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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Chic, Meticulously Maintained Cape Style Home, 3 bedrooms, 3 Baths, Sleeps 6, Walk to Oak Bluffs Town Center and Beaches, Tucked on a Large Beautifully Landscaped Lot

Nestled in a beautifully landscaped lot in a serene and private neighborhood, this meticulously maintained cottage in Oak Bluffs offers a perfect retreat for rental guests. With chic luxury amenities, it's...Read more

Location: 
Oak Bluffs
Sleeps: 
6
Bedrooms: 
3
Baths: 
3
Price Range:
$0 - $0
June 2026
SuMoTuWeThFrSaWeek
 1
2
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5
6
$3,750
7
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13
$3,750
14
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20
$4,350
21
22
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26
27
$4,600
28
29
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 $5,400
July 2026
SuMoTuWeThFrSaWeek
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2
3
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$5,400
5
6
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$5,400
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$5,600
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$5,600
26
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30
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 $5,600
August 2026
SuMoTuWeThFrSaWeek
 1
$5,600
2
3
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$6,850
9
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$6,850
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$6,850
23
24
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27
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29
$6,350
30
31
 $3,750
September 2026
SuMoTuWeThFrSaWeek
 1
2
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5
$3,750
6
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$3,750
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$3,750
20
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25
26
$3,750
27
28
29
30
 $3,750
Clean Fee: 
$425 per week
Tax: State & Local: 
11.7
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Property Details
Stunning Oak Bluffs Luxury Home with Heated Pool, Multiple Living Areas, Walk to Town 8/10ths mile from house.

This charming tri-level home is nestled on a peaceful street in the heart of Oak Bluffs, just a 10 to 15-minute walk from the town center, Inkwell Beach, Town Beaches,...Read more

Location: 
Oak Bluffs
Sleeps: 
10
Bedrooms: 
5
Baths: 
5
Price Range:
$0 - $0
June 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
$13,500
7
8
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11
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13
$13,500
14
15
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19
20
$13,500
21
22
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26
27
$13,500
28
29
30
 $13,500
July 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
$13,500
5
6
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11
$13,500
12
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$13,500
19
20
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$13,500
26
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30
31
 $15,000
August 2026
SuMoTuWeThFrSaWeek
 1
$15,000
2
3
4
5
6
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8
$15,000
9
10
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15
$15,000
16
17
18
19
20
21
22
$15,000
23
24
25
26
27
28
29
$13,500
30
31
 $13,500
September 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$13,500
6
7
8
9
10
11
12
$8,000
13
14
15
16
17
18
19
$8,000
20
21
22
23
24
25
26
$8,000
27
28
29
30
 
Clean Fee: 
$700 per week
Tax: State & Local: 
11.7

Pool Heated to 82 degrees, included in the rental rate!

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