Oak Bluffs Vacation Rentals, Homes, & More

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Oak Bluffs Massachusetts Vacation Rentals - Home
1 / 20

Oak Bluffs Home
2 Bedrooms / 1 Bathroom / Sleeps 4
Home / 2 Bedrooms / Sleeps 4

from

$215

/ night

Email Owner
Bedrooms:2
Bathrooms:1
Sleeps:4
Type:Home
Per night:$215
Per week:$1,500
Pets allowed:Yes
Internet:Yes

Great Getaway Cottage with a short walk to town, the harbor, and the Lagoon . A back yard picnic table, BBQ grill, and swing set. About a mile walk or bike ride to Town. The house has hardwood and fir floors throughout and also has air conditioning. This is a great "get away cottage"...

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Oak Bluffs Massachusetts Vacation Rentals - Home
1 / 15

Oak Bluffs Home
5 Bedrooms / 3.5 Bathrooms / Sleeps 10
Home / 5 Bedrooms / Sleeps 10

from

$572

/ night

Email Owner
Bedrooms:5
Bathrooms:3.5
Sleeps:10
Type:Home
Per night:$572 - $929
Per week:$4,000 - $6,500
Pets allowed:No
Internet:Yes

This beautiful fully renovated cottage beach house is available for weekly rent. Come enjoy the great ocean views. Sit out on the large front covered porch – enjoy friends, family and great times! Relax to the sights and sounds of the beautiful ocean. House comfortably sleeps ...

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Oak Bluffs Massachusetts Vacation Rentals - Home
1 / 13

Oak Bluffs Home
2 Bedrooms / 2 Bathrooms / Sleeps 5
Home / 2 Bedrooms / Sleeps 5

from

$372

/ night

Email Owner
Bedrooms:2
Bathrooms:2
Sleeps:5
Type:Home
Per night:$372 - $486
Per week:$2,600 - $3,400
Pets allowed:No
Internet:Yes

Beachfront living combined with the convenenience of in- town. This condo makes your Vineyard vacation easy. Enjoy sweeping ocean views of Nantucket Sound and Chappaquiddick, with Oak Bluffs' popular Inkwell Beach directly across the street. Enjoy a second floor condo with water ...

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Oak Bluffs Massachusetts Vacation Rentals - Home
1 / 5

Oak Bluffs Home
3 Bedrooms / 2 Bathrooms / Sleeps 7
Home / 3 Bedrooms / Sleeps 7

from

$300

/ night

Email Owner
Bedrooms:3
Bathrooms:2
Sleeps:7
Type:Home
Per night:$300 - $400
Per month:$9,000 - $12,000
Pets allowed:Yes
Internet:Yes

This 3. 5 Bedroom Home With Skylights, 52 Inch Tv, Computer, Internet, Printer, Fax, Is Your Home Away From Home. 1 Mile From Town 1. 5 Mile From Beach And 7 Miles From Airport Is Ideal Location. 2 Sets Of Golf Clubs And 4 Tennis Racquets For Your Use, 3 Cable Tv's, Master...

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Oak Bluffs Massachusetts Vacation Rentals - Home
1 / 10

Oak Bluffs Home
4 Bedrooms / 3 Bathrooms / Sleeps 8
Home / 4 Bedrooms / Sleeps 8

(1)“ Excellent ”1 Review

from

$258

/ night

Email Owner
Bedrooms:4
Bathrooms:3
Sleeps:8
Type:Home
Per night:$258 - $400
Per week:$1,800 - $2,800
Pets allowed:No
Internet:Yes

Newer immaculate four bedroom Cape style home located in a quiet area within easy access to town and beaches. The upper level has 2 master suites each with a private bath, one with a jacuzzi tub. Also has high speed internet....

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Visit to Martha's Vineyard

“ Excellent ”
July 12, 2014
Wonderful house. Great location. Fabulous outdoor shower. We had a great experience.
Diane Carr, Florida

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Oak Bluffs Massachusetts Vacation Rentals - Home
1 / 23

Oak Bluffs Home
4 Bedrooms / 2.5 Bathrooms / Sleeps 8
Home / 4 Bedrooms / Sleeps 8

(1)“ Excellent ”1 Review

from

$572

/ night

Email Owner
Bedrooms:4
Bathrooms:2.5
Sleeps:8
Type:Home
Per night:$572 - $643
Per week:$4,000 - $4,500
Pets allowed:Yes
Internet:Yes

Newly refurbished, stately 4262 sq ft. home with 4 bedrooms, 2. 5 baths situated within a five minute walk to the center of Oak Bluffs, beaches, and ride/jog to bike trail. Large fenced yard with tennis court and patio. Spacious, open 35x45 living room downstairs with smaller...

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Perfect Location

“ Excellent ”
August 16, 2013
This was the perfect location for my family vacation. We could walk to everything, however, we were far enough that we did not experience a lot of noise or traffic. The home was in mint condition and the homeowner likes it to stay that way. Not recommended for little children or elderly people, there are a lot of stairs and all the main amenities are on the second and third floor. We have teenagers, so they had their own floor. This gave all of us a lot of privacy and space.
Hillary Dunson, Atlanta, GA

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1 / 8

Oak Bluffs Home
4 Bedrooms / 3.5 Bathrooms / Sleeps 10
Home / 4 Bedrooms / Sleeps 10

from

$500

/ night

Email Owner
Bedrooms:4
Bathrooms:3.5
Sleeps:10
Type:Home
Per night:$500 - $1,429
Per week:$3,500 - $10,000
Pets allowed:No
Internet:Yes

A fully renovated four bedroom home with three and a half baths and separate garage, landscaped lot and a private dock. Dock can accommodate up to a 25 foot motor boat and is accessible to Vineyard Sound. Family room with cable TV, deck, fully equipped kitchen, wood burning stove,...

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Oak Bluffs Massachusetts Vacation Rentals - Home
1 / 24

Oak Bluffs Home
5 Bedrooms / 2 Bathrooms / Sleeps 8
Home / 5 Bedrooms / Sleeps 8

from

$315

/ night

Email Owner
Bedrooms:5
Bathrooms:2
Sleeps:8
Type:Home
Per night:$315 - $458
Per week:$2,200 - $3,200
Pets allowed:No
Internet:Yes

Renovated beach house in Oak Bluffs with 5 Bedrooms, 2 full baths, Sleeps 8; Large living/dining room, sliding door opens to deck, flagstone picnic area with gas grill, A/C, Washer/Dryer, Free WIFI, Large flat- screen LED TV's with cable service; Located 10- 20 min walk...

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Oak Bluffs Massachusetts Vacation Rentals - Home
1 / 30

Oak Bluffs Home
4 Bedrooms / 3 Bathrooms / Sleeps 9
Home / 4 Bedrooms / Sleeps 9

from

$786

/ night

Email Owner
Bedrooms:4
Bathrooms:3
Sleeps:9
Type:Home
Per night:$786
Per week:$5,500
Pets allowed:No
Internet:Yes

Located on almost two waterfront acres, this beach house sits directly on the shores of The Lagoon, with its own private sandy beach and water views of The Lagoon and beyond to Nantucket Sound. The Beach House On The Lagoon is designed around the water views, with large wraparound...

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Oak Bluffs Massachusetts Vacation Rentals - Home
1 / 16

Oak Bluffs Home
4 Bedrooms / 3 Bathrooms / Sleeps 8
Home / 4 Bedrooms / Sleeps 8

Bedrooms:4
Bathrooms:3
Sleeps:8
Type:Home
Per night:$1,072 - $1,715
Per week:$7,500 - $12,000
Pets allowed:No
Internet:Yes

Tucked away on the shores of The Lagoon, this deluxe waterfront retreat has been designed with an open layout to maximize grand water views and sunsets from its decks, screened porch and most rooms. The main level of Crow's Nest features a stylish wrap- around mahogany deck, and...

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Oak Bluffs Massachusetts Vacation Rentals - Home
1 / 23

Oak Bluffs Home
4 Bedrooms / 3 Bathrooms / Sleeps 8
Home / 4 Bedrooms / Sleeps 8

from

$643

/ night

Email Owner
Bedrooms:4
Bathrooms:3
Sleeps:8
Type:Home
Per night:$643 - $929
Per week:$4,500 - $6,500
Pets allowed:No
Internet:Yes

Quietly tucked away in prestigious Farm Neck Golf Club, this contemporary has sweeping waterviews of Sengekontacket Pond, State Beach and the Atlantic, as well as the 8th hole on the golf course. Situated on almost two landscaped acres, there are large wrap- around decks that ...

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Oak Bluffs Massachusetts Vacation Rentals - Home
1 / 27

Oak Bluffs Home
4 Bedrooms / 4 Bathrooms / Sleeps 8
Home / 4 Bedrooms / Sleeps 8

Bedrooms:4
Bathrooms:4
Sleeps:8
Type:Home
Per night:$1,572 - $1,900
Per week:$11,000 - $13,300
Pets allowed:No
Internet:Yes

This waterfront luxury retreat, designed by Hutker Architects, sits quietly perched above the Lagoon, with a large pool, private beach and sweeping water views. "Sandy Point" takes its name from the unique private beach below with its prominent point of sand that juts out into...

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Oak Bluffs Massachusetts Vacation Rentals - Home
1 / 2

Oak Bluffs Home
7 Bedrooms / 6 Bathrooms / Sleeps 14
Home / 7 Bedrooms / Sleeps 14

Bedrooms:7
Bathrooms:6
Sleeps:14
Type:Home
Per night:$1,000 - $1,358
Per week:$7,000 - $9,500
Pets allowed:No
Internet:No

Perfect for family and friends that want to vacation together, while maintaining their privacy, this unique home allows up to four families to stay together in the same home, while giving each of them total privacy. This 4, 000- square- foot, seven- bedroom, six- bathroom home...

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Oak Bluffs Massachusetts Vacation Rentals - Home
1 / 23

Oak Bluffs Home
3 Bedrooms / 4 Bathrooms / Sleeps 6
Home / 3 Bedrooms / Sleeps 6

from

$500

/ night

Email Owner
Bedrooms:3
Bathrooms:4
Sleeps:6
Type:Home
Per night:$500 - $629
Per week:$3,500 - $4,400
Pets allowed:No
Internet:Yes

This classic New England- style shingle home has a modern coastal- look throughout, and is conveniently tucked away in the Sunset Lake area of Oak Bluffs, with easy access to all of downtown, plus use of a private tennis court. The first floor features a bright, open Living Area...

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Oak Bluffs Massachusetts Vacation Rentals - Home
1 / 24

Oak Bluffs Home
4 Bedrooms / 2 Bathrooms / Sleeps 8
Home / 4 Bedrooms / Sleeps 8

from

$558

/ night

Email Owner
Bedrooms:4
Bathrooms:2
Sleeps:8
Type:Home
Per night:$558 - $872
Per week:$3,900 - $6,100
Pets allowed:No
Internet:Yes

Absolutely delightful Oak Bluffs Victorian with colorful and charming decorating touches. Spacious and homey, this house has been cared for and cherished. Old world charm with all of today's necessities combined transport you to another era and give you all the comfort of modern ...

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Oak Bluffs Massachusetts Vacation Rentals - Home
1 / 28

Oak Bluffs Home
4 Bedrooms / 3 Bathrooms / Sleeps 8
Home / 4 Bedrooms / Sleeps 8

from

$786

/ night

Email Owner
Bedrooms:4
Bathrooms:3
Sleeps:8
Type:Home
Per night:$786
Per week:$5,500
Pets allowed:No
Internet:Yes

This beautifully designed home features four bedrooms, three full and one half baths. The living spaces include a formal dining room, living room and sun porch and a deck that lead out to nicely landscaped grounds. Other Amenities: iPhone Dock & Play Station 3Additional amenities...

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Oak Bluffs Massachusetts Vacation Rentals - Home
1 / 38

Oak Bluffs Home
4 Bedrooms / 3 Bathrooms / Sleeps 9
Home / 4 Bedrooms / Sleeps 9

from

$550

/ night

Email Owner
Bedrooms:4
Bathrooms:3
Sleeps:9
Type:Home
Per night:$550 - $1,036
Per week:$3,850 - $7,250
Pets allowed:No
Internet:Yes

Sea breezes and fabulous water views from almost every room are the mainstay for this unique waterfront home on the Lagoon Pond in Oak Bluffs. Polished with soothing designer furnishings in layers of cappuccino and white neutral linen and cotton, you will enjoy this European- chic...

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Bedrooms:7
Bathrooms:3
Sleeps:14
Type:Home
Per night:$1,750
Per week:$12,250
Pets allowed:No
Internet:Yes

Delightful historic summer cottage sitting on the edge of Harthaven Harbor. Spectacular views of Vineyard Sound from all areas of the home. Private path leads you to a pristine private association beach, perfect for families of all ages. There is also a private dock in front of the...

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Oak Bluffs Massachusetts Vacation Rentals - Home
1 / 22
Bedrooms:6
Bathrooms:3
Sleeps:13
Type:Home
Per night:$422 - $758
Per week:$2,950 - $5,300
Pets allowed:No
Internet:Yes

This outstanding Oak Bluffs home is undergoing a complete face lift for the 2012 rental season and is sure to please. Spacious and perfect for extended families, featuring multiple attractively furnished living areas and sleeping 13 comfortably. The lower level of the house features...

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Oak Bluffs Massachusetts Vacation Rentals - Home
1 / 22

Oak Bluffs Home
5 Bedrooms / 3 Bathrooms / Sleeps 10
Home / 5 Bedrooms / Sleeps 10

from

$693

/ night

Email Owner
Bedrooms:5
Bathrooms:3
Sleeps:10
Type:Home
Per night:$693 - $1,108
Per week:$4,850 - $7,750
Pets allowed:No
Internet:Yes

Rose Cottage - Treasured Harborfront Home. Deepwater dock. Enjoy the harbor activity from the veranda. Just a short stroll along the harbor to beaches, town center, and gingerbread cottages in the historic campground, movies, family and fine dining, galleries. Amenities and ...

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Bedrooms:5
Bathrooms:2
Sleeps:8
Type:Home
Per night:$336 - $1,050
Per week:$2,350 - $7,350
Pets allowed:No
Internet:Yes

Set in a quiet community of homes just on the outskirts of OB, this outstanding home provides a peaceful get away yet is just a short drive to town center. The use of coastal colors and upscale furnishings throughout combine to make this gorgeous Oak Bluffs summer home a cut a above....

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Oak Bluffs Massachusetts Vacation Rentals - Home
1 / 24

Oak Bluffs Home
4 Bedrooms / 2 Bathrooms / Sleeps 8
Home / 4 Bedrooms / Sleeps 8

from

$743

/ night

Email Owner
Bedrooms:4
Bathrooms:2
Sleeps:8
Type:Home
Per night:$743 - $1,779
Per week:$5,200 - $12,450
Pets allowed:No
Internet:Yes

Custom built with extraordinary attention to detail. Located on Lagoon Pond with panoramic views up the lagoon. Large comfortably furnished deck and screened porch with dining create a most relaxing atmosphere overlooking the water. Luxury features throughout the house not seen in...

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Oak Bluffs Massachusetts Vacation Rentals - Home
1 / 19

Oak Bluffs Home
4 Bedrooms / 2 Bathrooms / Sleeps 8
Home / 4 Bedrooms / Sleeps 8

from

$522

/ night

Email Owner
Bedrooms:4
Bathrooms:2
Sleeps:8
Type:Home
Per night:$522 - $1,236
Per week:$3,650 - $8,650
Pets allowed:No
Internet:Yes

This unique and elegant four bedroom beach cottage is situated on the north shore of Martha's Vineyard. For your relaxation, there is a large porch/patio leading out to the beach affording magnificent views. Additional views from the tastefully decorated living area, bedrooms areas,...

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Oak Bluffs Massachusetts Vacation Rentals - Home
1 / 17

Oak Bluffs Home
4 Bedrooms / 2 Bathrooms / Sleeps 8
Home / 4 Bedrooms / Sleeps 8

from

$415

/ night

Email Owner
Bedrooms:4
Bathrooms:2
Sleeps:8
Type:Home
Per night:$415 - $629
Per week:$2,900 - $4,400
Pets allowed:No
Internet:Yes

10 minute walk to Oak Bluffs center and beach area from this lovely modern vacation home. Enjoy all that the summer community of Oak Bluffs has to offer, quaint shops, fine and family dining, harbor front stroll where you will and array of dining establishments, all waterside,...

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Bedrooms:4
Bathrooms:3
Sleeps:8
Type:Home
Per night:$986 - $1,486
Per week:$6,900 - $10,400
Pets allowed:No
Internet:Yes

A recent renovation has moved this home to the top of the list in terms of comfort in a tastefully decorated waterfront home. A new family media room has been added giving extended families lots of space to relax. The open concept kitchen, dining and living areas feature waterviews...

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Bedrooms:3
Bathrooms:2
Sleeps:7
Type:Home
Per night:$320 - $353
Per week:$2,240 - $2,465
Pets allowed:No
Internet:Yes

Owner Transfer Ferry Tickets - Please InquireSituated on quiet side street with a 15 minute walk or a 5 minute drive to town and beach, this light filled cape offers visiting families a well equipped vacation reprieve with comfortable living areas, modern kitchen, AC in all bedrooms....

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Oak Bluffs Massachusetts Vacation Rentals - Home
1 / 19
Bedrooms:3
Bathrooms:2
Sleeps:6
Type:Home
Per night:$308 - $465
Per week:$2,150 - $3,250
Pets allowed:No
Internet:Yes

Picturesque ocean views across Farm Pond to Vineyard Sound. Walk to beach and town. Bike path is one block away from this beautifully renovated three bedroom, two bathroom home. Open, airy with lots of glass. The dining and living areas open to deck. Amenities and Features include......

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Oak Bluffs Massachusetts Vacation Rentals - Home
1 / 16

Oak Bluffs Home
6 Bedrooms / 2 Bathrooms / Sleeps 11
Home / 6 Bedrooms / Sleeps 11

from

$243

/ night

Email Owner
Bedrooms:6
Bathrooms:2
Sleeps:11
Type:Home
Per night:$243 - $879
Per week:$1,700 - $6,150
Pets allowed:No
Internet:Yes

Amenities and Features include... In- Town, Walk to Beach, Wifi InternetAdditional amenities include: coffee maker, patio table and chairs, fans - portable, lobster pot, washer / dryer, cd player, landscaped, outside shower - enclosed, phone ld block, outdoor furniture,...

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Bedrooms:5
Bathrooms:2
Sleeps:10
Type:Home
Per night:$393 - $786
Per week:$2,750 - $5,500
Pets allowed:No
Internet:Yes

East Chop Victorian seasonal residence exudes the character and charm of the era is situated just a block from the East Chop Bluffs on a sleepy side street in a quiet wooded setting. This wonderful home has a family room with beamed cathedral ceiling, an eyebrow window and full bathroom....

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Bedrooms:7
Bathrooms:4
Sleeps:10
Type:Home
Per night:$643 - $1,072
Per week:$4,500 - $7,500
Pets allowed:No
Internet:Yes

Waterfront Compound on Lagoon with panoramic water views. The main house features an open and spacious living area with comfortable furnishings, a dining area and a spacious kitchen with new appliances. The master bedroom with king bed has a private bath and opens onto a private ...

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Oak Bluffs Massachusetts Vacation Rentals - Home
1 / 9

Oak Bluffs Home
4 Bedrooms / 2 Bathrooms / Sleeps 8
Home / 4 Bedrooms / Sleeps 8

from

$347

/ night

Email Owner
Bedrooms:4
Bathrooms:2
Sleeps:8
Type:Home
Per night:$347
Per week:$2,425
Pets allowed:No
Internet:No

Amenities and Features include... Meadow View Farms, Out of Town, Association Tennis, Hi Speed InternetAdditional amenities include: coffee maker, internet - ethernet cord required, fans - portable, lobster pot, food processor, washer / dryer, cd player, landscaped, patio...

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Bedrooms:4
Bathrooms:1
Sleeps:8
Type:Home
Per night:$329 - $358
Per week:$2,300 - $2,500
Pets allowed:No
Internet:Yes

This whimsical summer home located in Water View Farms, provides a peaceful retreat overlooking wild flower meadows. Launch canoes or kayaks from the private association beach on Sengekontacket Pond, just a short walk from the house. Great waterfront play area for young children...

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Oak Bluffs Massachusetts Vacation Rentals - Home
1 / 20

Oak Bluffs Home
4 Bedrooms / 3 Bathrooms / Sleeps 8
Home / 4 Bedrooms / Sleeps 8

from

$686

/ night

Email Owner
Bedrooms:4
Bathrooms:3
Sleeps:8
Type:Home
Per night:$686 - $779
Per week:$4,800 - $5,450
Pets allowed:No
Internet:No

Spectacular water view in desirable East Chop neighborhood. This 4 bedroom, 3 bath home is just 1. 5 miles from Oak Bluffs Center and Beach. There is a yard with multiple decks and waterviews. Features include central air and wifi internet. Beautifully decorated. Amenities and Features...

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Oak Bluffs Massachusetts Vacation Rentals - Home
1 / 23

Oak Bluffs Home
4 Bedrooms / 2 Bathrooms / Sleeps 8
Home / 4 Bedrooms / Sleeps 8

from

$386

/ night

Email Owner
Bedrooms:4
Bathrooms:2
Sleeps:8
Type:Home
Per night:$386 - $572
Per week:$2,700 - $4,000
Pets allowed:No
Internet:Yes

Spacious and pristine four bedroom contemporary located in lovely private down- island community. All new decor, air conditioning, association tennis courts and bike paths. Views from spacious deck across professionally landscaped yard to Sengekontacket Pond. Amenities and Features...

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Bedrooms:4
Bathrooms:3
Sleeps:8
Type:Home
Per night:$429 - $900
Per week:$3,000 - $6,300
Pets allowed:No
Internet:Yes

MVVR EXCLUSIVE: Custom crafted tri- level, this beautiful home features spacious open living spaces, hardwood floors throughout, 3 full baths, central A/C and WiFi. Exterior features include a large private deck at the back of the house, the perfect venue for summer dining or...

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Oak Bluffs Massachusetts Vacation Rentals - Home
1 / 10

Oak Bluffs Home
3 Bedrooms / 2 Bathrooms / Sleeps 6
Home / 3 Bedrooms / Sleeps 6

from

$200

/ night

Email Owner
Bedrooms:3
Bathrooms:2
Sleeps:6
Type:Home
Per night:$200 - $300
Per week:$1,400 - $2,100
Pets allowed:No
Internet:Yes

Adorable and immaculate three bedroom, two bath cottage located just 1. 5 miles from Oak Bluffs center and town beach area. Bike paths located at the end of the street for touring or access to town. Less that a half mile to Farm Neck golf course, tennis and dining. House features...

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Oak Bluffs Massachusetts Vacation Rentals - Home
1 / 16

Oak Bluffs Home
4 Bedrooms / 2 Bathrooms / Sleeps 6
Home / 4 Bedrooms / Sleeps 6

from

$236

/ night

Email Owner
Bedrooms:4
Bathrooms:2
Sleeps:6
Type:Home
Per night:$236 - $493
Per week:$1,650 - $3,450
Pets allowed:No
Internet:Yes

Pristine 4 bedroom waterfront hideaway. Enjoy spectacular views and sunsets across the lagoon. Private dock for boat enthusiasts. Kayak and boat rentals can be delivered to the property and kayaking on the lagoon is a fun and picturesque activity for the entire family. Centrally located,...

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Oak Bluffs Massachusetts Vacation Rentals - Home
1 / 14

Oak Bluffs Home
3 Bedrooms / 2 Bathrooms / Sleeps 6
Home / 3 Bedrooms / Sleeps 6

from

$247

/ night

Email Owner
Bedrooms:3
Bathrooms:2
Sleeps:6
Type:Home
Per night:$247 - $390
Per week:$1,725 - $2,725
Pets allowed:No
Internet:Yes

Amenities and Features include... Hidden Cove, Association Tennis Courts, Association Kayak LandingAdditional amenities include: coffee maker, fans - portable, lobster pot, food processor, washer / dryer, porch - screened, vacuum, outdoor furniture, tennis - association/shared,...

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Oak Bluffs Massachusetts Vacation Rentals - Home
1 / 19

Oak Bluffs Home
3 Bedrooms / 2 Bathrooms / Sleeps 7
Home / 3 Bedrooms / Sleeps 7

from

$286

/ night

Email Owner
Bedrooms:3
Bathrooms:2
Sleeps:7
Type:Home
Per night:$286 - $472
Per week:$2,000 - $3,300
Pets allowed:No
Internet:Yes

OAK BLUFFS, Water View Farms: Contemporary Vineyard summer vacation home overlooking conservation land with views of Sengekontacket Pond and Nantucket Sound. Easy access to bike path. High speed internet. Less than 2 miles to Oak Bluffs, State Beach and Oak Bluffs harbor. Association...

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Oak Bluffs Massachusetts Vacation Rentals - Home
1 / 14

Oak Bluffs Home
2 Bedrooms / 1 Bathroom / Sleeps 5
Home / 2 Bedrooms / Sleeps 5

from

$150

/ night

Email Owner
Bedrooms:2
Bathrooms:1
Sleeps:5
Type:Home
Per night:$150 - $236
Per week:$1,050 - $1,650
Pets allowed:No
Internet:Yes

"About Time" ....... Treat your wallet to a vacation. Come to SECOND AVE; Quiet neighborhood, Great outdoor space. A/C Neat clean and tidy. Sleeps five. Walk to town, beach, and all that historic Oak Bluffs has to offer. A great value! First floor has the living room with flat...

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Oak Bluffs Massachusetts Vacation Rentals - Home
1 / 15

Oak Bluffs Home
4 Bedrooms / 2 Bathrooms / Sleeps 6
Home / 4 Bedrooms / Sleeps 6

from

$308

/ night

Email Owner
Bedrooms:4
Bathrooms:2
Sleeps:6
Type:Home
Per night:$308 - $493
Per week:$2,150 - $3,450
Pets allowed:No
Internet:Yes

Waterview Farm boasts views across peaceful meadows to Sengekontacket Pond and beyond. Launch canoes and kayaks at private association beach on the pond. Great location for families. Close to bike paths, town and beaches. House has an open, airy floor plan and large deck. Amenities...

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Oak Bluffs Massachusetts Vacation Rentals - Home
1 / 14

Oak Bluffs Home
3 Bedrooms / 3 Bathrooms / Sleeps 6
Home / 3 Bedrooms / Sleeps 6

from

$172

/ night

Email Owner
Bedrooms:3
Bathrooms:3
Sleeps:6
Type:Home
Per night:$172 - $458
Per week:$1,200 - $3,200
Pets allowed:No
Internet:Yes

OAK BLUFFS, East Chop: Secluded immaculate single story Vineyard cottage. Sweeping views and spectacular sunsets over Crystal Lake and Vineyard Sound from the second story deck. Less than two miles to Oak Bluffs. Additional amenities include: beach chairs, twin bed: 4, walktobeach,...

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Oak Bluffs Massachusetts Vacation Rentals - Home
1 / 30

Oak Bluffs Home
7 Bedrooms / 7 Bathrooms / Sleeps 14
Home / 7 Bedrooms / Sleeps 14

(1)“ Excellent ”1 Review

Bedrooms:7
Bathrooms:7
Sleeps:14
Type:Home
Per night:$1,000 - $1,357
Per month:$30,000 - $40,710
Pets allowed:No
Internet:Yes

Located on over 1 acre of waterfront property on East Chop, an exclusive area of historic Oak Bluffs, this unique home is perfect for family and friends that want to vacation together while maintaining their privacy. This home allows up to 4 families to stay together in the same...

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Oak Bluffs Massachusetts Vacation Rentals - Home
1 / 22

Oak Bluffs Home
7 Bedrooms / 3 Bathrooms / Sleeps 14
Home / 7 Bedrooms / Sleeps 14

from

$414

/ night

Email Owner
Bedrooms:7
Bathrooms:3
Sleeps:14
Type:Home
Per night:$414 - $643
Per month:$12,420 - $19,290
Pets allowed:No
Internet:Yes

Classic, "Camp Ground" over sized 7 bedroom 3 bath home in a residential neighborhood within easy walking distance to the beach, shops, restaurants, galleries, etc. It offers double master bedrooms (1st and 2nd floor. ) Enjoy rocking on our huge front porch in over sized Georgia...

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Oak Bluffs Massachusetts Vacation Rentals - Home
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Oak Bluffs Home
6 Bedrooms / 4 Bathrooms / Sleeps 12
Home / 6 Bedrooms / Sleeps 12

from

$429

/ night

Email Owner
Bedrooms:6
Bathrooms:4
Sleeps:12
Type:Home
Per night:$429
Per month:$12,870
Pets allowed:No
Internet:Yes

Sitting on the "summer porch" (that is what they were called in the days of old) sipping your favorite beverage, strolling the short distant to the water, relaxing around the table, Well equipped kitchen, reading in the living room with your feet these are possible when you stay...

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Oak Bluffs Massachusetts Vacation Rentals - Home
1 / 23

Oak Bluffs Home
5 Bedrooms / 4 Bathrooms / Sleeps 10
Home / 5 Bedrooms / Sleeps 10

from

$286

/ night

Email Owner
Bedrooms:5
Bathrooms:4
Sleeps:10
Type:Home
Per night:$286 - $425
Per month:$8,580 - $12,750
Pets allowed:No
Internet:Yes

Our 'treehouse' is the tallest residence in the town of Oak Bluffs. Enjoy quiet and seclusion in this wooded setting, located in the exclusive Meadow View Farms community. There are panoramic views from the upper level, above the treetops. The bike path and MVTA (bus) are steps ...

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Oak Bluffs Massachusetts Vacation Rentals - Home
1 / 14

Oak Bluffs Home
4 Bedrooms / 3 Bathrooms / Sleeps 8
Home / 4 Bedrooms / Sleeps 8

from

$414

/ night

Email Owner
Bedrooms:4
Bathrooms:3
Sleeps:8
Type:Home
Per night:$414 - $629
Per month:$12,420 - $18,870
Pets allowed:No
Internet:Yes

This charming home sits atop the Lagoon bluffs w/stairs down to a narrow private beach It offers waterviews from many rooms (including a wonderful glassed in/screened porch). The living room sports bay windows to access the view, and there's a studio w/a private entrance and kitchenette....

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Oak Bluffs Massachusetts Vacation Rentals - Home
1 / 21

Oak Bluffs Home
4 Bedrooms / 3 Bathrooms / Sleeps 8
Home / 4 Bedrooms / Sleeps 8

from

$357

/ night

Email Owner
Bedrooms:4
Bathrooms:3
Sleeps:8
Type:Home
Per night:$357 - $429
Per month:$10,710 - $12,870
Pets allowed:No
Internet:Yes

Set in one of the Island's loveliest planned residential areas with beautiful landscaping, overlooking Sengekontacket Pond. Wonderful pond views from all bedrooms and living area. This spacious three floor house is well maintained and attractively decorated. Full deck across back...

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Oak Bluffs Massachusetts Vacation Rentals - Home
1 / 17

Oak Bluffs Home
4 Bedrooms / 3 Bathrooms / Sleeps 8
Home / 4 Bedrooms / Sleeps 8

from

$229

/ night

Email Owner
Bedrooms:4
Bathrooms:3
Sleeps:8
Type:Home
Per night:$229 - $543
Per month:$6,870 - $16,290
Pets allowed:No
Internet:Yes

This charming home is situated in an idyllic private wooded setting on Sengekontacket Pond, one of the largest salt- water ponds on Martha's Vineyard. Comfortably furnished, it has a newlyr renovated kitchen and a new dining area overlooking Major's Cove. There is also a new screened...

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Oak Bluffs Massachusetts Vacation Rentals - Home
1 / 14

Oak Bluffs Home
2 Bedrooms / 1 Bathroom / Sleeps 4
Home / 2 Bedrooms / Sleeps 4

(1)“ Excellent ”1 Review

from

$257

/ night

Email Owner
Bedrooms:2
Bathrooms:1
Sleeps:4
Type:Home
Per night:$257 - $286
Per month:$7,710 - $8,580
Pets allowed:No
Internet:Yes

The quintessential Vineyard cottage! ! ! This sweet cottage brings back visions of the lazydays of summer of bygone eras when life was lesshurried. The serene location overlooks a pond, abarrier beach with a few homes, and the Outer Harbor. It has a magnificent 180 degree view ...

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