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The Surfside Road bike path is well traveled with bikers, walkers, and roller bladers. You stop along the way at a sandwich shop or outdoor cafe. Housing ranges from the older summer cottages to newer homes off the main roads.

10 Vacation Properties in Surfside
Sleeps

Surfside vacation rentals that sleep 26

Surfside Nantucket
ID 6939
15 BR
17 baths
Sleeps 26
The Big House
Distance to beach: 1 1/2 miles to South Shore beaches via bike path
2 reviews read reviews
Description
This fifteen bedroom house is set on four and a half acres of landscaped yard and pine trees in a quiet Surfside neighborhood. A non-smoking house, it is perfect for reunions, large families, weddings... read more
Key amenities
screened porch, deck/porch/patio, washer&dryer, dishwasher, linens included, cable TV, DVD or VCR
Time active on this website
13 years, 6 months
Property ID 6939 listed by: Jacques Zimicki
Summer:
$6,445 - $9,500/wk
Off Season:
$5,000 - $7,000/wk
$8,000/mo

Surfside vacation rentals that sleep 12

Surfside
ID 18535
4 BR
3 ½ baths
Sleeps 12
Surfside Beach Cottage
Distance to beach: 4 min. walk & 6 min. to Lifeguard/Bus to Town
4 reviews read reviews
Description
Point O' Breakers is a sanctuary of amazing views and fresh air. A comfortable and practical beach house at the dead-end of Surfside's historic Western Avenue. A short walk to the beach or to the publ... read more
Key amenities
view of salt water, walk to a salt water beach, deck/porch/patio, outdoor shower, central A/C, washer&dryer, dishwasher, linens included, cable TV, DVD or VCR, wireless or wired internet, handicap accessibility
Time active on this website
7 years, 8 months
Property ID 18535 listed by: Dorothy Farrell
Summer:
$7,500 - $9,500/wk
Off Season:
$5,000 - $7,500/wk

Surfside vacation rentals that sleep 10

Nantucket, Nobadeer beach
ID 18054
4 BR
2 baths
Sleeps 10
Nobadeer Beach House
Distance to beach: 150 yards from Nobadeer Beach access
Description
This is a contemporary, casual but comfortable beach house located across the street from Nobadeer Beach (adjacent to Surfside Beach), with beach access just 150 yards from the front door. The second... read more
Key amenities
view of salt water, walk to a salt water beach, deck/porch/patio, outdoor shower, washer&dryer, dishwasher, linens included, cable TV, DVD or VCR, fireplace, wireless or wired internet, pet-friendly
Time active on this website
8 years
Property ID 18054 listed by: Caley
Summer:
$6,200 - $6,750/wk
Off Season:
$3,500 - $5,800/wk

Surfside vacation rentals that sleep 9

Surfside
ID 13650
4 BR
2 baths
Sleeps 9
''Bright & Airy'' -Charming 4 Bedroom Vacation Home
Distance to beach: just over 1/2 mile to Surfside
Description
Great value for a Nantucket vacation! - Located just over mile to Surfside, town, across from bike path, running path, very close to shuttle stop. 4 bedroom 2 bath light & bright house sleeps 9 an... read more
Key amenities
walk to beach, deck/porch/patio, outdoor shower, A/C unit(s), washer&dryer, dishwasher, linens included, cable TV, DVD or VCR, wireless or wired internet, pet-friendly
Time active on this website
10 years, 8 months
Property ID 13650 listed by: Allura
Summer:
$2,400 - $2,850/wk
Off Season:
$1,300 - $2,100/wk

Surfside vacation rentals that sleep 8

Mid-island
ID 22425
4 BR
3 baths
Sleeps 8
On Edge of Town -- Private but Convenient to All
Distance to beach: 2 miles to Madaket Beach
Description
On the edge of town with a patio and outdoor deck, this home features four bedrooms and central a/c. It is situated on a private dead end road and boasts plenty of privacy. It is within walking of the... read more
Key amenities
deck/porch/patio, outdoor shower, central A/C, washer&dryer, dishwasher, linens included, cable TV, DVD or VCR, wireless or wired internet
Time active on this website
Less than a month
Property ID 22425 listed by: Donna Elle
Summer:
$4,000 - $4,500/wk
Off Season:
$3,000 - $4,500/wk
$3,000 - $3,500/mo

Surfside vacation rentals that sleep 6

Surfside
ID 27521
3 BR
3 baths
Sleeps 6
Si Bheag Si Mhor
Distance to beach: 1/4 mile to Surfside Beach
Description
Si Bheag Si Mhor (shuh-BIG-shuh-moor) is a beautiful, 3 bedroom, 3 bathroom home located on the south shore side of Nantucket Island, in the residential neighborhood known as Surfside. Entrance to the... read more
Key amenities
walk to a salt water beach, deck/porch/patio, outdoor shower, central A/C, washer&dryer, dishwasher, linens included, cable TV, DVD or VCR, wireless or wired internet
Time active on this website
3 months
Property ID 27521 listed by: Galen
Summer:
$4,000 - $5,200/wk
Off Season:
$2,000 - $4,000/wk
Surfside
ID 29226
3 BR
2 baths
Sleeps 6
Charming Renovated Cottage near Surfside beaches
Distance to beach: 1/2 mile through the dunes to Surfside Beach
5 reviews read reviews
Description
Only about a half mile from Nantuckets stunning Surfside beaches, come home - through the lavender and thyme scented borders, behind the hydrangeas - to find your Nantucket porch swing waiting at the... read more
Key amenities
walk to a salt water beach, deck/porch/patio, outdoor shower, A/C unit(s), washer&dryer, dishwasher, linens included, cable TV, DVD or VCR, wireless or wired internet, pet-friendly
Time active on this website
1 month
Property ID 29226 listed by: Nancy
Summer:
$3,000 - $5,000/wk
Off Season:
$3,000 - $4,000/wk
Surfside Nantucket
ID 5200
2 BR
2 baths
Sleeps 6
Ocean Views Cottage at Nobadeer Beach
Distance to beach: 300 yards, 1 minute walk
3 reviews read reviews
Description
This cottage is a perfect getaway for all seasons. It is ideal for honeymooners or couples with one or two children. The hammock in the garden invites you to relax. A short, private walk brings you... read more
Key amenities
view of salt water, walk to a salt water beach, deck/porch/patio, outdoor shower, washer&dryer, dishwasher, linens included, cable TV, DVD or VCR, wireless or wired internet
Time active on this website
14 years, 8 months
Property ID 5200 listed by: Mark and Barbara White
Summer:
$2,200 - $3,000/wk
Off Season:
$1,000 - $3,000/wk

Surfside vacation rentals that sleep 5

Nantucket
ID 13744
3 BR
2 baths
Sleeps 5
Hear the Surf
Distance to beach: 1/2 mile to beach - 5-7 min walk Steps/Fisherman
3 reviews read reviews
Description
Hear the surf from this very private adorable 2 story cottage which is a short walk to Fisherman's, Nobadeer and Steps Beach in Surfside. The cottage is meticulously maintained and fully equipped for ... read more
Key amenities
walk to a salt water beach, deck/porch/patio, outdoor shower, washer&dryer, dishwasher, linens included, cable TV, DVD or VCR, wireless or wired internet
Time active on this website
10 years, 8 months
Property ID 13744 listed by: Karen
Summer:
$2,900 - $3,700/wk
Off Season:
$1,000 - $2,800/wk
Surfside
ID 26963
3 BR
2 baths
Sleeps 5
Hydrangea Cottage: Charming Nantucket Beach House
Distance to beach: 2/10s mile beach between Fisherman's & Surfside
Description
Late to list!!! Great availability! Hydrangea Cottage is the Nantucket home you thought no longer existed. A beach house with rustic charm, a short walk to a magnificent beach, it is perfect for coupl... read more
Key amenities
walk to a salt water beach, outdoor shower, washer&dryer, dishwasher, linens included, cable TV, DVD or VCR, wireless or wired internet
Time active on this website
1 year, 6 months
Property ID 26963 listed by: Diana Cooper
Summer:
$3,200 - $4,200/wk
Off Season:
$300 - $425/night
$2,275 - $3,200/wk