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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Waterview, Walk to the Beach and Town Center, Impeccably Maintained 4 bedroom Home set in the Heart of Oak Bluffs.

This restored historic J.A. Norton Main and Guest Suite Quarters seamlessly blends 1870s character with the modern comforts today’s travelers appreciate. Nestled in a peaceful  Oak Bluffs neighborhood, the property is just...Read more

Location: 
Oak Bluffs
Sleeps: 
8
Bedrooms: 
4
Baths: 
3
Price Range:
$4,400 - $61,600
June 2026
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July 2026
SuMoTuWeThFrSaWeek
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$8,800
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$8,800
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$8,900
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 $9,000
August 2026
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$9,000
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$12,000
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$12,000
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$13,000
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$13,000
30
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 $8,500
September 2026
SuMoTuWeThFrSaWeek
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$8,500
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$6,000
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$5,600
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$5,600
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 $5,600
Clean Fee: 
$400 per week
Tax: State & Local: 
11.7
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TRASJ

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Property Details
Owner offering 15% off all remaining weeks open 2026! Victorian East Chop Cottage all Newly updated, 4 Bedrooms, 3.5 Baths, Main House and Detached Guest Suite

Nestled in the highly sought-after East Chop neighborhood of Oak Bluffs, this charming Victorian cottage offers the perfect blend of classic Vineyard character and modern comfort. Ideally located within walking...Read more

Location: 
Oak Bluffs
Sleeps: 
8
Bedrooms: 
4
Baths: 
3
Price Range:
$3,800 - $59,850
June 2026
SuMoTuWeThFrSa
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July 2026
SuMoTuWeThFrSaWeek
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$10,000
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$8,550
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$8,550
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 $9,500
August 2026
SuMoTuWeThFrSaWeek
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$9,500
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$11,480
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$15,170
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$14,030
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$9,120
30
31
 $8,480
September 2026
SuMoTuWeThFrSaWeek
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$8,480
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$6,650
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$5,230
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$5,230
27
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29
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 $3,800
Clean Fee: 
$500 per week
Tax: State & Local: 
11.7

Owners are also open to weekday arrival and departure to accommodate the need for auto ferry ticket reservations. 

 

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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 - $30,000
June 2026
SuMoTuWeThFrSa
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July 2026
SuMoTuWeThFrSaWeek
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$18,000
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$18,000
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$20,000
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 $20,000
August 2026
SuMoTuWeThFrSaWeek
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$20,000
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$20,000
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$20,000
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$20,000
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$18,500
30
31
 $11,500
September 2026
SuMoTuWeThFrSaWeek
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$11,500
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$10,500
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$10,500
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$10,500
27
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 $10,500
Clean Fee: 
$800 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. The owner will activate the spa, see additional cost below

2 hours per day,  additional $350 per week

4 hours per day,  additional $600 per week

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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:
$7,000 - $22,000
June 2026
SuMoTuWeThFrSa
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July 2026
SuMoTuWeThFrSaWeek
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$12,000
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$13,000
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$14,000
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 $14,000
August 2026
SuMoTuWeThFrSaWeek
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$14,000
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$19,000
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$19,000
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$19,000
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$12,000
30
31
 $9,000
September 2026
SuMoTuWeThFrSaWeek
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$9,000
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$7,000
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$7,000
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30
 
Clean Fee: 
$550
Tax: State & Local: 
11.7
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CALWM

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Property Details
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 - $18,500
June 2026
SuMoTuWeThFrSa
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July 2026
SuMoTuWeThFrSaWeek
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$27,000
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$27,000
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$27,000
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 $28,500
August 2026
SuMoTuWeThFrSaWeek
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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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$30,000
30
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 $22,500
September 2026
SuMoTuWeThFrSaWeek
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$22,500
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$20,000
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$18,500
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$18,500
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 $17,000
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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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 - $17,800
June 2026
SuMoTuWeThFrSa
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July 2026
SuMoTuWeThFrSaWeek
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$15,700
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$15,700
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$16,800
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 $16,800
August 2026
SuMoTuWeThFrSaWeek
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$16,800
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$17,600
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$17,600
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$17,600
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$17,600
30
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 $10,000
September 2026
SuMoTuWeThFrSaWeek
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$10,000
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$7,500
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$7,500
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$7,500
27
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 $7,500
Clean Fee: 
$850 per week
Tax: State & Local: 
11.7

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:
$16,900 - $16,900
June 2026
SuMoTuWeThFrSa
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July 2026
SuMoTuWeThFrSaWeek
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$18,900
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$19,000
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$20,000
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 $20,000
August 2026
SuMoTuWeThFrSaWeek
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$20,000
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$20,000
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$20,000
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$20,000
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$20,000
30
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 $16,900
September 2026
SuMoTuWeThFrSaWeek
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$16,900
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$16,900
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$16,900
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$16,900
27
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30
 $16,900
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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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:
$16,500 - $16,500
June 2026
SuMoTuWeThFrSa
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July 2026
SuMoTuWeThFrSa
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August 2026
SuMoTuWeThFrSaWeek
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$19,500
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$16,500
30
31
 
September 2026
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Clean Fee: 
$650 per week
Tax: State & Local: 
11.7
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HUN24

Inquire
Property Details
Gorgeous Waterfront Home, Stunning Views, Spacious Vacation Home, Perfect for Extended Family & Friends

Note: Exterior photos were taken in the winter. The deck will be set up for summer relaxing and dining, not seen in the current photos.  New Sofas for 2026 in the office...Read more

Location: 
Oak Bluffs
Sleeps: 
8
Bedrooms: 
4
Baths: 
3
Price Range:
$10,000 - $16,000
June 2026
SuMoTuWeThFrSa
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July 2026
SuMoTuWeThFrSaWeek
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$13,500
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$14,000
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$14,000
26
27
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30
31
 $14,000
August 2026
SuMoTuWeThFrSaWeek
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$14,000
2
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$16,000
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$16,000
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$16,000
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$16,000
30
31
 $12,000
September 2026
SuMoTuWeThFrSaWeek
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$12,000
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$12,000
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$10,000
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$10,000
27
28
29
30
 
Clean Fee: 
$900 per week
Tax: State & Local: 
11.7
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ROSKH

Inquire
Property Details
East Chop Classic Waterfront Home, Private Dock, Mooring Available, Spectacular Sunsets

Experience refined coastal living at this exceptional cottage- style waterfront retreat in the coveted East Chop area of Oak Bluffs. 

This idyllic waterfront summer sanctuary is poised to create cherished...Read more

Location: 
Oak Bluffs
Sleeps: 
8
Bedrooms: 
4
Baths: 
3
Price Range:
$8,000 - $15,000
June 2026
SuMoTuWeThFrSa
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July 2026
SuMoTuWeThFrSaWeek
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$12,000
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$12,000
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$12,000
26
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30
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 $15,000
August 2026
SuMoTuWeThFrSaWeek
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$15,000
2
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$18,000
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$18,000
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$18,000
23
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$15,000
30
31
 $12,000
September 2026
SuMoTuWeThFrSaWeek
 1
2
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$12,000
6
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$8,000
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$8,000
20
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$8,000
27
28
29
30
 $8,000
Clean Fee: 
$650 per week
Tax: State & Local: 
11.7

Owner open to other than weekend to weekend dates.  Please inquire for details! 

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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:
$14,000 - $14,000
June 2026
SuMoTuWeThFrSa
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July 2026
SuMoTuWeThFrSaWeek
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 $14,000
August 2026
SuMoTuWeThFrSaWeek
 1
$14,000
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$14,000
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$14,000
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$14,000
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30
31
 
September 2026
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Clean Fee: 
$550
Tax: State & Local: 
11.7
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HUN28

Inquire
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

This stylish contemporary retreat is ideally located in a lovely, peaceful Oak Bluffs neighborhood, just a 10–15 minute stroll to the village center, parks, Inkwell Beach, Oak Bluffs Town Beach, and...Read more

Location: 
Oak Bluffs
Sleeps: 
8
Bedrooms: 
3
Baths: 
3
Price Range:
$5,250 - $13,960
June 2026
SuMoTuWeThFrSa
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July 2026
SuMoTuWeThFrSaWeek
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$10,460
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$10,460
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$10,460
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 $10,460
August 2026
SuMoTuWeThFrSaWeek
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$10,460
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$13,960
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$13,960
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$13,960
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$13,960
30
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 $9,060
September 2026
SuMoTuWeThFrSaWeek
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$9,060
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$6,650
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$6,650
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$6,650
27
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29
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 $6,650
Clean Fee: 
$600 per week
Tax: State & Local: 
11.7

2026, Owner offers 10% discount off rental rate - May, June, July weeks for 7 night stay or longer. 

 

3 night minimum stay required, May, June to last week, September 5 on &, October. 

 

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CORSB

Inquire
Property Details
Outstanding Impeccable,Waterfront Home, Private Dock, Spectacular Views & Sunsets across and up the Lagoon. Screened Porch, Larger Wrap Around Deck with Cushioned Chaise and Chair Seating, Additional Shady Lower Level Deck

Nestled hillside, this stunning, impeccably maintained contemporary residence offers an exquisite retreat overlooking the tranquil lagoon and the sunsets are magnificent. Featuring breathtaking water vistas, a private dock, a screened...Read more

Location: 
Oak Bluffs
Sleeps: 
8
Bedrooms: 
4
Baths: 
2
Price Range:
$6,000 - $13,850
June 2026
SuMoTuWeThFrSa
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July 2026
SuMoTuWeThFrSaWeek
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$10,750
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$11,750
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$13,850
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 $14,600
August 2026
SuMoTuWeThFrSaWeek
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$14,600
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$16,500
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$16,500
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$15,900
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$11,750
30
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 $7,750
September 2026
SuMoTuWeThFrSaWeek
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$7,750
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$7,750
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$6,500
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$6,000
27
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 $7,000
Clean Fee: 
$650 per week
Tax: State & Local: 
11.7

Ferry Tickets available for Purchase. 8/16 - 8/23 (mv) 

Owner is flexible with arrival & departure dates open weeks, June and July of 2026,  to accommodate the need for auto ferry tickets. Inquire for details! 

 

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

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MILTD

Inquire
Property Details
Perfect in Town Location. Just 1 to 2 blocks to Beach, Town Center & Harbor Area, Walk to and from the Ferry

Centrally located in the heart of Oak Bluffs, walk 1-2 blocks to the beach, public tennis courts, and town & harbor areas. This wonderful large home has a large wrap-around porch for relaxing, 7...Read more

Location: 
Oak Bluffs
Sleeps: 
14
Bedrooms: 
7
Baths: 
3
Price Range:
$8,500 - $13,500
June 2026
SuMoTuWeThFrSa
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July 2026
SuMoTuWeThFrSaWeek
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$13,500
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$13,500
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$13,500
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 $13,500
August 2026
SuMoTuWeThFrSaWeek
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$13,500
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$13,500
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$13,500
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$13,500
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$13,500
30
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 $12,500
September 2026
SuMoTuWeThFrSaWeek
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$12,500
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$12,500
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$12,500
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$12,500
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 $12,500
Clean Fee: 
$500 per week
Tax: State & Local: 
11.7
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WESTW

Inquire
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:
$5,300 - $12,000
June 2026
SuMoTuWeThFrSa
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July 2026
SuMoTuWeThFrSaWeek
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$8,500
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$9,000
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$10,000
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 $10,000
August 2026
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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$8,500
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 $6,300
September 2026
SuMoTuWeThFrSaWeek
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$6,300
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$6,300
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$5,300
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$5,300
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 $5,300
Clean Fee: 
$650 per week
Tax: State & Local: 
11.7

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