Oak Bluffs

Resort Swiper
Resort Swiper
Resort Swiper
Resort Swiper
Resort Swiper
Resort Swiper
Resort Swiper

Oak Bluffs - or 'OB' - is a classic beach town, filled with tons of fun! Enjoy the sandy beaches along the calm waters of Nantucket Sound, events held in Ocean Park and the Tabernacle, and the casual atmosphere of the harbor and Circuit Avenue. Popular attractions include the Flying Horses Carousel, the nation’s oldest operating platform carousel, and the Martha’s Vineyard Camp Meeting Association, a National Historic Landmark and community of over 300 charming Victorian gingerbread cottages surrounding a beautiful iron Tabernacle. Circuit Avenue is always bustling and has something for everyone – ice cream, coffee shops, eateries, bars and boutiques. The Harbor is entirely walkable and is a great place to relax and watch the boats coming and going. Outside of the downtown area, there are many areas in OB that offer a quieter atmosphere. Contact us and we'll help you find the perfect getaway!


Properties Available 136 properties available
BR1 Queen Bedroom with AC split, First FloorBR2 Bunk Room Queen on the bottom, Twin on the top, AC split, First FloorBedrooms 1 and 2 share a Hall BathroomBR3 Queen Bedroom with a water view, Second FloorBR4 Queen Bedroom with a water view, Second FloorBR5 Queen Bedroom Second FloorBedrooms 3-5 share a Hall BathroomBR6 King Bedroom en-suite, Flat s
Oak Bluffs 8153
Oak Bluffs 8153 2
Oak Bluffs 8153 3
Oak Bluffs 8153 4
Oak Bluffs 8153 5
Prev
Next
Oak Bluffs
$20,000.00 / per week
Beds 6 beds
Baths 3 Full, 1 Half Bath
Sleeps 12 sleeps
Oak Bluffs 8153
This beautiful property located in the heart of Oak Bluffs has been completely renovated and boasts six spacious bedrooms. It features Altec surround ... Read More
June 2025
Su Mo Tu We Th Fr Sa
1 2 3 4 5 6 $20000 7
8 9 10 11 12 13 $20000 14
15 16 17 18 19 20 $20000 21
22 23 24 25 26 27 28
29 30          
July 2025
Su Mo Tu We Th Fr Sa
    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 2025
Su Mo Tu We Th Fr Sa
          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            
Prev
Next
Available
Unavailable
Check-In
Check-Out
BR1 King, 2nd floorBR2 Queen, 2nd floorHall bath with shower stall, 2nd floorHalf Bath and Laundry facilities, 1st floor
Oak Bluffs 8077
Oak Bluffs 8077 2
Oak Bluffs 8077 3
Oak Bluffs 8077 4
Oak Bluffs 8077 5
Prev
Next
Oak Bluffs
$3,800.00 - $5,000.00 / per week
Beds 2 beds
Baths 1 Full, 1 Half Bath
Sleeps 4 sleeps
Rating 4.5 (2)
Oak Bluffs 8077
A classic Oak Bluffs Cottage has been renovated and revamped for 2023, adding air conditioning, a large sunroom and an additional half bath to this al... Read More
June 2025
Su Mo Tu We Th Fr Sa
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 2025
Su Mo Tu We Th Fr Sa
    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 2025
Su Mo Tu We Th Fr Sa
          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            
Prev
Next
Available
Unavailable
Check-In
Check-Out
BR1 King en suite with shower stall, 1st floorBR2 King en suite with tub/shower, 2nd floorBR3 Twin and queen sofa bed en suite with tub/shower, 2nd floorBR4 Double and twin bed, 2nd floorBR5 Queen and twin bed, 2nd floorHall bath with tub/shower, 2nd floorHalf bath, 1st floorLaundry facilities, lower level
Oak Bluffs 8129
Oak Bluffs 8129 2
Oak Bluffs 8129 3
Oak Bluffs 8129 4
Oak Bluffs 8129 5
Prev
Next
Oak Bluffs
$5,500.00 - $13,800.00 / per week
Beds 5 beds
Baths 4 Full, 1 Half Bath
Sleeps 12 sleeps
Oak Bluffs 8129
Pirate's Reef is a beautifully decorated residence that offers five spacious bedrooms (two primary suites!) with four and a half bathrooms and accommo... Read More
June 2025
Su Mo Tu We Th Fr Sa
1 2 3 4 5 6 $7700 7
8 9 10 11 12 13 $7700 14
15 16 17 18 19 20 $12000 21
22 23 24 25 26 27 28
29 30          
July 2025
Su Mo Tu We Th Fr Sa
    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 2025
Su Mo Tu We Th Fr Sa
          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            
Prev
Next
Available
Unavailable
Check-In
Check-Out
BR1 Queen En Suite with Shower Stall, Second FloorBR2 Double, Second FloorBR3 (2) Twin Beds, Second FloorHall Bath with Tub/Shower Combo, Second FloorTwin Sofa Bed, Living RoomPowder Room, First FloorLaundry Facilities, First Floor
Oak Bluffs 803
Oak Bluffs 803 2
Oak Bluffs 803 3
Oak Bluffs 803 4
Oak Bluffs 803 5
Prev
Next
Oak Bluffs
$4,500.00 - $8,500.00 / per week
Beds 3 beds
Baths 2 Full, 1 Half Bath
Sleeps 6 sleeps
Oak Bluffs 803
Oak Bluffs! Ready for your summer vacation! Beautifully furnished in a casually elegant style, this home allows you room to relax with friends and fam... Read More
June 2025
Su Mo Tu We Th Fr Sa
1 2 3 4 5 6 $5000 7
8 9 10 11 12 13 $5000 14
15 16 17 18 19 20 $5000 21
22 23 24 25 26 27 $6500 28
29 30          
July 2025
Su Mo Tu We Th Fr Sa
    1 2 3 4 $6500 5
6 7 8 9 10 11 $6500 12
13 14 15 16 17 18 19
20 21 22 23 24 25 26
27 28 29 30 31    
August 2025
Su Mo Tu We Th Fr Sa
          1 2
3 4 5 6 7 8 9
10 11 12 13 14 15 16
17 18 19 20 21 22 $8500 23
24 25 26 27 28 29 $6000 30
31            
Prev
Next
Available
Unavailable
Check-In
Check-Out
BR1 King, Second FloorBR2 Queen, First FloorBR3 Bunk Bed and a Double, Second Floor Hall Bath with Shower Stall, First FloorHall Bath with Tub/Shower, Second Floor
Oak Bluffs 830
Oak Bluffs 830 2
Oak Bluffs 830 3
Oak Bluffs 830 4
Oak Bluffs 830 5
Prev
Next
Oak Bluffs Pet Friendly
$3,500.00 - $6,200.00 / per week
Beds 3 beds
Baths 2 Full Bath
Sleeps 7 sleeps
Oak Bluffs 830
This rental home is a true gem, nestled in a peaceful, natural setting on a private, dead-end road. The exterior of the home features a large back dec... Read More
June 2025
Su Mo Tu We Th Fr Sa
1 2 3 4 5 6 $4440 7
8 9 10 11 12 13 $4440 14
15 16 17 18 19 20 21
22 23 24 25 26 27 28
29 30          
July 2025
Su Mo Tu We Th Fr Sa
    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 2025
Su Mo Tu We Th Fr Sa
          1 2
3 4 5 6 7 8 9
10 11 12 13 14 15 16
17 18 19 20 21 22 $6200 23
24 25 26 27 28 29 $4600 30
31            
Prev
Next
Available
Unavailable
Check-In
Check-Out
BR1 Queen En Suite with Tub/Shower Combo, First FloorBR2 King, Second FloorBR3 (2)Twin beds, Second FloorHall bath with Tub/Shower Combo, Second Floor
Oak Bluffs 841
Oak Bluffs 841 2
Oak Bluffs 841 3
Oak Bluffs 841 4
Oak Bluffs 841 5
Prev
Next
Oak Bluffs
$4,500.00 - $8,475.00 / per week
Beds 3 beds
Baths 2 Full Bath
Sleeps 6 sleeps
Oak Bluffs 841
Oak Bluffs off of County Road and close to the village, sits The Gladys Manor originally built in 1890. It has been exquisitely renovated as a three b... Read More
June 2025
Su Mo Tu We Th Fr Sa
1 2 3 4 5 6 $5000 7
8 9 10 11 12 13 $5000 14
15 16 17 18 19 20 $5000 21
22 23 24 25 26 27 28
29 30          
July 2025
Su Mo Tu We Th Fr Sa
    1 2 3 4 5
6 7 8 9 10 11 $6000 12
13 14 15 16 17 18 $6200 19
20 21 22 23 24 25 $6200 26
27 28 29 30 31    
August 2025
Su Mo Tu We Th Fr Sa
          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 $7450 30
31            
Prev
Next
Available
Unavailable
Check-In
Check-Out
BR1 Queen, 2nd FloorBR2 (2) Twins, 2nd floorHall bath with tub/shower, 2nd Floor floorHall Bath with Tub/Shower combo and Washer/Dryer, 2nd FloorHalf Bath, 1st floor
Oak Bluffs 813
Oak Bluffs 813 2
Oak Bluffs 813 3
Oak Bluffs 813 4
Oak Bluffs 813 5
Prev
Next
Oak Bluffs
$3,645.00 - $3,780.00 / per week
Beds 2 beds
Baths 1 Full, 1 Half Bath
Sleeps 4 sleeps
Rating 5 (1)
Oak Bluffs 813
This 2 story contemporary is located just outside Downtown Oak Bluffs with off-street parking for 2 cars. Immerse yourself in the hustle bustle of Cir... Read More
June 2025
Su Mo Tu We Th Fr Sa
1 2 3 4 5 6 $3645 7
8 9 10 11 12 13 $3645 14
15 16 17 18 19 20 $3645 21
22 23 24 25 26 27 $3645 28
29 30          
July 2025
Su Mo Tu We Th Fr Sa
    1 2 3 4 $3780 5
6 7 8 9 10 11 $3780 12
13 14 15 16 17 18 $3780 19
20 21 22 23 24 25 $3780 26
27 28 29 30 31    
August 2025
Su Mo Tu We Th Fr Sa
          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 $3780 30
31            
Prev
Next
Available
Unavailable
Check-In
Check-Out
BR1 King, 1st floorHall bath with shower stall, 1st floorBR2 Queen, 2nd floorBR3 (4)Twin beds, 2nd floorHall bath with tub/shower, 2nd floor
Oak Bluffs 810
Oak Bluffs 810 2
Oak Bluffs 810 3
Oak Bluffs 810 4
Oak Bluffs 810 5
Prev
Next
Oak Bluffs
$1,800.00 - $7,000.00 / per week
Beds 3 beds
Baths 2 Full Bath
Sleeps 8 sleeps
Oak Bluffs 810
Contemporary Cape on Martha's Vineyard. Open design, wood floors downstairs. Deck for extended summer living. Distance waterview of the Lagoon from ou... Read More
June 2025
Su Mo Tu We Th Fr Sa
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 2025
Su Mo Tu We Th Fr Sa
    1 2 3 4 5
6 7 8 9 10 11 $6000 12
13 14 15 16 17 18 $6000 19
20 21 22 23 24 25 $7000 26
27 28 29 30 31    
August 2025
Su Mo Tu We Th Fr Sa
          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            
Prev
Next
Available
Unavailable
Check-In
Check-Out
BR1 King, Second FloorHall Bath with Shower Tub Combo, Second FloorBR2 Queen, Second FloorBR3 Queen, First FloorHall Bath with Shower Tub Combo, First FloorBR4 Queen, First Floor
Oak Bluffs 8028
Oak Bluffs 8028 2
Oak Bluffs 8028 3
Oak Bluffs 8028 4
Oak Bluffs 8028 5
Prev
Next
Oak Bluffs Pet Friendly
$4,893.00 - $7,693.00 / per week
Beds 4 beds
Baths 2 Full Bath
Sleeps 8 sleeps
Oak Bluffs 8028
Looking for a cozy and inviting house for rent in Oak Bluffs? This beautiful property is located just a mile and a half from the beach, making it the ... Read More
June 2025
Su Mo Tu We Th Fr Sa
1 2 3 4 5 6 $6293 7
8 9 10 11 12 13 14
15 16 17 18 19 20 21
22 23 24 25 26 27 $6993 28
29 30          
July 2025
Su Mo Tu We Th Fr Sa
    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 2025
Su Mo Tu We Th Fr Sa
          1 2
3 4 5 6 7 8 9
10 11 12 13 14 15 16
17 18 19 20 21 22 $7693 23
24 25 26 27 28 29 $5593 30
31            
Prev
Next
Available
Unavailable
Check-In
Check-Out
BR 2 - Queen>Loft - King and two twins>Shared bath on main level
Oak Bluffs 847
Oak Bluffs 847 2
Oak Bluffs 847 3
Oak Bluffs 847 4
Oak Bluffs 847 5
Prev
Next
Oak Bluffs
$3,100.00 - $5,885.00 / per week
Beds 2 beds
Baths 1 Full Bath
Sleeps 8 sleeps
Oak Bluffs 847
Welcome to this charming rental on Martha's Vineyard on Circuit Avenue in Oak Bluffs. This delightful apartment offers comfortable and spacious accomm... Read More
June 2025
Su Mo Tu We Th Fr Sa
1 2 3 4 5 6 $4075 7
8 9 10 11 12 13 $4120 14
15 16 17 18 19 20 $3900 21
22 23 24 25 26 27 $3900 28
29 30          
July 2025
Su Mo Tu We Th Fr Sa
    1 2 3 4 $4120 5
6 7 8 9 10 11 $3900 12
13 14 15 16 17 18 $4120 19
20 21 22 23 24 25 $4120 26
27 28 29 30 31    
August 2025
Su Mo Tu We Th Fr Sa
          1 $5885 2
3 4 5 6 7 8 $5885 9
10 11 12 13 14 15 16
17 18 19 20 21 22 23
24 25 26 27 28 29 $4120 30
31            
Prev
Next
Available
Unavailable
Check-In
Check-Out
BR1 Double, First FloorBR2 Double Sofa Bed with Split Mattress, First FloorHall bath with Shower, First FloorLaundry, First Floor
Oak Bluffs 8044
Oak Bluffs 8044 2
Oak Bluffs 8044 3
Oak Bluffs 8044 4
Oak Bluffs 8044 5
Prev
Next
Oak Bluffs
$2,500.00 - $2,800.00 / per week
Beds 2 beds
Baths 1 Full Bath
Sleeps 4 sleeps
Oak Bluffs 8044
Newly constructed guesthouse with all the amenities of a Vineyard vacation home. Two bedrooms with shared hall bathroom. Fully equipped eat-in kitch... Read More
June 2025
Su Mo Tu We Th Fr Sa
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 2025
Su Mo Tu We Th Fr Sa
    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 2025
Su Mo Tu We Th Fr Sa
          1 2
3 4 5 6 7 8 9
10 11 12 13 14 15 16
17 18 19 20 21 22 $2800 23
24 25 26 27 28 29 $2500 30
31            
Prev
Next
Available
Unavailable
Check-In
Check-Out
BR1 Queen en suite with tub/shower, 1st floorBR2 Queen and twin bed, 2nd floorBR3 (4)Twin beds, 2nd floorHall bath with tub/shower, 2nd floorHalf bath, 1st floorLaundry facilities, 1st floor
Oak Bluffs 8155
Oak Bluffs 8155 2
Oak Bluffs 8155 3
Oak Bluffs 8155 4
Oak Bluffs 8155 5
Prev
Next
Oak Bluffs
$1,000.00 - $3,400.00 / per week
Beds 3 beds
Baths 2 Full, 1 Half Bath
Sleeps 9 sleeps
Rating 4.7 (4)
Oak Bluffs 8155
A contemporary cape located between the Lagoon Sailing Camp Park in Oak Bluffs, and the Farm Neck Golf Club. Step in from the farmer's porch to an inv... Read More
June 2025
Su Mo Tu We Th Fr Sa
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 2025
Su Mo Tu We Th Fr Sa
    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 2025
Su Mo Tu We Th Fr Sa
          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            
Prev
Next
Available
Unavailable
Check-In
Check-Out

Tell us what you're looking for and someone will contact you with available options.

I agree

Copyright © 2025 • Sandpiper Rentals

All Rights Reserved.