Discover Your Perfect Oak Bluffs Vacation Homes

Best Vacation Homes in Oak Bluffs

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10.0 (1 Review)
House
The Wayland Victorian
  • Air Conditioner
  • View
  • Wheelchair Accessible
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Oak Bluffs Luxury Rentals

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Oak Bluffs Pet Friendly Vacation Rentals

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Oak Bluffs Large Vacation Homes

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9.0 (1 Review)
House
Brewster House
  • Wheelchair Accessible
  • Balcony/Terrace
  • Accessibility
View Availability
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Why Choose Rent By Owner for your Oak Bluffs Vacation Rental Homes?

What makes our Vacation Rentals special?

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Verified Listings
Book with confidence knowing every property meets our quality and safety standards.
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Unbeatable Value
Enjoy competitive pricing with no hidden fees, providing exceptional value for every stay.
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Diverse Options
From cozy cabins to luxurious villas, find a rental that suits your style and needs.

Weekly Weather Forecast for Oak Bluffs

How to Book Your Oak Bluffs Vacation Rental Home

What's our booking process?

Our platform allows you to browse a curated selection of vacation rentals. Once you find the ideal property, you’ll be redirected to a trusted booking partner to complete your reservation securely.

Booking Steps

01

Search Properties

Use our filters to find the right property that fits your needs.
02

Select a Rental

Click on your preferred listing to view details, amenities, and pricing.
03

Book Online

Follow the link to finalize your reservation directly on the partner’s website.

Explore and book the perfect rental in Oak Bluffs

More Top-Rated Vacation Rentals in Oak Bluffs Area

Common Vacation Rentals Amenities

What amenities can you expect?

Our Vacation Rentals are designed to offer all the comforts of home, often with added perks to make your stay unforgettable. Here’s some common amenities to look forward to:

Indoor Features

  • Fully-equipped kitchens with modern appliances
  • Comfortable living areas with flat-screen TVs
  • Free Wi-Fi for staying connected
  • Air conditioning and heating for year-round comfort
  • In-unit washers and dryers for convenience
  • Luxurious bedrooms with premium bedding
  • Spa-like bathrooms with soaking tubs or walk-in showers

Other Places to Stay in Oak Bluffs, MA

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Joseph Sylvia State Beach Vacation Rentals
Farm Neck Golf Club
Farm Neck Golf Club Vacation Rentals
Oak Bluffs Public Library
Oak Bluffs Public Library Vacation Rentals
Martha's Vineyard Hospital
Martha's Vineyard Hospital Vacation Rentals
Martha's Vineyard Hospital Development
Martha's Vineyard Hospital Development Vacation Rentals
Trinity Park Tabernacle
Trinity Park Tabernacle Vacation Rentals
Cottage Museum
Cottage Museum Vacation Rentals
Circuit Avenue
Circuit Avenue Vacation Rentals
Oak Bluffs Harbor
Oak Bluffs Harbor Vacation Rentals
Ocean Park
Ocean Park Vacation Rentals
East Chop
East Chop Vacation Rentals
Lagoon Heights
Lagoon Heights Vacation Rentals
More Places to Stay Near Oak Bluffs

Oak Bluffs Vacation Rental Frequently Asked Questions

What are the top vacation rentals in Oak Bluffs?

There are a lot of options in Oak Bluffs. If you plan on staying in the Oak Bluffs area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Vacation Rentals in Oak Bluffs:

How many vacation rentals have private pools in Oak Bluffs?

There are 7 vacation rentals with private pools near Oak Bluffs. Top-rated RBO homes that have access to a swimming pool include:

Which vacation homes in Oak Bluffs are best for families?

If you are looking for a family-friendly vacation home in Oak Bluffs, check out one of the following properties as all are highly-rated places to stay with excellent review for families or groups staying in Oak Bluffs:

How many Rentbyowner vacation rentals are available in Oak Bluffs?

Currently, the total number of properties listed by Rent By Owner in 2025 is over 652 in the Oak Bluffs area, and still counting. By aggregating listings from multiple websites, Rent By Owner offers an immense amount of choice of the best RBO properties in Oak Bluffs.β€―

Oak Bluffs Top Rated Vacation Rentals

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