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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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22 Vacation Properties in Surfside    sleeping 26, 14, 12, 10, 9, 8, 7, 6, 5, 4

Location Price Description (click blue title for more...) Sleeps BRs Baths
Surfside vacation rentals that sleep 26  

Surfside Nantucket

Surfside Nantucket Nantucket vacation rental

Summer:
$7,000 - $9,000/wk,

Off Season:
$4,500 - $7,000/wk,

See a full calendar with detailed availability and pricing for this Surfside vacation rental.

The Big House

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....

Distance to beach: 1 1/2 miles to South Shore beaches via bike path

Key amenities: screened porch, deck/porch/patio, washer&dryer, dishwasher, linens included, cable TV, DVD or VCR

Time active on this website: 10 years

Guest Reviews: 1

Property ID# 6939, Listed by: Jacques Zimicki

26 15 17
Surfside vacation rentals that sleep 14  

Surfside Nantucket

Surfside Nantucket Nantucket vacation rental

Summer:
$15,000 - $20,000/wk,

Off Season:
$15,000 - $16,000/wk,

See a full calendar with detailed availability and pricing for this Surfside vacation rental.

New! ''Summer in Surfside!!'' Walk to Beach! Pool!! A.C.!

New Summer rental in Surfside with Pool!...Great Family Retreat! Eight (8) bedrooms and five (5) baths on very private 3-acre setting. Consisting of a 3 bedroom- 2 bath main house (with one 'daybed' ....

Distance to beach: 1/4 mile to Nobadeer , 1/2 mile to Surfside

Key amenities: view of salt water, walk to a salt water beach, deck/porch/patio, pool, 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# 8748, Listed by: Jenn Cabot

14 8 5
Surfside vacation rentals that sleep 12  

Surfside

Surfside Nantucket vacation rental

Summer:
$1,750 - $2,000/night,
$7,500 - $9,950/wk,
$40,000/mo,

Off Season:
$1,250 - $1,500/night,
$4,000 - $8,000/wk,

See a full calendar with detailed availability and pricing for this Surfside vacation rental.

Surfside Beach Cottage

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....

Distance to beach: 4 min. walk & 6 min. to Lifeguard/Bus to Town

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, 2 months

Guest Reviews: 1

Property ID# 18535, Listed by: Dorann Farrell, Farrell Realty Trust

12 4 3.5
Surfside vacation rentals that sleep 10  

Surfside Nantucket

Surfside Nantucket Nantucket vacation rental

Summer:
$1,000/night,
$5,000 - $7,000/wk,

Off Season:
$1,000/night,
$5,000 - $7,000/wk,

See a full calendar with detailed availability and pricing for this Surfside vacation rental.

Surfside Dream House

Much more than your typical rental, this luxury home is ideally located close to Surfside Beach, just a ten minute walk to Nantucket's # 1 beach. Great out door built in 8 person hot tub. The open li....

Distance to beach: 1/4 mile 10 minute walk / bike path

Key amenities: walk to a salt water beach, hot tub, outdoor shower, jacuzzi, A/C unit(s), washer&dryer, dishwasher, linens included, cable TV, DVD or VCR, fireplace, wireless or wired internet

Time active on this website: 5 years, 6 months

Guest Reviews: 1

Property ID# 10841, Listed by: Lia Humphrey

10 5 4

Surfside, Nantucket, Nobadeer beach

Surfside, Nantucket, Nobadeer beach Nantucket vacation rental

Summer:
$4,400 - $5,000/wk,
$18,000/mo,

Off Season:
$500 - $600/night,
$2,600 - $4,600/wk,

See a full calendar with detailed availability and pricing for this Surfside vacation rental.

Nobadeer Beach House

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....

Distance to beach: 150 yards from Nobadeer Beach access

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, 6 months

Property ID# 18054, Listed by: Caley

10 4 2
Surfside vacation rentals that sleep 9  

Surfside

Surfside Nantucket vacation rental

Summer:
$1,800 - $2,500/wk,

Off Season:
$180 - $290/night,
$1,100 - $1,800/wk,

See a full calendar with detailed availability and pricing for this Surfside vacation rental.

''Bright & Airy'' -Charming 4 Bedroom Vacation Home

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....

Distance to beach: just over 1/2 mile to Surfside

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, 2 months

Property ID# 13650, Listed by: Allura

9 4 2
Surfside vacation rentals that sleep 8  

Surfside, Nantucket

Surfside, Nantucket Nantucket vacation rental

Summer:
$8,500/wk,

Off Season:
$500 - $750/night,
$6,500/wk,

See a full calendar with detailed availability and pricing for this Surfside vacation rental.

Walk to Beautiful Surfside Beach in Minutes

''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 ....

Distance to beach: 1/4 mile to Nobadeer/Surfside/Fisherman's Beach

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: 6 years, 7 months

Property ID# 14335, Listed by: Pat Rossin

8 4 3.5

Surfside

Surfside Nantucket vacation rental

Summer:
$3,500 - $4,000/wk,

Off Season:
$3,500/wk,

See a full calendar with detailed availability and pricing for this Surfside vacation rental.

De's House

Nearly new house one mile from a drive-on (4x4) beach with great fishing and swimming. Professionally decorated with mahogany floors, wainscoating, two fireplaces (one in master suite), etc. and larg....

Distance to beach: exactly 1 mile from South Shore Road Beach (drive

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, 3 months

Property ID# 16744, Listed by: Lawrence

8 4 2.5

surfside

surfside Nantucket vacation rental

Summer:
$2,250 - $2,500/wk,

Off Season:
$325/night,
$2,250/wk,

See a full calendar with detailed availability and pricing for this Surfside vacation rental.

Post & Beam Beach House

A unique post and beam beach house located just off the Surfside bike path, one mile to either downtown or Surfside Beach. In the spacious Great Room with a 30 foot cathedral ceiling, the open living ....

Distance to beach: 1.5 mile to Surfside Beach

Key amenities: deck/porch/patio, outdoor shower, washer&dryer, dishwasher, linens included, cable TV, DVD or VCR, wireless or wired internet, pet-friendly

Time active on this website: 3 years, 5 months

Guest Reviews: 8

Property ID# 18389, Listed by: Matt or Valerie

8 3 2

Surfside

Surfside Nantucket vacation rental

Summer:
$2,800 - $3,500/wk,
$12,000 - $13,000/mo,

Off Season:
$280 - $300/night,
$1,500 - $2,200/wk,
$8,370 - $9,000/mo,

See a full calendar with detailed availability and pricing for this Surfside vacation rental.

Secluded and Serene, Designer Kitchen, 3 Bedroom, 3 Bath

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 ....

Distance to beach: 1/2 mile or 7 minute walk, Nobadeer Beach

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, 3 months

Guest Reviews: 5

Property ID# 19095, Listed by: Margaret Layton

8 3 2.5
Owner Special: Book for the whole month of SEPT. and get a $250. gift certificate to Stop and Shop.

Surfside Nantucket

Surfside Nantucket Nantucket vacation rental

Summer:
$2,600 - $2,900/wk,

Off Season:
$2,600 - $2,900/wk,

See a full calendar with detailed availability and pricing for this Surfside vacation rental.

Surfside Getaway

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....

Distance to beach: Just over a mile to beautiful Surfside Beach

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: 4 years, 9 months

Guest Reviews: 1

Property ID# 7216, Listed by: Samantha

8 3 2
Surfside vacation rentals that sleep 7  

Surfside Nantucket

Surfside Nantucket Nantucket vacation rental

Summer:
$3,300 - $3,500/wk,

Off Season:
$3,500/wk,

See a full calendar with detailed availability and pricing for this Surfside vacation rental.

Waterfront Cottage

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....

Distance to beach: 2/10 of a mile (1000 feet )

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, 1 month

Property ID# 9468, Listed by: Diane Kerr

7 3 2
Surfside vacation rentals that sleep 6  

Surfside Nantucket

Surfside Nantucket Nantucket vacation rental

Summer:
$3,500 - $4,000/wk,

Off Season:
$500 - $600/night,
$2,500 - $4,000/wk,

See a full calendar with detailed availability and pricing for this Surfside vacation rental.

Dunemoor Cottage

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....

Distance to beach: Walk on boardwalk to private beach 600 feet

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, 5 months

Guest Reviews: 2

Property ID# 3873, Listed by: Susan

6 3 1

Surfside

Surfside Nantucket vacation rental

Summer:
$3,600 - $4,200/wk,

Off Season:
$2,500 - $3,400/wk,

See a full calendar with detailed availability and pricing for this Surfside vacation rental.

Ocean Front on Surfside Beach

Come & enjoy a truly quintessential Nantucket vacation. ''Escape Hatch'', our ocean front 'cottage of yesteryear' has been a family treasure for 70 years. The southern exposure combined with the 180 d....

Distance to beach: 800' on private boardwalk to Surfside beach

Key amenities: on a salt water 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: 8 years, 4 months

Property ID# 11518, Listed by: James Mullen

6 3 2

Surfside

Surfside Nantucket vacation rental

Summer:
$1,500 - $3,200/wk,
$900 - $14,000/mo,

Off Season:
$300 - $350/night,
$1,000 - $1,500/wk,
$3,000 - $6,000/mo,

See a full calendar with detailed availability and pricing for this Surfside vacation rental.

Charming Cottage Within Walking Distance to the South Shore

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....

Distance to beach: 1/3 mile from Surfside/Fisherman's Beach

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: 5 years, 10 months

Property ID# 15752, Listed by: Laura

6 3 2

Surfside

Surfside Nantucket vacation rental

Summer:
$3,000 - $5,500/wk,

Off Season:
$3,000 - $4,000/wk,

See a full calendar with detailed availability and pricing for this Surfside vacation rental.

'Summer of '42'! Walk to Beach! Sleep to Sound of the Surf!

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.....

Distance to beach: 1/4 mile

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: 5 years, 7 months

Property ID# 16195, Listed by: Jenn Cabot

6 3 2

Surfside Nantucket

Surfside Nantucket Nantucket vacation rental

Summer:
$1,500 - $3,000/wk,

Off Season:
$1,000 - $2,500/wk,

See a full calendar with detailed availability and pricing for this Surfside vacation rental.

Ocean Views Cottage at Nobadeer Beach

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....

Distance to beach: 300 yards, 1 minute walk

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, 2 months

Guest Reviews: 1

Property ID# 5200, Listed by: Mark and Barbara White

6 2 2

Surfside

Surfside Nantucket vacation rental

Summer:
$2,400 - $2,500/wk,

Off Season:
$1,800 - $2,500/wk,

See a full calendar with detailed availability and pricing for this Surfside vacation rental.

Beautiful post and beam

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....

Distance to beach: 10-15 min. walk down wooded dirt road and across d

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: 7 years, 7 months

Guest Reviews: 10

Property ID# 12339, Listed by: Sue

6 2 2

Surfside

Surfside Nantucket vacation rental

Summer:
$900 - $1,700/wk,
$6,000/mo,

Off Season:
$100 - $175/night,
$750 - $900/wk,
$1,900 - $2,400/mo,

See a full calendar with detailed availability and pricing for this Surfside vacation rental.

Starswept Cottage, Nantucket Island

This sweet 2 story retreat is nestled in the pines on three and a half acres of unspoiled wilderness. Sunny and breezy during daylight, at night stargaze from the three skylights in the master bedroom....

Distance to beach: Surfside or Miacomet within a mile

Key amenities: 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: 8 months

Property ID# 21532, Listed by: Nan

6 2 1
Surfside vacation rentals that sleep 5  

Surfside, Nantucket

Surfside, Nantucket Nantucket vacation rental

Summer:
$3,000/wk,

Off Season:
$1,200 - $1,900/wk,

See a full calendar with detailed availability and pricing for this Surfside vacation rental.

Hear the Surf

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....

Distance to beach: 1/2 mile to beach - 5-7 minute walk Steps/Fisherma

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, 2 months

Guest Reviews: 1

Property ID# 13744, Listed by: Karen

5 3 2
Surfside vacation rentals that sleep 4  

Surfside Nantucket

Surfside Nantucket Nantucket vacation rental

Summer:
$2,000 - $2,100/wk,

Off Season:
$1,800 - $2,000/wk,
$5,000 - $7,000/mo,

See a full calendar with detailed availability and pricing for this Surfside vacation rental.

Oceanfront Vintage Cottage

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....

Distance to beach: directly on the beach

Key amenities: on a salt water beach, outdoor shower, linens included

Time active on this website: 4 years

Guest Reviews: 1

Property ID# 5988, Listed by: Joy or Emily

4 2 1

Surfside, Nantucket

Surfside, Nantucket Nantucket vacation rental

Summer:
$1,800/wk,

Off Season:
$1,300 - $1,800/wk,

See a full calendar with detailed availability and pricing for this Surfside vacation rental.

Carriage House

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....

Distance to beach: 1.5 mile Surfside Beach

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

Guest Reviews: 2

Property ID# 16737, Listed by: Samantha

4 1 1