Oak Bluffs Vacation Rentals

Oak Bluffs is a beautiful peninsula on the north eastern coast of Martha’s Vineyard that is bordered by Nantucket Sound. Renting a vacation home in Oak Bluffs gives you so many options. Our list of vacations rentals include luxury waterfront properties with exceptional views of the sound and quaint Victorian homes that allow you to glimpse deeply into Martha’s Vineyard’s historic past. Vacationing in Oak Bluffs is like taking a trip back in time. Ocean air and private beaches make you feel as though you have Martha’s Vineyard all to yourself.

Displaying 61 - 75 of 96

View Result on Map
Depart OnlyArrive OnlyBookedAvailable
Add Favorite
tothg13-03-exterior.jpg
Get My Quote

Note: Older style TVs seen in photos have been replaced. 

This bright and classic summer cottage is ideally located just one mile from Oak Bluffs town center and all the...Read more

Location: 
Oak Bluffs
Sleeps: 
5
Bedrooms: 
3
Baths: 
1
Price Range:
$4,000 - $4,950
June 2027
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 2027
SuMoTuWeThFrSaWeek
 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
$4,950
August 2027
SuMoTuWeThFrSaWeek
1
2
3
4
5
6
7
$4,950
8
9
10
11
12
13
14
$4,950
15
16
17
18
19
20
21
$4,950
22
23
24
25
26
27
28
$4,950
29
30
31
 $4,000
September 2027
SuMoTuWeThFrSaWeek
 1
2
3
4
$4,000
5
6
7
8
9
10
11
$4,000
12
13
14
15
16
17
18
$4,000
19
20
21
22
23
24
25
$4,000
26
27
28
29
30
 $4,000
Clean Fee: 
$250 per week
Tax: State & Local: 
14.45
Add Favorite
Get My Quote
Lovely Oak Bluffs Home, 3 Bedrooms, 2.5 Baths, Sleeps 7. Set just on the Outskirts of Oak Bluffs Center

Lovely 3 bedroom, 2.5 bath home that sleeps 7. This sweet home is bordered by a large yard and is located just on the outskirts of Oak Bluffs. The patio...Read more

Location: 
Oak Bluffs
Sleeps: 
8
Bedrooms: 
3
Baths: 
2
Price Range:
$2,000 - $4,800
June 2027
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$2,500
6
7
8
9
10
11
12
$2,500
13
14
15
16
17
18
19
$3,000
20
21
22
23
24
25
26
$3,000
27
28
29
30
 $4,800
July 2027
SuMoTuWeThFrSaWeek
 1
2
3
$4,800
4
5
6
7
8
9
10
$4,800
11
12
13
14
15
16
17
$4,800
18
19
20
21
22
23
24
$4,800
25
26
27
28
29
30
31
August 2027
SuMoTuWeThFrSaWeek
1
2
3
4
5
6
7
$5,000
8
9
10
11
12
13
14
$5,000
15
16
17
18
19
20
21
$5,000
22
23
24
25
26
27
28
$5,000
29
30
31
 $4,500
September 2027
SuMoTuWeThFrSaWeek
 1
2
3
4
$4,500
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
 
Clean Fee: 
$500 per week
Tax: State & Local: 
14.45
Add Favorite
Get My Quote
Lovely Cape, 7 minute walk to town and harbor area, 4 bedrooms, 3 baths, sleeps 7

Lovely 4 bedroom, 3 bath home, pristinely maintained and ideally located just on the outskirts of Oak Bluffs on a quiet street. Short walk to town center and Oak Bluffs town...Read more

Location: 
Oak Bluffs
Sleeps: 
7
Bedrooms: 
4
Baths: 
3
Price Range:
$3,000 - $4,700
June 2027
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$3,000
6
7
8
9
10
11
12
$3,000
13
14
15
16
17
18
19
$3,000
20
21
22
23
24
25
26
$3,800
27
28
29
30
 $4,700
July 2027
SuMoTuWeThFrSaWeek
 1
2
3
$4,700
4
5
6
7
8
9
10
$4,700
11
12
13
14
15
16
17
$4,700
18
19
20
21
22
23
24
$4,700
25
26
27
28
29
30
31
$5,350
August 2027
SuMoTuWeThFrSaWeek
1
2
3
4
5
6
7
$5,400
8
9
10
11
12
13
14
$5,600
15
16
17
18
19
20
21
$5,400
22
23
24
25
26
27
28
$4,400
29
30
31
 $3,200
September 2027
SuMoTuWeThFrSaWeek
 1
2
3
4
$3,200
5
6
7
8
9
10
11
$3,200
12
13
14
15
16
17
18
$3,000
19
20
21
22
23
24
25
$3,000
26
27
28
29
30
 $3,000
Clean Fee: 
$450 per week
Tax: State & Local: 
14.45
Add Favorite
Get My Quote
Adorable Updated 2 Bedroom 1.5 Bath Cottage, Walk to Town, Harbor and Beach

If you are looking for an adorable cottage-style home in the center of Oak Bluffs this newly updated, tastefully decorated 2 bedroom, with one full bath and a half bath, is sure to...Read more

Location: 
Oak Bluffs
Sleeps: 
5
Bedrooms: 
2
Baths: 
1
Price Range:
$2,600 - $4,600
June 2027
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$2,600
6
7
8
9
10
11
12
$2,600
13
14
15
16
17
18
19
$2,800
20
21
22
23
24
25
26
$2,800
27
28
29
30
 $3,900
July 2027
SuMoTuWeThFrSaWeek
 1
2
3
$3,900
4
5
6
7
8
9
10
$3,900
11
12
13
14
15
16
17
$3,900
18
19
20
21
22
23
24
$3,900
25
26
27
28
29
30
31
$3,900
August 2027
SuMoTuWeThFrSaWeek
1
2
3
4
5
6
7
$4,600
8
9
10
11
12
13
14
$4,600
15
16
17
18
19
20
21
22
23
24
25
26
27
28
29
30
31
 $3,100
September 2027
SuMoTuWeThFrSaWeek
 1
2
3
4
$3,100
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
 $2,600
Clean Fee: 
$275 per week
Tax: State & Local: 
14.45
Add Favorite
Get My Quote
Contemporary 4 Bedroom, 4 Bath, Multiple Living Spaces, Walk to Oak Bluffs Center and Inkwell Beach-10 minutes

Perfect for extended families and friends, this spacious tri-level contemporary home offers multiple gathering spaces, comfortable accommodations, and an ideal location just a short stroll from the heart of Oak Bluffs....Read more

Location: 
Oak Bluffs
Sleeps: 
8
Bedrooms: 
4
Baths: 
4
Price Range:
$4,000 - $4,500
June 2027
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
7
8
9
10
11
12
$4,000
13
14
15
16
17
18
19
$4,000
20
21
22
23
24
25
26
$4,500
27
28
29
30
 $5,500
July 2027
SuMoTuWeThFrSaWeek
 1
2
3
$5,500
4
5
6
7
8
9
10
$6,500
11
12
13
14
15
16
17
$6,500
18
19
20
21
22
23
24
$6,500
25
26
27
28
29
30
31
$6,500
August 2027
SuMoTuWeThFrSaWeek
1
2
3
4
5
6
7
$7,500
8
9
10
11
12
13
14
$8,800
15
16
17
18
19
20
21
$8,800
22
23
24
25
26
27
28
$7,500
29
30
31
 $5,500
September 2027
SuMoTuWeThFrSaWeek
 1
2
3
4
$5,500
5
6
7
8
9
10
11
$4,000
12
13
14
15
16
17
18
$4,000
19
20
21
22
23
24
25
$4,000
26
27
28
29
30
 $4,000
Clean Fee: 
$600 per week
Tax: State & Local: 
14.45
Add Favorite
Get My Quote
Hidden Cove Retreat, Walk to Association Tennis/Pickleball Courts, 3 Bedrooms, 2.5 Baths, Screened Porch and Deck

Nestled in the charming Hidden Cove community, this adorable contemporary home resides on a tranquil street within walking distance of the association's tennis/pickleball courts. Its central location places it just a...Read more

Location: 
Oak Bluffs
Sleeps: 
7
Bedrooms: 
3
Baths: 
2
Price Range:
$4,000 - $4,500
June 2027
SuMoTuWeThFrSaWeek
 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
 $4,500
July 2027
SuMoTuWeThFrSaWeek
 1
2
3
$4,500
4
5
6
7
8
9
10
$4,500
11
12
13
14
15
16
17
$4,500
18
19
20
21
22
23
24
$4,500
25
26
27
28
29
30
31
$4,500
August 2027
SuMoTuWeThFrSaWeek
1
2
3
4
5
6
7
$6,500
8
9
10
11
12
13
14
$6,500
15
16
17
18
19
20
21
$5,000
22
23
24
25
26
27
28
$5,000
29
30
31
 $4,000
September 2027
SuMoTuWeThFrSaWeek
 1
2
3
4
$4,000
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
 
Clean Fee: 
$350 per week
Tax: State & Local: 
14.45
Add Favorite
Get My Quote
Lagoon Waterfront & Beachfront, Spectacular Water views, Room A/C, WIFI

Adorable waterfront & beachfront cottage.   Immaculately maintained, lots of summer charm, fantastic views of the Vineyard Sound and Lagoon from the large patio area. Stairs lead directly to a...Read more

Location: 
Oak Bluffs
Sleeps: 
4
Bedrooms: 
2
Baths: 
1
Price Range:
$2,460 - $4,390
June 2027
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$2,960
6
7
8
9
10
11
12
$3,260
13
14
15
16
17
18
19
$3,270
20
21
22
23
24
25
26
$3,640
27
28
29
30
 $3,980
July 2027
SuMoTuWeThFrSaWeek
 1
2
3
$3,980
4
5
6
7
8
9
10
$4,070
11
12
13
14
15
16
17
$4,090
18
19
20
21
22
23
24
$4,200
25
26
27
28
29
30
31
$4,300
August 2027
SuMoTuWeThFrSaWeek
1
2
3
4
5
6
7
$4,390
8
9
10
11
12
13
14
$4,390
15
16
17
18
19
20
21
$4,200
22
23
24
25
26
27
28
$3,850
29
30
31
 $3,300
September 2027
SuMoTuWeThFrSaWeek
 1
2
3
4
$3,300
5
6
7
8
9
10
11
$2,820
12
13
14
15
16
17
18
$2,560
19
20
21
22
23
24
25
$2,460
26
27
28
29
30
 
Clean Fee: 
$250 per week
Tax: State & Local: 
14.45
Add Favorite
Get My Quote
Hidden Cove, Centrally Located to Beaches and Towns, Association Tennis Courts, A/C, WiFi

Centrally located in the Hidden Cove community of homes on the outskirts of Oak Bluffs. Lovely area to bike, walk, or play tennis at the association courts. 

The main level features an...Read more

Location: 
Oak Bluffs
Sleeps: 
6
Bedrooms: 
3
Baths: 
2
Price Range:
$2,400 - $4,300
June 2027
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$2,400
6
7
8
9
10
11
12
$3,050
13
14
15
16
17
18
19
$3,050
20
21
22
23
24
25
26
$3,200
27
28
29
30
 $4,100
July 2027
SuMoTuWeThFrSaWeek
 1
2
3
$4,100
4
5
6
7
8
9
10
$4,100
11
12
13
14
15
16
17
$4,300
18
19
20
21
22
23
24
$4,300
25
26
27
28
29
30
31
$4,600
August 2027
SuMoTuWeThFrSaWeek
1
2
3
4
5
6
7
$4,720
8
9
10
11
12
13
14
$4,720
15
16
17
18
19
20
21
$4,720
22
23
24
25
26
27
28
$3,570
29
30
31
 $4,100
September 2027
SuMoTuWeThFrSaWeek
 1
2
3
4
$4,100
5
6
7
8
9
10
11
$4,100
12
13
14
15
16
17
18
$4,100
19
20
21
22
23
24
25
$4,100
26
27
28
29
30
 $4,100
Clean Fee: 
$375 per week
Tax: State & Local: 
14.45
Add Favorite
gratd13-01-exterior.jpg
Get My Quote
Located in the Heart of Oak Bluffs, 5 Minute Walk to OB Center and 2 Blocks to the Beach
Location: 
Oak Bluffs
Sleeps: 
10
Bedrooms: 
5
Baths: 
2
Price Range:
$3,400 - $4,200
June 2027
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$4,000
6
7
8
9
10
11
12
$4,000
13
14
15
16
17
18
19
$4,100
20
21
22
23
24
25
26
$4,400
27
28
29
30
 $4,800
July 2027
SuMoTuWeThFrSaWeek
 1
2
3
$4,800
4
5
6
7
8
9
10
$4,800
11
12
13
14
15
16
17
$4,800
18
19
20
21
22
23
24
$4,800
25
26
27
28
29
30
31
$4,800
August 2027
SuMoTuWeThFrSaWeek
1
2
3
4
5
6
7
$4,800
8
9
10
11
12
13
14
$4,800
15
16
17
18
19
20
21
$4,800
22
23
24
25
26
27
28
$4,800
29
30
31
 $4,800
September 2027
SuMoTuWeThFrSaWeek
 1
2
3
4
$4,800
5
6
7
8
9
10
11
$4,200
12
13
14
15
16
17
18
$4,000
19
20
21
22
23
24
25
$3,400
26
27
28
29
30
 
Clean Fee: 
$270 per week
Tax: State & Local: 
14.45
Add Favorite
Get My Quote
Waterview Farms, Water view

Lovely contemporary home in one of the island's premier community settings, Waterview Farms. Close to Farm Neck Golf Course and tennis and a short distance to town and beaches....Read more

Location: 
Oak Bluffs
Sleeps: 
5
Bedrooms: 
3
Baths: 
1
Price Range:
$2,800 - $4,160
June 2027
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$3,100
6
7
8
9
10
11
12
$3,100
13
14
15
16
17
18
19
$3,100
20
21
22
23
24
25
26
$3,100
27
28
29
30
 $3,850
July 2027
SuMoTuWeThFrSaWeek
 1
2
3
$3,850
4
5
6
7
8
9
10
$3,850
11
12
13
14
15
16
17
$3,850
18
19
20
21
22
23
24
$3,850
25
26
27
28
29
30
31
$3,850
August 2027
SuMoTuWeThFrSaWeek
1
2
3
4
5
6
7
$4,160
8
9
10
11
12
13
14
$4,160
15
16
17
18
19
20
21
$4,160
22
23
24
25
26
27
28
$4,160
29
30
31
 $4,160
September 2027
SuMoTuWeThFrSaWeek
 1
2
3
4
$4,160
5
6
7
8
9
10
11
$3,800
12
13
14
15
16
17
18
$3,800
19
20
21
22
23
24
25
$3,800
26
27
28
29
30
 $3,800
Clean Fee: 
$250 per week
Tax: State & Local: 
14.45
Add Favorite
Get My Quote
Lovely Waterfront Home, Oak Bluffs, Gorgeous Water Views, Association Tennis Courts, AC, Wi-fi, Bike Paths Nearby

MVVR Exclusive! Spacious, traditional waterfront Cape Cod style home tucked away on the shores of Sengekontacket Lagoon in a community of homes - featuring gorgeous views, mini-split AC units in main living areas,...Read more

Location: 
Oak Bluffs
Sleeps: 
8
Bedrooms: 
4
Baths: 
2
Price Range:
$2,700 - $4,100
June 2027
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$2,700
6
7
8
9
10
11
12
$2,700
13
14
15
16
17
18
19
$3,000
20
21
22
23
24
25
26
$3,000
27
28
29
30
 $3,500
July 2027
SuMoTuWeThFrSaWeek
 1
2
3
$3,500
4
5
6
7
8
9
10
$4,100
11
12
13
14
15
16
17
$3,900
18
19
20
21
22
23
24
$3,900
25
26
27
28
29
30
31
$4,100
August 2027
SuMoTuWeThFrSaWeek
1
2
3
4
5
6
7
$4,100
8
9
10
11
12
13
14
$4,100
15
16
17
18
19
20
21
$4,100
22
23
24
25
26
27
28
$4,100
29
30
31
 $3,400
September 2027
SuMoTuWeThFrSaWeek
 1
2
3
4
$3,400
5
6
7
8
9
10
11
$2,800
12
13
14
15
16
17
18
$2,800
19
20
21
22
23
24
25
$2,800
26
27
28
29
30
 $2,800
Clean Fee: 
$475 per week
Tax: State & Local: 
14.45
Add Favorite
Get My Quote
Classic Lovely Vineyard Cottage, Approximately 1.5 Miles to Oak Bluffs Center and Beaches. Mature Landscaped Yard, Spacious Deck

The Perfect Cozy Cottage, is pristinely maintained and situated in a quiet neighborhood just on the outskirts of Oak Bluffs.  This spacious 2 bedroom, 2 bath home sleeps 4. The...Read more

Location: 
Oak Bluffs
Sleeps: 
4
Bedrooms: 
2
Baths: 
2
Price Range:
$2,700 - $4,000
June 2027
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$2,700
6
7
8
9
10
11
12
$2,700
13
14
15
16
17
18
19
$2,700
20
21
22
23
24
25
26
$2,700
27
28
29
30
 $3,500
July 2027
SuMoTuWeThFrSaWeek
 1
2
3
$3,500
4
5
6
7
8
9
10
$3,500
11
12
13
14
15
16
17
$3,500
18
19
20
21
22
23
24
$3,500
25
26
27
28
29
30
31
$4,000
August 2027
SuMoTuWeThFrSaWeek
1
2
3
4
5
6
7
$4,000
8
9
10
11
12
13
14
$4,000
15
16
17
18
19
20
21
$4,000
22
23
24
25
26
27
28
$4,000
29
30
31
 $3,000
September 2027
SuMoTuWeThFrSaWeek
 1
2
3
4
$3,000
5
6
7
8
9
10
11
$2,700
12
13
14
15
16
17
18
$2,700
19
20
21
22
23
24
25
$2,700
26
27
28
29
30
 $2,700
Clean Fee: 
$300, additional may apply multiple week rentals
Tax: State & Local: 
14.45
Add Favorite
Get My Quote
Modern, Light filled Home, Located at end of Quiet Street, 1.5 Miles to Oak Bluffs center, Harbor Area and one of many Public Beaches

Perfect Oak Bluffs vacation home.  Located just 1.5 miles to the village center, town beach, and centrally located to the towns of Vineyard Haven, Edgartown, and multiple public beaches.  This...Read more

Location: 
Oak Bluffs
Sleeps: 
7
Bedrooms: 
3
Baths: 
2
Price Range:
$2,800 - $3,800
June 2027
SuMoTuWeThFrSaWeek
 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
$3,800
27
28
29
30
 $3,800
July 2027
SuMoTuWeThFrSaWeek
 1
2
3
$3,800
4
5
6
7
8
9
10
$3,800
11
12
13
14
15
16
17
$3,800
18
19
20
21
22
23
24
$3,800
25
26
27
28
29
30
31
$3,800
August 2027
SuMoTuWeThFrSaWeek
1
2
3
4
5
6
7
$3,800
8
9
10
11
12
13
14
$3,800
15
16
17
18
19
20
21
$3,800
22
23
24
25
26
27
28
$3,800
29
30
31
 $3,100
September 2027
SuMoTuWeThFrSaWeek
 1
2
3
4
$3,100
5
6
7
8
9
10
11
$2,800
12
13
14
15
16
17
18
$2,800
19
20
21
22
23
24
25
$2,800
26
27
28
29
30
 
Clean Fee: 
$400 per week
Tax: State & Local: 
14.45
Add Favorite
Get My Quote
Meadow View Farms, Out of Town, Association Tennis, Hi Speed Internet
Location: 
Oak Bluffs
Sleeps: 
6
Bedrooms: 
3
Baths: 
2
Price Range:
$3,200 - $3,200
June 2027
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
7
8
9
10
11
12
13
14
15
16
17
18
19
$3,200
20
21
22
23
24
25
26
$3,200
27
28
29
30
 $3,200
July 2027
SuMoTuWeThFrSaWeek
 1
2
3
$3,200
4
5
6
7
8
9
10
$3,200
11
12
13
14
15
16
17
$3,200
18
19
20
21
22
23
24
$3,200
25
26
27
28
29
30
31
$3,200
August 2027
SuMoTuWeThFrSaWeek
1
2
3
4
5
6
7
$3,200
8
9
10
11
12
13
14
$3,200
15
16
17
18
19
20
21
$3,200
22
23
24
25
26
27
28
$3,200
29
30
31
 $3,200
September 2027
SuMoTuWeThFrSaWeek
 1
2
3
4
$3,200
5
6
7
8
9
10
11
$3,200
12
13
14
15
16
17
18
$3,200
19
20
21
22
23
24
25
26
27
28
29
30
 
Clean Fee: 
$360 per week
Tax: State & Local: 
14.45
Add Favorite
Get My Quote
Waterfront, Private Beach, Gorgeous Water Views, Room AC, Wifi

MVVR EXCLUSIVE:  Classic, beach cottage with spectacular views across the sound, calm water swimming, and a great area for kayaking. The open kitchen, dining, and living areas are enhanced by the wall of windows...Read more

Location: 
Oak Bluffs
Sleeps: 
4
Bedrooms: 
3
Baths: 
1
Price Range:
$2,000 - $3,200
June 2027
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$2,250
6
7
8
9
10
11
12
$2,300
13
14
15
16
17
18
19
$2,700
20
21
22
23
24
25
26
$2,900
27
28
29
30
 $3,250
July 2027
SuMoTuWeThFrSaWeek
 1
2
3
$3,250
4
5
6
7
8
9
10
$3,250
11
12
13
14
15
16
17
$3,250
18
19
20
21
22
23
24
$3,250
25
26
27
28
29
30
31
$3,350
August 2027
SuMoTuWeThFrSaWeek
1
2
3
4
5
6
7
$3,400
8
9
10
11
12
13
14
$3,400
15
16
17
18
19
20
21
$3,400
22
23
24
25
26
27
28
$3,200
29
30
31
 $2,000
September 2027
SuMoTuWeThFrSaWeek
 1
2
3
4
$2,000
5
6
7
8
9
10
11
$2,000
12
13
14
15
16
17
18
$2,000
19
20
21
22
23
24
25
$2,000
26
27
28
29
30
 $2,000
Clean Fee: 
$325 per week
Tax: State & Local: 
14.45

Cottage books Tuesday to Tuesday July & August weeks

Pages