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Surfside Vacation Rentals

info & map

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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24 Vacation Properties in Surfside    sleeping 26, 14, 12, 10, 9, 8, 6, 5

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:
$8,000 - $9,000/week,
Off Season:
$3,500 - $7,000/week,

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 and small business groups. The house accommodates twenty-six and is surrounded on three sides by a ....
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, VCR or DVD
Time active on this website: 5 years, 4 months

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

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! Seven( 7) bedrooms and five(5) baths on very private 3-acre setting. Consisting of a 3 bedroom- 2 bath main house, a 3-bedroom- 2 bath cottage and a 1 bedroom carriage house studio - all either brand new or just renovated. Immaculate....
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, VCR or DVD, fireplace, high speed internet
Time active on this website: 2 years, 3 months

Property ID# 8748, Listed by: Jenn Cabot

14 7 5
Surfside vacation rentals that sleep 12  

Surfside

Surfside Nantucket vacation rental
New as of 11/6/2009  

Summer:
$7,000 - $7,500/week,

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

Private Retreat in Surfside - Short Walk to Beaches!

This custom built 5 bedroom house is within 1/2 mile of Surfside Beach, bike paths and bus stop. The open floor plan and large outdoor entertaining area make this the perfect vacation home for a large group or family. Private wooded lot abuts the State Forest. Enjoy the serenity of Surfside from o....
Distance to beach: 1/2 mile to Surfside Beach
Key amenities: walk to a salt water beach, deck/porch/patio, outdoor shower, central A/C, washer&dryer, dishwasher, linens included, cable TV, VCR or DVD, fireplace, high speed internet
Time active on this website: Less than a month

Property ID# 17986, Listed by: Patrick and Jodi Levesque

12 5 4.5
Surfside vacation rentals that sleep 10  

Surfside Nantucket

Surfside Nantucket Nantucket vacation rental

Summer:
$8,500 - $11,000/week,
Off Season:
$2,500 - $6,000/week,

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

Wonderful House with Heated Swimming Pool and Maid Service

This wonderful multi-level vacation home located off Nonantum Avenue in Surfside offers every amenity. The main floor consists of an entry foyer, huge kitchen with rare blue azul marble countertops, cathedral ceiling, tiled dining room table, living room with fireplace, flat screen TV, library, bedr....
Distance to beach: less than 5 minute walk
Key amenities: view of salt water, walk to a salt water beach, deck/porch/patio, pool, outdoor shower, hot tub, jacuzzi, central A/C, washer&dryer, dishwasher, linens included, cable TV, VCR or DVD, fireplace, high speed internet, pets considered
Time active on this website: 7 years, 11 months

Property ID# 3689, Listed by: Edith Delker Real Estate, Licensed in MA

10 5 5

Surfside Nantucket

Surfside Nantucket Nantucket vacation rental

Summer:
$3,000 - $4,500/week,
Off Season:
$500 - $1,000/night, $2,000 - $3,000/week,

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

Smugglers Luck 200 yards to the steps of Fishermans beach

Surfside beach house. 5 bedrooms. 2.5 bath. 200 yards to Fisherman's Beach. Wonderful large deck with a 6 person hot tub. Large gas grill. Outside shower. Horseshoes and everything you need for a great island getaway. 2 miles to town. Nearby bike and public transportation. Great ....
Distance to beach: 200 yards to Fisherman's Beach
Key amenities: view of salt water, walk to a salt water beach, deck/porch/patio, outdoor shower, hot tub, washer&dryer, dishwasher, linens included, cable TV, VCR or DVD, fireplace, high speed internet, handicap accessibility
Time active on this website: 5 years, 4 months

Property ID# 8025, Listed by: Melissa

10 5 2.5

Surfside Nantucket

Surfside Nantucket Nantucket vacation rental

Summer:
$7,000/week,
Off Season:
$3,000 - $6,000/week,

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

Surfside Dream House/ first time it will be rented

Much more than your typical rental. This luxury home is ideally located close to Surfside Beach, just a ten minute walk to Nantucket # 1 beach. Great out door built in 8 person hot tub. The open living plan consist of a large kitchen that is open to a sitting area and dinning with French doors to....
Distance to beach: 1/4 mile 10 minute walk / bike path
Key amenities: walk to a salt water beach, outdoor shower, hot tub, jacuzzi, A/C units, washer&dryer, dishwasher, linens included, cable TV, VCR or DVD, fireplace, high speed internet
Time active on this website: 1 year, 2 months

Property ID# 10841, Listed by: Lia Humphrey

10 5 4
Surfside vacation rentals that sleep 9  

Surfside

Surfside Nantucket vacation rental


Off Season:
$170 - $280/night, $1,000 - $1,800/week,

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 and is located at the back of an acre with plenty of privacy. Beautiful new multi-level mahogany deck....
Distance to beach: just over 1/2 mile to Surfside
Key amenities: deck/porch/patio, outdoor shower, washer&dryer, dishwasher, linens included, cable TV, VCR or DVD, high speed internet, pets considered
Time active on this website: 2 years, 6 months

Property ID# 13650, Listed by: Allura

9 4 2
Surfside vacation rentals that sleep 8  

Surfside/Nobadeer

Surfside/Nobadeer Nantucket vacation rental

Summer:
$4,300 - $4,500/week, $18,000 - $18,900/month,
Off Season:
$4,300/week, $17,500/month,

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

Nantucket Island/Close to South Shore Beaches

Very unique and private house built by island craftsman and owner on 2.8 acres wooded lot, close to Nantucket's best southernfacing beaches (20 minute walk). The house is located between Surfside and Nobadeer in a quiet residential neighborhood. You can hear the surf with a southwest wind (just abou....
Distance to beach: < 1 mile, 20 minute walk, < 5 minutes by bike
Key amenities: walk to a salt water beach, deck/porch/patio, outdoor shower, jacuzzi, washer&dryer, dishwasher, linens included, cable TV, VCR or DVD, fireplace, high speed internet, pets considered
Time active on this website: 6 years, 8 months

Property ID# 4911, Listed by: Sybille Stillger Andersen

8 4 2

Surfside/Southshore

Surfside/Southshore Nantucket vacation rental

Summer:
$5,500 - $6,500/week,
Off Season:
$5,500/week,

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

2 Morgan Square

Classic Nantucket beach house, designed by Neil Parent and completed in 2001. Beautiful, light, and airy with all contemporary amenities. Many comfortable design elements, including window seats, bar, island in kitchen, heated floor tiles in (two) baths, room-by-room audio, jacuzzi in master bedroom....
Distance to beach: 3/10 mile to Surfside Beach
Key amenities: on fresh water, walk to a salt water beach, deck/porch/patio, outdoor shower, jacuzzi, washer&dryer, dishwasher, linens included, cable TV, VCR or DVD, high speed internet, handicap accessibility
Time active on this website: 4 years, 4 months

Property ID# 9682, Listed by: Steve Calabrese

8 4 4.5

Surfside, Nantucket

Surfside, Nantucket Nantucket vacation rental

Summer:
$6,500 - $8,500/week, $30,000 - $40,000/month,
Off Season:
$6,500/week, $3,500 - $5,000/month,

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 cathedral great room, granite/stainless kitchen, large cathedral master suite, and a spacious family....
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, VCR or DVD, fireplace, high speed internet
Time active on this website: 1 year, 10 months

Property ID# 14335, Listed by: Pat Rossin

8 4 3.5

Surfside

Surfside Nantucket vacation rental
New as of 10/5/2009  

Summer:
$10,000/week,
Off Season:
$10,000/week,

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

New! Summer in Surfside! Pool! AC! Walk to Beach!

New Summer rental in Surfside...Great family retreat!! Four (4) bedrooms and three (3) baths on 2 of 3 very private acre setting. Central air conditioning in main house. Casual elegance and fantastic outdoor living with huge yard, pool, and decks. Central air conditioning in main house. Terrif....
Distance to beach: 1/4 mile or 10 minute walk
Key amenities: view of salt water, walk to a salt water beach, deck/porch/patio, pool, central A/C, washer&dryer, dishwasher, linens included, cable TV, VCR or DVD, fireplace, high speed internet
Time active on this website: 1 month

Property ID# 17862, Listed by: Jenn Cabot

8 4 3

Surfside

Surfside Nantucket vacation rental

Summer:
$2,500 - $2,800/week,
Off Season:
$2,500 - $2,800/week,

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

3 Bedroom, 2.5 Bath New Home with Indoor Pool

New home in a quiet neighborhood. The house has 3 bedrooms, 2.5 baths. Large open plan includes an ''eat in'' kitchen with deck and living room. Master bedroom has a walk-in closet, walk-in shower, hot tub and an 13' x 7' ''endless pool.'' The house is close to the bike path and the shuttle bus. Su....
Distance to beach: 1.5 miles
Key amenities: deck/porch/patio, jacuzzi, washer&dryer, dishwasher, linens included, cable TV, VCR or DVD, fireplace, high speed internet, pets considered
Time active on this website: 11 months

Property ID# 15652, Listed by: James Robinson

8 3 2
Owner Special: AVAILABLE FOR CHRISTMAS STROLL.Thursday 3rd through monday 7th ($2'400).
Surfside vacation rentals that sleep 6  

Surfside

Surfside Nantucket vacation rental

Summer:
$3,400/week,
Off Season:
$2,500 - $3,400/week,

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

Charming Home Close to Surfside Beach

This adorable home is located on a large private lot which is beautifully landscaped. There is a great back deck with an area for dining and grilling overlooking the manicured back yard and flower gardens. The home is a short walk or bicycle ride to Surfside Beach, which has life guards and a conces....
Distance to beach: 1/4 of a mile to Surfside Beach
Key amenities: deck/porch/patio, A/C units, washer&dryer, dishwasher, linens included, cable TV, VCR or DVD, fireplace, high speed internet
Time active on this website: 2 years, 3 months

Property ID# 12783, Listed by: Great Point Properties

6 4 2

Surfside

Surfside Nantucket vacation rental

Summer:
$400/night, $4,500 - $5,000/week,
Off Season:
$400/night, $2,750 - $4,500/week,

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

Surfside Beach Cottage - Newly Updated!

Enjoy the charm and convenience of Nantucket Beach living in ''TURF'' - a newly updated Surfside Beach House on Nonantum Avenue.  Located only 100 yards down a sandy lane from beautiful Surfside beaches.  Spend more time at the beach and less time getting to it.  This professionally decorated home f....
Distance to beach: 100 yards to Fisherman's beach
Key amenities: view of salt water, walk to a salt water beach, deck/porch/patio, outdoor shower, washer&dryer, dishwasher, linens included, cable TV, VCR or DVD, fireplace, high speed internet
Time active on this website: 1 year, 8 months

Property ID# 14851, Listed by: Robert Earl

6 4 3

Surfside

Surfside Nantucket vacation rental

Summer:
$1,500 - $2,700/week, $8,000 - $8,500/month,
Off Season:
$150/night, $1,000 - $1,500/week, $3,800 - $4,000/month,

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 in 2003, this home is quaint and comfortable and sleeps 6 comfortably with a huge master bedroom. Wi....
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, VCR or DVD, high speed internet
Time active on this website: 1 year, 2 months

Property ID# 15752, Listed by: Laura

6 3 2

Surfside, Nantucket

Surfside, Nantucket Nantucket vacation rental

Summer:
$2,600/week,

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

Beautiful Home Located 2 Miles From Surfside Beach

For the ideal vacation opportunity, come enjoy the relaxed charm and beauty of Nantucket living in this immaculate, charming home complete with hot tub, farmer’s porch, deck and gorgeous landscaping. Just 2 miles from Surfside Beach, the house is located in a quiet neighborhood on a beautiful, spac....
Distance to beach: 2 miles to Surfside Beach
Key amenities: deck/porch/patio, outdoor shower, hot tub, A/C units, washer&dryer, dishwasher, linens included, cable TV, VCR or DVD, fireplace
Time active on this website: 1 year, 1 month

Property ID# 15006, Listed by: Ben Cartwright

6 3 2.5

Surfside

Surfside Nantucket vacation rental

Summer:
$3,500 - $4,500/week,
Off Season:
$3,500/week,

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. An easy 10 minute walk to Fisherman's, Step's and Nobadeer beaches!! Beautiful interiors. Brand new....
Distance to beach: 1/4 mile
Key amenities: water view, walk to beach, deck/porch/patio, outdoor shower, A/C units, washer&dryer, dishwasher, linens included, cable TV, VCR or DVD, fireplace, high speed internet
Time active on this website: 10 months

Property ID# 16195, Listed by: Jenn Cabot

6 3 2

Surfside Nantucket

Surfside Nantucket Nantucket vacation rental

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

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

Dunemoor Cottage

This quaint, bright, and airy cottage has three bedrooms and one bath, and comfortably sleeps a maximum of six. The kitchen opens to a living/dining room and views beyond. The sunsets are gorgeous from the secluded brick patio on the side of the cottage. Outdoor shower is enclosed. Panoramic....
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, linens included, cable TV, VCR or DVD, high speed internet, pets considered
Time active on this website: 7 years, 9 months

Property ID# 3873, Listed by: Susan McMaster

6 3 1

Surfside

Surfside Nantucket vacation rental

Summer:
$400/night, $4,500 - $5,000/week,
Off Season:
$400/night, $2,750 - $4,500/week,

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

Surfside Beach Gem

''SURF'' is an open and airy cottage set-up for enjoyable beachside living. It is located directly across the street from Fisherman's Beach and has recently undergone a complete renovation from top to bottom. See and hear the ocean from every room on both floors. An ideal location for seaside fami....
Distance to beach: 30 yards to Fisherman's Beach
Key amenities: on water, walk to beach, deck/porch/patio, outdoor shower, washer&dryer, dishwasher, linens included, cable TV, VCR or DVD, high speed internet
Time active on this website: 1 year, 6 months

Property ID# 15226, Listed by: Robert Earl

6 3 2

Surfside Nantucket

Surfside Nantucket Nantucket vacation rental


Off Season:
$1,775 - $3,175/week,

Ocean Front on Surfside Beach

Ocean front cottage of yesteryear, with modern conveniences & 180 degree unobstructed panoramic view of dunes & ocean. Three bedrooms, two baths. Newer kitchen & baths, enclosed sun porch, ocean front deck & brick patio, BBQ, fireplace, cable TV/VCR, dishwasher, washer & dryer, linens. Private board....
Distance to beach: 800' on private boardwalk to Surfside beach
Key amenities: on a salt water beach, deck/porch/patio, outdoor shower, washer&dryer, dishwasher, linens included, cable TV, VCR or DVD, fireplace
Time active on this website: 3 years, 8 months

Property ID# 11518, Listed by: James Mullen

6 3 2

Surfside

Surfside Nantucket vacation rental

Summer:
$1,600 - $2,300/week,
Off Season:
$1,500 - $1,700/week,

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 private upstairs deck and listen to the surf. Well equipped kitchen, clawfoot tub, fireplace. This ho....
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, VCR or DVD, fireplace, high speed internet, pets considered
Time active on this website: 3 years, 3 months

Property ID# 12339, Listed by: Sue

6 2 2

Surfside, Nantucket

Surfside, Nantucket Nantucket vacation rental

Summer:
$500 - $1,000/night, $3,000 - $3,700/week,
Off Season:
$250 - $500/night, $2,000 - $3,700/week,

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

Short Walk to Beach in Surfside

This large one bedroom house with king bed also has a den with a trundle bed, a queen in the living room and two twin beds in the loft. New in 2008, there are hardwood floors, stone tile in the baths, a whirlpool tub and separate shower in the master bath, lots of decks...even a great view of the oc....
Distance to beach: .2 miles
Key amenities: view of salt water, walk to a salt water beach, deck/porch/patio, outdoor shower, jacuzzi, central A/C, washer&dryer, dishwasher, linens included, cable TV, VCR or DVD, high speed internet
Time active on this website: 1 year, 2 months

Property ID# 15804, Listed by: Steve Backus

6 2 2.5

Surfside Nantucket

Surfside Nantucket Nantucket vacation rental

Summer:
$2,400/week,
Off Season:
$200/night, $1,000 - $2,000/week,

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. A short, private walk brings you to Nobadeer Beach, a popular beach on the surf side of the island, about 2 and a half miles from the town center. For those seeking privacy, a ....
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, VCR or DVD, high speed internet
Time active on this website: 6 years, 6 months

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

6 2 2
Surfside vacation rentals that sleep 5  

Surfside, Nantucket

Surfside, Nantucket Nantucket vacation rental

Summer:
$2,200 - $2,700/week,
Off Season:
$900 - $1,800/week,

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 washer and dryer. Small bedroom with single bed.  Second floor:  master bedroom with queen bed and ....
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, VCR or DVD, high speed internet
Time active on this website: 2 years, 5 months

Property ID# 13744, Listed by: Karen

5 3 2