Entire home
Oak Bluffs Family Retreat - Private Roundabout, Walk to the Beach & Downtown OB.
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Reviews
10 out of 10, Loved by Guests
Top 10% of guest reviews in this area
3 bedrooms2+ bathroomsSleeps 6
Popular amenities
Explore the area

Oak Bluffs, MA
- Place, Oak Bluffs Harbor8 min walk
- Place, Circuit Avenue13 min walk
- Place, Inkwell Beach3 min drive
- Airport, Vineyard Haven, MA (MVY-Martha's Vineyard)19 min drive
Rooms & beds
3 bedrooms (sleeps 6)
Bedroom 1
2 Single Beds
Bedroom 2
1 King Bed
Bedroom 3
1 Queen Bed
Lower Level has a Pull Out Couch
1 Double Futon
2 bathrooms, 1 half bathroom
Bathroom 1
Toilet
Bathroom 2
Toilet · Shower only
Bathroom 3
Bathtub or shower · Bathtub · Toilet · Shower only
Spaces
Deck or patio
Kitchen
Outdoor play area
About this property
Oak Bluffs Family Retreat - Private Roundabout, Walk to the Beach & Downtown OB.
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House Rules
Important information
You need to know
Property Registration Number C2050898600
About the area
Oak Bluffs
Oak Bluffs is home to this holiday home. While the natural beauty of Inkwell Beach and Cape Cod Beaches can be enjoyed by anyone, those looking for an activity can explore Woods Hole Ferry Terminal.
Flying Horses Carousel and Island Cove Adventures are also worth visiting.

Oak Bluffs, MA
What's nearby
- Oak Bluffs Public Library - 5 min walk - 0.4 km
- Oak Bluffs Harbor - 8 min walk - 0.7 km
- Circuit Avenue - 13 min walk - 1.1 km
- Oak Bluffs Town Beach - 18 min walk - 1.5 km
- Inkwell Beach - 3 min drive - 1.5 km
Getting around
Restaurants
- Offshore Ale Co. - 3 min drive
- The Barn Bowl & Bistro - 16 min walk
- Lookout Tavern - 20 min walk
- Mo's Lunch - 10 min walk
- Portuguese-American Club - 14 min walk
Frequently asked questions
Reviews
10
Exceptional
Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labelled.
Learn moreOpens in a new window10/10
Cleanliness
10/10
Check-in
10/10
Communication
9.8/10
Location
10/10
Listing accuracy
Reviews
Verified
22 September 2025
Liked: Cleanliness, check-in, communication, location, listing accuracy
Stayed 3 nights in Sep 2025
Verified
10/10 Excellent
Camille U.
2 August 2025
Liked: Cleanliness, check-in, communication, location, listing accuracy
Camille U.
Stayed 6 nights in Jul 2025
Verified
10/10 Excellent
Catherine G.
22 June 2025
Liked: Cleanliness, check-in, communication, location, listing accuracy
Perfect weekend
Catherine G.
Stayed 3 nights in Jun 2025
Verified
10/10 Excellent
Katisha V.
28 May 2023
Liked: Cleanliness, check-in, communication, location, listing accuracy
Charming in Martha’s Vineyard
Katisha V.
Stayed 3 nights in May 2023
Verified
10/10 Excellent
Katharyn F.
14 July 2025
Liked: Cleanliness, check-in, communication, location, listing accuracy
Oak Bluffs Retreat
Katharyn F.
Stayed 3 nights in Jul 2025
Verified
10/10 Excellent
Ashley G.
26 July 2024
Liked: Cleanliness, check-in, communication, location, listing accuracy
Great property!
Ashley G.
Stayed 4 nights in Jul 2024
Verified
10/10 Excellent
Jennifer T.
27 September 2023
Liked: Cleanliness, check-in, communication, location, listing accuracy
Jennifer T
Jennifer T.
Stayed 3 nights in Sep 2023
Verified
10/10 Excellent
Patrick M.
6 June 2023
Liked: Cleanliness, check-in, communication, location, listing accuracy
Excellent
Patrick M.
Stayed 5 nights in Jun 2023
Verified
10/10 Excellent
Sarah S.
1 July 2024
Liked: Cleanliness, check-in, communication, location, listing accuracy
Sister Weekend Getaway
Sarah S.
Stayed 3 nights in Jun 2024
Verified
10/10 Excellent
Karen G.
15 August 2024
Liked: Cleanliness, check-in, communication, location, listing accuracy
Great home, Great hospitality!
Karen G.
Stayed 7 nights in Aug 2024
Verified
10/10 Excellent
Angela L.
5 September 2024
Liked: Cleanliness, check-in, communication, location, listing accuracy
As advertised
Angela L.
Stayed 7 nights in Aug 2024
Verified
10/10 Excellent
Constance K.
15 August 2023
Liked: Cleanliness, check-in, communication, location, listing accuracy
Magical Stay!!
Constance K.
Stayed 8 nights in Aug 2023
Verified
10/10 Excellent
David S.
29 July 2025
Liked: Cleanliness, check-in, communication, location, listing accuracy
Beautiful home, comfortable stay!




David S.
Stayed 7 nights in Jul 2025
Verified
10/10 Excellent
Scott M.
30 June 2023
Liked: Cleanliness, check-in, communication, location, listing accuracy
Great house for a family or two
Scott M.
Stayed 4 nights in Jun 2023
Verified
10/10 Excellent
Clifford R.
5 August 2022
Liked: Cleanliness, check-in, communication, location, listing accuracy
Responsive and considerate communication and oversight
Clifford R.
Stayed 21 nights in Jul 2022
Verified
10/10 Excellent
Alicia O.
26 August 2022
Liked: Cleanliness, check-in, communication, location, listing accuracy
Fantastic time
Alicia O.
Stayed 5 nights in Aug 2022
Verified
10/10 Excellent
natalie t.
18 July 2022
Liked: Cleanliness, check-in, communication, location, listing accuracy
Stunning home! Great layout for families.
natalie t.
Stayed 3 nights in Jul 2022
About the host
Hosted by Jason
We only recently discovered the serenity and magic of Martha's Vineyard. We continue to meet really amazing old and new friends, who live, visit and vacation on Martha's Vineyard. My wife and I have been VRBO (formerly HomeAway) hosts since 2013. We have earned over 200 5-Star ratings mostly because we truly care about the experiences that our guests have while staying in our rental home and spending time in our neighborhood.
Why they chose this property
This property is special because it is a short walk away from the center of Oak Bluffs and also close to the beach. The property itself feels tucked away, so after a long day, you will feel and experience privacy similar to a house located on lots of land, while having breakfast or an afternoon dinner with family.
What makes this property unique
The lower level adds a great outlet for quiet reading and/or media entertainment before or after a day out for the day.
Premier Host
They consistently provide great experiences for their guests
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