Surfside holiday homes

We found 722 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:13 Nov - 20 Nov

60ft Salt H2O heated pool, 6 chaise lounges, new bluestone patio (not in photo)
Living room, slipcovered sofas, airy,bright, with access to deck, fantastic view
New Kitchen, caesarstone counters, open to freshly painted greatroom
Even off season, the view is gorgeous!
Exceptional
(33 reviews)

XLG PRIVATE POOL&TENNIS,WALK TO BEACH,VIEWS,SLEEPS 8. 10% Discount for 2 weeks.

Nantucket

8% off
NZ$38,711
for 7 nights, 1 home
NZ$5,530 per night
includes taxes & fees
XLG PRIVATE POOL&TENNIS,WALK TO BEACH,VIEWS,SLEEPS 8. 10% Discount for 2 weeks.
Living area
Outdoor dining
Exterior
Private kitchen
Exceptional
(5 reviews)

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

Nantucket

8% off
NZ$36,525
for 7 nights, 1 home
NZ$5,218 per night
includes taxes & fees
Cliff - 5 min walk to the beach / downtown. NEW Outdoor Patio/BBQ/fire pit
Living area
Private kitchen
Master Bedroom - 2nd floor
On 1 acre of land surrounded by a beautiful meadow
Exceptional
(10 reviews)

Spacious Surfside home just a short walk to Nobadeer Beach!

Nantucket

8% off
NZ$14,517
for 7 nights, 1 home
NZ$2,074 per night
includes taxes & fees
Spacious Surfside home just a short walk to Nobadeer Beach!
Interior
Private kitchen
Property grounds
Outdoor dining
Exceptional
(54 reviews)

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

Nantucket

8% off
NZ$58,966
for 7 nights, 1 home
NZ$8,424 per night
includes taxes & fees
LUXURIOUS HOUSE AND COTTAGE - Total 8 BR suites, pool, home theater.
BACKYARD
DEN
SIDE VIEW
KING SECOND FLOOR
Exceptional
(21 reviews)

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

Nantucket

8% off
NZ$20,202
for 7 nights, 1 home
NZ$2,886 per night
includes taxes & fees
Walk to Children's Beach- house w/ Yard + Firepit
Sconset Roses
DOWN TOWN
Guest House front view
living room
Exceptional
(86 reviews)

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

Nantucket

8% off
NZ$10,015
for 7 nights, 1 home
NZ$1,431 per night
includes taxes & fees
OCEAN VIEWS! Immaculate Quintessential Nantucket Beach Cottage see virtual tour.
Exterior
Back deck
Living area
Dining
Exceptional
(13 reviews)

West of Town, a quiet corner of luxury

Nantucket

8% off
NZ$18,983
for 7 nights, 1 home
NZ$2,712 per night
includes taxes & fees
West of Town, a quiet corner of luxury
1st Floor
1st Floor TV Room
Our lovely home - located next door to communal pool and tennis courts.
Outdoor space to hang out and enjoy the gorgeous weather - including Fire Pit
Exceptional
(40 reviews)

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

Nantucket

8% off
NZ$13,608
for 7 nights, 1 home
NZ$1,944 per night
includes taxes & fees
Hog Heaven-Quintessential ACK in Naushop w/ Pool & Tennis ~ Near Beaches & Town
Common Room adjacent to kitchen and dining area. Plenty of natural light.
Quiet location with off-street parking for two vehicles. Security camera.
Fully-equipped kitchen
Master Bedroom with access to shared bath, desk, and high-resolution monitor.
Exceptional
(58 reviews)

Beautiful House Minutes from Town, on Bike Path

Nantucket

8% off
NZ$11,297
for 7 nights, 1 home
NZ$1,614 per night
includes taxes & fees
Beautiful House Minutes from Town, on Bike Path
Eat in kitchen and living room shown.
Living room and tv area 
high above union street so remains quiet and private
Living room. Smart tv.
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
NZ$23,144
for 7 nights, 1 home
NZ$3,306 per night
includes taxes & fees
100 Steps to Main Street. 5 bedrooms and 6.5 baths. New and Completely renovated
Laundry/Back patio
Terrace/patio
Downstairs living area (pull out sofa pictured)
Kitchen
Exceptional
(66 reviews)

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

Nantucket

6% off
NZ$10,754
for 7 nights, 1 cottage
NZ$1,536 per night
includes taxes & fees
Classic Gem! Nothing Like it! Private cottage on Main St.
Room
Private kitchen
Interior
Living area
Exceptional
(39 reviews)

Newly constructed 3 BR house . Walk to town, harbor and restaurants

Nantucket

8% off
NZ$12,343
for 7 nights, 1 home
NZ$1,763 per night
includes taxes & fees
Newly constructed 3 BR house . Walk to town, harbor and restaurants
Dining
Private kitchen
Living area
“ACK About Time”
Exceptional
(8 reviews)

Cheerful 5 br Nantucket home; perfect for families

Nantucket

8% off
NZ$22,944
for 7 nights, 1 home
NZ$3,278 per night
includes taxes & fees
Cheerful 5 br Nantucket home; perfect for families
Mid level entrance with stairs to back terrace
Dinning area and kitchen.  Open floor plan 2nd floor
Front entrance on Angola street
Mid level entrance - up to living room down to 1st floor suite.
Exceptional
(88 reviews)

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

Nantucket

8% off
NZ$18,705
for 7 nights, 1 home
NZ$2,672 per night
includes taxes & fees
Charming home tucked on a lovely lane - 10 min walk to main street
Exterior detail
Beach
Terrace/patio
Room
Exceptional
(23 reviews)

Charming Historic Downtown Cottage

Nantucket

7% off
NZ$13,345
for 7 nights, 1 cottage
NZ$1,906 per night
includes taxes & fees
Charming Historic Downtown Cottage
Living area
Living area
Pool
Exterior detail
Exceptional
(7 reviews)

Mid island oasis with large pool and outdoor entertainment area. Pet friendly!

Nantucket

8% off
NZ$16,179
for 7 nights, 1 home
NZ$2,311 per night
includes taxes & fees
Mid island oasis with large pool and outdoor entertainment area. Pet friendly!
Marina
Marina
Private kitchen
Living area
Exceptional
(65 reviews)

Luxurious Harbor View “Cindy” Cottage. Walk & Bike To Everything!

Nantucket

8% off
NZ$6,393
for 7 nights, 1 cottage
NZ$913 per night
includes taxes & fees
Luxurious Harbor View “Cindy” Cottage. Walk & Bike To Everything!
Private kitchen
Property grounds
Private kitchen
Property grounds
Exceptional
(15 reviews)

Renovated 2024, Blocks From the Inner Harbor/ Downtown - King, Twins, Pull out.

Nantucket

8% off
NZ$15,107
for 7 nights, 1 home
NZ$2,158 per night
includes taxes & fees
Renovated 2024, Blocks From the Inner Harbor/ Downtown - King, Twins, Pull out.
Exterior detail
Property grounds
Master bedroom
Dining room
Exceptional
(17 reviews)

4 Bedroom Gem, 10 minute walk to town!

Nantucket

8% off
NZ$16,277
for 7 nights, 1 home
NZ$2,325 per night
includes taxes & fees
4 Bedroom Gem, 10 minute walk to town!
Room
Outdoor dining
Private kitchen
Living area
Exceptional
(20 reviews)

Newly renovated beach cottage

Nantucket

8% off
NZ$13,290
for 7 nights, 1 home
NZ$1,899 per night
includes taxes & fees
Newly renovated beach cottage
Private kitchen
Private kitchen
Room
Outdoor dining
Exceptional
(25 reviews)

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

Nantucket

8% off
NZ$8,102
for 7 nights, 1 apartment
NZ$1,157 per night
includes taxes & fees
Charming new renovated 3 bed/ 1 Bath condo sleeps 6+Walk & Bike to everything
Alternate view of main stairway and hallway
Front of home from street
Fall view from deck and kitchen
Grill with patio table and chairs
Exceptional
(55 reviews)

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

Nantucket

8% off
NZ$10,561
for 7 nights, 1 home
NZ$1,509 per night
includes taxes & fees
Beautiful Intown Nantucket Home with parking.Short walk to downtown and ferries
Beach
Property grounds
Room
Exterior detail
Exceptional
(34 reviews)

Charming Pet Friendly Cottage

Nantucket

7% off
NZ$14,503
for 7 nights, 1 cottage
NZ$2,072 per night
includes taxes & fees
Charming Pet Friendly Cottage
Great custom kitchen to meet all of your needs.
Outdoor dining
Interior
Large, spacious bright master bedroom w/2 closets, plenty of storage.
Exceptional
(18 reviews)

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

Nantucket

8% off
NZ$7,082
for 7 nights, 1 cottage
NZ$1,012 per night
includes taxes & fees
Escape to Nantucket's charm, just a 6-min drive from Surfside Beach
  • 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)
  • Nantucket Golf Club (5.6 mi / 9 km)
  • Siasconset Golf Course (5.7 mi / 9.2 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)
  • Hummock Pond (3.4 mi / 5.5 km)
  • Jetties 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 most popular type of holiday home accommodation in Surfside?
Houses are the most popular kind of holiday home in Surfside, according to our data. Even if you've got something bigger or smaller in mind, Bookabach has properties in a variety of sizes and shapes. Compare our options to find your perfect fit.
How much does it cost to rent a holiday home in Surfside?
Length of stay, property type and season are among the factors that can influence the price of a holiday home. Simply add your dates of travel to find your perfect match. From comfy cottages to plush villas, all Bookabach holiday homes offer terrific value.
How much does it cost to rent a beach house in Surfside?
Prices for beach houses in Surfside will vary depending on the size and style of the property and time of year you're travelling. Simply enter your dates of travel into Bookabach and how many guests to see your home options and prices. From there you can use our filter tool to refine your search by nearby activities, ratings, amenities and more.
Are there pet-friendly holiday homes in Surfside?
With 25 holiday homes that welcome pets, your little buddy can also come along on your Surfside getaway. Use our filter tool to search our pet-friendly holiday homes and find a stay that's pawfect on Bookabach.
Can I rent a house with a pool in Surfside?
Grab your swimwear and pool noodle, because there are 10 houses with a private pool in Surfside. Stay at one of these sought-after holiday homes and you'll enjoy pool days every day. Simply enter your dates into Bookabach, then check the "pool" filter to find the perfect place for a splashing good time!
What are popular home amenities in Surfside?
When it comes to home amenities that guests are on the lookout for in Surfside, a firepit, a nearby waterfront and a garden are at the top of the list. With Bookabach holiday homes, you'll enjoy options to match your style and taste, whether you're travelling with family members, friends or even pets.
Are there large group holiday homes in Surfside?
Surfside has 10 holiday homes that can host 10 or more people. These stays come with all the space you need to share good times with friends and family.
Are there holiday homes in Surfside that welcome kids?
Surfside has 25 family-friendly holiday homes to choose from. And finding a stay that welcomes kiddos is a cinch with our "Properties good for families" filter. Besides having the entire place to yourselves, you can also look forward to amenities and perks such as multiple bedrooms, kitchens and private pools.
What are the top attractions for families in Surfside?
Keeping the kids amused during your holiday in Surfside is child's play with these cool family-friendly attractions:
  • Surfside Beach
  • Cisco Beach
  • Jetties Beach
Are there holiday homes with WiFi in Surfside?
Surfside has nine holiday homes with WiFi, so you'll be able to stay connected while travelling. Simply check the "WiFi" box in our handy search filter for a list of properties with this feature. From streaming TV shows with the family to scrolling social media, these Bookabach homes make it a breeze to go online.
How can I find holiday homes with air conditioning in Surfside?
You'll have a choice of 19 holiday homes with air conditioning in Surfside giving you that gentle, cool breeze and extra level of comfort. Simply enter your chosen travel dates and then use our handy filters to help you locate stays with air conditioning.
How old do you have to be to rent a holiday home in Surfside?
The minimum age allowed can differ between properties on Bookabach, so be sure to look at the rules of the holiday home in Surfside you want to book. But in general, it's 16, 18 or 21.
How long can I rent a holiday home in Surfside for?
The amount of time you can rent a Surfside holiday home for varies depending on the property. Just tap in your preferred travel dates to see available options that offer long-term stays. They come with everything you need to make your extended trip more comfortable and convenient, such as kitchens and laundries. Some holiday homes may also offer weekly or monthly discounted prices, so you can have a longer stay for less.

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