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.

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Meadow View Farms, Out of Town, Association Tennis, Hi Speed Internet
Location: 
Oak Bluffs
Sleeps: 
6
Bedrooms: 
3
Baths: 
2
Price Range:
$2,900 - $2,900
June 2025
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July 2025
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 $3,000
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 $2,900
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$2,900
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Clean Fee: 
$360 per week
Tax: State & Local: 
11.7
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ST304

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Property Details
Sea View Condominium, Water View, Walk to town and beach

Sea View Condominium with a breathtaking view of Nantucket Sound from almost every room. Just steps from the beach.Read more

Location: 
Oak Bluffs
Sleeps: 
5
Bedrooms: 
2
Baths: 
2
Price Range:
$2,900 - $2,900
June 2025
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July 2025
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 $4,800
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 $3,600
September 2025
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$2,900
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$2,900
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 $2,900
Clean Fee: 
$275 per week
Tax: State & Local: 
11.7
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FRANL

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Property Details
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:
$2,300 - $2,800
June 2025
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July 2025
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 $2,800
September 2025
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$2,800
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$2,800
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 $2,300
Clean Fee: 
$400 per week
Tax: State & Local: 
11.7
Add Favorite
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GRATD

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Property Details
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:
$2,000 - $2,500
June 2025
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July 2025
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$2,000
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Clean Fee: 
$260 per week
Tax: State & Local: 
11.7
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PEOTA

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Property Details
Pristine Water view Home, Located in the Community of Homes known as Water View Farms, Walk to Private Association Waterfront, Great Play Beach, Launch Kayaks

This charming updated home is set in idyllic Water View Farms overlooking Sengekontacket pond.  This well-thought-out home offers a beautifully landscaped yard and cottage-style living with indoor spaces that transition...Read more

Location: 
Oak Bluffs
Sleeps: 
4
Bedrooms: 
2
Baths: 
2
Price Range:
$2,000 - $2,500
June 2025
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July 2025
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 $5,770
August 2025
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$4,720
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 $3,500
September 2025
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$2,500
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 $2,000
Clean Fee: 
$300 per week
Tax: State & Local: 
11.7
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CASHK

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Property Details
Lovely Home, Centrally Located, Bike Paths, AC all Rooms

This lovely 3 bedroom home features an open floor plan on the living level, colorful decor, window AC in all rooms, and a well-equipped modern kitchen. The home is nicely situated...Read more

Location: 
Oak Bluffs
Sleeps: 
5
Bedrooms: 
3
Baths: 
2
Price Range:
$0 - $0
June 2025
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July 2025
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 $7,800
August 2025
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September 2025
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Clean Fee: 
$200 per week
Tax: State & Local: 
11.7
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WHARG

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Property Details
Lovely Home in a quiet Neighborhood. Walk to Town Center and Inkwell Beach, Large Private Deck, Room AC

Spacious sun-filled contemporary home located on a quiet private street, a 10-minute walk to town center, Inkwell Beach, and the harborfront.

The first level features a spacious kitchen with stainless steel...Read more

Location: 
Oak Bluffs
Sleeps: 
6
Bedrooms: 
3
Baths: 
3
Price Range:
$0 - $0
June 2025
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July 2025
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$6,400
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 $7,200
August 2025
SuMoTuWeThFrSaWeek
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$7,200
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 $5,700
September 2025
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$5,700
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Clean Fee: 
$375 per week
Tax: State & Local: 
11.7
Add Favorite
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FRIEM

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Property Details
Beautiful East Chop Home , Walk to Town & Beach, Outdoor Patio Area with Patio Dining

Lovely Spacious East Chop Area home features elegant custom craftsmanship throughout, a light-filled open kitchen, living and dining areas, and a family/TV room. 3 bedrooms on the 2nd level and 2...Read more

Location: 
Oak Bluffs
Sleeps: 
6
Bedrooms: 
3
Baths: 
2
Price Range:
$0 - $0
June 2025
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July 2025
SuMoTuWeThFrSaWeek
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$5,800
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$6,050
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 $6,500
August 2025
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$6,500
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Clean Fee: 
$400 per week
Tax: State & Local: 
11.7
Add Favorite
 
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KLEIB

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Property Details
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:
$0 - $0
June 2025
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July 2025
SuMoTuWeThFrSaWeek
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$3,800
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$3,800
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 $4,020
August 2025
SuMoTuWeThFrSaWeek
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$4,020
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$4,100
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$3,920
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$3,720
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 $2,770
September 2025
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$2,540
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$2,390
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$2,300
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 $2,190
Clean Fee: 
$250 per week
Tax: State & Local: 
11.7
Add Favorite
 
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PRIAN

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Property Details
Beautiful Upscale Contemporary Home, Designer Details Throughout, 4 Bedrooms, 4.5 Baths, Muliple Living Areas

Discover this stunning tri-level vacation home nestled in a peaceful community just on the outskirts of Oak Bluffs and minutes away from Oak Bluffs center, Edgartown Village, downtown Vineyard Haven, and several...Read more

Location: 
Oak Bluffs
Sleeps: 
7
Bedrooms: 
4
Baths: 
4
Price Range:
$0 - $0
June 2025
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July 2025
SuMoTuWeThFrSaWeek
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 $8,000
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$7,500
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Clean Fee: 
$750 per week
Tax: State & Local: 
11.7
Add Favorite
 
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ROCHA

(0)Inquire/Share
Property Details
Bridle Path House, Quiet Lovely Neighborhood, Porch and Deck Areas, Large Yard, Central Location to all 3 Down Island Towns and Beaches

Lovely 3 bedroom 3 bath home sleeps 8, bordered by a large landscaped yard. The exterior features a shady wrap-around porch with rockers, a perfect place to relax, read a book,  and enjoy...Read more

Location: 
Oak Bluffs
Sleeps: 
8
Bedrooms: 
3
Baths: 
2
Price Range:
$0 - $0
June 2025
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July 2025
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$5,900
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$5,900
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 $5,900
August 2025
SuMoTuWeThFrSaWeek
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$5,900
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$6,500
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$6,500
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$6,500
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Clean Fee: 
$300 per week
Tax: State & Local: 
11.7
Add Favorite
 
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TRAVM

(0)Inquire/Share
Property Details
Updated East Chop Area Summer Retreat, Great Proximity to Town Center and Beaches, Cottage Styling with All the Modern Amenities, Central A/C. Covered Porch and Open Patio Areas.

Visitors will enjoy this delightful &  comfortable 4 bedroom, 3 bath home in the desirable East Chop area of Oak Bluffs. 

Relax in the breeze with your morning coffee on the front...Read more

Location: 
Oak Bluffs
Sleeps: 
8
Bedrooms: 
4
Baths: 
2
Price Range:
$0 - $0
June 2025
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July 2025
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30
31
 $6,800
August 2025
SuMoTuWeThFrSaWeek
 1
2
$6,800
3
4
5
6
7
8
9
$7,000
10
11
12
13
14
15
16
$7,250
17
18
19
20
21
22
23
24
25
26
27
28
29
30
31
 
September 2025
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
 
Clean Fee: 
$475 per week
Tax: State & Local: 
11.7
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CURRM

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Property Details
Outstanding Designer Home, 15 Min Walk to Oak Bluffs Center, 4 Bedrooms each en suite with TV, Occupancy Limit 9

Stylish Dreamy Home on Dreamer's Way, less than a mile from the town center and beach area! The owners have left nothing out in the way of design and comfort in...Read more

Location: 
Oak Bluffs
Sleeps: 
9
Bedrooms: 
4
Baths: 
4
Price Range:
$0 - $0
June 2025
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 2025
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
7
8
9
10
11
12
$8,500
13
14
15
16
17
18
19
$8,800
20
21
22
23
24
25
26
$9,000
27
28
29
30
31
 $9,200
August 2025
SuMoTuWeThFrSaWeek
 1
2
$9,200
3
4
5
6
7
8
9
$9,700
10
11
12
13
14
15
16
$10,500
17
18
19
20
21
22
23
$11,000
24
25
26
27
28
29
30
$9,500
31
 $8,000
September 2025
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
$8,000
7
8
9
10
11
12
13
$6,500
14
15
16
17
18
19
20
$5,500
21
22
23
24
25
26
27
$4,500
28
29
30
 
Clean Fee: 
$500 per week
Tax: State & Local: 
11.7

Owner ACCEPTS 3 NIGHT MINIMUM STAYS, MEMORIAL DAY WEEKEND TO JUNE 16TH, AND SEPT 7TH TO THE END OF OCTOBER.

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LANLL

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Property Details
Outstanding Waterfront Home & Guest House, Panoramic Views, Beach on the Lagoon, 5 Bedrooms, 4 Baths, AC

Gorgeous Expansive Waterfront Main & Guest Cottage, perfect for a multigenerational family vacation.  Spectacular views across and up the lagoon, this pristine home and guest cottage sits on just under two...Read more

Location: 
Oak Bluffs
Sleeps: 
9
Bedrooms: 
5
Baths: 
4
Price Range:
$0 - $0
June 2025
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 2025
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
7
8
9
10
11
12
13
14
15
16
17
18
19
$14,000
20
21
22
23
24
25
26
$14,000
27
28
29
30
31
 $16,000
August 2025
SuMoTuWeThFrSaWeek
 1
2
$16,000
3
4
5
6
7
8
9
$16,000
10
11
12
13
14
15
16
$18,000
17
18
19
20
21
22
23
$16,000
24
25
26
27
28
29
30
$16,000
31
 $14,000
September 2025
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
$14,000
7
8
9
10
11
12
13
$12,000
14
15
16
17
18
19
20
$12,000
21
22
23
24
25
26
27
$12,000
28
29
30
 
Clean Fee: 
$600 per week
Tax: State & Local: 
11.7

Two Week Minimum Stay Required per Owner

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GRACM

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Property Details
Beautful Oak Bluffs Home. Pool, Tucked on a Large Private &Extensively Landscaped Lot, 4 Bedrooms, Sleeps 9

Modern, spacious recently updated vacation home with a heated pool tucked on 1.5 acres of landscaped grounds provides an ideal setting for families and friends to enjoy their time together. The...Read more

Location: 
Oak Bluffs
Sleeps: 
9
Bedrooms: 
4
Baths: 
2
Price Range:
$0 - $0
June 2025
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 2025
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
7
8
9
10
11
12
$7,500
13
14
15
16
17
18
19
$9,250
20
21
22
23
24
25
26
$9,250
27
28
29
30
31
 $9,250
August 2025
SuMoTuWeThFrSaWeek
 1
2
$9,250
3
4
5
6
7
8
9
$12,250
10
11
12
13
14
15
16
$12,250
17
18
19
20
21
22
23
$12,250
24
25
26
27
28
29
30
$7,500
31
 $7,500
September 2025
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
$7,500
7
8
9
10
11
12
13
14
15
16
17
18
19
20
$6,250
21
22
23
24
25
26
27
$6,250
28
29
30
 $6,250
Clean Fee: 
$500 per week
Tax: State & Local: 
11.7

Pool Heated to 81 degrees July & August weeks included in the rental rate. 

Pool Heated to 81 degrees,  additional $275 per week June& September weeks 2023

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