucket | 1755 Home, Cottage & Hot Tub

Rare 8BR Nantucket | 1755 Home, Cottage & Hot Tub
Nantucket Town
$3,592 nightly
The price is $3,925
Sep 7 - Sep 8
Total with taxes and fees
Rare 8BR Nantucket | 1755 Home, Cottage & Hot Tub
A residential area with a house featuring a front porch, a wooden fence, and a well-maintained hedge.

15. 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, (27 reviews)
"It’s was perfect for our family. Very close to everything."
United States
Patrick&Suzi S.
$743 nightly
The price is $830
Aug 30 - Aug 31
Total with taxes and fees
Cozy upper studio- fully equipped & close to town, harbor, shops & restaurants!
A white building with a black door, a sign reading 'Union Suits,' and a number '36' above the door.

16. 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.
$1,621 nightly
The price is $1,811
Sep 16 - Sep 17
Total with taxes and fees
Three bedrooms Four Blocks to Town and Harbor with parking
A modern room with a wooden bench, clear chairs, a staircase, and a view of boats through a window.

17. 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, (118 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
$1,145 nightly
The price is $1,279
Sep 8 - Sep 9
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.

18. 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 3 - Sep 4
Total with taxes and fees
Luxurious Harbor View “Cindy” Cottage. Walk & Bike To Everything!
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, (56 reviews)
"Great stay, close enough to town but still private and quiet. Would highly recommend the home."
United States
Edward S.
$2,493 nightly
The price is $2,785
Sep 8 - Sep 9
Total with taxes and fees
6 BDR, Pet-friendly, newly remodeled whaling captain’s house downtown Nantucket!
A spacious living room with a staircase, white sofas, a coffee table, and a large window.

20. 100 Steps to Main Street. 5 bedrooms and 6.5 baths. New and Completely renovated

100 Steps to Main Street. 5 bedrooms and 6.5 baths. New and Completely renovated
Nantucket Town
10.0 out of 10, Exceptional, (19 reviews)
"Great location close to town. Lots of bedrooms for a big group but we had only 6 adults so we loved the King bedrooms!"
United States
Terri W.
$3,290 nightly
The price is $3,674
Sep 1 - Sep 2
Total with taxes and fees
100 Steps to Main Street. 5 bedrooms and 6.5 baths. New and Completely renovated
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

Jared Coffin House

Jared Coffin House

10/10 Excellent
"excellent location, great staff"
david 2-night trip
Posted 13 hours ago
Jared Coffin House

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 $642 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?

Chill beach 3-bedroom getaway on Nobadeer beach: This highly rated vacation home rental in Surfside has air-conditioning and laundry facilities to help you feel perfectly comfortable in your new surroundings.

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.