Oak Bluffs Vacation Rentals

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Waterfront Deck Area has 3 Chaise Lounge and 2 Chairs not shown in this Photo

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CENCP

East Chop Waterfront, Extraordinary Sunsets &Views Across the Sound , Deck directly on the Beach, Casual Interior

Classic, casual beachfront home combines cottage styling with modern amenities. spectacular views, quietly lapping waves right outside your windows, and breathtaking sunsets. Ideally located in the East Chop Area of Oak Bluffs just a short distance...Read more

Location:

Oak Bluffs

Sleeps:

Bedrooms:

Baths:

Price Range:

$14 - $13,804

Clean Fee:

$480 per week

Tax: State & Local:

11.7

Rates reduced for available weeks - see calendar for adjusted rates

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JOSEJ

Exquisite Coastal Style Home, Pool, Patio, Landscaped Yard! 10 minute walk to Oak Bluffs Center, Luxury Interior, 3 bedrooms, 4 baths, Multiple Living Spaces

This newly constructed, luxurious home offers the perfect blend of comfort, style, and convenience. Featuring a heated 16 x 32' pool with varying depths of 3 to 8 feet, a...Read more

Location:

Oak Bluffs

Sleeps:

Bedrooms:

Baths:

Price Range:

$14 - $13,503

Clean Fee:

$700 per week

Tax: State & Local:

11.7

Rates just reduced for available weeks in July & August by 15% - see calendar for adjusted rates

Pool Heated to 81 degrees included in rental rate last Sat in June to first Sat in September. Pool Depth 3 feet to 8 Feet

Pool Heated to 81 degrees June and September weeks additional $275 per week

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MILTD

Perfect in Town Location. Just 1 to 2 blocks to Beach, Town Center & Harbor Area, Walk to and from the Ferry

Centrally located in the heart of Oak Bluffs, walk 1-2 blocks to the beach, public tennis courts, and town & harbor areas. This wonderful large home has a large wrap-around porch for relaxing, 7...Read more

Location:

Oak Bluffs

Sleeps:

Bedrooms:

Baths:

Price Range:

$14 - $12,502

Clean Fee:

$500 per week

Tax: State & Local:

11.7

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WESTW

Tri Level Oak Bluffs Home, Central A/C, Set in Private Community of Sengekontacket, Multiple Living Spaces, Large Deck, Patio Area, Association Tennis

Privately situated on a hilltop in Sengekontacket, -spacious tri-level, 4000 sq ft contemporary home. Set in a wonderful, family friendly community, offering association tennis courts, and an association dock on Sengekontacket Pond...Read more

Location:

Oak Bluffs

Sleeps:

Bedrooms:

Baths:

Price Range:

$14 - $12,287

Clean Fee:

$600 per week

Tax: State & Local:

11.7

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GRACM

Beautful Oak Bluffs Home. Pool, Tucked on a Large Private &Extensively Landscaped Lot, 4 Bedrooms, Sleeps 9

Modern, spacious recently updated vacation home with a heated pool tucked on 1.5 acres of landscaped grounds provides an ideal setting for families and friends to enjoy their time together. The...Read more

Location:

Oak Bluffs

Sleeps:

Bedrooms:

Baths:

Price Range:

$14 - $12,250

Clean Fee:

$500 per week

Tax: State & Local:

11.7

Pool Heated to 81 degrees July & August weeks included in the rental rate.

Pool Heated to 81 degrees, additional $275 per week June& September weeks 2023

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BAKE7

Waterview, Walk to the Beach and Town Center, Impeccably Maintained 4 bedroom Home set in the Heart of Oak Bluffs.

Location:

Oak Bluffs

Sleeps:

Bedrooms:

Baths:

Price Range:

$14 - $12,005

Clean Fee:

$400 per week

Tax: State & Local:

11.7

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POWDA

Beautiful Newly Updated Oak Bluffs Home, Nestled on a Large Landscaped Lot in a Quiet Enclave of Homes. 4 Bedrooms. 4.5 Baths

Step inside to discover a welcoming interior, highlighted by a sunroom featuring comfortable seating around the TV. The open first-floor plan seamlessly integrates the main family room complete with a media...Read more

Location:

Oak Bluffs

Sleeps:

Bedrooms:

Baths:

Price Range:

$14 - $12,005

Clean Fee:

$600 per week

Tax: State & Local:

11.7

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CENCR

Oak Bluffs Summer Retreat, Large Private Deck, Lagoon Beach Rights -Great Area for Kayaking.

Spacious sun-filled home features open living spaces, hardwood floors throughout, 4 bedrooms and sleeps 8.

Exterior features include two decks, one sunny deck at the front of the house, and a large private...Read more

Location:

Oak Bluffs

Sleeps:

Bedrooms:

Baths:

Price Range:

$14 - $11,802

Clean Fee:

$480 per week

Tax: State & Local:

11.7

Rates just reduced on available weeks - see calendar for adjusted rates

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PIN15

Beautiful Oak Bluffs Home, Screened Porch & Open Porch, Association Tennis Courts, 4 bedrooms, 3.5 baths, Ideally Located just 2 miles to Town and Beach

Spacious contemporary home nestled in the lovely community of homes Meadow View Farms just on the outskirts of Oak Bluffs and 2 miles to town center and Oak Bluffs beaches....Read more

Location:

Oak Bluffs

Sleeps:

Bedrooms:

Baths:

Price Range:

$14 - $11,753

Clean Fee:

$500 per week

Tax: State & Local:

11.7

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STEJE

Charming Oak Bluffs Home, Waterfront on the Lagoon, Patio & Deck Areas. Spectacular Views & Sunsets

Waterfront on the Lagoon! The highlight of this home is its breathtaking views across the lagoon and beautiful sunsets. Whether you're inside or outside on the deck or patio, you can...Read more

Location:

Oak Bluffs

Sleeps:

Bedrooms:

Baths:

Price Range:

$14 - $11,501

Clean Fee:

$450 per week

Tax: State & Local:

11.7

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CURRM

Outstanding Designer Home, 15 Min Walk to Oak Bluffs Center, 4 Bedrooms each en suite with TV, Occupancy Limit 9

Stylish Dreamy Home on Dreamer's Way, less than a mile from the town center and beach area! The owners have left nothing out in the way of design and comfort in...Read more

Location:

Oak Bluffs

Sleeps:

Bedrooms:

Baths:

Price Range:

$14 - $11,200

Clean Fee:

$500 per week

Tax: State & Local:

11.7

Owner ACCEPTS 3 NIGHT MINIMUM STAYS, MEMORIAL DAY WEEKEND TO JUNE 16TH, AND SEPT 7TH TO THE END OF OCTOBER.

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View across Pool to House, Patio areas and Yard

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GOLDF

Outstanding Oak Bluffs Summer Home with Heated Pool and Patio Surround, Screened Porch with Living and Dining Area, Association Tennis Courts.

MVVR Exclusive Listing: Set in a quiet community of homes just on the outskirts of OB, this outstanding home provides a peaceful getaway yet is just a short drive to the...Read more

Location:

Oak Bluffs

Sleeps:

Bedrooms:

Baths:

Price Range:

$14 - $11,004

Clean Fee:

$550 per week

Tax: State & Local:

11.7

Pool Heated to 80 July & August and the 1st week in September included in the rental rate!

Pool Heated to 80 May, June & September weeks at additional cost ($400).

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INGAE

Location:

Oak Bluffs

Sleeps:

Bedrooms:

Baths:

Price Range:

$14 - $11,004

Clean Fee:

$500 per week

Tax: State & Local:

11.7

Rates reduce for available weeks in June & July - see calendar for adjusted rates

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MANUC

Hart Haven, Spacious Contemporary Colonial, Private Association Beach .8 mi from house, Private Association Tennis, 5 min walk from house

Located in the desirable enclave of homes known as Hart Haven just on the outskirts of Oak Bluffs Center, rental guests will surely enjoy this beautifully maintained home bordered by...Read more

Location:

Oak Bluffs

Sleeps:

Bedrooms:

Baths:

Price Range:

$14 - $11,004

Clean Fee:

$600 per week

Tax: State & Local:

11.7

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HOD28