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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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:
$3,400 - $7,600
June 2025
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 $7,200
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Clean Fee: 
$575 per week
Tax: State & Local: 
11.7
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VANAL

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Property Details
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 - $7,500
June 2025
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$3,000
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 $3,000
Clean Fee: 
$350 per week
Tax: State & Local: 
11.7
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TRAVM

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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:
$5,350 - $7,500
June 2025
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 $6,800
August 2025
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Clean Fee: 
$500 per week
Tax: State & Local: 
11.7
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JOHNL

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Property Details
"Endless Summer Vacation" Stylish, Newly Update 3 + Bedroom, Sleeps 8, East Chop Area of Oak Bluffs, Deck Living & Dining Area, Screened Porch,
Location: 
Oak Bluffs
Sleeps: 
8
Bedrooms: 
4
Baths: 
2
Price Range:
$3,500 - $7,500
June 2025
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 $4,500
September 2025
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 $4,500
Clean Fee: 
$450 per week
Tax: State & Local: 
11.7

Owner will rent off weekend dates to accommodate the need for ferry tickets July weeks. 

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BICKE

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Property Details
East Chop Area, Tri-Level Home with Distant Water views, Located just 1.5 Mi to Oak Bluffs Center

Beautiful summer home with distant water views, located in the desirable East Chop neighborhood.  This 4 bedroom, 3 bath home is located just 1.5 miles from Oak Bluffs Center & Beach. 

The...Read more

Location: 
Oak Bluffs
Sleeps: 
8
Bedrooms: 
4
Baths: 
3
Price Range:
$6,500 - $7,150
June 2025
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 $7,000
September 2025
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$6,500
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 $6,500
Clean Fee: 
$600 per week
Tax: State & Local: 
11.7
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BURBS

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Property Details
Set Just on the ouskirts of Oak Bluffs. Central AC, Screened Porch

Lovely spacious 3+ bedroom, 3.5 bedroom home within a mile from Oak Bluffs center and beach area.  Fully furnished screen porch and shady porch.  This lovely home sleeps families of 8 comfortably.

The main...Read more

Location: 
Oak Bluffs
Sleeps: 
8
Bedrooms: 
3
Baths: 
3
Price Range:
$6,000 - $7,000
June 2025
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August 2025
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Clean Fee: 
$425 per week
Tax: State & Local: 
11.7
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DONAK

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Property Details
Stunning Luxury Home, Complete Renovation in Main House, Sweet Updated Guest House, Walk to Oak Bluffs Center

Gorgeous Luxury Home, Newly Renovated with Stylish Updates, Walking Distance to Oak Bluffs Center

This stunning bungalow-style home has undergone a complete renovation, blending luxury designer decor with the original...Read more

Location: 
Oak Bluffs
Sleeps: 
8
Bedrooms: 
4
Baths: 
4
Price Range:
$7,000 - $7,000
June 2025
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 $15,000
August 2025
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 $7,000
September 2025
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$7,000
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Clean Fee: 
$550 per week
Tax: State & Local: 
11.7
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HANRJ

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Property Details
Spacious Oak Bluffs Contemporary Home, 4 Bedrooms & 4 Baths, Quiet Private Location in Bayes Hill Community of Homes

Privately situated on the outskirts of Oak Bluffs, yet centrally located to towns and beaches. The home features a large patio area with outdoor dining and grill area and a spacious...Read more

Location: 
Oak Bluffs
Sleeps: 
8
Bedrooms: 
4
Baths: 
4
Price Range:
$3,500 - $7,000
June 2025
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August 2025
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$4,000
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 $3,500
Clean Fee: 
$575
Tax: State & Local: 
11.7

Owner reduced rates for available weeks in June, July & August - see calendar for adjusted rates

 

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HOL14

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Property Details
Gorgeous Waterfront Home on the Lagoon Oak Bluffs, Kayak, Swim, Enjoy the Sunsets, 4 bedrooms 4.5 Baths

Stunning Waterfront home nestled just in the outskirts of Oak Bluffs, 1 mile from town center and Oak Bluffs beaches. This home offers 150 feet of private lagoon beach perfect...Read more

Location: 
Oak Bluffs
Sleeps: 
8
Bedrooms: 
4
Baths: 
4
Price Range:
$5,000 - $7,000
June 2025
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August 2025
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$7,000
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 $7,000
Clean Fee: 
$750 per week
Tax: State & Local: 
11.7
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GUCOB

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Property Details
Spacious Home with Heated Pool, Pool Bar with TV, Patio Surround, Deck Overlooking the Pool & Yard, Centrally Located

Spacious home with private heated pool & hot tub, tucked away in a quiet neighborhood, centrally located providing easy access to beaches and towns.  The pool, patio area, deck, & pool bar...Read more

Location: 
Oak Bluffs
Sleeps: 
8
Bedrooms: 
4
Baths: 
2
Price Range:
$6,820 - $6,820
June 2025
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Clean Fee: 
$400 per week
Tax: State & Local: 
11.7

Pool Heated to 80 degrees included in the rental rate, July & August

Pool Heated to 80 degrees, June & September, additional 350 per week surcharge

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FISHJ

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Property Details
Stylish Contemporary Vacation Home situated in Meadow View Farms, Open Light Filled Design, Expansive Private Deck

Come and enjoy this light-filled, beautifully maintained, three-level contemporary home complete with gardens, landscaped yard, and a children’s backyard playground.  

The main level features an open kitchen, dining, and TV/living...Read more

Location: 
Oak Bluffs
Sleeps: 
8
Bedrooms: 
4
Baths: 
4
Price Range:
$3,900 - $6,800
June 2025
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$6,800
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Clean Fee: 
$425 per week
Tax: State & Local: 
11.7
Add Favorite
 
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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 - $6,500
June 2025
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27
28
29
30
31
 $8,000
August 2025
SuMoTuWeThFrSaWeek
 1
2
$8,000
3
4
5
6
7
8
9
$8,000
10
11
12
13
14
15
16
$8,000
17
18
19
20
21
22
23
$8,000
24
25
26
27
28
29
30
$6,500
31
 $4,500
September 2025
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
$4,500
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
 
Clean Fee: 
$400 per week
Tax: State & Local: 
11.7
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LIJOY

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Property Details
Hidden Cove Summer Retreat, Newly Updated, Association Tennis Courts, Bike Paths at Entrance to Neighborhood, Multiple Beaches Near By

Summer Dream offers the opportunity for a relaxing vacation in a beautiful environment. This 4 bedroom, 2 ½ bath home has a beautiful new kitchen and new living room furnishings...Read more

Location: 
Oak Bluffs
Sleeps: 
8
Bedrooms: 
4
Baths: 
2
Price Range:
$4,200 - $6,500
June 2025
SuMoTuWeThFrSa
1
2
3
4
5
6
7
8
9
10
11
12
13
14
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21
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29
30
 
July 2025
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
 $6,500
August 2025
SuMoTuWeThFrSaWeek
 1
2
$6,500
3
4
5
6
7
8
9
$6,500
10
11
12
13
14
15
16
$6,900
17
18
19
20
21
22
23
$6,500
24
25
26
27
28
29
30
$6,500
31
 $6,500
September 2025
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
$6,500
7
8
9
10
11
12
13
$5,500
14
15
16
17
18
19
20
$4,700
21
22
23
24
25
26
27
$4,700
28
29
30
 
Clean Fee: 
$390 per week
Tax: State & Local: 
11.7
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JOSEJ

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Property Details
Exquisite Coastal Style Home, Pool, Patio, Landscaped Yard! 10 minute walk to Oak Bluffs Center, Luxury Interior, 3 bedrooms, 4 baths, Multiple Living Spaces

This newly constructed, luxurious home offers the perfect blend of comfort, style, and convenience. Featuring a heated 16 x 32' pool with varying depths of 3 to 8 feet, a...Read more

Location: 
Oak Bluffs
Sleeps: 
8
Bedrooms: 
4
Baths: 
4
Price Range:
$6,500 - $6,500
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
20
21
22
23
24
25
26
27
28
29
30
31
 $13,500
August 2025
SuMoTuWeThFrSaWeek
 1
2
$13,500
3
4
5
6
7
8
9
$13,500
10
11
12
13
14
15
16
$13,500
17
18
19
20
21
22
23
$13,500
24
25
26
27
28
29
30
$9,350
31
 $7,000
September 2025
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
$7,000
7
8
9
10
11
12
13
$6,500
14
15
16
17
18
19
20
$6,500
21
22
23
24
25
26
27
$6,500
28
29
30
 
Clean Fee: 
$700 per week
Tax: State & Local: 
11.7

Rates just reduced for available weeks in July & August by 15% - see calendar for adjusted rates

 

Pool Heated to  81 degrees included in rental rate last Sat in June to first Sat in September. Pool Depth 3 feet to 8 Feet 

Pool Heated to 81 degrees June and September weeks additional $275 per week  

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HOD28

(0)Inquire/Share
Property Details
Beautiful Oak Bluffs home just blocks from the Center of Town, Ocean Park and Inkwell Beach.

Note: the kitchen is being completely remodeled for summer 2024 and will have all new high-end appliances, Subzero, Thermador, and new cabinets, and counters. 

Summer Joy!  Set in the heart of...Read more

Location: 
Oak Bluffs
Sleeps: 
9
Bedrooms: 
5
Baths: 
2
Price Range:
$5,000 - $6,500
June 2025
SuMoTuWeThFrSa
1
2
3
4
5
6
7
8
9
10
11
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17
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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
20
21
22
23
24
25
26
27
28
29
30
31
 $8,750
August 2025
SuMoTuWeThFrSaWeek
 1
2
$8,750
3
4
5
6
7
8
9
$8,750
10
11
12
13
14
15
16
$10,350
17
18
19
20
21
22
23
$10,350
24
25
26
27
28
29
30
$8,750
31
 $6,500
September 2025
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
$6,500
7
8
9
10
11
12
13
$6,500
14
15
16
17
18
19
20
$6,500
21
22
23
24
25
26
27
$6,500
28
29
30
 $5,000
Clean Fee: 
$650 per week
Tax: State & Local: 
11.7

Rates reduced for available weeks in June & July - see calendar for adjusted rates

 

8-minute walk from the ferry dock in Oak Bluffs and 5 minute walk to the Ink Well Beach, and Oak Bluffs Center from the house. 

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