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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Exquisite New Luxurious Home, Tucked in the Private Enclave, Known as -The Preserve, Heated Saltwater Pool 18' x 45, Screened Porch, Propane Fire pit with Adirondack Seating, Designer Interior

"The Preserve" in Oak Bluffs is a desirable enclave of homes that offers a serene and alluring living environment. This expansive luxury home designed by noted architect Chuck Sullivan was completed...Read more

Location: 
Oak Bluffs
Sleeps: 
12
Bedrooms: 
6
Baths: 
5
Price Range:
$17,000 - $32,500
June 2025
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July 2025
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 $28,500
August 2025
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$28,500
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$30,000
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$32,500
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$32,500
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$27,000
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 $20,000
September 2025
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$20,000
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$17,500
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$17,500
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$17,500
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Clean Fee: 
$960 per week
Tax: State & Local: 
11.7

Pool Heated to 82 degrees  July & August  weeks, included in the rental rate

Pool Heated to 82 degrees June & September weeks, additional $300 per week surcharge

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GLEDE

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Property Details
Stunning New Custom Luxury Home, Oak Bluffs, 18 x 36 Heated Saltwater Pool, Bluestone Patio, 4 Bedrooms 3.5 baths

Tucked just on the outskirts of Oak Bluffs downtown area this spacious architect-designed custom home offers families and friends an outstanding vacation experience. 

Professionally designed by a noted architect this outstanding...Read more

Location: 
Oak Bluffs
Sleeps: 
8
Bedrooms: 
4
Baths: 
3
Price Range:
$7,500 - $21,500
June 2025
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July 2025
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 $18,000
August 2025
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$18,000
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$19,500
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$20,000
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$20,000
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$18,000
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 $9,500
September 2025
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$9,500
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$7,500
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$7,500
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 $7,500
Clean Fee: 
$600 per week
Tax: State & Local: 
11.7

Pool Heated to 81 degrees July & August included in Rental Rate

Pool Heated to 81 degrees June & September additional $300 Propane Surcharge

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TAYLC

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Property Details
Luxurious Home located in The Preserve, 18 x 36 Heated Pool , Multiple Indoo/Outdoor Entertainment Areas

Welcome to this stunning, expansive luxury residence nestled within the exclusive enclave of homes known as The Preserve!

Situated on the outskirts of Oak Bluffs, The Preserve is a lovely community...Read more

Location: 
Oak Bluffs
Sleeps: 
10
Bedrooms: 
5
Baths: 
4
Price Range:
$10,500 - $20,000
June 2025
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July 2025
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 $20,000
August 2025
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$20,000
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$20,000
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$20,000
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$18,500
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 $11,500
September 2025
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$11,500
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$10,500
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$10,500
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$10,500
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Clean Fee: 
$650 per week
Tax: State & Local: 
11.7

Pool Heated to 82 July and August weeks included in Rental Rate. 

Pool Heated to 82 June & September weeks additional $350 per week.  

 

The poolside spa maintains the same temperature as the pool itself, and the jets are not activated. However, should you desire, the spa can be heated for a duration of 4 hours daily, subject to an additional weekly charge. For more information, kindly reach out to the agent for further details.

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HODGW

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Property Details
New Tri Level Luxury Home, Heated Pool with Bluestone Patio Surround

Location location!

Just 1 mile from Oak Bluffs center this stunning 5 bedroom, 4.5 bath features a gunite pool with a bluestone patio surround, sure to be the focal point...Read more

Location: 
Oak Bluffs
Sleeps: 
10
Bedrooms: 
5
Baths: 
4
Price Range:
$7,500 - $17,600
June 2025
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July 2025
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 $16,500
August 2025
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$16,500
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$17,300
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$17,300
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$17,300
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$17,300
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 $17,050
September 2025
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$17,050
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$15,400
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$15,400
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$15,400
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 $12,500
Clean Fee: 
$850 per week
Tax: State & Local: 
11.7

Rate reduced by $4000 for week of 6/28-7/5 - see calendar for adjusted rate

 

Pool Heated to 81 included in rental rate, July and August weeks

 

June & September weeks to 81 degrees additional $500 fee. Higher temp upon request additional fee

 

Notice: Ring doorbell cameras are located on the front entry door and door on the left/parking side of the house:

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EW138

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Property Details
Beautiful Oak Bluffs Home, 20 x 40 Heated Pool, 6 Bedrooms, 4 baths, Sleeps 14, Screened Porch, Multiple Living Spaces

Oak Bluffs vacation retreat with multiple indoor, and outdoor living and entertaining areas. The highlight of this spacious summer home is the heated Gunite pool with waterfall, bluestone patio, and...Read more

Location: 
Oak Bluffs
Sleeps: 
14
Bedrooms: 
6
Baths: 
4
Price Range:
$9,100 - $16,900
June 2025
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July 2025
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 $20,000
August 2025
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$20,000
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$20,000
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$20,000
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$20,000
31
 $16,900
September 2025
SuMoTuWeThFrSaWeek
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$16,900
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$16,900
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$12,000
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$12,000
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 $12,000
Clean Fee: 
$750 per week
Tax: State & Local: 
11.7

Pool Heated to 82 included in rental rate July and August, Spa in pool is heated to same the temperature as pool.

 

Additional Spa Heat 6 to 10pm, $250 per week. Available upon request. 

 

Pool Heated to 82 June & Sept additional $275 per week. May & October additional $350 per week. 

 

Firepit seen in photos is not for renter use. 

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BRANF

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Property Details
Spacious Colonial with Contemporary Detailing in Fresh Pond Estates, Mulitpe Living Spaces, Screened Porch, Spacious Deck, AC, Wifi, Beautifully Furnished, Bike Paths at the head of the Road

Spacious, 4 bedroom 3.5 bath contemporary home set in a quiet lovely community on the outskirts of Oak Bluffs. . The main living level features an open concept and hosts a family...Read more

Location: 
Oak Bluffs
Sleeps: 
8
Bedrooms: 
4
Baths: 
3
Price Range:
$4,900 - $15,000
June 2025
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July 2025
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31
 $6,900
August 2025
SuMoTuWeThFrSaWeek
 1
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$6,900
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$12,000
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$9,500
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$15,000
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$7,500
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 $5,010
September 2025
SuMoTuWeThFrSaWeek
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$5,010
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$5,000
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$5,000
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$5,000
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 $4,900
Clean Fee: 
$500 per week ($375 for interim cleaning on multiple week rentals)
Tax: State & Local: 
11.7

Rate just reduced for 8/24 week - see calendar for adjusted rate

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HUN28

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Property Details
Lovely New 3 Bedroom, 3.5 Bath Home, 15 min walk to Oak Bluffs Center, Inkwell Beach and Town Beach, Sleeps 8, 3 Bedrooms, Plus Loft, 3.5 Baths

Please note: This beautiful new home is in the process of being furnished into April. The photos provided are a sampling of the decor. All furnishings and household items will...Read more

Location: 
Oak Bluffs
Sleeps: 
8
Bedrooms: 
3
Baths: 
3
Price Range:
$5,230 - $13,960
June 2025
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July 2025
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 $8,010
August 2025
SuMoTuWeThFrSaWeek
 1
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$8,010
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$11,230
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$11,230
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$11,230
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$8,010
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 $8,010
September 2025
SuMoTuWeThFrSaWeek
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$8,010
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$6,040
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$6,040
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$6,040
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 $5,230
Clean Fee: 
$600 per week
Tax: State & Local: 
11.7

3 night minimum stay required, May, June, September, October,  4 night minimum July to 7/19

 

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CENCP

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Property Details
East Chop Waterfront, Extraordinary Sunsets &Views Across the Sound , Deck directly on the Beach, Casual Interior

Classic, casual beachfront home combines cottage styling with modern amenities. spectacular views, quietly lapping waves right outside your windows, and breathtaking sunsets. Ideally located in the East Chop Area of Oak Bluffs just a short distance...Read more

Location: 
Oak Bluffs
Sleeps: 
6
Bedrooms: 
3
Baths: 
2
Price Range:
$6,000 - $13,800
June 2025
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July 2025
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 $9,700
August 2025
SuMoTuWeThFrSaWeek
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$9,700
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$13,800
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$13,800
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$13,800
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$11,200
31
 $6,000
September 2025
SuMoTuWeThFrSaWeek
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$6,000
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$6,000
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$6,000
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30
 
Clean Fee: 
$480 per week
Tax: State & Local: 
11.7

Rates reduced for available weeks - see calendar for adjusted rates

 

 

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ALVEN

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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:
$13,000 - $13,000
June 2025
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July 2025
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 $13,000
August 2025
SuMoTuWeThFrSaWeek
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$13,000
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$13,000
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$13,000
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$13,000
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$13,000
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September 2025
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Clean Fee: 
$550
Tax: State & Local: 
11.7
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WESTC

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Property Details
Summer Wind in the Heart of Oak Bluffs, Water views. 2 minute Walk to Inkwell Beach & 5 minute walk to town, All Newly Remodeled 5 Bedroom, 3 Bath Home With Deluxe Amenities

Set in the heart of Oak Bluffs center, this newly renovated home features water views, walk to Inkwell Beach and Pay Beach and walk to the town center all within...Read more

Location: 
Oak Bluffs
Sleeps: 
10
Bedrooms: 
5
Baths: 
3
Price Range:
$6,000 - $13,000
June 2025
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July 2025
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31
 $16,000
August 2025
SuMoTuWeThFrSaWeek
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$16,000
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$17,000
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$17,000
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$17,000
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30
$9,000
31
 $8,000
September 2025
SuMoTuWeThFrSaWeek
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$8,000
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$7,000
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$7,000
21
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27
$7,000
28
29
30
 $6,000
Clean Fee: 
$550
Tax: State & Local: 
11.7
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WESTW

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Property Details
Tri Level Oak Bluffs Home, Central A/C, Set in Private Community of Sengekontacket, Multiple Living Spaces, Large Deck, Patio Area, Association Tennis

Privately situated on a hilltop in Sengekontacket, -spacious tri-level, 4000 sq ft contemporary home. Set in a wonderful, family friendly community, offering association tennis courts, and an association dock on Sengekontacket Pond...Read more

Location: 
Oak Bluffs
Sleeps: 
14
Bedrooms: 
5
Baths: 
2
Price Range:
$5,000 - $12,000
June 2025
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July 2025
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31
 $10,000
August 2025
SuMoTuWeThFrSaWeek
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$10,000
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$12,000
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$12,000
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$12,000
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29
30
$8,500
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
$5,500
21
22
23
24
25
26
27
$5,000
28
29
30
 $5,000
Clean Fee: 
$650 per week
Tax: State & Local: 
11.7
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BAKE7

(0)Inquire/Share
Property Details
Waterview, Walk to the Beach and Town Center, Impeccably Maintained 4 bedroom Home set in the Heart of Oak Bluffs.
Location: 
Oak Bluffs
Sleeps: 
8
Bedrooms: 
4
Baths: 
3
Price Range:
$4,400 - $12,000
June 2025
SuMoTuWeThFrSa
1
2
3
4
5
6
7
8
9
10
11
12
13
14
15
16
17
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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
 $12,000
August 2025
SuMoTuWeThFrSaWeek
 1
2
$12,000
3
4
5
6
7
8
9
$12,000
10
11
12
13
14
15
16
$12,000
17
18
19
20
21
22
23
$12,000
24
25
26
27
28
29
30
$8,500
31
 $5,700
September 2025
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
$5,700
7
8
9
10
11
12
13
$5,700
14
15
16
17
18
19
20
$5,700
21
22
23
24
25
26
27
$5,700
28
29
30
 $5,600
Clean Fee: 
$400 per week
Tax: State & Local: 
11.7
Add Favorite
 
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POWDA

(0)Inquire/Share
Property Details
Beautiful Newly Updated Oak Bluffs Home, Nestled on a Large Landscaped Lot in a Quiet Enclave of Homes. 4 Bedrooms. 4.5 Baths

Step inside to discover a welcoming interior, highlighted by a sunroom featuring comfortable seating around the TV. The open first-floor plan seamlessly integrates the main family room complete with a media...Read more

Location: 
Oak Bluffs
Sleeps: 
8
Bedrooms: 
4
Baths: 
4
Price Range:
$6,000 - $12,000
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
 $9,000
August 2025
SuMoTuWeThFrSaWeek
 1
2
$9,000
3
4
5
6
7
8
9
$12,000
10
11
12
13
14
15
16
$12,000
17
18
19
20
21
22
23
$10,000
24
25
26
27
28
29
30
$8,500
31
 $7,000
September 2025
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
$7,000
7
8
9
10
11
12
13
$6,000
14
15
16
17
18
19
20
$6,000
21
22
23
24
25
26
27
$6,000
28
29
30
 
Clean Fee: 
$600 per week
Tax: State & Local: 
11.7
Add Favorite
 
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LORJU

(0)Inquire/Share
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:
$8,000 - $12,000
June 2025
SuMoTuWeThFrSa
1
2
3
4
5
6
7
8
9
10
11
12
13
14
15
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21
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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
 $12,000
August 2025
SuMoTuWeThFrSaWeek
 1
2
$12,000
3
4
5
6
7
8
9
$15,000
10
11
12
13
14
15
16
$15,000
17
18
19
20
21
22
23
$15,000
24
25
26
27
28
29
30
$12,000
31
 $12,000
September 2025
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
$12,000
7
8
9
10
11
12
13
$8,000
14
15
16
17
18
19
20
$8,000
21
22
23
24
25
26
27
$8,000
28
29
30
 
Clean Fee: 
$700 per week
Tax: State & Local: 
11.7

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

6/29 to 7/6 week 3 Night Stay  $7000

Labor Day Weekend 3 Night Stay $7000

 

 

 

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

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CENCR

(0)Inquire/Share
Property Details
Oak Bluffs Summer Retreat, Large Private Deck, Lagoon Beach Rights -Great Area for Kayaking.

Spacious sun-filled home features open living spaces, hardwood floors throughout, 4 bedrooms and sleeps 8.

Exterior features include two decks, one sunny deck at the front of the house, and a large private...Read more

Location: 
Oak Bluffs
Sleeps: 
8
Bedrooms: 
4
Baths: 
3
Price Range:
$3,000 - $11,800
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
 $5,800
August 2025
SuMoTuWeThFrSaWeek
 1
2
$5,800
3
4
5
6
7
8
9
$8,800
10
11
12
13
14
15
16
$9,900
17
18
19
20
21
22
23
$11,800
24
25
26
27
28
29
30
$5,800
31
 $4,000
September 2025
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
$3,500
21
22
23
24
25
26
27
$3,000
28
29
30
 $3,000
Clean Fee: 
$480 per week
Tax: State & Local: 
11.7

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