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Oak Bluffs Homes for Rent

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  • /41

    $8,750 per month

    • 4 Beds
    • 2.5 Baths
    • 1,811 Sq Ft
    • House for Rent

    11 High Meadow Ln, Vineyard Haven, MA 02568

    Discover the perfect summer retreat in this beautifully updated Meadow View Farms home. Nestled on a private hilltop and minutes from beaches, bike paths, Farm Neck Gand Downtown Oak Bluffs, this home offers a serene escape close to the island’s best attractions. 4 spacious bedrooms, first floor primary ensuite, shared secondary floor full bath, plus additional half bath on main level. The

    Allison Cameron Parry Douglas Elliman Real Estate - Nantucket

    11 High Meadow Ln, Vineyard Haven, MA 02568
  • /20

    $14,000 per month

    • 5 Beds
    • 3 Baths
    • 3,000 Sq Ft
    • House for Rent

    55 Samoset Ave, Oak Bluffs, MA 02557

    Modernized 5 bed, 3 full bath Victorian in the heart of Downtown Oak Bluffs. Steps to restaurants, shopping, harbor, ferries and beaches. Accommodates 10 guests. Easy breezy outdoor living, dining, bluestone patio and BBQ grill. Relax on the covered porch surrounded by a lush flower garden or unwind in the outdoor shower. Updated stone and stainless kitchen. Formal dining for eight. A/C, WIFI and

    Allison Cameron Parry Douglas Elliman Real Estate - Nantucket

    55 Samoset Ave, Oak Bluffs, MA 02557
  • /30

    $28,500 per month

    • 9 Beds
    • 6.5 Baths
    • 3,500 Sq Ft
    • House for Rent

    9 Tuckernuck Ave, Oak Bluffs, MA 02557

    **PEAK SUMMER WEEKLY RATE** Water view Victorian fronting Waban Park, steps to Inkwell Beach. Newly restored 9-bed, 6+ bath Main and Guest House houses 18 guests. Internet, A/C and cable TV. Coastal chic interior with all new furnishings. Large open floor plan, ample gathering and relaxation spaces. Dining for 10, Wet Bar, gourmet kitchen, gas range, stainless appliances and distinctive design.

    Allison Cameron Parry Douglas Elliman Real Estate - Nantucket

    9 Tuckernuck Ave, Oak Bluffs, MA 02557
  • /10

    $20,000 per month

    • 5 Beds
    • 3 Baths
    • 2,352 Sq Ft
    • House for Rent

    55 Samoset Ave Unit 1, Oak Bluffs, MA 02557

    THIS PROPERTY IS A WEEKLY RENTAL PROPERTY!! Newly renovated, Great for Family Gatherings, Corporate Retreats, Central Air & Heat, very close to Circuit Ave and Beach, 5 Bedrooms, 3 full baths, galley kitchen, new appliances, dining room, family room, Flat Screen TV, FREE Wifi, washer & dryer, bay window breakfast nook, Oak and Pine wood flooring, outdoor shower, wrap around porch, blue stone

    Karen Overtoom Karen M. Overtoom R.E.

    55 Samoset Ave Unit 1, Oak Bluffs, MA 02557
  • /20

    $20,000 per month

    • 3 Beds
    • 3 Baths
    • House for Rent

    40 Hidden Cove Rd, Oak Bluffs, MA 02557

    THIS IS A WEEKLY SUMMER RENTAL ONLY.SEE WEB SITE FOR WEEKLY PRICING. Welcome to "Shangri-la" A beautiful townhouse condominium end unit with magnificent views. Located midway between Oak Bluffs and Edgartown. You can enjoy the beautiful pool or one of the close local beaches. You will want to sit and enjoy the water views on the deck. The townhouse has a great living room with views and bedrooms

    Karen Overtoom Karen M. Overtoom R.E.

    40 Hidden Cove Rd, Oak Bluffs, MA 02557
  • /29

    $64,000 per month

    • 4 Beds
    • 7 Baths
    • 3,600 Sq Ft
    • House for Rent

    385 Barnes Rd Ob534, Oak Bluffs, MA 02557

    THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $18,000. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING. This is a beautiful waterfront home with a pool on the Lagoon. Enter through the impressive foyer with water views over the pool and lawn. There is a large living room with cathedral ceilings and dining area on the main level. There is a gourmet kitchen with eat-in

    Karen Overtoom Karen M. Overtoom R.E.

    385 Barnes Rd Ob534, Oak Bluffs, MA 02557
  • /25

    $24,000 per month

    • 3 Beds
    • 2 Baths
    • 1,257 Sq Ft
    • House for Rent

    5 Laurel Ave, Oak Bluffs, MA 02557

    THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $6,500. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING. Wonderful, fully redecorated Gingerbread house on East Chop, just minutes from the excitement of Oak Bluffs. There are three bedrooms and two full baths. The interior is clean and crisp, with beach cottage décor and beautiful bamboo floors. Entertainment options include

    Karen Overtoom Karen M. Overtoom R.E.

    5 Laurel Ave, Oak Bluffs, MA 02557
  • /30

    $20,000 per month

    • 4 Beds
    • 2 Baths
    • 1,920 Sq Ft
    • House for Rent

    291 Barnes Rd Ob516, Oak Bluffs, MA 02557

    THIS IS A WEEKLY SUMMER RENTAL ONLY.SEE WEB SITE FOR WEEKLY PRICING. Feel the ocean breezes from this classic waterfront home. There are four bedrooms, an open living room and dining room that open up to large deck overlooking beautiful views across the Lagoon. Walking path to private sandy beach. BOAT MOORING INCLUDED.

    Karen Overtoom Karen M. Overtoom R.E.

    291 Barnes Rd Ob516, Oak Bluffs, MA 02557
  • /14

    $14,200 per month

    • 3 Beds
    • 2 Baths
    • 1,500 Sq Ft
    • House for Rent

    59 Prospect Ave Ob502, Oak Bluffs, MA 02557

    THIS IS A WEEKLY SUMMER RENTAL ONLY. SEE WEB SITE FOR WEEKLY PRICING. This immaculate home is located in a quiet neighborhood that is just a bike ride's distance from several lovely beaches as well as the center of Oak Bluffs. The home offers open living spaces, generously proportioned sunny bedrooms and is well equipped.

    Karen Overtoom Karen M. Overtoom R.E.

    59 Prospect Ave Ob502, Oak Bluffs, MA 02557
  • /15

    $21,000 per month

    • 6 Beds
    • 2 Baths
    • 1,700 Sq Ft
    • House for Rent

    12 John Wesley Ave Ob519, Oak Bluffs, MA 02557

    THIS IS A SUMMER RENTAL ONLY. EAST CHOP LOCATION!! Located across from the historic Baptist Temple Town Park. This charming 1885 Victorian cottage is original to days gone by and a significant part of the Vineyard Highlands. Six bedrooms and two full bathrooms allow for friends and family to visit along with a cozy, bright vintage kitchen. This is a house of distinctive "Carpenter Gothic"

    Karen Overtoom Karen M. Overtoom R.E.

    12 John Wesley Ave Ob519, Oak Bluffs, MA 02557
  • /11

    $12,500 per month

    • 4 Beds
    • 1.5 Baths
    • 1,413 Sq Ft
    • House for Rent

    11 Wamsutta Ave Ob540, Oak Bluffs, MA 02557

    THIS IS A SUMMER RENTAL ONLY. This antique Vineyard home is thoughtfully styled with classic country-chic interior decor. The wraparound porch has plenty of room to enjoy people watching or sipping ice cold tea, perfect for a hot summer day. Alternatively, you can enjoy peering down the street from the master bedroom which opens up to a charming porch with plenty of room for two to enjoy

    Karen Overtoom Karen M. Overtoom R.E.

    11 Wamsutta Ave Ob540, Oak Bluffs, MA 02557
  • /9

    $6,500 per month

    • 3 Beds
    • 3 Baths
    • 1,645 Sq Ft
    • House for Rent

    23 Ocean Ave Unit OB539, Edgartown, MA 02539

    THIS IS A SUMMER WEEKLY RENTAL ONLY. PRICES ARE WEEKLY NOT MONTHLY. Victorian Cottage located on Ocean Park in the heart of Oak Bluffs with fully equipped and updated kitchen, five bedrooms and three baths, cozy living spaces and multiple amenities will accommodate your family and friends. Smell the sea air and watch the waves break from your front porch. This charming beach house is steps away

    Karen Overtoom Karen M. Overtoom R.E.

    23 Ocean Ave Unit OB539, Edgartown, MA 02539
  • /11

    $21,000 per month

    • 3 Beds
    • 2 Baths
    • 1,481 Sq Ft
    • House for Rent

    24 Deer Run Rd Unit OB521, Vineyard Haven, MA 02568

    THIS IS A SUMMER RENTAL ONLY. Centrally located to Edgartown, Vineyard Haven and Oak Bluffs. Just a short drive will take you to any of the town beaches and the Sailing Camp Park is a quick bike ride away. The home is located on over a 1/2 acre of landscaped property in a beautiful, private, neighborhood, with private roads great for biking and is wonderful for families, friends or even a

    Karen Overtoom Karen M. Overtoom R.E.

    24 Deer Run Rd Unit OB521, Vineyard Haven, MA 02568
  • /14

    $20,000 per month

    • 3 Beds
    • 1 Bath
    • 1,629 Sq Ft
    • House for Rent

    67 New York Ave Unit OB536, Oak Bluffs, MA 02557

    THIS IS A SUMMER RENTAL ONLY. 1900 Oak Bluffs Victorian. Ten minute walk to Nancy’s restaurant/downtown OB and 1/2 mile walk to Jetty beach in East Chop. The house was purchased empty in 2018 so all furnishings are new and the house is freshly painted. On the second floor, there are 3 bedrooms and a full bathroom, which connects to hall and master bedroom. Two bedrooms include queen beds and

    Karen Overtoom Karen M. Overtoom R.E.

    67 New York Ave Unit OB536, Oak Bluffs, MA 02557
  • /16

    $40,000 per month

    • 4 Beds
    • 3 Baths
    • 2,748 Sq Ft
    • House for Rent

    38 Farm Pond Ob524, Oak Bluffs, MA 02557

    THIS IS A SUMMER RENTAL ONLY. Gracious 4 bedroom home with private beach access and tennis. This home has a reverse design that has been fully renovated and thoughtfully decorated. There is a large deck overlooking gardens and a peep of the water. A separate studio is attached by the deck. You are a short distance from town, less than a mile to the public beach and a minutes to a beautiful

    Karen Overtoom Karen M. Overtoom R.E.

    38 Farm Pond Ob524, Oak Bluffs, MA 02557
  • /21

    $13,000 per month

    • 4 Beds
    • 3 Baths
    • 2,500 Sq Ft
    • House for Rent

    14 Pulpit Rock Rd, Oak Bluffs, MA 02557

    PRICES ARE WEEKLY NOT MONTHLY. Located in Waterview Farms, this four bedroom home features a private beach on Sengekontacket Pond, private dock access to Land Bank boat launch and several walking trails. Just minutes to Farm Neck Golf Course, beaches and town.

    Karen Overtoom Karen M. Overtoom R.E.

    14 Pulpit Rock Rd, Oak Bluffs, MA 02557
  • /15

    $40,000 per month

    • 6 Beds
    • 3 Baths
    • 1,704 Sq Ft
    • House for Rent

    120 Eastville Ave Ob520, Oak Bluffs, MA 02557

    THIS IS A SUMMER RENTAL ONLY. Watch the boats come and go from the harbor while you picnic and relax on your beach. This fabulous waterfront three bedroom main house and three bedroom guest house also offers your own dock and mooring.

    Karen Overtoom Karen M. Overtoom R.E.

    120 Eastville Ave Ob520, Oak Bluffs, MA 02557
  • /8

    $56,000 per month

    • 4 Beds
    • 2.5 Baths
    • 3,000 Sq Ft
    • House for Rent

    337 Barnes Rd Ob526, Oak Bluffs, MA 02557

    THIS IS A SUMMER RENTAL ONLY. This home offers a spacious open floor plan providing a comfortable yet elegant retreat, truly an upscale surprise, perfect for relaxing or entertaining. With an expansive mahogany wraparound deck, sweeping views and a screened-in porch, enjoying the evening sunsets while grilling and dining al fresco or try a nearby bistro or 5 star restaurant----the choice is

    Karen Overtoom Karen M. Overtoom R.E.

    337 Barnes Rd Ob526, Oak Bluffs, MA 02557
  • /8

    $12,000 per month

    • 3 Beds
    • 1.5 Baths
    • 820 Sq Ft
    • House for Rent

    8 Beach Plum Path Ob525, Oak Bluffs, MA 02557

    THIS IS A SUMMER RENTAL ONLY. This irresistible home is a 3-minute walk away from a deeded, sandy, sheltered beach and only a 5-minute drive to the center of Oak Bluffs and all the fun activities that Circuit Avenue has to offer. The casual getaway has wonderful ambiance enhanced by its soaring ceilings, a wood-burning fireplace, and delightful furnishings.

    Karen Overtoom Karen M. Overtoom R.E.

    8 Beach Plum Path Ob525, Oak Bluffs, MA 02557
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