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Surfside Vacation Rentals

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 café. Housing ranges from the older summer cottages to newer homes off the main roads.

Surfside Beach is a great family destination for picnics, kite flying, beach games, and surfcasting. The surf can be heavy at times. Accommodations include lifeguards, a snack bar, parking, restrooms, and cold showe... more info and map.

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15 Vacation Properties in Surfside

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
1 review read review
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
10 years, 5 months
Property ID 6939 listed by: Jacques Zimicki
Summer:
$7,500 - $9,500/wk
Off Season:
$2,500 - $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
1 review read review
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, 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
4 years, 7 months
Property ID 18535 listed by: Dorann Farrell, Farrell Realty Trust
Summer:
$1,750 - $2,000/night
$7,500 - $9,000/wk
Off Season:
$1,250 - $1,500/night
$4,000 - $8,000/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
4 years, 11 months
Property ID 18054 listed by: Caley
Summer:
$4,800 - $5,500/wk
Off Season:
$650/night
$1,000 - $5,200/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
7 years, 7 months
Property ID 13650 listed by: Allura
Summer:
$250 - $350/night
$1,900 - $2,600/wk
Off Season:
$180 - $290/night
$1,100 - $1,900/wk

Surfside vacation rentals that sleep 8

Nantucket
ID 14335
4 BR
3 ½ baths
Sleeps 8
Walk to Beautiful Surfside Beach in Minutes
Distance to beach: 1/4 mile to Nobadeer/Surfside/Fisherman's Beach
Description
''At Last'' is a spacious home located in a private setting, a short walk from the Surfside beaches. Completely renovated in '05, this beautifully decorated upside down beach house features a soaring ... 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, fireplace, wireless or wired internet
Time active on this website
7 years
Property ID 14335 listed by: Pat Rossin
Summer:
$8,500/wk
Off Season:
$500 - $750/night
$8,500/wk
Surfside Nantucket
ID 7216
3 BR
2 baths
Sleeps 8
Surfside Getaway
Distance to beach: Just over a mile to beautiful Surfside Beach
3 reviews read reviews
Description
Renovated Spring 2012. House is located on Surfside Road. Surfside beach is a little over a mile and town is about 3/4 of a mile. On bike path and close to bus route. 3 bedrooms, two upstairs (king... read more
Key amenities
deck/porch/patio, A/C unit(s), washer&dryer, dishwasher, linens included, cable TV, DVD or VCR, wireless or wired internet
Time active on this website
5 years, 2 months
Property ID 7216 listed by: Samantha
Summer:
$2,800 - $3,000/wk
Off Season:
$200 - $450/night
$2,600 - $2,800/wk
Surfside
ID 19095
3 BR
2 ½ baths
Sleeps 8
Secluded and Serene, Designer Kitchen, 3 Bedroom, 3 Bath
Distance to beach: 1/2 mile or 7 minute walk, Nobadeer Beach
6 reviews read reviews
Description
Open, airy, bright and fresh, this secluded home just 7 minutes walking from Nobadeer beach is just right for one or two families.Imagine the 'Big Chill' with all of your friends and family movin' to ... read more
Key amenities
walk to a salt water beach, hot tub, deck/porch/patio, outdoor shower, central A/C, washer&dryer, dishwasher, linens included, cable TV, fireplace, wireless or wired internet, pet-friendly, handicap accessibility
Time active on this website
3 years, 8 months
Property ID 19095 listed by: Margaret Layton
Summer:
$2,800 - $3,500/wk
Off Season:
$280 - $300/night
$1,500 - $2,200/wk
$8,370 - $9,000/mo

Surfside vacation rentals that sleep 7

Surfside Nantucket
ID 9468
3 BR
2 baths
Sleeps 7
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
5 years, 6 months
Property ID 9468 listed by: Diane Kerr
Off Season:
$3,500/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
12 years, 9 months
Property ID 3873 listed by: Susan
Summer:
$3,700 - $4,200/wk
$16,000/mo
Off Season:
$600 - $700/night
$3,000 - $4,200/wk
Surfside
ID 16195
3 BR
2 baths
Sleeps 6
'Summer of '42'! Walk to Beach! Sleep to Sound of the Surf!
Distance to beach: 1/4 mile
Description
Immaculate, bright and fresh! New (2005) classic Nantucket beach cottage. Designed by renowned architects and beautifully decorated. Crisp, classic simplicity. Terrific ocean breezes a near constant.... read more
Key amenities
water view, walk to beach, 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
6 years
Property ID 16195 listed by: Jenn Cabot
Summer:
$4,000 - $5,500/wk
Off Season:
$3,000 - $5,000/wk
Surfside
ID 15752
3 BR
2 baths
Sleeps 6
Charming Cottage Within Walking Distance to the South Shore
Distance to beach: 1/3 mile from Surfside/Fisherman's Beach
Description
Adorable 3 bedroom cottage located on large landscaped lot within walking distance to the best surf beach on the island. Located at 38 Boulevard it sits between Surfside and Nobadeer beaches. Built i... 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
6 years, 3 months
Property ID 15752 listed by: Laura
Summer:
$1,500 - $3,500/wk
$9,000 - $14,000/mo
Off Season:
$300 - $350/night
$1,000 - $1,500/wk
$3,000 - $6,000/mo
Surfside Nantucket
ID 5200
2 BR
2 baths
Sleeps 6
Ocean Views Cottage at Nobadeer Beach
Distance to beach: 300 yards, 1 minute walk
1 review read review
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
11 years, 7 months
Property ID 5200 listed by: Mark and Barbara White
Summer:
$1,500 - $2,500/wk
Off Season:
$1,000 - $2,500/wk
Surfside
ID 12339
2 BR
2 baths
Sleeps 6
Beautiful post and beam
Distance to beach: 10-15 min. walk down wooded dirt road and across
10 reviews read reviews
Description
Come relax and unwind in this house where old meets new. Nice old post and beam frame house with all new amenities nestled into a quiet wooded neighborhood. Walk to the beach or sit on the totally pr... 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, fireplace, wireless or wired internet
Time active on this website
8 years
Property ID 12339 listed by: Sue
Summer:
$2,200 - $2,800/wk
Off Season:
$2,200 - $2,800/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
1 review read review
Description
Hear the surf from this very private adorable 2 story cottage which is a short walk to Surfside Beach. First floor: kitchen open to dining and living room with gas wood stove, full bathroom with stack... 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
7 years, 6 months
Property ID 13744 listed by: Karen
Summer:
$2,000 - $3,500/wk
Off Season:
$950 - $2,500/wk

Surfside vacation rentals that sleep 4

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
4 years, 5 months
Property ID 16737 listed by: Samantha
Summer:
$1,800 - $2,000/wk
Off Season:
$200 - $450/night
$1,100 - $2,000/wk