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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.

14 Vacation Properties in Surfside
sleeping

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
12 years
Property ID 6939 listed by: Jacques Zimicki
Summer:
$7,000 - $9,500/wk
Off Season:
$4,000 - $7,000/wk
$8,000/mo

Surfside vacation rentals that sleep 12

Nantucket
ID 26421
6 BR
3 baths
Sleeps 12
Nantucket Home for Large Group or Family
Distance to beach: 1.1 mile to Surfside Beach
8 reviews read reviews
Description
Our 6 bedroom, 3 full bath home sleeps 12 and is conveniently located with just a 2 minute walk to the RTA shuttle stop. Bike or jog to town or beach via the bike path across the street. This is a com... read more
Key amenities
deck/porch/patio, outdoor shower, A/C unit(s), washer&dryer, dishwasher, cable TV, DVD or VCR, fireplace, wireless or wired internet, handicap accessibility
Time active on this website
3 months
Property ID 26421 listed by: Janet Amorello
Summer:
$5,000 - $6,000/wk
Off Season:
$800/night
$4,000/wk
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
6 years, 2 months
Property ID 18535 listed by: Dorothy Farrell
Summer:
$7,500 - $9,500/wk
Off Season:
$4,000 - $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
6 years, 6 months
Property ID 18054 listed by: Caley
Summer:
$6,100 - $6,600/night
$6,300 - $6,500/wk
Off Season:
$5,000 - $5,500/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
9 years, 2 months
Property ID 13650 listed by: Allura
Summer:
$300 - $400/night
$2,300 - $2,750/wk
Off Season:
$200 - $250/night
$1,300 - $2,000/wk

Surfside vacation rentals that sleep 8

Surfside
ID 16744
4 BR
2 ½ baths
Sleeps 8
De's House
Distance to beach: exactly 1 mile from South Shore Road Beach
Description
Nearly new house one mile from beach with great fishing and swimming. Professionally decorated with mahogany floors, wainscoating, two fireplaces (one in master suite), etc. and large professionally ... read more
Key amenities
deck/porch/patio, outdoor shower, A/C unit(s), washer&dryer, dishwasher, linens included, cable TV, DVD or VCR, fireplace, wireless or wired internet
Time active on this website
2 years, 10 months
Property ID 16744 listed by: Lawrence
Summer:
$4,500/wk

Surfside vacation rentals that sleep 6

Surfside Nantucket
ID 3873
3 BR
1 bath
Sleeps 6
Dunemoor Cottage
Distance to beach: Walk on boardwalk to private beach 600 feet
2 reviews read reviews
Description
Offering panoramic views of moorlands, dunes, and the ocean east, south, and west, this quaint, bright, and airy cottage has three bedrooms and one bath, and comfortably sleeps a maximum of six. It ha... read more
Key amenities
on a salt water beach, deck/porch/patio, outdoor shower, washer&dryer, cable TV, DVD or VCR, wireless or wired internet, pet-friendly
Time active on this website
14 years, 2 months
Property ID 3873 listed by: Susan
Summer:
$750 - $8,509/night
$4,500 - $4,900/wk
Off Season:
$3,000 - $4,500/wk
Surfside Nantucket
ID 9468
3 BR
2 baths
Sleeps 6
Waterfront Cottage
Distance to beach: 2/10 of a mile (1000 feet )
Description
This cottage is a favorite with families. It is located on the Island's most popular surf beach at Surfside. A boardwalk off our large deck brings you to the beach adjacent to the public beach and lif... read more
Key amenities
on a salt water beach, deck/porch/patio, outdoor shower, jacuzzi, washer&dryer, dishwasher, linens included, cable TV, DVD or VCR
Time active on this website
7 years, 1 month
Property ID 9468 listed by: Diane Kerr
Summer:
$3,600 - $3,800/wk
Off Season:
$3,600/wk
SURFSIDE
ID 25910
3 BR
4 baths
Sleeps 6
THE Best of Surfside
Distance to beach: Surfside and Miacomet Beaches - 1 mile
13 reviews read reviews
Description
Nantucket is oh, so special and your vacation should be too ... and it is at 8 Maclean!! Our home is a beautiful vacation retreat located in the heart of the island. It is well appointed - with attent... read more
Key amenities
deck/porch/patio, outdoor shower, jacuzzi, A/C unit(s), washer&dryer, dishwasher, linens included, cable TV, wireless or wired internet
Time active on this website
5 months
Property ID 25910 listed by: Paul Vineis
Summer:
$5,000 - $5,665/wk
Off Season:
$2,950 - $5,665/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
13 years, 2 months
Property ID 5200 listed by: Mark and Barbara White
Summer:
$1,600 - $2,700/wk
Off Season:
$1,000 - $2,700/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
2 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
9 years, 2 months
Property ID 13744 listed by: Karen
Summer:
$2,900 - $3,500/wk
Off Season:
$950 - $1,700/wk
Surfside
ID 26963
3 BR
2 baths
Sleeps 5
Hydragea 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
Less than a month
Property ID 26963 listed by: Diana Cooper
Summer:
$500/night
$3,000 - $4,200/wk
$16,000 - $16,800/mo
Off Season:
$300 - $350/night
$1,750 - $4,000/wk
$8,000 - $12,000/mo

Surfside vacation rentals that sleep 4

Surfside Nantucket
ID 5988
2 BR
1 bath
Sleeps 4
Oceanfront Vintage Cottage
Distance to beach: directly on the beach
3 reviews read reviews
OWNER SPECIAL:
Prime (Thurs.-Thurs.) week of Aug.4 - Aug. 11 available for $2800/wk.
Description
Waterfront vintage guest cottage directly on the ocean. Perfect for a relaxing, romantic getaway. Enjoy the sunsets, surf, and stars. Listen to the sound of the waves as you fall asleep. The cot... read more
Key amenities
on a salt water beach, outdoor shower, linens included
Time active on this website
4 years, 7 months
Property ID 5988 listed by: Joy or Emily
Summer:
$2,500 - $2,800/wk
$9,000 - $10,000/mo
Off Season:
$400/night
$2,800/wk
Nantucket
ID 16737
1 BR
1 bath
Sleeps 4
Carriage House
Distance to beach: 1.5 mile Surfside Beach
2 reviews read reviews
Description
Nantucket carriage House located on the bike path. Walking distance to the beach and town. - Full kitchen with refrigerator stove and microwave. - Bathroom with shower and full size washer and drye... read more
Key amenities
deck/porch/patio, outdoor shower, washer&dryer, linens included, cable TV, DVD or VCR, wireless or wired internet
Time active on this website
6 years, 1 month
Property ID 16737 listed by: Samantha
Summer:
$1,800 - $2,000/wk
Off Season:
$1,600 - $1,800/wk