Surfside holiday rentals

We found 726 holiday rentals — enter your dates for availability
Discover a selection of 10 homes and other holiday rentals in Surfside that are perfect for your trip. Whether you’re staying in a holiday home with your children and pets or just with friends, you'll have the best amenities for spending time at your home away from home, which might include parking and a pool. At the end of the day, you'll be sure to find a property to rent for everyone's needs, including accessible or non-smoking choices.

Holiday rentals with weekly discounts – Surfside

Showing deals for:1 Jan - 8 Jan

Living area
Private kitchen
Backyard patio and detached post and beam garage
On 1 acre of land surrounded by a beautiful meadow
Exceptional
(12 reviews)

Spacious Surfside home just a short walk to Nobadeer Beach!

Nantucket

8% off
AU$8,012
for 7 nights, 1 home
AU$1,145 per night
includes taxes & fees
Spacious Surfside home just a short walk to Nobadeer Beach!
Kitchen Sub zero refrigerator and freezer draws. Wolf oven. Pantry on right
Living room and tv area high above union street so remains quiet and private
Outdoor shower and private, secluded patio
Living room. Smart tv.
Exceptional
(20 reviews)

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

Nantucket

8% off
AU$20,041
for 7 nights, 1 home
AU$2,863 per night
includes taxes & fees
100 Steps to Main Street. 5 bedrooms and 6.5 baths. New and Completely renovated
SIDE VIEW
DEN
KING SECOND FLOOR
KITCHEN
Exceptional
(22 reviews)

Walk to Children's Beach- house w/ Yard + Firepit

Nantucket

8% off
AU$23,525
for 7 nights, 1 home
AU$3,361 per night
includes taxes & fees
Walk to Children's Beach- house w/ Yard + Firepit
Exterior
Interior
Living area
Private kitchen
Exceptional
(7 reviews)

Walk to ferry, town and beaches!

Nantucket

9% off
AU$19,198
for 7 nights, 1 home
AU$2,743 per night
includes taxes & fees
Walk to ferry, town and beaches!
Front of house
Front entrance
Kitchen Area - 2nd Floor
Living room #2 - 2nd floor
Exceptional
(24 reviews)

Prime Brant Point Location – 5-Minute Walk to Beach & Downtown

Nantucket

8% off
AU$29,724
for 7 nights, 1 home
AU$4,246 per night
includes taxes & fees
Prime Brant Point Location – 5-Minute Walk to Beach & Downtown
Guest House front view
DOWN TOWN
Court yard
living room
Exceptional
(86 reviews)

OCEAN VIEWS! Immaculate Quintessential Nantucket Beach Cottage see virtual tour.

Nantucket

8% off
AU$8,253
for 7 nights, 1 home
AU$1,179 per night
includes taxes & fees
OCEAN VIEWS! Immaculate Quintessential Nantucket Beach Cottage see virtual tour.
Private kitchen
Private kitchen
Exterior
Front Entrance
Exceptional
(15 reviews)

Secluded Nantucket Retreat: Newly Renovated Home with Deck on 2 Acres!

Nantucket

5% off
AU$6,238
for 7 nights, 1 home
AU$891 per night
includes taxes & fees
Secluded Nantucket Retreat: Newly Renovated Home with Deck on 2 Acres!
Large, spacious bright master bedroom w/2 closets, plenty of storage.
Outdoor dining
Exterior
Great custom kitchen to meet all of your needs.
Exceptional
(22 reviews)

Escape to Nantucket's charm, just a 6-min drive from Surfside Beach

Nantucket

8% off
AU$6,194
for 7 nights, 1 cottage
AU$885 per night
includes taxes & fees
Escape to Nantucket's charm, just a 6-min drive from Surfside Beach
Fireplace
Kitchen & Pantry
3rd floor en-suite Bathroom
Kitchen with Wolf Range & warming Drawer
Exceptional
(59 reviews)

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

Nantucket

8% off
AU$11,964
for 7 nights, 1 home
AU$1,709 per night
includes taxes & fees
6 BDR, Pet-friendly, newly remodeled whaling captain’s house downtown Nantucket!
Living room
Private driveway leading up to the house
Master suite
Pool & Hot Tub
Exceptional
(40 reviews)

Private Beach House in Surfside

Nantucket

9% off
AU$21,253
for 7 nights, 1 home
AU$3,036 per night
includes taxes & fees
Private Beach House in Surfside
Quaint village of Sconset
Marina
Exterior
Interior
Exceptional
(71 reviews)

Cute, Quiet, Comfortable, Centrally Located, Outdoor Shower, Large Yard, BBQ

Nantucket

8% off
AU$4,811
for 7 nights, 1 home
AU$687 per night
includes taxes & fees
Cute, Quiet, Comfortable, Centrally Located, Outdoor Shower, Large Yard, BBQ
1st Floor
1st Floor TV Room
1st Floor
Outdoor space to hang out and enjoy the gorgeous weather - including Fire Pit
Exceptional
(41 reviews)

Hog Heaven-Quintessential ACK in Naushop w/ Pool & Tennis ~ Near Beaches & Town

Nantucket

8% off
AU$10,930
for 7 nights, 1 home
AU$1,561 per night
includes taxes & fees
Hog Heaven-Quintessential ACK in Naushop w/ Pool & Tennis ~ Near Beaches & Town
Outdoor dining
Private kitchen
“ACK About Time”
Living area
Exceptional
(8 reviews)

Cheerful 5 br Nantucket home; perfect for families

Nantucket

8% off
AU$19,149
for 7 nights, 1 home
AU$2,736 per night
includes taxes & fees
Cheerful 5 br Nantucket home; perfect for families
Front entrance on Angola street
Dinning area and kitchen. Open floor plan 2nd floor
Mid level entrance - up to living room down to 1st floor suite.
Dining area - 2nd floor- doors to back terrace and keypad lock
Exceptional
(91 reviews)

Charming home tucked on a lovely lane - 10 min walk to main street

Nantucket

8% off
AU$13,607
for 7 nights, 1 home
AU$1,944 per night
includes taxes & fees
Charming home tucked on a lovely lane - 10 min walk to main street
Property grounds
Exterior detail
Interior
Terrace/patio
Exceptional
(61 reviews)

Rebuilt Captains Home A Couple Blocks From Town Center

Nantucket

17% off
AU$23,944
for 7 nights, 1 home
AU$3,421 per night
includes taxes & fees
Rebuilt Captains Home A Couple Blocks From Town Center
Master bedroom
Property grounds
Exterior detail
Beach shed on left, back cottage on right, main house in the middle
Exceptional
(17 reviews)

6 BR Nantucket, Main House and Cottage, 10 min walk into town with parking

Nantucket

13% off
AU$20,845
for 7 nights, 1 home
AU$2,978 per night
includes taxes & fees
6 BR Nantucket, Main House and Cottage, 10 min walk into town with parking
Living area
Outdoor dining
Private kitchen
Exterior detail
Exceptional
(21 reviews)

Newly renovated beach cottage

Nantucket

8% off
AU$10,669
for 7 nights, 1 home
AU$1,524 per night
includes taxes & fees
Newly renovated beach cottage
Private kitchen
Private kitchen
Room
Interior
Exceptional
(25 reviews)

Charming new renovated 3 bed/ 1 Bath condo sleeps 6+Walk & Bike to everything

Nantucket

8% off
AU$6,717
for 7 nights, 1 apartment
AU$960 per night
includes taxes & fees
Charming new renovated 3 bed/ 1 Bath condo sleeps 6+Walk & Bike to everything
Terrace/patio
Beach
Private kitchen
Room
Exceptional
(26 reviews)

Charming Historic Downtown Cottage

Nantucket

8% off
AU$10,715
for 7 nights, 1 cottage
AU$1,531 per night
includes taxes & fees
Charming Historic Downtown Cottage
Dining
Open concept kitchen
Gas stove
Room
Exceptional
(26 reviews)

Mid island oasis! 3-bedroom, 4 bath in the middle of “second downtown”

Nantucket

8% off
AU$10,394
for 7 nights, 1 home
AU$1,485 per night
includes taxes & fees
Mid island oasis! 3-bedroom, 4 bath in the middle of “second downtown”
Interior
Living area
Private kitchen
Room
Exceptional
(46 reviews)

Newly Renovated Condo in the heart of downtown Nantucket

Nantucket

12% off
AU$9,087
for 7 nights, 1 apartment
AU$1,298 per night
includes taxes & fees
Newly Renovated Condo in the heart of downtown Nantucket
North-facing side of house. NOTE: Outdoor shower on left.
Terrace/patio
Kitchen
Downstairs living area (pull out sofa pictured)
Exceptional
(67 reviews)

Classic Gem! Nothing Like it! Private cottage on Main St.

Nantucket

6% off
AU$8,864
for 7 nights, 1 cottage
AU$1,266 per night
includes taxes & fees
Classic Gem! Nothing Like it! Private cottage on Main St.
Private kitchen
Interior
Exterior detail
Room
Exceptional
(12 reviews)

Noddy - Cozy & cute 1st Floor Studio close to town with everything you need.

Nantucket

11% off
AU$2,335
for 7 nights, 1 apartment
AU$334 per night
includes taxes & fees
Noddy - Cozy & cute 1st Floor Studio close to town with everything you need.
Beach
Property grounds
Exterior detail
Room
Exceptional
(36 reviews)

Charming Pet Friendly Cottage

Nantucket

8% off
AU$11,662
for 7 nights, 1 cottage
AU$1,666 per night
includes taxes & fees
Charming Pet Friendly Cottage

  • Peace of mind

    Our Book with Confidence Guarantee gives you 24/7 support

  • More quality time

    From booking to staying, the whole process is simple and enjoyable

  • All the privacy of home

    Enjoy full kitchens, laundry, pools, gardens and more

  • More for less

    More space, more privacy, more amenities — more value

Book a holiday rental for your Surfside getaway

Learn about the unique charm of Surfside with a stay in a holiday home rental. This city has something for everyone. Whether you're planning a family holiday, romantic stay or trip with friends, holiday rentals offer features like full kitchens and laundry facilities for a more convenient stay.

Sightseeing in and around Surfside

Are you looking for attractions to see while you're in the area? Venture out of your holiday home and experience everything that Surfside has to offer. Here are some of the major attractions to put on your list, all within 30 miles (48.2 km) of the city centre:

  • Miacomet Golf Course (2 mi / 3.2 km)
  • Siasconset Golf Course (5.7 mi / 9.2 km)
  • Nantucket Golf Club (5.6 mi / 9 km)

Exploring the natural landscape of Surfside

Whether you're looking for adventure or just want to take in the scenery, Surfside is a great spot to appreciate mother nature. Here are a few of the area's most enchanting sights, all within 30 miles (48.2 km) of the city centre:

  • Surfside Beach (0.3 mi / 0.4 km)
  • Nobadeer Beach (0.4 mi / 0.7 km)
  • Children's Beach (3 mi / 4.8 km)
  • Cisco Beach (3.4 mi / 5.4 km)
  • Jetties Beach (3.7 mi / 5.9 km)
  • Tom Nevers Beach (3.7 mi / 5.9 km)

Transport options to and around Surfside

Fly into Nantucket, MA (ACK-Nantucket Memorial), the closest airport, located 1.5 mi (2.4 km) from the city centre. If you can't find a flight that's convenient for your trip, you could book a flight to Vineyard Haven, MA (MVY-Martha's Vineyard), which is 29 mi (46.6 km) away.

Frequently asked questions

What is the best area to stay in Surfside when booking a holiday rental?
When looking for the best area to stay in Surfside, Massachusetts, a popular choice is the quaint neighbourhood of Surfside itself. This charming area is known for its beautiful beaches, making it a great spot for a relaxing holiday by the sea. Visitors can enjoy the sandy shores and the stunning views of the Atlantic Ocean, ideal for sunbathing, swimming, or simply taking a leisurely stroll.Another appealing aspect of Surfside is its proximity to local attractions. One must-visit spot is the nearby Cisco Brewery, where guests can sample a variety of craft beers and enjoy a lovely outdoor setting. Additionally, the area is close to the picturesque Miacomet Pond, offering opportunities for kayaking and birdwatching, making it a haven for nature enthusiasts.In terms of holiday rentals, Surfside boasts a variety of properties, ranging from cosy cottages to spacious family homes, allowing for a wide selection that caters to different preferences and budgets.
What are the top attractions in Surfside?
In Surfside, Massachusetts, visitors can enjoy the serene beauty of the beaches, particularly Surfside Beach, which is known for its soft sands and family-friendly atmosphere. This area is ideal for sunbathing, swimming, and beachcombing, making it a popular spot for families and those seeking relaxation by the sea.Nearby, the picturesque Nantucket Town offers charming cobblestone streets lined with distinctive grey shingle houses, where you can explore boutique shops, art galleries, and local eateries. The Whaling Museum is also a highlight, providing insight into the island's rich maritime history.For those interested in outdoor activities, the nearby Miacomet and Cisco beaches are great for surfing and paddleboarding, while the surrounding landscapes offer lovely walking trails and opportunities for cycling.
Are all fees included in the Surfside holiday homes prices shown on Stayz?
Stayz provides upfront pricing from the moment you start your search. There are no hidden fees added during the check-out process. This allows you to compare properties with ease and plan your trip with confidence.
Are there any Surfside holiday homes with parking?
Stayz offers a wide selection of holiday homes in Surfside with parking available—perfect for families or travellers who value the convenience of having a car during their stay. To easily find these properties, simply enter your travel details and use the "Parking available" filter under the amenities section. This makes it quick and easy to browse listings that suit your needs, whether you're planning a short city break or a longer stay.
Are there any discounts for Surfside holiday homes?
You can find great discounts on holiday homes in Surfside on Stayz, including special rates on new listings and savings for weekly or monthly stays with top amenities such as a pool or parking. There are several discounts for last-minute bookings, and early-bird bookings too. The best part is, there's no need for a discount code—just enter your travel dates and apply the discount filters to view the top rates.
Can I change or cancel my Surfside holiday home booking on Stayz?
To find Surfside holiday rentals with free cancellation, just use Stayz's handy "Free cancellation" search filter. We get that plans can change, so it's easy to filter properties that give you flexibility. If you need to make changes to an existing booking, drop your host a message. Go to "My Trips" in your account, click "Change or Cancel" and then "Message Host". Whether you're adjusting your plans or looking for flexible payment options, Stayz makes it easy to book with confidence.
Can I find long-stay holiday homes in Surfside?
A long-stay holiday home in Surfside is the best way to experience local living. Plus, you can make the most of long-stay discounts. Long-stay discounts are applied automatically when you enter your vacation dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
Can I plan a group trip on Stayz?
Stayz's Trip Planner makes organising group trips easy and stress-free. Whether you're planning with friends or coordinating a large group, you can collaborate in one place, save and share properties, vote on favourites, and build the perfect itinerary together.
How early should I book a Surfside holiday home?
Book your Surfside holiday home at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your vacation rental, the better the price. *Based on analysis of Stayz booking and occupancy data for 2024 stays.
How much does it cost to rent a holiday home in Surfside?
Prices for holiday homes in Surfside vary based on factors like travel dates, length of stay, accommodation type, and location. Simply enter your trip details to explore a wide range of options—whether you're travelling solo, as a couple, with family, or in a group. Stayz offers something for every taste and budget, from affordable homes in Surfside to more spacious homes.
What can I expect from Stayz customer service and StayzCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, StayzCare™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, StayzCare™ customer service is available 24/7 to support you every step of the way. Stayz also offers support via live chat through our Help Centre, where you can find helpful resources on bookings, payments, property management, and safety, making it easy to get instant answers to many common questions.
What is StayzCare™ and how does it work?
Stayz's mission is to help guests relax, reconnect, and enjoy precious time together. With StayzCare™, you can have peace of mind knowing you're protected and that if something goes wrong, we will do our best to make it right as applicable. If a significant issue arises that your host can't resolve, we'll help you address it, find a similar property, or get your reservation refunded if applicable. That's our promise. If a home is significantly different than listed, we'll get you into a new space that meets your needs and makes it right, or if a host cancels before your stay, you have a dedicated support team to get you into a similar home as applicable.
Why should I join Stayz as a host?
Joining Stayz as a host opens the door to a global community of travellers seeking unique stays, giving you the opportunity to earn income from your property on your terms. With user-friendly tools, dedicated support, and exposure on major travel sites, Stayz makes it easy to list, manage, and succeed. Whether it's a cosy cabin or a beach house, you can turn your space into a standout destination, become a host and let Stayz handle the heavy lifting to help you thrive. Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.

More holiday ideas