Surfside holiday homes

We found 725 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:25 Dec - 1 Jan

Exterior
Outdoor dining
Living area
Private kitchen
Exceptional
(6 reviews)

Cliff - 5 min walk to the beach / downtown. NEW Outdoor Patio/BBQ/fire pit

Nantucket

8% off
NZ$37,739
for 7 nights, 1 home
NZ$5,391 per night
includes taxes & fees
Cliff - 5 min walk to the beach / downtown. NEW Outdoor Patio/BBQ/fire pit
Living area
Private kitchen
Dining
Living area
Exceptional
(20 reviews)

Prime location Cliff Rd retreat w private pond - steps to town/beach/bike path

Nantucket

8% off
NZ$22,165
for 7 nights, 1 home
NZ$3,166 per night
includes taxes & fees
Prime location Cliff Rd retreat w private pond - steps to town/beach/bike path
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
NZ$8,692
for 7 nights, 1 cottage
NZ$1,242 per night
includes taxes & fees
Escape to Nantucket's charm, just a 6-min drive from Surfside Beach
Living area
Private kitchen
Master Bedroom - 2nd floor
Backyard patio and detached post and beam garage
Exceptional
(12 reviews)

Spacious Surfside home just a short walk to Nobadeer Beach!

Nantucket

8% off
NZ$12,000
for 7 nights, 1 home
NZ$1,714 per night
includes taxes & fees
Spacious Surfside home just a short walk to Nobadeer Beach!
Garden Tour
Town Harbor
Dining Room
Entry Way/Outside Deck/ Very private
Exceptional
(109 reviews)

In-Town • Walk to Beaches • Charming Cottage • Private Patio & Easy Parking

Nantucket

6% off
NZ$5,599
for 7 nights, 1 cottage
NZ$800 per night
includes taxes & fees
In-Town • Walk to Beaches • Charming Cottage • Private Patio & Easy Parking
Guest House front view
DOWN TOWN
Court yard
Sconset Roses
Exceptional
(86 reviews)

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

Nantucket

8% off
NZ$10,348
for 7 nights, 1 home
NZ$1,478 per night
includes taxes & fees
OCEAN VIEWS! Immaculate Quintessential Nantucket Beach Cottage see virtual tour.
Eat in kitchen and living room shown.
Living room and tv area 
high above union street so remains quiet and private
Outdoor shower and private, secluded patio
Kitchen 
Sub zero refrigerator and freezer draws. 
Wolf oven. 
Pantry on right
Exceptional
(20 reviews)

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

Nantucket

8% off
NZ$27,774
for 7 nights, 1 home
NZ$3,968 per night
includes taxes & fees
100 Steps to Main Street. 5 bedrooms and 6.5 baths. New and Completely renovated
Dining
Marina
Quaint village of Sconset
Interior
Exceptional
(71 reviews)

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

Nantucket

8% off
NZ$6,070
for 7 nights, 1 home
NZ$867 per night
includes taxes & fees
Cute, Quiet, Comfortable, Centrally Located, Outdoor Shower, Large Yard, BBQ
Mid level entrance with stairs to back terrace
Dinning area and kitchen.  Open floor plan 2nd floor
Mid level entrance - up to living room down to 1st floor suite.
Front entrance on Angola street
Exceptional
(91 reviews)

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

Nantucket

8% off
NZ$19,327
for 7 nights, 1 home
NZ$2,761 per night
includes taxes & fees
Charming home tucked on a lovely lane - 10 min walk to main street
Property grounds
Private kitchen
Interior
Outdoor dining
Exceptional
(55 reviews)

LUXURIOUS HOUSE AND COTTAGE - Total 8 BR suites, pool, home theater.

Nantucket

8% off
NZ$60,925
for 7 nights, 1 home
NZ$8,704 per night
includes taxes & fees
LUXURIOUS HOUSE AND COTTAGE - Total 8 BR suites, pool, home theater.
Our lovely home - located next door to communal pool and tennis courts.
1st Floor TV Room
1st Floor
1st Floor
Exceptional
(41 reviews)

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

Nantucket

8% off
NZ$14,061
for 7 nights, 1 home
NZ$2,009 per night
includes taxes & fees
Hog Heaven-Quintessential ACK in Naushop w/ Pool & Tennis ~ Near Beaches & Town
Pool & Hot Tub
Private driveway leading up to the house
Kitchen
Living room
Exceptional
(40 reviews)

Private Beach House in Surfside

Nantucket

9% off
NZ$26,359
for 7 nights, 1 home
NZ$3,766 per night
includes taxes & fees
Private Beach House in Surfside
GOURMET KITCHEN WITH LARGE DINING BAR
INTERIOR
FIREPLACE
ROOM
Exceptional
(55 reviews)

Great 5 Bedroom Compound Off Cliff Rd! Short Walk to Town & Beach!

Nantucket

7% off
NZ$8,511
for 7 nights, 1 home
NZ$1,216 per night
includes taxes & fees
Great 5 Bedroom Compound Off Cliff Rd! Short Walk to Town & Beach!
Outdoor dining
Private kitchen
Living area
Dining
Exceptional
(8 reviews)

Cheerful 5 br Nantucket home; perfect for families

Nantucket

8% off
NZ$23,707
for 7 nights, 1 home
NZ$3,387 per night
includes taxes & fees
Cheerful 5 br Nantucket home; perfect for families
Private kitchen
Beach
Exterior detail
Terrace/patio
Exceptional
(26 reviews)

Charming Historic Downtown Cottage

Nantucket

7% off
NZ$13,695
for 7 nights, 1 cottage
NZ$1,956 per night
includes taxes & fees
Charming Historic Downtown Cottage
Living area
Property grounds
Exterior detail
Master bedroom
Exceptional
(17 reviews)

4 Bedroom Gem, 10 minute walk to town!

Nantucket

8% off
NZ$16,818
for 7 nights, 1 home
NZ$2,403 per night
includes taxes & fees
4 Bedroom Gem, 10 minute walk to town!
Private kitchen
Outdoor dining
Exterior detail
Room
Exceptional
(21 reviews)

Newly renovated beach cottage

Nantucket

8% off
NZ$13,732
for 7 nights, 1 home
NZ$1,962 per night
includes taxes & fees
Newly renovated beach cottage
Fall view from deck and kitchen
Front of home from street
Alternate view of main stairway and hallway
Grill with patio table and chairs
Exceptional
(57 reviews)

Beautiful Intown Nantucket Home with parking.Short walk to downtown and ferries

Nantucket

8% off
NZ$10,912
for 7 nights, 1 home
NZ$1,559 per night
includes taxes & fees
Beautiful Intown Nantucket Home with parking.Short walk to downtown and ferries
Interior
Private kitchen
Room
Private kitchen
Exceptional
(25 reviews)

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

Nantucket

8% off
NZ$8,371
for 7 nights, 1 apartment
NZ$1,196 per night
includes taxes & fees
Charming new renovated 3 bed/ 1 Bath condo sleeps 6+Walk & Bike to everything
Exterior
Nantucket Harbor
Property grounds
Interior
Excellent
(95 reviews)

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

Nantucket

8% off
NZ$5,321
for 7 nights, 1 apartment
NZ$760 per night
includes taxes & fees
Duplex Sunny Condo in residential neighborhood, 5min walk to bike paths!!!
Downstairs living area (pull out sofa pictured)
Terrace/patio
Kitchen
North-facing side of house.  NOTE: Outdoor shower on left.
Exceptional
(67 reviews)

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

Nantucket

6% off
NZ$11,111
for 7 nights, 1 cottage
NZ$1,587 per night
includes taxes & fees
Classic Gem! Nothing Like it! Private cottage on Main St.
Studio entrance off patio
Living room with 52" flat screen tv and gas fireplace (available only in winter)
View from bathroom of studio
 indoor staircase at far end of photo
Fully equipped kitchenette with Sub-Zero fridge and Meile gas cooktop
Exceptional
(6 reviews)

Beautiful, Private Studio Close to Town and Beaches

Nantucket

8% off
NZ$8,223
for 7 nights, 1 apartment
NZ$1,175 per night
includes taxes & fees
Beautiful, Private Studio Close to Town and Beaches
Living area
Property grounds
Beach
Exterior detail
Exceptional
(36 reviews)

Charming Pet Friendly Cottage

Nantucket

7% off
NZ$14,796
for 7 nights, 1 cottage
NZ$2,114 per night
includes taxes & fees
Charming Pet Friendly Cottage
Exterior detail
Interior
Room
Private kitchen
Exceptional
(12 reviews)

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

Nantucket

12% off
NZ$4,317
for 7 nights, 1 apartment
NZ$617 per night
includes taxes & fees
Noddy - Cozy & cute 1st Floor Studio close to town with everything you need.
  • Peace of mind

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    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 Bookabach?
Bookabach 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?
Bookabach 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 Bookabach, 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 Bookabach?
To find Surfside holiday rentals with free cancellation, just use Bookabach'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, Bookabach 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 Bookabach?
Bookabach'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 Bookabach 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. Bookabach offers something for every taste and budget, from affordable homes in Surfside to more spacious homes.
What can I expect from Bookabach customer service and Bookabach Care™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, Bookabach Care™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, Bookabach customer service is available 24/7 to support you every step of the way. Bookabach 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 Bookabach Care™ and how does it work?
Bookabach's mission is to help guests relax, reconnect, and enjoy precious time together. With Bookabach Care™, 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 Bookabach as a host?
Joining Bookabach 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, Bookabach 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 Bookabach handle the heavy lifting to help you thrive. Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.

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