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:
$14 - $32,501
June 2025
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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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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:
$14 - $20,006
June 2025
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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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EW138

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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:
$14 - $20,006
June 2025
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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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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:
$14 - $20,006
June 2025
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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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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:
$14 - $19,005
June 2025
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Clean Fee: 
$550
Tax: State & Local: 
11.7
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LANLL

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Property Details
Outstanding Waterfront Home & Guest House, Panoramic Views, Beach on the Lagoon, 5 Bedrooms, 4 Baths, AC

Gorgeous Expansive Waterfront Main & Guest Cottage, perfect for a multigenerational family vacation.  Spectacular views across and up the lagoon, this pristine home and guest cottage sits on just under two...Read more

Location: 
Oak Bluffs
Sleeps: 
9
Bedrooms: 
5
Baths: 
4
Price Range:
$14 - $17,997
June 2025
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Clean Fee: 
$600 per week
Tax: State & Local: 
11.7

Two Week Minimum Stay Required per Owner

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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:
$14 - $17,605
June 2025
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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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BROWL

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Property Details
Stunning Tri-Level Home, Heated Pool, Screened Porch, Beautifully Landscaped, Walk to Association Tennis Courts

Featured MVVR Listing:

Beautiful Coastal Inspired Retreat features multiple living spaces, a pool, a bluestone patio area, and a deck with an outdoor dining and grill area.  This beautiful home is...Read more

Location: 
Oak Bluffs
Sleeps: 
8
Bedrooms: 
4
Baths: 
4
Price Range:
$14 - $17,500
June 2025
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Clean Fee: 
$550 per week
Tax: State & Local: 
11.7

Pool Heated to 80 degrees included in rental rate last Saturday in June to the first Saturday in September. 

 

Pool Heated to 80 degrees, June & September weeks additional $300 propane surcharge per week. 

   

 

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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:
$14 - $17,003
June 2025
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Clean Fee: 
$550 per week
Tax: State & Local: 
11.7
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CORSB

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

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

Location: 
Oak Bluffs
Sleeps: 
8
Bedrooms: 
4
Baths: 
2
Price Range:
$14 - $16,506
June 2025
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Clean Fee: 
$575 per week
Tax: State & Local: 
11.7

Ferry Tickets Availalble 8/10-8/17. Please inquire for details! (mv)

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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:
$14 - $15,806
June 2025
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Clean Fee: 
$750 per week
Tax: State & Local: 
11.7
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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:
$14 - $15,001
June 2025
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Clean Fee: 
$500 per week ($350 for interim cleaning on multiple week rentals)
Tax: State & Local: 
11.7

Ferry Tickets Available 8/24-8/31 - please inquire

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

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LORJU

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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:
$14 - $15,001
June 2025
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July 2025
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August 2025
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September 2025
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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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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:
$14 - $14,504
June 2025
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July 2025
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August 2025
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September 2025
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Clean Fee: 
$550
Tax: State & Local: 
11.7
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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:
$14 - $13,965
June 2025
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July 2025
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August 2025
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September 2025
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Clean Fee: 
$450 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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