$1,650
Total Monthly Price
53 Pondview Dr, Oak Bluffs, MA 02557
New construction colonial winter rental 3 br ( 1 master with bath ) renting by bedroom $1500 for the 2 bedrooms and $1650 for the master. cable, trash included. electric will be split 3 way. ele heat pump is the heating and ac. The house in very efficient, 25 in of insulation in attic, we have insulation every under the siding. all led lights, the electric should be reasonable.
$64,000 Per Month
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.
$7,323
Total Monthly Price
25 Simpson Ave Unit SI ID1514679P, Oak Bluffs, MA 02568
The advertised rate of $7,323/month is the lowest available price, based on a 30 day(s) stay with a move-in date of December 4, 2026.Rates vary depending on the duration of stay, season, and other parameters. For exact pricing and additional pricing components, please visit our website and enter your desired move-in and move-out dates. The rate is applicable when billed upfront; it can be
$15,000 Per Month
41 Naushon Rd Wt116, Aquinnah, MA 02575
Stunning water views from this expansive beachfront estate in Makonikey off Lambert's Cove Rd. Enjoy the large living area with comfortable couches, floor to ceiling windows and french doors for seamless indoor to outdoor living and dining. There is a fully equipped kitchen. Some folks will enjoy the treadmill and elliptical while watching boats pass by or even play squash in the indoor squash
Karen Overtoom Karen M. Overtoom R.E.
$7,389
Total Monthly Price
13 N Meadow Ln Unit SI ID1514673P, Oak Bluffs, MA 02568
The advertised rate of $7,390/month is the lowest available price, based on a 30 day(s) stay with a move-in date of December 2, 2026.Rates vary depending on the duration of stay, season, and other parameters. For exact pricing and additional pricing components, please visit our website and enter your desired move-in and move-out dates. The rate is applicable when billed upfront; it can be
$20,000 Per Month
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.
$50,000 Per Month
29 Naushon Rd Wt142, West Tisbury, MA 02575
THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $12,500. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING. Waterfront home in spectacular location overlooking the Vineyard Sound and the Elizabeth Islands. This casual and comfortable single level 4 BR 3 bath home has central air and heat. Enjoy summer star-studded skies from your patio or through skylights in each bedroom.
Karen Overtoom Karen M. Overtoom R.E.
$15,000 Per Month
55 Samoset Ave, Oak Bluffs, MA 02557
AVAILABLE SUMMER 2026: JULY 12-AUGUST 9. 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
Allison Cameron Parry Douglas Elliman Real Estate - Nantucket
$19,000 Per Month
40 Sweet William Way, West Tisbury, MA 02575
THIS PROPERTY IS A WEEKLY RENTAL PROPERTY! This stunning home is situated right in the heart of West Tisbury, yet set back enough for a completely private feel. On a property that encompasses 10 acres with your own private pond, you will feel the stress melt away as soon as you get to this luxury vacation home. Keys to private Quansoo Beach Association come with the house. Spend your days on the
Karen Overtoom Karen M. Overtoom R.E.
$24,000 Per Month
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.
$6,800 Per Month
27 Beach Plum Ln, Chilmark, MA 02535
September Availability weekly rental rate negotiable, cost $600-$975 per night depending on season and month 3 night min stay The "Grapevine" is located on a private road .The house has 3 generous size bedrooms all with private baths, 2 of the bedrooms are located on the second floor, 1 bedroom is located on the first floor as well as the Open concept living with a chefs Kitchen, living room
Bryan Hummel Commonwealth Realty Group
$6,000 Per Month
33 Kennebago Ave Vh414, Tisbury, MA 02568
THIS PROPERTY IS A WEEKLY RENTAL PROPERTY!! This beautiful home has lots of open space for cooking, yard activities or just plain relaxing. Private association beach overlooking the Elizabethan Islands. Plan a sunset picnic on the beach or plan in the morning to see the rays of sun break on the water.
Karen Overtoom Karen M. Overtoom R.E.
$32,000 Per Month
37 Mempremagog Ave Vh410, Tisbury, MA 02568
THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $8,200. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING. Fabulous custom designed and decorated four bedroom home is located in a wooded setting that offers total privacy and is with-in walking distance to a private association beach. And yet is only 3 miles from downtown Vineyard Haven. This lovely home offers a gourmet eat-in
Karen Overtoom Karen M. Overtoom R.E.
$18,840 Per Month
21 William St Vh430, Tisbury, MA 02568
THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $4,710. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING. Lovely elegant home with wonderful art and furnishings. Once you step in the front door you will fall in love with this lovely home. Each room is a delight. Large nicely appointed kitchen with easy access to a beautiful dining room. A formal living room is next to a less
Karen Overtoom Karen M. Overtoom R.E.
$17,600 Per Month
50 Carls Way, West Tisbury, MA 02575
THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $4,400. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING. Looking for that perfect setting with a water view? This is the one!!This cute cape is privately set with a water view and direct water access to Town Pond. You can dock your canoes and kyacks here and access Tisbury Great Pond and then right out to the beach. There are
Karen Overtoom Karen M. Overtoom R.E.
$19,000 Per Month
17 Umbagog Ave Wt109, West Tisbury, MA 02575
THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $4,750. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING. This three story home is located in a very desirable area off of Lambert's Cove Road, Makonikey, with access to a private association beach and walking trails. There are four plus bedrooms and bright and open living spaces that lead out to a deck and a screened-in porch.
Karen Overtoom Karen M. Overtoom R.E.
$10,000 Per Month
15 Crowell Lane Wt119, West Tisbury, MA 02575
THIS IS A WEEKLY RENTAL NOT A MONTHLY!!!!!!!Seven Gates Farm. This property has three ponds, overlooks rolling meadows and is very charming. Located in Seven Gates Farm association, the property affords access to association tennis and two miles of private beach as well as miles of walking trails. Bookings for tennis are available at the office for a slight fee.There is a $25 trash charge per
Karen Overtoom Karen M. Overtoom R.E.
$25,000 Per Month
100 Connie's Way Vh401, Tisbury, MA 02568
THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $6,250. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING. Located in Mink Meadows Association, this wonderful four bedroom, three full and one half bath home has many nice features that include a large eat-in kitchen/family room, a more formal living room with fireplace, dining room and den. Televisions in every bedroom, living
Karen Overtoom Karen M. Overtoom R.E.
$20,000 Per Month
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.
$7,500 Per Month
43 Edgartown Rd, Vineyard Haven, MA 02568
Located off of Edgartown-Vineyard Haven Road, close to down-town and bike path, this 3 bedroom, 2 bath property is being offered year round to the right tenants. The home has been completely renovated, is being offered fully furnished and features an open floor plan with wood floors on the first level, wall to wall carpet in the upstairs bedrooms and an in-ground pool in the backyard. Available
Karen Overtoom Karen M. Overtoom R.E.
$13,600 Per Month
64 Bartimus Luce Road Wt125, West Tisbury, MA 02575
THIS IS A WEEKLY RENTAL NOT A MONTHLY!!!!!!!!!!Idyllic location right above a sandy private beach on the North Shore. This beach cottage affords views of the Sound and the Elizabeth Islands with a front row seat on unrivaled sunsets. It is rustic and cozy with a large screened porch overlooking the view. Have a getaway like in days of yore when life was simple and the beach at your doorstep.Take
Karen Overtoom Karen M. Overtoom R.E.
$18,500 Per Month
4 Windy Way Wt143, West Tisbury, MA 02575
THIS PROPERTY IS A WEEKLY RENTAL PROPERTY!! The 3.3 acre private setting is most picturesque with its positioning in private Upper Makonikey , the long circular driveway , its grassy lawn, and rolling landscape fields . Only a short distance away is over 3,000 feet of PRIVATE sandy association Beaches , directly below , with two nearby parking lot access-ways . Nestled onto this promontory is a
Karen Overtoom Karen M. Overtoom R.E.
$8,250 Per Month
227 S Gate Rd Wt120, West Tisbury, MA 02575
THIS PROPERTY IS A WEEKLY PROPERTY!! Set on 12 acres of peaceful woods, meadows, stone walls and its own pond, this charming 18th century 4 bedroom farmhouse and 3 bedroom rustic barn sleeps 12 and is perfect for larger groups wanting peace and tranquility all within a short distance to private swimming beaches. The setting, on exclusive Seven Gates Farm, offers miles of sandy trails through open
Karen Overtoom Karen M. Overtoom R.E.
$17,500 Per Month
550 Chappaquonsett Rd Vh424 Unit 1, Tisbury, MA 02568
THIS PROPERTY IS A WEEKLY RENTAL PROPERTY!!!!!! Classic vineyard cottage with large open indoor and outdoor spaces to choose from while you and your family create memories to last a lifetime. Enjoy creating appetizers or three course meals in the newly renovated kitchen, bask in the light filled sun room or one of several covered porches while you take in the smell of fresh ocean air and relaxing
Karen Overtoom Karen M. Overtoom R.E.
$17,600 Per Month
40 Summer Cir, West Tisbury, MA 02575
THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $4,400. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING. This beautiful tasteful modern home has many charming elements. The bright open airy floor plan offers a generous kitchen, welcoming dining room and living room surrounded by windows and decks with an outdoor table and extra seating. An "upside down" house with the living
Karen Overtoom Karen M. Overtoom R.E.
$18,000 Per Month
71 Bartmus Luce Road Wt154, West Tisbury, MA 02575
THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $5,000. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING. Finest Views on the Island!! This house is set high on a hill surrounded by nature. The expansive views from the front of this house are spectacular. Enjoy the large deck or the screened porch and gaze upon one of the most amazing Vineyard Views available. It is a short
Karen Overtoom Karen M. Overtoom R.E.
$28,500 Per Month
9 Tuckernuck Ave, Oak Bluffs, MA 02557
**SHORT TERM ONLY - WEEKLY RATE ADVERTISED ** 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
Allison Cameron Parry Douglas Elliman Real Estate - Nantucket
$3,000 Per Month
41 Oak Lane Wt147, West Tisbury, MA 02575
THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $3,200. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING. Inside the front entrance is a large open living room with a comfortable L-shaped couch facing the floor to ceiling windows which look out onto the spacious tree lined back yard and a wall mounted flat screen television. Off the open concept living/dining room is a large
Karen Overtoom Karen M. Overtoom R.E.
$20,000 Per Month
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.
$10,000 Per Month
100 Franklin Terrace Vh411, Tisbury, MA 02568
THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $2,500. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING. This charming 3 bedroom home offers open living, dining and kitchen space that open to a screened-in porch and patio. You are located in a peaceful setting yet with-in walking distance to Lake Tashmoo, town beaches, and the Vineyard Haven Village for dining, shopping and
Karen Overtoom Karen M. Overtoom R.E.
$10,800 Per Month
256 Sandpiper Lane Vh417, Tisbury, MA 02568
THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $2,700. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING. This well appointed condo will make you feel comfortable and at home the moment you walk in. Swimming, kayaking, tennis, walking trails, and shopping are all at your finger tips. Mink Meadows Golf Course is just a stroll down the street as well. Enjoy all the Island has
Karen Overtoom Karen M. Overtoom R.E.
$7,500 Per Month
83 Ashtons Way, Vineyard Haven, MA 02568
THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $1,875. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING. This two bedroom cottage is set in a private setting in the woods, just a short distance to downtown Vineyard Haven. Sleeps four comfortably, open living space, deck and outside shower. If rented with the main house, access to private association beach and golf would be
Karen Overtoom Karen M. Overtoom R.E.
$8,000 Per Month
10 James Pond Way, West Tisbury, MA 02575
THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $2,000. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING. This spacious and well appointed one bedroom guest house has a cozy living area and kitchen which opens up to a large second story deck with outdoor furniture, table and chairs where you can enjoy dining amidst the trees. One A/C unit is in the bedroom along with a
Karen Overtoom Karen M. Overtoom R.E.
$12,000 Per Month
76 Ben Chase Rd Wt136, West Tisbury, MA 02575
Experience a wonderful glimpse of country living in the peaceful, quiet setting of Serene Pond Cottage! This charming Martha's Vineyard retreat features a cozy interior with ample natural light, a private deck where you can take your breakfast and coffee, and a tree-lined backyard to enjoy on lazy summer days. Comfortable three bedroom single story home with one brand new renovated full bath with
Karen Overtoom Karen M. Overtoom R.E.
$12,000 Per Month
223 Sandpiper Lane Vh405, Tisbury, MA 02568
THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $3,000. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING. This three bedroom two bath condo is just a short walk to association tennis, pool and the beach. Comfortable easy summer living with outdoor shower, spacious deck, and central AC for those really hot August days!Amenities include Direct TV DVD set up. There is an open
Karen Overtoom Karen M. Overtoom R.E.
$112,000 Per Month
31 Lamberts Cove Road Vh434, Tisbury, MA 02568
Karen Overtoom Karen M. Overtoom R.E.
$10,000 Per Month
24 Nat's Farm Lane Wt113, West Tisbury, MA 02575
THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $2,500. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING. Charming three bedroom home located in a private neighborhood close to bike path, walking trails and public tennis courts. Just a short drive to Lambert's Cove Beach, West Tisbury Village and down island restaurants and shops.Amenities include High definition TV, wifi
Karen Overtoom Karen M. Overtoom R.E.
$8,500 Per Month
29 Bea Lane Wt160 Unit 1, West Tisbury, MA 02575
THIS IS A WEEKLY RENTAL PROPERTY!! Red Farm, Off Lambert's Cove Road West Tisbury. This newly built Contemporary Home is privately sited overlooking a peaceful meadow and wooded setting. The spacious floor plan features an open living, dining and a well equipped chef's kitchen, cathedral ceilings, wood floors and sliders that lead to a nicely landscaped yard. Three spacious bedrooms, the primary
Karen Overtoom Karen M. Overtoom R.E.
$13,500 Per Month
14 Bernard Cir, Vineyard Haven, MA 02568
** SUMMER WEEKLY RATE ** Private and luxurious BRAND NEW contemporary chic 5 BED 5.5 BATH home perfectly situated close to downtown Vineyard Haven yet set amongst a rural and peaceful WEST CHOP adjacent neighborhood. Indulge and unwind in the PRIVATE HEATED SALTWATER IN-GROUND POOL surrounded by opulent outdoor living and dining area highlighted by covered al-fresco kitchen, BBQ grill and bar -
Allison Cameron Parry Douglas Elliman Real Estate - Nantucket
$5,000 Per Month
90 Edgartown Rd, Vineyard Haven, MA 02568
*Summer Weekly Rate** Inquire For Long-term Off-Season Rates. Renovated Studio Cottage on Martha's Vineyard w/private feel. Within walking distance to shops, dining, and the ferry. Lots of trees for year-round enjoyment. Open floor plan with Murphy bed for additional space and a large comfortable sofa, galley kitchen with granite countertops, stainless steel appliances, amazing tiled bathroom
Kim Seawright Generations Realty Group
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