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100 Rentals
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Featured 
$575/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
$1,357/night
Copeland Gem downtown Oak Bluffs | 77
28 Pequot Ave. Oak Bluffs, MA 02557- 5 Bedrooms
- 2.5 Baths
- 10 Guests
- House
Featured
$2,557/night
Downtown Oak Bluffs Walk to beach and Town | 56
16 Pequot Avenue, Oak Bluffs, MA 02557- 6 Bedrooms
- 3 Baths
- 12 Guests
- House
Featured
$715/night
Oak Bluffs -Waterview Home on the lagoon | 102
12 Mae Avenue, Oak Bluffs- 3 Bedrooms
- 2 Baths
- 8-10 Guests
- House
Featured
$372/night
Oak Bluffs downtown Condo | 110
21 Kennebec Ave.- 2 Bedrooms
- 1 Baths
- 4 Guests
- Condo
Featured
$1,214/night
Cinderella Cottage in Oak Bluffs | 188
26 Pequot Avenue, Oak Bluffs, MA 02557- 3 plus sleep area Bedrooms
- 3 Baths
- 8 Guests
- Cottage|House
Featured
$1,250/night
East Chop Waterfront on the beach sleeps 12! | 202
283 East Chop Drive, Oak Bluffs, MA 02557- 4 Bedrooms
- 2.5 Baths
- 12 Guests
- House
Featured
$1,214/night
Renovated Victorian steps from Inkwell with a/c | 210
10 Pequot Avenue, Oak Bluffs, MA 02557- 4 Bedrooms
- 2.5 Baths
- 8 Guests
- Cottage
Featured
$650/night
Bayes Hill/with A/C and brand new pool!! /253
26 Bayes Hill Road, Oak Bluffs, MA 02557- 4 Bedrooms
- 2.5 Baths
- 8 Guests
- House
Featured
$257/night
Contemporary Cape with open floor plan/271
23 Beacon Avenue, Oak Bluffs, MA 02557- 3 Bedrooms
- 2 Baths
- 5 Guests
- House
Featured
$429/night
Ocean Park 2 bedroom condo- waterview/200
61 Ocean Ave. #3 Oak Bluffs, MA 02557 USA- 2 Bedrooms
- 1 Baths
- 4 Guests
- Condo
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
$857/night
- 4 Bedrooms
- 2.5 Baths
- 8 Guests
Featured
$1,143/night
Tranquility in Oak Bluffs/292
7 Hidden Cove Road, Oak Bluffs- 4 Bedrooms
- 2.5 Baths
- 9 Guests
Featured
$571/night
Updated Saltbox WALK TO TOWN Oak Bluffs/293
44 Barnes Road, Oak Bluffs, MA 02557- 3 Bedrooms
- 2 Baths
- 6 Guests
- House
Featured
$429/night
Seaside Cottage near Inkwell/294
101A Ocean Avenue, Oak Bluffs, MA 02557- 1 Bedrooms
- 1 Baths
- 3 Guests
- Cottage
Featured
$1,160/night
Brand New Large Family Home with Central Air in Oak Bluffs/295
35 Gull Landing, Oak Bluffs- 3 Bedrooms
- 3.5 Baths
- 10 Guests
Featured
$1,929/night
- 6 Bedrooms
- 4 plus 2 half baths Baths
- 16 Guests
- House
Featured
$1,429/night
Classic Vineyard home with guesthouse A/C and water view/299
7 Canonicus Avenue Oak Bluffs, MA- 4 Bedrooms
- 3 Baths
- 8 Guests
- House