Aerial view of a Martha’s Vineyard coastal town, with homes, a waterfront pier, and blue ocean.
Aerial view of Oak Bluffs homes, waterfront park, and pier beside the blue ocean.
Aerial view of a coastal neighborhood with tree-lined streets, a broad grassy field, and oceanfront homes.
Aerial view of a blue-gray shingle house with white trim among Oak Bluffs homes.
Gray shingle house with a prominent upper bay window and covered porch on a sunny residential street.
Gray shingle-style house with a covered porch, front gable, and detached garage.
Rental patio with a striped umbrella over a wooden picnic table beside the gray-sided house.
Furnished living and dining room with white paneling, hardwood floors, and a wood-railed staircase.
Furnished living and dining room with white paneling, warm wood floors, and garden-facing French doors.
Bedroom with pale green bedding, a wicker armchair, and a window air conditioner.
Bedroom with a white bed, wicker chair, window air conditioner, and television.
Furnished living room with arched shuttered windows, white sofas, and a wooden staircase.
Furnished living room with white sofas, arched shuttered windows, a wood coffee table, and a ceiling fan.
Living room with a vaulted white ceiling, wide windows, pale blue sofa, and wooden coffee table.
Living room with a vaulted white ceiling, blue media cabinet, wood coffee table, and whale wall art.
Enclosed porch with pale blue ceiling beams, large windows, and wicker chairs overlooking a residential street.
Covered porch with wicker chairs, white shingle siding, and tall windows overlooking the street.
Living room with white sofas, red accent pillows, hardwood floors, and an open view to the kitchen.
Furnished living room with a white sofa, colorful cushions, wood floors, and adjoining dining area.
Dining room with a long wooden table, wide windows, and an open kitchen beyond.
Kitchen with green cabinetry, a large island and breakfast bar, and stainless steel appliances.
Kitchen with sage-green cabinets, dark countertops, stainless steel appliances, and wood-look flooring.
Kitchen with sage-green cabinets, stainless steel appliances, and wood-look flooring.
Kitchen with mint-green cabinets, stainless steel appliances, and wooden steps beside the cooking area.
Kitchen with sage-green cabinetry and island, wood entry door, and dining area beyond.
Bright kitchen with green cabinetry, a stainless steel dishwasher, and a wooden entry door.
Laundry room with washer and dryer, woven baskets, and an open doorway to a small bathroom.
Bathroom with olive-green trim, a tiled walk-in shower, and a compact toilet area.
Tiled shower with a recessed shelf holding toiletries and a wall-mounted shower fixture.
Bathroom with a sage-green vanity, brass fixtures, ornate round mirror, and patterned tile floor.
Bedroom with a white bed beneath a sloped beamed ceiling and beside tall windows.
Bedroom with two beds beneath a vaulted white ceiling, opening to a small bathroom.
Bedroom with two beds in green patterned quilts beneath a high, beam-lined ceiling.
Bedroom with two beds, pale green patterned bedding, and a white beamed ceiling.
Bedroom with two beds beneath a vaulted white ceiling and a hanging red model airplane.
Bathroom with a glass walk-in shower and vessel sink, looking through to a bedroom with pale blue bedding.
Bedroom with a large white bed beneath shuttered windows and a white-beamed ceiling.
Bright bedroom with a white bed and open turquoise doors leading to an enclosed porch.
Bedroom with turquoise arched doors opening to a balcony and gray chairs beside shuttered windows.
Furnished bedroom with a gray bed beneath a white vaulted ceiling and windows behind it.
Bedroom with a gray bed beneath a white vaulted ceiling and exposed beams
SEE ALL PHOTOS
Aerial view of a Martha’s Vineyard coastal town, with homes, a waterfront pier, and blue ocean.
Aerial view of Oak Bluffs homes, waterfront park, and pier beside the blue ocean.
Aerial view of a coastal neighborhood with tree-lined streets, a broad grassy field, and oceanfront homes.
Aerial view of a blue-gray shingle house with white trim among Oak Bluffs homes.
Gray shingle house with a prominent upper bay window and covered porch on a sunny residential street.
Gray shingle-style house with a covered porch, front gable, and detached garage.
Rental patio with a striped umbrella over a wooden picnic table beside the gray-sided house.
Furnished living and dining room with white paneling, hardwood floors, and a wood-railed staircase.
Furnished living and dining room with white paneling, warm wood floors, and garden-facing French doors.
Bedroom with pale green bedding, a wicker armchair, and a window air conditioner.
Bedroom with a white bed, wicker chair, window air conditioner, and television.
Furnished living room with arched shuttered windows, white sofas, and a wooden staircase.
Furnished living room with white sofas, arched shuttered windows, a wood coffee table, and a ceiling fan.
Living room with a vaulted white ceiling, wide windows, pale blue sofa, and wooden coffee table.
Living room with a vaulted white ceiling, blue media cabinet, wood coffee table, and whale wall art.
Enclosed porch with pale blue ceiling beams, large windows, and wicker chairs overlooking a residential street.
Covered porch with wicker chairs, white shingle siding, and tall windows overlooking the street.
Living room with white sofas, red accent pillows, hardwood floors, and an open view to the kitchen.
Furnished living room with a white sofa, colorful cushions, wood floors, and adjoining dining area.
Dining room with a long wooden table, wide windows, and an open kitchen beyond.
Kitchen with green cabinetry, a large island and breakfast bar, and stainless steel appliances.
Kitchen with sage-green cabinets, dark countertops, stainless steel appliances, and wood-look flooring.
Kitchen with sage-green cabinets, stainless steel appliances, and wood-look flooring.
Kitchen with mint-green cabinets, stainless steel appliances, and wooden steps beside the cooking area.
Kitchen with sage-green cabinetry and island, wood entry door, and dining area beyond.
Bright kitchen with green cabinetry, a stainless steel dishwasher, and a wooden entry door.
Laundry room with washer and dryer, woven baskets, and an open doorway to a small bathroom.
Bathroom with olive-green trim, a tiled walk-in shower, and a compact toilet area.
Tiled shower with a recessed shelf holding toiletries and a wall-mounted shower fixture.
Bathroom with a sage-green vanity, brass fixtures, ornate round mirror, and patterned tile floor.
Bedroom with a white bed beneath a sloped beamed ceiling and beside tall windows.
Bedroom with two beds beneath a vaulted white ceiling, opening to a small bathroom.
Bedroom with two beds in green patterned quilts beneath a high, beam-lined ceiling.
Bedroom with two beds, pale green patterned bedding, and a white beamed ceiling.
Bedroom with two beds beneath a vaulted white ceiling and a hanging red model airplane.
Bathroom with a glass walk-in shower and vessel sink, looking through to a bedroom with pale blue bedding.
Bedroom with a large white bed beneath shuttered windows and a white-beamed ceiling.
Bright bedroom with a white bed and open turquoise doors leading to an enclosed porch.
Bedroom with turquoise arched doors opening to a balcony and gray chairs beside shuttered windows.
Furnished bedroom with a gray bed beneath a white vaulted ceiling and windows behind it.
Bedroom with a gray bed beneath a white vaulted ceiling and exposed beams
For Rent

Oak Bluffs Rental

Oak Bluffs Rental

Experience a piece of Oak Bluffs history in this stunning 5-bedroom Tuckernuck home, just 0.2 miles from iconic Inkwell Beach. New to the rental market, this spacious retreat offers classic Vineyard charm with modern comfort and convenience. Enjoy easy walks to the beach, shops, restaurants, ferry, and all that Oak Bluffs has to offer. Perfect for families and groups seeking an unforgettable Martha’s Vineyard summer escape. 5 Beds 2 baths outdoor shower!

August 22 2026-September 6 2026 $8,400/ week
 9/7/2026-12/1/2026 900/night 5 night minimum

  • 2027 Summer Rentals 

    Jun 05, 2027 Jun 18, 2027 $8,000.00

    Jun 19, 2027 Jul 16, 2027 $10,000.00

    Jul 17, 2027 Jul 30, 2027 $12,000.00

    Jul 31, 2027 Aug 20, 2027 $15,000.00

    Aug 21, 2027 Aug 27, 2027 $12,000.00

    Aug 28, 2027 Sep 03, 2027 $9,000.00

    Sep 04, 2027 Sep 17, 2027 $8,000.00

    Sep 18, 2027 Oct 01, 2027 $7,000.00

    Oct 02, 2027 Oct 29, 2027 $5,500.00

Work With Us

With our extensive background in real estate, our intimate knowledge of the island and its amazing community- we are here to make your Vineyard Dream come true. We take pride in specializing in YOU- prioritizing your dreams and needs every step of the way.
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Contact Details

Vineyard Dream Realty

Phone

(508) 254-8034

Email

[email protected]

Address

22 WINTER ST, #2 EDGARTOWN, MA 02539

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