Oak Bluffs Rentals


Our Oak Bluffs rentals are the prime destination for your summer vacation to Martha's Vineyard. Its fun and active ambiance really opens up with the arrival of Memorial weekend and stays in full swing until Columbus weekend. It has historically been a summer destination dating back to the mid 1800’s when the camp ground cottages were developed as a Methodist summer retreat which actually started with camp sites and developed into the quaint, colorful gingerbread cottages that we see today.

For attractions near your Oak Bluffs vacation rentals, visit the town center,  located on the harbor where you will find a high energy level with hundreds of boats coming and going. Circuit Avenue is the commercial heart of Oak Bluffs. It has ice cream and sunscreen, coffee stands and souvenir shops. It has Reliable Self-Serve Market, family owned and operated, and Giordano's Restaurant and Clam Bar, offering up family style meals since 1930. It has Back Door Doughnuts (on a summer's night, between 9 p.m. and 12:30 a.m., buy them fresh from the oven in the parking lot behind Reliable Market.). Circuit Avenue starts with the Flying Horses Carousel, the nation's oldest operating platform carousel and a National Historical Landmark owned by the Martha's Vineyard Preservation Trust and ends with the start of the Art District on the other end. Oak Bluffs also hosts the "summer” steamship authority terminal adding to its high summer foot traffic.

There are many residential areas outside of the downtown that offer quiet privacy for your summer vacation yet have easy access to downtown Oak Bluffs, Edgartown and Vineyard Haven. Contact us for more information about any of the Oak Bluffs rentals on our site.


Leave this field empty

Map All Results

Available Unavailable Check In Check Out
  • Property Highlights
    Area: Oak Bluffs
    Turnover Day: Saturday
    Pets Allowed: No
    • 4Bedrooms:
    • 2.5Baths:
    • 8Sleeps:
  • Description:
    BR1 King, en suite with shower stall, BR2 Queen, BR3 Double, BR4 (2)Twin beds. All bedrooms located on first floor. Hal...Read More
June 2019
SuMoTuWeThFrSa
1
2 3 4 5 6 7 8
9 10 11 12 13 14 15
16 17 18 19 20 21 22
23 24 25 26 27 28 29
30
July 2019
SuMoTuWeThFrSa
1 2 3 4 5 6
7 8 9 10 11 12 13
14 15 16 17 18 19 20
21 22 23 24 25 26 27
28 29 30 31
August 2019
SuMoTuWeThFrSa
1 2 3
4 5 6 7 8 9 10
11 12 13 14 15 16 17
18 19 20 21 22 23 24
25 26 27 28 29 30 31
September 2019
SuMoTuWeThFrSa
1 2 3 4 5 6 7
8 9 10 11 12 13 14
15 16 17 18 19 20 21
22 23 24 25 26 27 28
29 30
  • Property Highlights
    Area: Oak Bluffs
    Turnover Day: Sunday
    Pets Allowed: No
    • 4Bedrooms:
    • 2.5Baths:
    • 8Sleeps:
  • Description:
    BR#1 Queen Bedroom first floor, BR#2 Queen Bedroom first floor, BR#3 Queen Bedroom second floor, BR#4 (2) Twins and a Fu...Read More
June 2019
SuMoTuWeThFrSa
1
2 3 4 5 6 7 8
9 10 11 12 13 14 15
16 17 18 19 20 21 22
23 24 25 26 27 28 29
30
July 2019
SuMoTuWeThFrSa
1 2 3 4 5 6
7 8 9 10 11 12 13
14 15 16 17 18 19 20
21 22 23 24 25 26 27
28 29 30 31
August 2019
SuMoTuWeThFrSa
1 2 3
4 5 6 7 8 9 10
11 12 13 14 15 16 17
18 19 20 21 22 23 24
25 26 27 28 29 30 31
September 2019
SuMoTuWeThFrSa
1 2 3 4 5 6 7
8 9 10 11 12 13 14
15 16 17 18 19 20 21
22 23 24 25 26 27 28
29 30
  • Property Highlights
    Area: Oak Bluffs
    Turnover Day: Saturday
    Pets Allowed: No
    • 3Bedrooms:
    • 2.5Baths:
    • 8Sleeps:
  • Description:
    BR1 King en suite shower stall first floor, BR2 Queen, second floor, BR3 (2) Queen beds with shared hall bathroom of tub...Read More
June 2019
SuMoTuWeThFrSa
1
2 3 4 5 6 7 8
9 10 11 12 13 14 15
16 17 18 19 20 21 22
23 24 25 26 27 28 29
30
July 2019
SuMoTuWeThFrSa
1 2 3 4 5 6
7 8 9 10 11 12 13
14 15 16 17 18 19 20
21 22 23 24 25 26 27
28 29 30 31
August 2019
SuMoTuWeThFrSa
1 2 3
4 5 6 7 8 9 10
11 12 13 14 15 16 17
18 19 20 21 22 23 24
25 26 27 28 29 30 31
September 2019
SuMoTuWeThFrSa
1 2 3 4 5 6 7
8 9 10 11 12 13 14
15 16 17 18 19 20 21
22 23 24 25 26 27 28
29 30
  • Property Highlights
    Area: Oak Bluffs
    Turnover Day: Saturday
    Pets Allowed: No
    • 3Bedrooms:
    • 2.0Baths:
    • 8Sleeps:
  • Description:
    BR1 Queen first floor en suite shower stall, BR2 Double second floor, BR3 Double second floor, hall bath with claw-foot ...Read More
June 2019
SuMoTuWeThFrSa
1
2 3 4 5 6 7 8
9 10 11 12 13 14 15
16 17 18 19 20 21 22
23 24 25 26 27 28 29
30
July 2019
SuMoTuWeThFrSa
1 2 3 4 5 6
7 8 9 10 11 12 13
14 15 16 17 18 19 20
21 22 23 24 25 26 27
28 29 30 31
August 2019
SuMoTuWeThFrSa
1 2 3
4 5 6 7 8 9 10
11 12 13 14 15 16 17
18 19 20 21 22 23 24
25 26 27 28 29 30 31
September 2019
SuMoTuWeThFrSa
1 2 3 4 5 6 7
8 9 10 11 12 13 14
15 16 17 18 19 20 21
22 23 24 25 26 27 28
29 30
  • Property Highlights
    Area: Oak Bluffs
    Turnover Day: Sunday
    Pets Allowed: Yes, with approval
    • 3Bedrooms:
    • 2.0Baths:
    • 6Sleeps:
  • Description:
    BR 1 (2) Twin beds, first floor, BR 2 (2) Twin beds, second floor (with option to convert to KING bed) BR 3 Queen, Maste...Read More
June 2019
SuMoTuWeThFrSa
1
2 3 4 5 6 7 8
9 10 11 12 13 14 15
16 17 18 19 20 21 22
23 24 25 26 27 28 29
30
July 2019
SuMoTuWeThFrSa
1 2 3 4 5 6
7 8 9 10 11 12 13
14 15 16 17 18 19 20
21 22 23 24 25 26 27
28 29 30 31
August 2019
SuMoTuWeThFrSa
1 2 3
4 5 6 7 8 9 10
11 12 13 14 15 16 17
18 19 20 21 22 23 24
25 26 27 28 29 30 31
September 2019
SuMoTuWeThFrSa
1 2 3 4 5 6 7
8 9 10 11 12 13 14
15 16 17 18 19 20 21
22 23 24 25 26 27 28
29 30
  • Property Highlights
    Area: Oak Bluffs
    Turnover Day: Saturday
    Pets Allowed: No
    • 4Bedrooms:
    • 2.5Baths:
    • 8Sleeps:
  • Description:
    BR 1 - Two twins, BR 2 - Two twins, BR 3 - Two twins, BR 4 - Queen...Read More
June 2019
SuMoTuWeThFrSa
1
2 3 4 5 6 7 8
9 10 11 12 13 14 15
16 17 18 19 20 21 22
23 24 25 26 27 28 29
30
July 2019
SuMoTuWeThFrSa
1 2 3 4 5 6
7 8 9 10 11 12 13
14 15 16 17 18 19 20
21 22 23 24 25 26 27
28 29 30 31
August 2019
SuMoTuWeThFrSa
1 2 3
4 5 6 7 8 9 10
11 12 13 14 15 16 17
18 19 20 21 22 23 24
25 26 27 28 29 30 31
September 2019
SuMoTuWeThFrSa
1 2 3 4 5 6 7
8 9 10 11 12 13 14
15 16 17 18 19 20 21
22 23 24 25 26 27 28
29 30
  • Property Highlights
    Area: Oak Bluffs
    Turnover Day: Sunday
    Pets Allowed: No
    • 1Bedrooms:
    • 1.0Baths:
    • 3Sleeps:
  • Description:
    BR1 Queen bedroom with a Jack and Jill type bathroom of shower stall. A small office area with (1)Twin bed. Washer/Dryer...Read More
June 2019
SuMoTuWeThFrSa
1
2 3 4 5 6 7 8
9 10 11 12 13 14 15
16 17 18 19 20 21 22
23 24 25 26 27 28 29
30
July 2019
SuMoTuWeThFrSa
1 2 3 4 5 6
7 8 9 10 11 12 13
14 15 16 17 18 19 20
21 22 23 24 25 26 27
28 29 30 31
August 2019
SuMoTuWeThFrSa
1 2 3
4 5 6 7 8 9 10
11 12 13 14 15 16 17
18 19 20 21 22 23 24
25 26 27 28 29 30 31
September 2019
SuMoTuWeThFrSa
1 2 3 4 5 6 7
8 9 10 11 12 13 14
15 16 17 18 19 20 21
22 23 24 25 26 27 28
29 30
  • Property Highlights
    Area: Oak Bluffs
    Turnover Day: Saturday
    Pets Allowed: No
    • 3Bedrooms:
    • 2.5Baths:
    • 12Sleeps:
  • Description:
    BR1 Queen, second floor with full bathroom, BR2 (2) Twin beds, lower level with shared full hall bath, BR3 (2) Double be...Read More
June 2019
SuMoTuWeThFrSa
1
2 3 4 5 6 7 8
9 10 11 12 13 14 15
16 17 18 19 20 21 22
23 24 25 26 27 28 29
30
July 2019
SuMoTuWeThFrSa
1 2 3 4 5 6
7 8 9 10 11 12 13
14 15 16 17 18 19 20
21 22 23 24 25 26 27
28 29 30 31
August 2019
SuMoTuWeThFrSa
1 2 3
4 5 6 7 8 9 10
11 12 13 14 15 16 17
18 19 20 21 22 23 24
25 26 27 28 29 30 31
September 2019
SuMoTuWeThFrSa
1 2 3 4 5 6 7
8 9 10 11 12 13 14
15 16 17 18 19 20 21
22 23 24 25 26 27 28
29 30
  • Property Highlights
    Area: Oak Bluffs
    Turnover Day: Saturday
    Pets Allowed: No
    • 5Bedrooms:
    • 4.5Baths:
    • 12Sleeps:
  • Description:
    BR1 King en suite first floor, BR2 King en suite second floor, BR3 (1) Twin and Queen sleeper sofa en suite second floor...Read More
June 2019
SuMoTuWeThFrSa
1
2 3 4 5 6 7 8
9 10 11 12 13 14 15
16 17 18 19 20 21 22
23 24 25 26 27 28 29
30
July 2019
SuMoTuWeThFrSa
1 2 3 4 5 6
7 8 9 10 11 12 13
14 15 16 17 18 19 20
21 22 23 24 25 26 27
28 29 30 31
August 2019
SuMoTuWeThFrSa
1 2 3
4 5 6 7 8 9 10
11 12 13 14 15 16 17
18 19 20 21 22 23 24
25 26 27 28 29 30 31
September 2019
SuMoTuWeThFrSa
1 2 3 4 5 6 7
8 9 10 11 12 13 14
15 16 17 18 19 20 21
22 23 24 25 26 27 28
29 30
  • Property Highlights
    Area: Oak Bluffs
    Turnover Day: N/A
    Pets Allowed: No
    • 2Bedrooms:
    • 1.0Baths:
    • 4Sleeps:
  • Description:
    BR1 King, with flat screened TV, main level, BR2 (2) Twin beds, main level. Both bedrooms share a hall bathroom equipped...Read More
June 2019
SuMoTuWeThFrSa
1
2 3 4 5 6 7 8
9 10 11 12 13 14 15
16 17 18 19 20 21 22
23 24 25 26 27 28 29
30
July 2019
SuMoTuWeThFrSa
1 2 3 4 5 6
7 8 9 10 11 12 13
14 15 16 17 18 19 20
21 22 23 24 25 26 27
28 29 30 31
August 2019
SuMoTuWeThFrSa
1 2 3
4 5 6 7 8 9 10
11 12 13 14 15 16 17
18 19 20 21 22 23 24
25 26 27 28 29 30 31
September 2019
SuMoTuWeThFrSa
1 2 3 4 5 6 7
8 9 10 11 12 13 14
15 16 17 18 19 20 21
22 23 24 25 26 27 28
29 30

This website uses cookies to ensure you get the best experience on our website. Learn More

Ok