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 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: 
4
Bedrooms: 
2
Baths: 
2
Price Range:
$4,100 - $4,500
June 2027
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July 2027
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August 2027
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September 2027
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Clean Fee: 
$275 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 & Beach-Across the Street

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: 
4
Bedrooms: 
2
Baths: 
2
Price Range:
$4,500 - $4,500
June 2027
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July 2027
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September 2027
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Clean Fee: 
$275 per week
Tax: State & Local: 
11.7
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LECAY

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Property Details
Boutique Sweet with Designer Interior, Large Screened Porch, AC all Bedrooms, 15 Minute Walk to Oak Bluffs Center and Inkwell Beach

All newly remodeled and furnished and tucked away on a quiet Oak Bluffs lane for the perfect reprieve after a day at the beach and shopping in town, all just a...Read more

Location: 
Oak Bluffs
Sleeps: 
8
Bedrooms: 
4
Baths: 
2
Price Range:
$4,500 - $4,500
June 2027
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July 2027
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August 2027
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September 2027
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Clean Fee: 
$400 per week
Tax: State & Local: 
11.7
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SACHE

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Property Details
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
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2
3
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5
$3,100
6
7
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$3,100
13
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$3,100
20
21
22
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26
$3,100
27
28
29
30
 $3,850
July 2027
SuMoTuWeThFrSaWeek
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2
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$3,850
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$3,850
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$3,850
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$3,850
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30
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$3,850
August 2027
SuMoTuWeThFrSaWeek
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$4,160
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$4,160
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$4,160
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$4,160
29
30
31
 $4,160
September 2027
SuMoTuWeThFrSaWeek
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$4,160
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$3,800
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$3,800
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25
$3,800
26
27
28
29
30
 $3,800
Clean Fee: 
$250 per week
Tax: State & Local: 
11.7
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PETEV

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Property Details
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: 
6
Bedrooms: 
4
Baths: 
2
Price Range:
$2,460 - $4,100
June 2027
SuMoTuWeThFrSaWeek
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$2,700
6
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$2,700
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$3,000
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21
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25
26
$3,000
27
28
29
30
 $3,500
July 2027
SuMoTuWeThFrSaWeek
 1
2
3
$3,500
4
5
6
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$4,100
11
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$3,900
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$3,900
25
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31
$4,100
August 2027
SuMoTuWeThFrSaWeek
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$4,100
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$4,100
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$4,100
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$4,100
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 $3,400
September 2027
SuMoTuWeThFrSaWeek
 1
2
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$3,400
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$2,800
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$2,800
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$2,800
26
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29
30
 $2,800
Clean Fee: 
$475 per week
Tax: State & Local: 
11.7

Owner just reduced rates for available weeks in July - see calendar for adjusted rates

 

Owner will rent weekday to weekday the middle two weeks of July with a 7 night minimum to accommodate the need for auto ferry tickets if none available the weekend dates. 

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ROLAJ

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Property Details
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 - $4,000
June 2027
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July 2027
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August 2027
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September 2027
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Clean Fee: 
$250 per week
Tax: State & Local: 
11.7
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CAH48

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Property Details
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
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12
$2,700
13
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$2,700
20
21
22
23
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25
26
$2,700
27
28
29
30
 $3,500
July 2027
SuMoTuWeThFrSaWeek
 1
2
3
$3,500
4
5
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$3,500
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$3,500
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$3,500
25
26
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30
31
$4,000
August 2027
SuMoTuWeThFrSaWeek
1
2
3
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$4,000
8
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$4,000
15
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$4,000
22
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$4,000
29
30
31
 $3,000
September 2027
SuMoTuWeThFrSaWeek
 1
2
3
4
$3,000
5
6
7
8
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11
$2,700
12
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$2,700
19
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21
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25
$2,700
26
27
28
29
30
 $2,700
Clean Fee: 
$300, additional may apply multiple week rentals
Tax: State & Local: 
11.7

Owner will rent off weekend dates, with a 7-night minimum, to accommodate the need for auto ticket reservations.  

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FRANL

Inquire
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 - $3,600
June 2027
SuMoTuWeThFrSaWeek
 1
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8
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$3,600
27
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29
30
 $3,600
July 2027
SuMoTuWeThFrSaWeek
 1
2
3
$3,600
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$3,600
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$3,600
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$3,600
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$3,600
August 2027
SuMoTuWeThFrSaWeek
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2
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$3,600
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$3,600
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$3,600
22
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27
28
$3,600
29
30
31
 $3,100
September 2027
SuMoTuWeThFrSaWeek
 1
2
3
4
$3,100
5
6
7
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10
11
$2,800
12
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$2,800
19
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21
22
23
24
25
$2,800
26
27
28
29
30
 
Clean Fee: 
$400 per week
Tax: State & Local: 
11.7
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GOLLB

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Property Details
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:
$1,900 - $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
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$3,250
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19
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23
24
$3,250
25
26
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29
30
31
$3,350
August 2027
SuMoTuWeThFrSaWeek
1
2
3
4
5
6
7
$3,400
8
9
10
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14
$3,400
15
16
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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
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$2,000
12
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$2,000
19
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25
$2,000
26
27
28
29
30
 $2,000
Clean Fee: 
$325 per week
Tax: State & Local: 
11.7

Cottage books Tuesday to Tuesday July & August weeks

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LODGJ

Inquire
Property Details
Meadow View Farms, Out of Town, Association Tennis, Hi Speed Internet
Location: 
Oak Bluffs
Sleeps: 
6
Bedrooms: 
3
Baths: 
2
Price Range:
$2,900 - $3,000
June 2027
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
7
8
9
10
11
12
13
14
15
16
17
18
19
$2,900
20
21
22
23
24
25
26
$2,900
27
28
29
30
 $3,000
July 2027
SuMoTuWeThFrSaWeek
 1
2
3
$3,000
4
5
6
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8
9
10
$3,000
11
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17
$3,000
18
19
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21
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23
24
$3,000
25
26
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29
30
31
$3,000
August 2027
SuMoTuWeThFrSaWeek
1
2
3
4
5
6
7
$3,000
8
9
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$3,000
15
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21
$3,000
22
23
24
25
26
27
28
$3,000
29
30
31
 $2,900
September 2027
SuMoTuWeThFrSaWeek
 1
2
3
4
$2,900
5
6
7
8
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10
11
$2,900
12
13
14
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18
$2,900
19
20
21
22
23
24
25
26
27
28
29
30
 
Clean Fee: 
$360 per week
Tax: State & Local: 
11.7
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ALVEN

Inquire
Property Details
Spacious Oak Bluffs Home, Heated Pool 16 x 32, 4 bedrooms & 3.5 baths sleeps 8

This charming and spacious 4-bedroom, 3.5-bath home offers multiple living areas, including a main living room with TV, a cozy sitting room, and a lower-level family room featuring a TV,...Read more

Location: 
Oak Bluffs
Sleeps: 
8
Bedrooms: 
4
Baths: 
3
Price Range:
$0 - $0
June 2027
SuMoTuWeThFrSa
 1
2
3
4
5
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7
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July 2027
SuMoTuWeThFrSaWeek
 1
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$14,000
August 2027
SuMoTuWeThFrSaWeek
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$14,000
8
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$14,000
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$14,000
22
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31
 
September 2027
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26
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29
30
 
Clean Fee: 
$550
Tax: State & Local: 
11.7
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ALLER

Inquire
Property Details
Oak Bluffs 4 Bedroom Home, Walk to Town & Beach!

10-minute walk to Oak Bluffs center and beach area from this lovely modern vacation home.  Enjoy all that the summer community of Oak Bluffs has to offer with quaint shops,...Read more

Location: 
Oak Bluffs
Sleeps: 
8
Bedrooms: 
4
Baths: 
2
Price Range:
$0 - $0
June 2027
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$3,680
6
7
8
9
10
11
12
$3,680
13
14
15
16
17
18
19
$3,680
20
21
22
23
24
25
26
$3,900
27
28
29
30
 $5,250
July 2027
SuMoTuWeThFrSaWeek
 1
2
3
$5,250
4
5
6
7
8
9
10
$5,250
11
12
13
14
15
16
17
$5,250
18
19
20
21
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23
24
$5,250
25
26
27
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29
30
31
$5,250
August 2027
SuMoTuWeThFrSaWeek
1
2
3
4
5
6
7
$6,000
8
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$6,000
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$6,000
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$5,750
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 $4,500
September 2027
SuMoTuWeThFrSaWeek
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$4,500
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$4,200
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$4,200
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$4,200
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 $4,200
Clean Fee: 
$475 per week
Tax: State & Local: 
11.7
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KLEIB

Inquire
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 2027
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July 2027
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August 2027
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September 2027
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Clean Fee: 
$250 per week
Tax: State & Local: 
11.7
Add Favorite
 
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WOODO

Inquire
Property Details
Weku House, Luxury Living, Features Outstanding Entertainment Level, Guest Apartment, Custom Interior and Coastal Design

The Weku House is a luxury, 5,000 square foot home located in Oak Bluffs. Elegantly decorated with designer furnishings and interior appointments, the meticulous attention to detail makes this home a unique vacation retreat. With a total of 5 bedrooms and 5 1/2 baths, the home...Read more

Location: 
Oak Bluffs
Sleeps: 
10
Bedrooms: 
5
Baths: 
5
Price Range:
$0 - $0
June 2027
SuMoTuWeThFrSa
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July 2027
SuMoTuWeThFrSa
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August 2027
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$19,500
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$16,500
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September 2027
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Clean Fee: 
$650 per week
Tax: State & Local: 
11.7
Add Favorite
 
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PETEO

Inquire
Property Details
Beautiful Custom Built Home Overlooking Little Duarte Pond, Beautifully Landscaped

Outstanding vacation home, centrally located to all three down-island town centers and multiple public beaches. This lovely home in a serene setting overlooks the picturesque Little Duarte Pond in the Iron Hill...Read more

Location: 
Oak Bluffs
Sleeps: 
8
Bedrooms: 
4
Baths: 
5
Price Range:
$0 - $0
June 2027
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July 2027
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August 2027
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September 2027
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Clean Fee: 
$575 per week
Tax: State & Local: 
11.7

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