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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.

15 Vacation Properties in Surfside
Sleeps
A fee-based feature highlighting availability within the next 4 weeks.

Surfside vacation rentals that sleep 26

Surfside Nantucket
ID 6939
15 BR
17 baths
Sleeps 26
The Big House
The Big House
Distance to beach: 1 1/2 miles to South Shore beaches via bike path
2 reviews read reviews
Summer:
$6,445 - $9,500/wk
Off Season:
$5,000 - $6,500/wk

Surfside vacation rentals that sleep 12

Nantucket
ID 26421
6 BR
3 baths
Sleeps 12
Nantucket Home for Large Group or Family
Nantucket Home for Large Group or Family
Distance to beach: 1.1 mile to Surfside Beach
8 reviews read reviews
LAST MINUTE ALERT 8/19 - 8/26
OWNER SPECIAL:
Save $1800/wk NOW $5000 for week of August 19 - August 26.
Summer:
$800 - $900/night
$5,000 - $7,000/wk
$58/mo
Off Season:
$750 - $900/night
$3,800 - $5,000/wk
Nantucket
ID 30964
5 BR
4 baths
Sleeps 12
Your Perfect Getaway: Main House Plus Pool & Cabana
Your Perfect Getaway: Main House Plus Pool & Cabana
Distance to beach: 7/10 mi to Nobadeer Beach
1 review read review
Summer:
$16,000 - $20,000/wk
$60,000 - $100,000/mo
Off Season:
$20,000/wk
$10,000 - $80,000/mo

Surfside vacation rentals that sleep 10

Nantucket, Nobadeer beach
ID 18054
4 BR
2 baths
Sleeps 10
Nobadeer Beach House
Nobadeer Beach House
Distance to beach: 150 yards from Nobadeer Beach access
Summer:
$6,200 - $6,750/wk
Off Season:
$5,000/wk

Surfside vacation rentals that sleep 9

Surfside
ID 13650
4 BR
2 baths
Sleeps 9
''Bright & Airy'' -Charming 4 Bedroom Vacation Home
''Bright & Airy'' -Charming 4 Bedroom Vacation Home
Distance to beach: just over 1/2 mile to Surfside
Summer:
$2,400 - $2,850/wk
Off Season:
$1,300 - $2,100/wk

Surfside vacation rentals that sleep 8

Mid-island
ID 22425
Summer:
$4,000 - $4,500/wk
Off Season:
$3,500 - $4,500/wk
$3,000/mo
Surfside
ID 30762
4 BR
3 ½ baths
Sleeps 8
Quiet Skyline Home - Bike paths leading to Surfside Beaches
Quiet Skyline Home - Bike paths leading to Surfside Beaches
Distance to beach: 1 mile to Surside and Nobadeer Beaches
Summer:
$6,000 - $6,500/wk
$25,000 - $25,500/mo
Off Season:
$6,000/wk

Surfside vacation rentals that sleep 7

Surfside
ID 31058
4 BR
2 ½ baths
Sleeps 7
New Listing: Charming ocean view house 3 minutes to beach!
New Listing: Charming ocean view house 3 minutes to beach!
Distance to beach: Stones and Fishermans less than 200 yards
OWNER SPECIAL:
Save $1000/wk Due to late cancellation for Aug.17-24 Just reduced to only $4700!!
Summer:
$4,700 - $5,700/wk
Off Season:
$500 - $600/night
$3,000 - $4,500/wk
$14,000/mo

Surfside vacation rentals that sleep 6

Surfside
ID 27521
3 BR
3 baths
Sleeps 6
Si Bheag Si Mhor
Si Bheag Si Mhor
Distance to beach: 1/4 mile to Surfside Beach
1 review read review
Summer:
$4,500 - $5,200/wk
Off Season:
$2,000 - $2,200/wk
Surfside
ID 29226
3 BR
2 baths
Sleeps 6
Charming Renovated Cottage near Surfside beaches
Charming Renovated Cottage near Surfside beaches
Distance to beach: 1/2 mile through the dunes to Surfside Beach
5 reviews read reviews
Summer:
$4,000 - $6,000/wk
Off Season:
$3,000 - $4,000/wk
Surfside Nantucket
ID 9468
3 BR
2 baths
Sleeps 6
Waterfront Cottage
Waterfront Cottage
Distance to beach: 2/10 of a mile (1000 feet )
Off Season:
$2,700 - $3,000/wk
Surfside Nantucket
ID 5200
2 BR
2 baths
Sleeps 6
Ocean Views Cottage at Nobadeer Beach
Ocean Views Cottage at Nobadeer Beach
Distance to beach: 300 yards, 1 minute walk
3 reviews read reviews
Summer:
$3,000/wk
Off Season:
$1,200 - $3,000/wk

Surfside vacation rentals that sleep 5

Nantucket
ID 13744
3 BR
2 baths
Sleeps 5
Hear the Surf
Hear the Surf
Distance to beach: 1/2 mile to beach - 5-7 min walk Steps/Fisherman
3 reviews read reviews
Summer:
$3,350 - $3,700/wk
Off Season:
$1,300 - $1,800/wk
Surfside
ID 26963
3 BR
2 baths
Sleeps 5
Hydrangea Cottage: Charming Nantucket Beach House
Hydrangea Cottage: Charming Nantucket Beach House
Distance to beach: 2/10s mile beach between Fisherman's & Surfside
Summer:
$3,200 - $4,200/wk
Off Season:
$325 - $425/night
$2,275 - $2,975/wk

Surfside vacation rentals that sleep 4

Nantucket
ID 16737
1 BR
1 bath
Sleeps 4
Carriage House
Carriage House
Distance to beach: 1.5 miles Surfside Beach
2 reviews read reviews
OWNER SPECIAL:
Due to recent cancellations, property is available at discounted rate of $2K per week.
Summer:
$2,000 - $2,500/wk
Off Season:
$200 - $400/night
$1,800 - $2,500/wk