Surfside holiday lettings

We found 729 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:18 Dec - 25 Dec

Living area
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
£16,834
for 7 nights, 1 home
£2,405 per night
includes taxes & fees
Cliff - 5 min walk to the beach / downtown. NEW Outdoor Patio/BBQ/fire pit
Room
Private kitchen
Living area
Living area
Exceptional
(19 reviews)

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

Nantucket

8% off
£9,872
for 7 nights, 1 home
£1,410 per night
includes taxes & fees
Prime location Cliff Rd retreat w private pond - steps to town/beach/bike path
Guest House front view
DOWN TOWN
living room
Court yard
Exceptional
(86 reviews)

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

Nantucket

8% off
£4,451
for 7 nights, 1 home
£636 per night
includes taxes & fees
OCEAN VIEWS! Immaculate Quintessential Nantucket Beach Cottage see virtual tour.
Mid level entrance - up to living room down to 1st floor suite.
Dinning area and kitchen.  Open floor plan 2nd floor
Dining area - 2nd floor- doors to back terrace and keypad lock
Front entrance on Angola street
Exceptional
(91 reviews)

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

Nantucket

8% off
£8,497
for 7 nights, 1 home
£1,214 per night
includes taxes & fees
Charming home tucked on a lovely lane - 10 min walk to main street
Backyard patio and detached post and beam garage
Private kitchen
On 1 acre of land surrounded by a beautiful meadow
Master Bedroom - 2nd floor
Exceptional
(12 reviews)

Spacious Surfside home just a short walk to Nobadeer Beach!

Nantucket

7% off
£5,247
for 7 nights, 1 home
£750 per night
includes taxes & fees
Spacious Surfside home just a short walk to Nobadeer Beach!
Outdoor dining
Private kitchen
Property grounds
Interior
Exceptional
(54 reviews)

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

Nantucket

8% off
£26,306
for 7 nights, 1 home
£3,758 per night
includes taxes & fees
LUXURIOUS HOUSE AND COTTAGE - Total 8 BR suites, pool, home theater.
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
(19 reviews)

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

Nantucket

8% off
£11,932
for 7 nights, 1 home
£1,705 per night
includes taxes & fees
100 Steps to Main Street. 5 bedrooms and 6.5 baths. New and Completely renovated
Exterior
Marina
Interior
Quaint village of Sconset
Exceptional
(70 reviews)

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

Nantucket

7% off
£2,604
for 7 nights, 1 home
£372 per night
includes taxes & fees
Cute, Quiet, Comfortable, Centrally Located, Outdoor Shower, Large Yard, BBQ
1st Floor
1st Floor TV Room
Outdoor space to hang out and enjoy the gorgeous weather - including Fire Pit
Our lovely home - located next door to communal pool and tennis courts.
Exceptional
(40 reviews)

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

Nantucket

8% off
£6,067
for 7 nights, 1 home
£867 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
Master suite
Exceptional
(39 reviews)

Private Beach House in Surfside

Nantucket

8% off
£11,639
for 7 nights, 1 home
£1,663 per night
includes taxes & fees
Private Beach House in Surfside
ROOM
INTERIOR
GOURMET KITCHEN WITH LARGE DINING BAR
FIREPLACE
Exceptional
(55 reviews)

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

Nantucket

7% off
£3,731
for 7 nights, 1 home
£533 per night
includes taxes & fees
Great 5 Bedroom Compound Off Cliff Rd! Short Walk to Town & Beach!
Exterior detail
Beach
Private kitchen
Terrace/patio
Exceptional
(25 reviews)

Charming Historic Downtown Cottage

Nantucket

7% off
£5,945
for 7 nights, 1 cottage
£849 per night
includes taxes & fees
Charming Historic Downtown Cottage
Dining
Private kitchen
Outdoor dining
Living area
Exceptional
(8 reviews)

Cheerful 5 br Nantucket home; perfect for families

Nantucket

8% off
£10,345
for 7 nights, 1 home
£1,478 per night
includes taxes & fees
Cheerful 5 br Nantucket home; perfect for families
Private kitchen
Outdoor dining
Living area
Exterior detail
Exceptional
(21 reviews)

Newly renovated beach cottage

Nantucket

8% off
£5,784
for 7 nights, 1 home
£826 per night
includes taxes & fees
Newly renovated beach cottage
Living area
Property grounds
Dining room
Exterior detail
Exceptional
(17 reviews)

4 Bedroom Gem, 10 minute walk to town!

Nantucket

8% off
£7,406
for 7 nights, 1 home
£1,058 per night
includes taxes & fees
4 Bedroom Gem, 10 minute walk to town!
Private kitchen
Private kitchen
Interior
Room
Exceptional
(25 reviews)

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

Nantucket

7% off
£3,750
for 7 nights, 1 apartment
£536 per night
includes taxes & fees
Charming new renovated 3 bed/ 1 Bath condo sleeps 6+Walk & Bike to everything
Room
Interior
Interior
Exterior detail
Exceptional
(12 reviews)

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

Nantucket

12% off
£1,704
for 7 nights, 1 apartment
£243 per night
includes taxes & fees
Noddy - Cozy & cute 1st Floor Studio close to town with everything you need.
Kitchen
Terrace/patio
North-facing side of house.  NOTE: Outdoor shower on left.
Laundry/Back patio
Exceptional
(67 reviews)

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

Nantucket

6% off
£4,818
for 7 nights, 1 cottage
£688 per night
includes taxes & fees
Classic Gem! Nothing Like it! Private cottage on Main St.
Room
Property grounds
Beach
Living area
Exceptional
(35 reviews)

Charming Pet Friendly Cottage

Nantucket

7% off
£6,412
for 7 nights, 1 cottage
£916 per night
includes taxes & fees
Charming Pet Friendly Cottage
Interior
Living area
Private kitchen
Exterior
Exceptional
(45 reviews)

Newly Renovated Condo in the heart of downtown Nantucket

Nantucket

11% off
£5,546
for 7 nights, 1 apartment
£792 per night
includes taxes & fees
Newly Renovated Condo in the heart of downtown Nantucket
Room
Open concept kitchen
Gas stove
Dining
Exceptional
(22 reviews)

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

Nantucket

8% off
£5,463
for 7 nights, 1 home
£780 per night
includes taxes & fees
Mid island oasis! 3-bedroom, 4 bath in the middle of “second downtown”
Exterior
Outdoor dining
Great custom kitchen to meet all of your needs.
Large, spacious bright master bedroom w/2 closets, plenty of storage.
Exceptional
(21 reviews)

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

Nantucket

8% off
£3,219
for 7 nights, 1 cottage
£460 per night
includes taxes & fees
Escape to Nantucket's charm, just a 6-min drive from Surfside Beach
View from bathroom of studio
 indoor staircase at far end of photo
Living room with 52" flat screen tv and gas fireplace (available only in winter)
Studio entrance off patio
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
£3,576
for 7 nights, 1 apartment
£511 per night
includes taxes & fees
Beautiful, Private Studio Close to Town and Beaches
Master bedroom
Property grounds
Back Cottage: Living Room
Exterior detail
Exceptional
(17 reviews)

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

Nantucket

7% off
£6,475
for 7 nights, 1 home
£925 per night
includes taxes & fees
6 BR Nantucket, Main House and Cottage, 10 min walk into town with parking
  • 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, 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.
How much does it cost to rent a holiday home in Surfside?
Prices for holiday rentals 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 traveling solo, as a couple, with family, or in a group. Vrbo offers something for every taste and budget, from affordable rentals in Surfside to more spacious homes. To get the best value, book early and take advantage of Vrbo's free rewards program.
Are there any discounts for Surfside holiday house rentals?
You can find great discounts on house rentals in Surfside on Vrbo, 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 find long-stay holiday rentals in Surfside?
A long-stay holiday rental 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 travel dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
Are there any Surfside holiday rentals with parking?
Vrbo offers a wide selection of holiday rentals 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 on Vrbo 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.
How early should I book a Surfside holiday rental?
Book your Surfside holiday rental at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your holiday rental, the better the price. *Based on analysis of Vrbo booking and occupancy data for 2024 stays.
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.
Can I change or cancel my Surfside home rental booking on Vrbo?
To find Surfside holiday rentals with free cancellation, just use Vrbo'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". Vrbo makes it easy to book with confidence.
Why should I join Vrbo as a host?
Joining Vrbo 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, Vrbo 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 Vrbo handle the heavy lifting to help you thrive. Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.
Are all fees included in the Surfside holiday rental prices shown on Vrbo?
Vrbo 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.
What is VrboCare™ and how does it work?
Vrbo's mission is to help guests relax, reconnect, and enjoy precious time together. With VrboCare™, 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.
What can I expect from Vrbo customer service and VrboCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, VrboCare™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, Vrbo customer service is available 24/7 to support you every step of the way. Vrbo 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.
Can I plan a group trip on Vrbo?
Vrbo'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 favorites, and build the perfect itinerary together.

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