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Oak Bluffs Vacation Rentals

One of the island’s most popular destinations, Oak Bluffs offers a broad range of attractions for kids and adults, from ice cream parlors and an arcade to the dozens of shops, restaurants, and bars along and around Circuit Avenue. The town hosts annual special events, including late-summer fireworks at Ocean Park and Illumination Night, when Campground residents put thousands of unique and colorful Chinese lanterns on display. 

You can also view all of our Martha's Vineyard Vacation Rentals.  Or search for rentals in EdgartownEdgartown VillageKatamaChilmarkVineyard Haven Tisbury, or West Tisbury.

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discount tag Summer Savings 2025

Looking for some special summer 2025 rate savings and deals? We assembled a collection of our top picks with savings up to $4,000/week off. Please contact our Rental Team if you'd like to book one of these special Martha's Vineyard vacation rental deals -- call us at 508.939.9422 or email

Luxurious Coastal-Style Living With Pool And Hot Tub In The Preserve $10,000 - $30,000/week

  • Property Highlights
    Unit Code: OB RSMI-16
    Pets Considered: No
    Town/Area: Oak Bluffs
    • Bedrooms:5
    • Bath: 6.5
    • Sleeps:12
  • Description:
    **JULY+AUGUST SPECIAL: SAVE $4,000/WEEK OFF ANY OPEN WEEKS (7/6 - 8/31) | NEW RATES PROGRAMMED** POINT B EXCLUSIVE -... Read More

discount tag Ferry Tickets Available

While most peak July and August summer weekends have already sold out, we do have a collection of vacation rentals where the owner already has some transferable car ferry tickets in place. Check with us for availability and cost (expect around $340). You can email the Rental Team or call us 508.939.9422.

Luxurious Oak Bluffs Contemporary With Water Views $5,500 - $13,000/week

  • Property Highlights
    Unit Code: OB EVAN-07
    Pets Considered: No
    Town/Area: Oak Bluffs
    • Bedrooms:4
    • Bath: 4.5
    • Sleeps:8
  • Description:
    POINT B EXCLUSIVE - This freshly renovated Luxurious Contemporary combines water views out to Sengekontacket Pond from... Read More

discount tag JAWS 50th Anniversary Festival

Summer 2025 marks the 50th anniversary of the classic scary beach movie JAWS. Much of it was filmed right here on Amity Island -- as Martha's Vineyard was called in the movie -- and there are a large variety of Jaws festival events during the third week of June (June 20 - 29). Thinking of coming? We've got some great vacation rental options across the island. Our Rental Team is here and ready to help you. Please reach out to us by phone 508-939-9422 or email.

Coastal Farmhouse With Connected Carriage House $6,600 - $12,500/week

  • Property Highlights
    Unit Code: OB KMCD-09
    Pets Considered: No
    Town/Area: Oak Bluffs
    • Bedrooms:5
    • Bath: 4.5
    • Sleeps:10
  • Description:
    POINT B EXCLUSIVE - This newly built Farmhouse with Connected Carriage House features a modern coastal-style with nice... Read More

discount tag Ferry Tickets Available

While most peak July and August summer weekends have already sold out, we do have a collection of vacation rentals where the owner already has some transferable car ferry tickets in place. Check with us for availability and cost (expect around $340). You can email the Rental Team or call us 508.939.9422.

Sengekontacket Contemporary With Water Views $4,000 - $10,500/week

  • Property Highlights
    Unit Code: OB SVIC-20
    Pets Considered: Yes
    Town/Area: Oak Bluffs
    • Bedrooms:4
    • Bath: 4.5
    • Sleeps:8
  • Description:
    POINT B EXCLUSIVE - Tucked away in the desirable Waterview Farm enclave on Sengekontacket Pond, this newly outfitted... Read More

discount tag JAWS 50th Anniversary Festival

Summer 2025 marks the 50th anniversary of the classic scary beach movie JAWS. Much of it was filmed right here on Amity Island -- as Martha's Vineyard was called in the movie -- and there are a large variety of Jaws festival events during the third week of June (June 20 - 29). Thinking of coming? We've got some great vacation rental options across the island. Our Rental Team is here and ready to help you. Please reach out to us by phone 508-939-9422 or email.

Modern Farmhouse In Central Oak Bluffs Neighborhood $5,600 - $9,317/week

  • Property Highlights
    Unit Code: OB EEXU-29
    Pets Considered: No
    Town/Area: Oak Bluffs
    • Bedrooms:3
    • Bath: 3.5
    • Sleeps:8
  • Description:
    POINT B EXCLUSIVE - This newly-built Modern Farmhouse is tucked away in a quiet and centrally located neighborhood in... Read More

discount tag July 4th Week

The fourth of July week on Martha's Vineyard is one of the iconic weeks to enjoy the Vineyard. During the day, there is the quintessential July 4th parade in Edgartown followed by the fireworks over Edgartown Harbor and Edgartown Lighthouse. Both events -- truly epic and totally Martha's Vineyard. We have a curated collection of the best vacation rentals on Martha's Vineyard that are available during this magic time period (June 28th - July 11th). Our Rental Team is here and ready to help you. Please reach out to us by phone 508-939-9422 or email.

Modern Colonial Near The Lagoon $2,700 - $7,500/week

  • Property Highlights
    Unit Code: OB GASH-12
    Pets Considered: No
    Town/Area: Oak Bluffs
    • Bedrooms:3
    • Bath: 3.5
    • Sleeps:6
  • Description:
    POINT B EXCLUSIVE - This recently built Modern Colonial has a stylish Vineyard vibe throughout, and is tucked away in a... Read More

Water View Cottage At Sunset Lake $5,000 - $7,500/week

  • Property Highlights
    Unit Code: OB MLLO-14
    Pets Considered: No
    Town/Area: Oak Bluffs
    • Bedrooms:3
    • Bath: 2.0
    • Sleeps:6
  • Description:
    POINT B EXCLUSIVE -- This classic Oak Bluffs cottage sits at the edge of Sunset Lake and enjoys views across the Lake on... Read More

discount tag JAWS 50th Anniversary Festival

Summer 2025 marks the 50th anniversary of the classic scary beach movie JAWS. Much of it was filmed right here on Amity Island -- as Martha's Vineyard was called in the movie -- and there are a large variety of Jaws festival events during the third week of June (June 20 - 29). Thinking of coming? We've got some great vacation rental options across the island. Our Rental Team is here and ready to help you. Please reach out to us by phone 508-939-9422 or email.

Contemporary Cape In Central Oak Bluffs $3,300 - $7,000/week

  • Property Highlights
    Unit Code: OB EEXU-71
    Pets Considered: No
    Town/Area: Oak Bluffs
    • Bedrooms:3
    • Bath: 2.0
    • Sleeps:6
  • Description:
    POINT B EXCLUSIVE - This newly renovated Cape is quietly located in a convenient central Oak Bluffs neighborhood. Newly... Read More

discount tag JAWS 50th Anniversary Festival

Summer 2025 marks the 50th anniversary of the classic scary beach movie JAWS. Much of it was filmed right here on Amity Island -- as Martha's Vineyard was called in the movie -- and there are a large variety of Jaws festival events during the third week of June (June 20 - 29). Thinking of coming? We've got some great vacation rental options across the island. Our Rental Team is here and ready to help you. Please reach out to us by phone 508-939-9422 or email.

Architect Designed Getaway In Bayes Hill $3,900 - $6,695/week

  • Property Highlights
    Unit Code: OB MSKE-41
    Pets Considered: Yes
    Town/Area: Oak Bluffs
    • Bedrooms:3
    • Bath: 2.5
    • Sleeps:8
  • Description:
    POINT B EXCLUSIVE - This architect-designed home is tucked away back in the Bayes Hill enclave, surrounded by... Read More
  • Property Highlights!
    Unit Code: OB VBUT-09
    Pets Considered: No
    Town/Area: Oak Bluffs
    • Bedrooms:9
    • Bath:5.5
    • Sleeps:18
  • Description:
    This water view Compound with a recently renovated six-Bedroom Main House and a newly built three-Bedroom Guest House... Read More
  • Property Highlights!
    Unit Code: OB BFLO-48
    Pets Considered: No
    Town/Area: Oak Bluffs
    • Bedrooms:6
    • Bath:9.5
    • Sleeps:16
  • Description:
    This deluxe compound at The Preserve makes a grand multi-generation or larger group Vineyard getaway destination. There... Read More
  • Property Highlights!
    Unit Code: OB PMOR-12
    Pets Considered: No
    Town/Area: Oak Bluffs
    • Bedrooms:4
    • Bath:6.5
    • Sleeps:8
  • Description:
    This luxurious home at The Preserve is designed for indoor-outdoor living, with modern styling throughout its deluxe... Read More