Oak Bluffs

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 121 properties available
This charming waterfront two story Cape sits atop the Lagoon bluffs. Boasts spectacular sunsets and panoramic waterfront views of Lagoon, outer Vineyard Haven Harbor and Cape Cod from the patios, living room, dining room and two upstairs bedrooms. Stairs down to private beach. You are just minutes to the center of Oak Bluffs village. It truly is a
Hot HOT 15
Oak Bluffs 805
Oak Bluffs 805 2
Oak Bluffs 805 3
Oak Bluffs 805 4
Oak Bluffs 805 5
Prev
Next
Oak Bluffs
$4,000.00 - $5,900.00 / per week
Beds 4 beds
Baths 2 Full, 1 Half Bath
Sleeps 8 sleeps
Oak Bluffs 805
This charming waterfront two story Cape sits atop the Lagoon bluffs. Boasts spectacular sunsets and panoramic waterfront views of Lagoon, outer Vineya... Read More
June 2027
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 2027
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 2027
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
Indulge in the ultimate vacation experience at this well-appointed cape-style home, designed to provide peace and comfort to its guests. Step outside and bask in the enchanting outdoor sitting area with high-quality furniture, surrounded by a fenced-in yard and welcoming farmer's porch, perfect for savoring your morning cup of coffee. Inside, you'l
Oak Bluffs 8119
Oak Bluffs 8119 2
Oak Bluffs 8119 3
Oak Bluffs 8119 4
Oak Bluffs 8119 5
Prev
Next
Oak Bluffs
$3,500.00 - $4,200.00 / per week
Beds 3 beds
Baths 2 Full Bath
Sleeps 6 sleeps
Rating 5 (2)
Oak Bluffs 8119
Indulge in the ultimate vacation experience at this well-appointed cape-style home, designed to provide peace and comfort to its guests. Step outside ... Read More
June 2027
Su Mo Tu We Th Fr Sa
    1 2 3 4 $3500 5
6 7 8 9 10 11 $3500 12
13 14 15 16 17 18 $3500 19
20 21 22 23 24 25 $3500 26
27 28 29 30      
July 2027
Su Mo Tu We Th Fr Sa
        1 2 $4200 3
4 5 6 7 8 9 $3800 10
11 12 13 14 15 16 $3800 17
18 19 20 21 22 23 24
25 26 27 28 29 30 31
August 2027
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 $3800 28
29 30 31        
Prev
Next
Available
Unavailable
Check-In
Check-Out
Nestled on 1.5 private, wooded acres in Hidden Cove, this beautifully appointed multi-level home offers an ideal blend of tranquility and space for gathering. The open living and dining areas create a welcoming atmosphere, while the thoughtful layout provides quiet retreats for guests. The home sleeps seven and features three bedrooms and four and
Oak Bluffs 8013
Oak Bluffs 8013 2
Oak Bluffs 8013 3
Oak Bluffs 8013 4
Oak Bluffs 8013 5
Prev
Next
Oak Bluffs
$4,200.00 - $8,400.00 / per week
Beds 3 beds
Baths 4 Full, 1 Half Bath
Sleeps 7 sleeps
Rating 5 (1)
Oak Bluffs 8013
Nestled on 1.5 private, wooded acres in Hidden Cove, this beautifully appointed multi-level home offers an ideal blend of tranquility and space for ga... Read More
June 2027
Su Mo Tu We Th Fr Sa
    1 2 3 4 $7350 5
6 7 8 9 10 11 $7350 12
13 14 15 16 17 18 $7350 19
20 21 22 23 24 25 $7350 26
27 28 29 30      
July 2027
Su Mo Tu We Th Fr Sa
        1 2 $8400 3
4 5 6 7 8 9 $8400 10
11 12 13 14 15 16 $8400 17
18 19 20 21 22 23 $8400 24
25 26 27 28 29 30 $8400 31
August 2027
Su Mo Tu We Th Fr Sa
1 2 3 4 5 6 $8400 7
8 9 10 11 12 13 $8400 14
15 16 17 18 19 20 $8400 21
22 23 24 25 26 27 $8400 28
29 30 31        
Prev
Next
Available
Unavailable
Check-In
Check-Out
Enjoy this expansive five bedroom home, ideal for extended family or friends. Spanning four levels, there is ample space for everyone to spread out. The main level includes the kitchen, dining, half bath and a couple of sitting areas with access to the back deck. The deck is perfect for outdoor dining and ample room in the backyard for those outdoo
Oak Bluffs 8109
Oak Bluffs 8109 2
Oak Bluffs 8109 3
Oak Bluffs 8109 4
Oak Bluffs 8109 5
Prev
Next
Oak Bluffs
$7,950.00 - $8,450.00 / per week
Beds 5 beds
Baths 3 Full, 1 Half Bath
Sleeps 13 sleeps
Rating 4.5 (2)
Oak Bluffs 8109
Enjoy this expansive five bedroom home, ideal for extended family or friends. Spanning four levels, there is ample space for everyone to spread out. T... Read More
June 2027
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 2027
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 2027
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 $7950 28
29 30 31        
Prev
Next
Available
Unavailable
Check-In
Check-Out
Welcome to your perfect Oak Bluffs getaway! This inviting 4-bedroom, 3-bath home is located in the heart of downtown and comfortably sleeps up to 10 guests, with central air conditioning throughout for a cool, relaxing stay. Designed for easy vacation living, the home features a well-equipped kitchen and a spacious living room with plenty of seatin
Oak Bluffs 8075
Oak Bluffs 8075 2
Oak Bluffs 8075 3
Oak Bluffs 8075 4
Oak Bluffs 8075 5
Prev
Next
Oak Bluffs
$10,500.00 - $22,900.00 / per week
Beds 4 beds
Baths 3 Full Bath
Sleeps 10 sleeps
Oak Bluffs 8075
Welcome to your perfect Oak Bluffs getaway! This inviting 4-bedroom, 3-bath home is located in the heart of downtown and comfortably sleeps up to 10 g... Read More
June 2027
Su Mo Tu We Th Fr Sa
    1 2 3 4 $17800 5
6 7 8 9 10 11 $17800 12
13 14 15 16 17 18 $17800 19
20 21 22 23 24 25 $17800 26
27 28 29 30      
July 2027
Su Mo Tu We Th Fr Sa
        1 2 $17800 3
4 5 6 7 8 9 $17800 10
11 12 13 14 15 16 $17800 17
18 19 20 21 22 23 24
25 26 27 28 29 30 31
August 2027
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 $17800 28
29 30 31        
Prev
Next
Available
Unavailable
Check-In
Check-Out
Prime Oak Bluffs location in a serene setting. This home has plenty of room to spread out and enjoy your vacation. The main level has a generous and spacious kitchen that opens to both the dining and living areas. Off of the dining area is a lovely screened porch, perfect for that extra space. There is also a bedroom and full bath, along with laund
Hot HOT 10
Oak Bluffs 802
Oak Bluffs 802 2
Oak Bluffs 802 3
Oak Bluffs 802 4
Oak Bluffs 802 5
Prev
Next
Oak Bluffs
$2,600.00 - $3,900.00 / per week
Beds 4 beds
Baths 2 Full, 1 Half Bath
Sleeps 8 sleeps
Oak Bluffs 802
Prime Oak Bluffs location in a serene setting. This home has plenty of room to spread out and enjoy your vacation. The main level has a generous and s... Read More
June 2027
Su Mo Tu We Th Fr Sa
    1 2 3 4 $3200 5
6 7 8 9 10 11 $3900 12
13 14 15 16 17 18 $3900 19
20 21 22 23 24 25 $3900 26
27 28 29 30      
July 2027
Su Mo Tu We Th Fr Sa
        1 2 $3900 3
4 5 6 7 8 9 $3900 10
11 12 13 14 15 16 $3900 17
18 19 20 21 22 23 24
25 26 27 28 29 30 31
August 2027
Su Mo Tu We Th Fr Sa
1 2 3 4 5 6 7
8 9 10 11 12 13 $3900 14
15 16 17 18 19 20 $3900 21
22 23 24 25 26 27 $2600 28
29 30 31        
Prev
Next
Available
Unavailable
Check-In
Check-Out
Dramatic views! Enjoy the perfect vacation spot for all families. Located on the Barnes Road side of the Lagoon, this single level, 3 bedroom home includes a small beach, and dock. Newly updated with many amenities such as split unit AC, gas grill, spacious deck, Adirondack chairs, enclosed shower and a full outside dining area. The staircase down
Oak Bluffs 8032
Oak Bluffs 8032 2
Oak Bluffs 8032 3
Oak Bluffs 8032 4
Oak Bluffs 8032 5
Prev
Next
Oak Bluffs
$7,000.00 - $13,000.00 / per week
Beds 3 beds
Baths 2 Full Bath
Sleeps 8 sleeps
Oak Bluffs 8032
Dramatic views! Enjoy the perfect vacation spot for all families. Located on the Barnes Road side of the Lagoon, this single level, 3 bedroom home inc... Read More
June 2027
Su Mo Tu We Th Fr Sa
    1 2 3 4 $7000 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 2027
Su Mo Tu We Th Fr Sa
        1 2 $10000 3
4 5 6 7 8 9 10
11 12 13 14 15 16 $10000 17
18 19 20 21 22 23 $13000 24
25 26 27 28 29 30 31
August 2027
Su Mo Tu We Th Fr Sa
1 2 3 4 5 6 7
8 9 10 11 12 13 $13000 14
15 16 17 18 19 20 $12000 21
22 23 24 25 26 27 $7000 28
29 30 31        
Prev
Next
Available
Unavailable
Check-In
Check-Out
A classic Oak Bluffs Cottage recently renovated and refreshed, adding air conditioning, a large sunroom and an additional half bath to this already charming two-bedroom cottage overlooking Niantic Park. The new sunroom, complete with a gas log stove, flatscreen television and vinyl turntable with in-ceiling speakers, creates an opportunity to unwin
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 4.6 (3)
Oak Bluffs 8077
A classic Oak Bluffs Cottage recently renovated and refreshed, adding air conditioning, a large sunroom and an additional half bath to this already ch... Read More
June 2027
Su Mo Tu We Th Fr Sa
    1 2 3 4 $3800 5
6 7 8 9 10 11 $3800 12
13 14 15 16 17 18 $3800 19
20 21 22 23 24 25 $4500 26
27 28 29 30      
July 2027
Su Mo Tu We Th Fr Sa
        1 2 $4500 3
4 5 6 7 8 9 10
11 12 13 14 15 16 $4500 17
18 19 20 21 22 23 $5000 24
25 26 27 28 29 30 31
August 2027
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 $5000 21
22 23 24 25 26 27 $5000 28
29 30 31        
Prev
Next
Available
Unavailable
Check-In
Check-Out
A Frank Lloyd Wright-inspired home in Harthaven with a reverse style 3-bedroom main house and a 2-bedroom guest house offers an abundance of privacy and a spectacular location. The open concept living spaces open to both the screened porch and expansive deck, which creates an abundance of living space and ample opportunity to relax and soak in all
Hot HOT 44
Oak Bluffs 8010
Oak Bluffs 8010 2
Oak Bluffs 8010 3
Oak Bluffs 8010 4
Oak Bluffs 8010 5
Prev
Next
Oak Bluffs
$12,500.00 - $15,000.00 / per week
Beds 5 beds
Baths 5 Full Bath
Sleeps 10 sleeps
Oak Bluffs 8010
A Frank Lloyd Wright-inspired home in Harthaven with a reverse style 3-bedroom main house and a 2-bedroom guest house offers an abundance of privacy a... Read More
June 2027
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 2027
Su Mo Tu We Th Fr Sa
        1 2 3
4 5 6 7 8 9 $12500 10
11 12 13 14 15 16 $12500 17
18 19 20 21 22 23 $12500 24
25 26 27 28 29 30 $12500 31
August 2027
Su Mo Tu We Th Fr Sa
1 2 3 4 5 6 $15000 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
This six bedroom Oak Bluffs Gingerbread home is well appointed with a grand open floor plan, chef's kitchen, formal dining, front living space, spilling into a cordial verandah where you will view many beautiful sunrises and sights of the Atlantic Ocean. You are minutes to the beach, village, tennis, basketball, and the bike path. Inside you will f
Hot HOT 14
Oak Bluffs 8014
Oak Bluffs 8014 2
Oak Bluffs 8014 3
Oak Bluffs 8014 4
Oak Bluffs 8014 5
Prev
Next
Oak Bluffs
$8,000.00 - $13,000.00 / per week
Beds 6 beds
Baths 3 Full, 1 Half Bath
Sleeps 14 sleeps
Oak Bluffs 8014
This six bedroom Oak Bluffs Gingerbread home is well appointed with a grand open floor plan, chef's kitchen, formal dining, front living space, spilli... Read More
June 2027
Su Mo Tu We Th Fr Sa
    1 2 3 4 $10550 5
6 7 8 9 10 11 $10550 12
13 14 15 16 17 18 $10550 19
20 21 22 23 24 25 $10550 26
27 28 29 30      
July 2027
Su Mo Tu We Th Fr Sa
        1 2 $10550 3
4 5 6 7 8 9 $10550 10
11 12 13 14 15 16 $10550 17
18 19 20 21 22 23 $11500 24
25 26 27 28 29 30 31
August 2027
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 $8000 28
29 30 31        
Prev
Next
Available
Unavailable
Check-In
Check-Out
This cozy well maintained and tastefully decorated Martha's Vineyard summer home is perfect for vacationers. It is located on a carriage road in a quiet neighborhood with association tennis, just minutes away. The large yard is fenced in to accommodate a heated in ground pool with lots of chairs for lounging. The lovely screened porch, right off th
Hot HOT 10
Oak Bluffs 8143
Oak Bluffs 8143 2
Oak Bluffs 8143 3
Oak Bluffs 8143 4
Oak Bluffs 8143 5
Prev
Next
Oak Bluffs
$5,500.00 - $14,000.00 / per week
Beds 4 beds
Baths 3 Full, 1 Half Bath
Sleeps 8 sleeps
Oak Bluffs 8143
This cozy well maintained and tastefully decorated Martha's Vineyard summer home is perfect for vacationers. It is located on a carriage road in a qui... Read More
June 2027
Su Mo Tu We Th Fr Sa
    1 2 3 4 $10000 5
6 7 8 9 10 11 $10000 12
13 14 15 16 17 18 $10000 19
20 21 22 23 24 25 $10000 26
27 28 29 30      
July 2027
Su Mo Tu We Th Fr Sa
        1 2 $10000 3
4 5 6 7 8 9 $10000 10
11 12 13 14 15 16 17
18 19 20 21 22 23 24
25 26 27 28 29 30 31
August 2027
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
Set on a quiet cul de sac, yet one mile to the heart of Oak Bluffs. Step into this light filled, newly decorated home and let the vacation begin. With multiple living spaces, there is plenty of room to spread out. The open floorplan is spacious with a modern kitchen. There is also a bedroom with a queen bed and full bath on the main level. The fini
Oak Bluffs 8012
Oak Bluffs 8012 2
Oak Bluffs 8012 3
Oak Bluffs 8012 4
Oak Bluffs 8012 5
Prev
Next
Oak Bluffs
$7,000.00 - $12,500.00 / per week
Beds 3 beds
Baths 3 Full Bath
Sleeps 8 sleeps
Oak Bluffs 8012
Set on a quiet cul de sac, yet one mile to the heart of Oak Bluffs. Step into this light filled, newly decorated home and let the vacation begin. With... Read More
June 2027
Su Mo Tu We Th Fr Sa
    1 2 3 4 $7000 5
6 7 8 9 10 11 $7000 12
13 14 15 16 17 18 $7000 19
20 21 22 23 24 25 $7000 26
27 28 29 30      
July 2027
Su Mo Tu We Th Fr Sa
        1 2 $8250 3
4 5 6 7 8 9 $7500 10
11 12 13 14 15 16 $7500 17
18 19 20 21 22 23 $7500 24
25 26 27 28 29 30 $8000 31
August 2027
Su Mo Tu We Th Fr Sa
1 2 3 4 5 6 7
8 9 10 11 12 13 $10500 14
15 16 17 18 19 20 $12500 21
22 23 24 25 26 27 $8000 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 © 2026 • Sandpiper Rentals

All Rights Reserved.