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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Seaview Condo Unit, Gorgeous Water Views, In Town Location, Modern updated Interior!

Note: Seavies Condos is a 3-minute walk from the Steamship Authority dock in Oak Bluffs and two blocks from the Island Queen ferry dock. Perfect location if you cannot or...Read more

Location: 
Oak Bluffs
Sleeps: 
4
Bedrooms: 
2
Baths: 
2
Price Range:
$1,850 - $4,850
June 2024
SuMoTuWeThFrSaWeek
 1
$1,850
2
3
4
5
6
7
8
$1,940
9
10
11
12
13
14
15
$1,900
16
17
18
19
20
21
22
$2,000
23
24
25
26
27
28
29
$3,300
30
 $3,350
July 2024
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
$3,350
7
8
9
10
11
12
13
$3,850
14
15
16
17
18
19
20
$3,950
21
22
23
24
25
26
27
$3,950
28
29
30
31
 $4,850
August 2024
SuMoTuWeThFrSaWeek
 1
2
3
$4,850
4
5
6
7
8
9
10
$4,850
11
12
13
14
15
16
17
$4,850
18
19
20
21
22
23
24
$4,850
25
26
27
28
29
30
31
$4,750
September 2024
SuMoTuWeThFrSaWeek
1
2
3
4
5
6
7
$2,550
8
9
10
11
12
13
14
$2,350
15
16
17
18
19
20
21
$1,950
22
23
24
25
26
27
28
$1,950
29
30
 $1,950
Clean Fee: 
$230 per week
Tax: State & Local: 
11.7

5 minute walk from Steamship Authority Oak Bluffs dock to the Seaview Condos.  2 blocks from the Island Queen ferry dock.  

 
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CLARO

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New Contemporary Farmhouse Design, Multiple Living Areas, Screened Porch and Farmers Porch, Bike or Walk to Oak Bluffs Center.

Situated just on the outskirts of Oak Bluffs, this lovely new vacation home offers renters modern styling with multiple living spaces and all the conveniences renters look for in a vacation...Read more

Location: 
Oak Bluffs
Sleeps: 
7
Bedrooms: 
3
Baths: 
2
Price Range:
$2,800 - $4,800
June 2024
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
7
8
$3,000
9
10
11
12
13
14
15
$3,000
16
17
18
19
20
21
22
$3,300
23
24
25
26
27
28
29
$3,950
30
 $4,300
July 2024
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
$4,300
7
8
9
10
11
12
13
$4,300
14
15
16
17
18
19
20
$4,300
21
22
23
24
25
26
27
$4,300
28
29
30
31
 $4,600
August 2024
SuMoTuWeThFrSaWeek
 1
2
3
$4,600
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
$4,600
25
26
27
28
29
30
31
$3,600
September 2024
SuMoTuWeThFrSaWeek
1
2
3
4
5
6
7
$3,300
8
9
10
11
12
13
14
$3,300
15
16
17
18
19
20
21
$2,800
22
23
24
25
26
27
28
$2,800
29
30
 
Clean Fee: 
$300 per week
Tax: State & Local: 
11.7
 
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NEWMJ

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Newly update mid-century modern beach house set in the private community of homes surrounding Sengekontacket pond. The cozy summer cottage offers indoor and outdoor living at its best with a...Read more

Location: 
Oak Bluffs
Sleeps: 
6
Bedrooms: 
3
Baths: 
2
Price Range:
$2,450 - $4,720
June 2024
SuMoTuWeThFrSaWeek
 1
$3,670
2
3
4
5
6
7
8
$3,670
9
10
11
12
13
14
15
$3,670
16
17
18
19
20
21
22
$4,720
23
24
25
26
27
28
29
$4,720
30
 $5,800
July 2024
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
$5,800
7
8
9
10
11
12
13
$5,800
14
15
16
17
18
19
20
$5,800
21
22
23
24
25
26
27
28
29
30
31
 
August 2024
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
$5,800
September 2024
SuMoTuWeThFrSaWeek
1
2
3
4
5
6
7
$5,800
8
9
10
11
12
13
14
$3,670
15
16
17
18
19
20
21
$3,670
22
23
24
25
26
27
28
$3,670
29
30
 $3,080
Clean Fee: 
$400 per week
Tax: State & Local: 
11.7
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GRATD

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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 - $4,600
June 2024
SuMoTuWeThFrSaWeek
 1
$3,000
2
3
4
5
6
7
8
$3,900
9
10
11
12
13
14
15
$3,900
16
17
18
19
20
21
22
$3,900
23
24
25
26
27
28
29
$4,200
30
 $4,600
July 2024
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
$4,600
7
8
9
10
11
12
13
$4,600
14
15
16
17
18
19
20
$4,600
21
22
23
24
25
26
27
$4,600
28
29
30
31
 $4,600
August 2024
SuMoTuWeThFrSaWeek
 1
2
3
$4,600
4
5
6
7
8
9
10
$4,600
11
12
13
14
15
16
17
$4,600
18
19
20
21
22
23
24
$4,600
25
26
27
28
29
30
31
$4,600
September 2024
SuMoTuWeThFrSaWeek
1
2
3
4
5
6
7
$4,600
8
9
10
11
12
13
14
$4,000
15
16
17
18
19
20
21
$2,500
22
23
24
25
26
27
28
$2,000
29
30
 
Clean Fee: 
$250 per week
Tax: State & Local: 
11.7
 
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ST203

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Seaview Condominium, Waterview, Walk to Town and Beach

Beachfront Condominium with breathtaking views of Nantucket Sound. Just steps to the beach.Read more

Location: 
Oak Bluffs
Sleeps: 
5
Bedrooms: 
2
Baths: 
2
Price Range:
$3,850 - $4,550
June 2024
SuMoTuWeThFrSaWeek
 1
$3,850
2
3
4
5
6
7
8
$2,600
9
10
11
12
13
14
15
$3,850
16
17
18
19
20
21
22
$3,850
23
24
25
26
27
28
29
$3,850
30
 $4,550
July 2024
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
$4,550
7
8
9
10
11
12
13
$4,550
14
15
16
17
18
19
20
$4,550
21
22
23
24
25
26
27
$4,550
28
29
30
31
 $4,550
August 2024
SuMoTuWeThFrSaWeek
 1
2
3
$4,550
4
5
6
7
8
9
10
$4,550
11
12
13
14
15
16
17
$4,550
18
19
20
21
22
23
24
$4,550
25
26
27
28
29
30
31
$4,550
September 2024
SuMoTuWeThFrSaWeek
1
2
3
4
5
6
7
$3,850
8
9
10
11
12
13
14
$3,850
15
16
17
18
19
20
21
$3,850
22
23
24
25
26
27
28
$3,850
29
30
 $3,850
Clean Fee: 
$275 per week
Tax: State & Local: 
11.7
 
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DONOP

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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 - $4,500
June 2024
SuMoTuWeThFrSaWeek
 1
$2,400
2
3
4
5
6
7
8
$2,400
9
10
11
12
13
14
15
$3,050
16
17
18
19
20
21
22
$3,050
23
24
25
26
27
28
29
$3,200
30
 $4,000
July 2024
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
$4,000
7
8
9
10
11
12
13
$4,000
14
15
16
17
18
19
20
$4,200
21
22
23
24
25
26
27
$4,200
28
29
30
31
 $4,500
August 2024
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
$3,400
September 2024
SuMoTuWeThFrSaWeek
1
2
3
4
5
6
7
$2,600
8
9
10
11
12
13
14
$2,600
15
16
17
18
19
20
21
$2,600
22
23
24
25
26
27
28
$2,600
29
30
 $2,600
Clean Fee: 
$375 per week
Tax: State & Local: 
11.7

Ferry Tickets Available, 7/14 and 7/21 weeks, Inquire for details! (mv)

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ROLAJ

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Waterfront, Water View, Lagoon Beach

This charming, recently renovated, waterfront home atop the lagoon bluffs, boasts spectacular sunsets and panoramic waterfront views of the Lagoon, outer Vineyard Haven Harbor, and Cape Cod from patios, living...Read more

Location: 
Oak Bluffs
Sleeps: 
8
Bedrooms: 
4
Baths: 
2
Price Range:
$4,000 - $4,500
June 2024
SuMoTuWeThFrSaWeek
 1
$4,300
2
3
4
5
6
7
8
$4,300
9
10
11
12
13
14
15
$4,300
16
17
18
19
20
21
22
$5,100
23
24
25
26
27
28
29
$6,000
30
 $6,200
July 2024
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
$6,200
7
8
9
10
11
12
13
$6,200
14
15
16
17
18
19
20
$6,200
21
22
23
24
25
26
27
$6,200
28
29
30
31
 $6,300
August 2024
SuMoTuWeThFrSaWeek
 1
2
3
$6,300
4
5
6
7
8
9
10
$6,300
11
12
13
14
15
16
17
$6,300
18
19
20
21
22
23
24
$6,300
25
26
27
28
29
30
31
$5,800
September 2024
SuMoTuWeThFrSaWeek
1
2
3
4
5
6
7
$4,500
8
9
10
11
12
13
14
$4,500
15
16
17
18
19
20
21
$4,500
22
23
24
25
26
27
28
$4,500
29
30
 $4,000
Clean Fee: 
$250 per week
Tax: State & Local: 
11.7
 
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KEANM

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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:
$2,950 - $4,300
June 2024
SuMoTuWeThFrSaWeek
 1
$2,950
2
3
4
5
6
7
8
$2,950
9
10
11
12
13
14
15
$2,950
16
17
18
19
20
21
22
$2,950
23
24
25
26
27
28
29
$3,500
30
 $4,300
July 2024
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
$4,300
7
8
9
10
11
12
13
$4,300
14
15
16
17
18
19
20
$4,300
21
22
23
24
25
26
27
$4,300
28
29
30
31
 $4,300
August 2024
SuMoTuWeThFrSaWeek
 1
2
3
$4,300
4
5
6
7
8
9
10
$4,300
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
$3,500
September 2024
SuMoTuWeThFrSaWeek
1
2
3
4
5
6
7
$2,950
8
9
10
11
12
13
14
$2,950
15
16
17
18
19
20
21
$2,950
22
23
24
25
26
27
28
$2,950
29
30
 $2,950
Clean Fee: 
$500 per week
Tax: State & Local: 
11.7
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TOTHG

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Adorable Updated Vineyard Cottage, Lovely Landscaped Yard, Central A/C, Flat Screen TV, Bike Paths at end of Drive, One Mile to Oak Bluffs Center

Bright and classic summer cottage. Conveniently located just one mile from Oak Bluffs town center, Inkwell Beach, shops, fine and family dining, historic Flying Horses Carousel, public tennis courts, Ocean...Read more

Location: 
Oak Bluffs
Sleeps: 
5
Bedrooms: 
3
Baths: 
1
Price Range:
$2,500 - $4,200
June 2024
SuMoTuWeThFrSaWeek
 1
$2,700
2
3
4
5
6
7
8
$2,700
9
10
11
12
13
14
15
$3,000
16
17
18
19
20
21
22
$3,000
23
24
25
26
27
28
29
$3,200
30
 $4,200
July 2024
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
$4,200
7
8
9
10
11
12
13
$4,200
14
15
16
17
18
19
20
$4,200
21
22
23
24
25
26
27
$4,200
28
29
30
31
 $4,200
August 2024
SuMoTuWeThFrSaWeek
 1
2
3
$4,200
4
5
6
7
8
9
10
$4,200
11
12
13
14
15
16
17
$4,200
18
19
20
21
22
23
24
$4,200
25
26
27
28
29
30
31
$4,000
September 2024
SuMoTuWeThFrSaWeek
1
2
3
4
5
6
7
$3,600
8
9
10
11
12
13
14
$2,600
15
16
17
18
19
20
21
$2,600
22
23
24
25
26
27
28
$2,600
29
30
 $2,600
Clean Fee: 
$175 per week
Tax: State & Local: 
11.7
 
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WILCM

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Hidden Cove, Association Tennis Courts, 3 Bedrooms, 2.5 Baths, Screened Porch and Deck

New for 2024. All new kitchen to be completed mid April.

Set in a lovely community of homes known as Hidden Cove, this lovely contemporary home is tucked in on a...Read more

Location: 
Oak Bluffs
Sleeps: 
7
Bedrooms: 
3
Baths: 
2
Price Range:
$3,100 - $4,200
June 2024
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
7
8
9
10
11
12
13
14
15
16
17
18
19
20
21
22
$3,200
23
24
25
26
27
28
29
$3,200
30
 $3,900
July 2024
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
$3,900
7
8
9
10
11
12
13
$3,900
14
15
16
17
18
19
20
$3,900
21
22
23
24
25
26
27
$4,200
28
29
30
31
 $4,200
August 2024
SuMoTuWeThFrSaWeek
 1
2
3
$4,200
4
5
6
7
8
9
10
$4,500
11
12
13
14
15
16
17
$4,600
18
19
20
21
22
23
24
$4,600
25
26
27
28
29
30
31
$3,900
September 2024
SuMoTuWeThFrSaWeek
1
2
3
4
5
6
7
$3,100
8
9
10
11
12
13
14
$3,100
15
16
17
18
19
20
21
$3,100
22
23
24
25
26
27
28
$3,100
29
30
 
Clean Fee: 
$325 per week
Tax: State & Local: 
11.7

Rates reduced for available weeks in July and 8/25 week - see calendar for adjusted rates

 
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PETEV

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Lovely Waterfront Home, Oak Bluffs, Gorgeous Water Views, Association Tennis Courts, AC, Wi-fi, Bike Paths Nearby

Note: Pricing for this waterfront home takes into account that this is an older-style home. Please note that baths and kitchen have not been updated

MVVR Exclusive! Spacious, traditional waterfront Cape Cod style home...Read more

Location: 
Oak Bluffs
Sleeps: 
6
Bedrooms: 
4
Baths: 
2
Price Range:
$2,460 - $4,100
June 2024
SuMoTuWeThFrSaWeek
 1
$3,600
2
3
4
5
6
7
8
$3,600
9
10
11
12
13
14
15
$3,600
16
17
18
19
20
21
22
$3,600
23
24
25
26
27
28
29
$3,600
30
 $4,100
July 2024
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
$4,100
7
8
9
10
11
12
13
$4,100
14
15
16
17
18
19
20
$4,100
21
22
23
24
25
26
27
$4,100
28
29
30
31
 $4,100
August 2024
SuMoTuWeThFrSaWeek
 1
2
3
$4,100
4
5
6
7
8
9
10
$4,100
11
12
13
14
15
16
17
$4,100
18
19
20
21
22
23
24
$4,100
25
26
27
28
29
30
31
$3,910
September 2024
SuMoTuWeThFrSaWeek
1
2
3
4
5
6
7
$3,660
8
9
10
11
12
13
14
$3,660
15
16
17
18
19
20
21
$3,660
22
23
24
25
26
27
28
$2,460
29
30
 $2,460
Clean Fee: 
$475 per week
Tax: State & Local: 
11.7
 
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VANAL

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Classic Updated Gingerbread Cottage, 5 Minute Stroll Along Harbor to Beach and Town Center,

Classic Vineyard Oak Bluffs Cottage, tastefully and comfortably furnished. Large open deck on both the main and 2nd levels. The main living level features a lovely kitchen, very well stocked with...Read more

Location: 
Oak Bluffs
Sleeps: 
6
Bedrooms: 
3
Baths: 
2
Price Range:
$3,000 - $4,000
June 2024
SuMoTuWeThFrSaWeek
 1
$3,000
2
3
4
5
6
7
8
$3,000
9
10
11
12
13
14
15
$3,000
16
17
18
19
20
21
22
$3,000
23
24
25
26
27
28
29
$4,000
30
 $5,000
July 2024
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
$5,000
7
8
9
10
11
12
13
$4,500
14
15
16
17
18
19
20
$4,500
21
22
23
24
25
26
27
$4,500
28
29
30
31
 $6,500
August 2024
SuMoTuWeThFrSaWeek
 1
2
3
$6,500
4
5
6
7
8
9
10
$6,500
11
12
13
14
15
16
17
$7,500
18
19
20
21
22
23
24
$5,000
25
26
27
28
29
30
31
$4,500
September 2024
SuMoTuWeThFrSaWeek
1
2
3
4
5
6
7
$4,500
8
9
10
11
12
13
14
$3,000
15
16
17
18
19
20
21
$3,000
22
23
24
25
26
27
28
$3,000
29
30
 $3,000
Clean Fee: 
$325 per week
Tax: State & Local: 
11.7
 
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MAHAB

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Sweet Updated 3 Bedroom Home, Nicely Tucked in Lightly Wooded Area, Central Location, Beaches and Towns just a short Drive!

Lovely reverse contemporary home with a large deck, outdoor dining, and grill area. The upper level of this home features an open kitchen, living, and dining area stylishly furnished.  Nicely equipped kitchen...Read more

Location: 
Oak Bluffs
Sleeps: 
6
Bedrooms: 
3
Baths: 
1
Price Range:
$2,900 - $4,000
June 2024
SuMoTuWeThFrSaWeek
 1
$3,500
2
3
4
5
6
7
8
$3,500
9
10
11
12
13
14
15
$3,500
16
17
18
19
20
21
22
$3,500
23
24
25
26
27
28
29
$3,500
30
 $4,000
July 2024
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
$4,000
7
8
9
10
11
12
13
$4,000
14
15
16
17
18
19
20
$4,000
21
22
23
24
25
26
27
$4,000
28
29
30
31
 $4,000
August 2024
SuMoTuWeThFrSaWeek
 1
2
3
$4,000
4
5
6
7
8
9
10
$4,000
11
12
13
14
15
16
17
$4,000
18
19
20
21
22
23
24
$4,000
25
26
27
28
29
30
31
$3,500
September 2024
SuMoTuWeThFrSaWeek
1
2
3
4
5
6
7
$3,500
8
9
10
11
12
13
14
$3,500
15
16
17
18
19
20
21
$3,500
22
23
24
25
26
27
28
$3,500
29
30
 $3,500
Clean Fee: 
$300 per week
Tax: State & Local: 
11.7
 
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CAH48

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Classic Lovely Vineyard Cottage, Pristine Condition, Approximately 1.5 Miles to Town 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 2024
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
7
8
$2,700
9
10
11
12
13
14
15
$2,700
16
17
18
19
20
21
22
$2,700
23
24
25
26
27
28
29
$2,900
30
 $3,500
July 2024
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
$3,500
7
8
9
10
11
12
13
$3,500
14
15
16
17
18
19
20
$3,500
21
22
23
24
25
26
27
$3,500
28
29
30
31
 $4,000
August 2024
SuMoTuWeThFrSaWeek
 1
2
3
$4,000
4
5
6
7
8
9
10
$4,000
11
12
13
14
15
16
17
$4,000
18
19
20
21
22
23
24
$4,000
25
26
27
28
29
30
31
$4,000
September 2024
SuMoTuWeThFrSaWeek
1
2
3
4
5
6
7
$2,700
8
9
10
11
12
13
14
$2,700
15
16
17
18
19
20
21
$2,700
22
23
24
25
26
27
28
$2,700
29
30
 
Clean Fee: 
$300, additional may apply multiple week rentals
Tax: State & Local: 
11.7
 
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ST304

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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:
$3,850 - $3,850
June 2024
SuMoTuWeThFrSaWeek
 1
$3,850
2
3
4
5
6
7
8
$2,700
9
10
11
12
13
14
15
$3,850
16
17
18
19
20
21
22
$3,850
23
24
25
26
27
28
29
$3,850
30
 $4,550
July 2024
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
$4,550
7
8
9
10
11
12
13
$4,550
14
15
16
17
18
19
20
$4,550
21
22
23
24
25
26
27
$4,550
28
29
30
31
 $5,070
August 2024
SuMoTuWeThFrSaWeek
 1
2
3
$5,070
4
5
6
7
8
9
10
$5,070
11
12
13
14
15
16
17
$5,070
18
19
20
21
22
23
24
$5,070
25
26
27
28
29
30
31
$5,070
September 2024
SuMoTuWeThFrSaWeek
1
2
3
4
5
6
7
$3,850
8
9
10
11
12
13
14
$3,850
15
16
17
18
19
20
21
$3,850
22
23
24
25
26
27
28
$3,850
29
30
 
Clean Fee: 
$199 per week
Tax: State & Local: 
11.7

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