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98 Rentals
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Featured 
$857/night
Near Beach & Harbor Oak Bluffs | 001
7 Gorham Avenue, Oak Bluffs, MA 02558- 4 Bedrooms
- 2 Baths
- 6 Guests
- Cottage
Featured
$850/night
Oak Bluffs Victorian less than block from Beach | 30
10 Narragansett Avenue, Oak Bluffs, MA 02557- 5 Bedrooms
- 2 Baths
- 8 Guests
- House
Featured
$1,000/night
In Town Victorian with large back yard | 69
77 Pennacook Avenue, Oak Bluffs MA 02557- 5 Bedrooms
- 1.5 Baths
- 8 Guests
- Cottage
Featured
$2,142/night
In-town Historic Copeland District | 165
28 Narragansett Avenue, Oak Bluffs, MA 02557- 8 Bedrooms
- 2.5 Baths
- 16 Guests
- House
Featured
$1,214/night
Newly Renovated Meadow View Farms Colonial with association tennis near Farm Neck Golf Course | 185
18 High Meadow Lane, Oak Bluffs- 4 Bedrooms
- 3 Baths
- 8 Guests
- House
Featured
$714/night
Beachy Classic home with reverse floor plan | 266
39 California Avenue Oak Bluffs, MA 02557- 4 Bedrooms
- 2 Baths
- 8 Guests
- House
Featured
$1,900/night
Classic Home on Ocean Park with views of Nantucket Sound/160
19 Ocean Avenue, Oak Bluffs, MA 02557- 7 Bedrooms
- 3.5 Baths
- 13 Guests
- House
Featured
$571/night
Updated Saltbox Close to town Oak Bluffs/293
44 Barnes Road, Oak Bluffs, MA 02557- 3 Bedrooms
- 2 Baths
- 6 Guests
- House
Featured
$925/night
Vineyard Haven- Swimming pool close to town!/304
344 Greenwood Avenue- 4 Bedrooms
- 2.5 Baths
- 8 Guests
Featured
$929/night
Sun Filled Waterfront Home with a Beautiful Pond View 4 BR/305
Sengekontacket Association, Oak Bluffs- 4 Bedrooms
- 2 Baths
- 8 Guests
- House
Featured
$1,271/night
- 4 Bedrooms
- 2 Baths
- 8 Guests
- House
$486/night
Katama- near beach | 6
19 Sutton Way, Edgartown, MA 02539- 3 Bedrooms
- 2 Baths
- 8 Guests
- House
$1,428/night
In Town 7 Bedroom Home near Niantic Park | 2
2 Pocasset Avenue, Oak Bluffs, MA 02557- 7 Bedrooms
- 4 Baths
- 14 Guests
- House
$486/night
Katama guest house | 7
19A Sutton Way, Edgartown, MA 02539- 2 Bedrooms
- 1.5 Baths
- 4 Guests
- House
$1,214/night
Lovely Home in Fresh Pond Estates | 19
6 Fresh Pond Road, Oak Bluffs, MA 02557- 4 Bedrooms
- 3.5 Baths
- 8 Guests
- House
$1,179/night
Upscale 5 BR Vineyard Haven Home near town | 21
169 Greenwood Avenue, Vineyard Haven MA 02568- 5 Bedrooms
- 4.5 Baths
- 10 Guests
- House
$585/night
Cottage in the heart of Oak Bluffs | 23
47 Tuckernuck Avenue, Oak Bluffs, MA 02557- 4 Bedrooms
- 2 Baths
- 8 Guests
- House
$500/night
Quintessential Campground Cottage | 28
50 Clinton Avenue, Oak Bluffs, MA 02557- 3 Bedrooms
- 1.5 Baths
- 6 Guests
- Cottage
$858/night
Brand new Luxury Home in Oak Bluffs! Central a/c! | 32
25 Dreamers Way, Oak Bluffs, MA 02557- 4 Bedrooms
- 4 Baths
- 9 Guests
- House
$715/night
Nashawena Park Steps from Inkwell Beach | 34
38 Nashawena Avenue, Oak Bluffs. MA 02557- 4 Bedrooms
- 2 Baths
- 8 Guests
- House