589+ Private Villas and Holiday Rentals in Oak Bluffs |
  1. USA
  2. Massachusetts
  3. Oak Bluffs

Oak Bluffs Holiday Rentals

About Casai's Private Villas and Holiday Rentals in Oak Bluffs

Discover more than 589 vacation rentals available in Oak Bluffs. These rentals, ranging from vacation rentals to Casai Homes and other short-term private accommodations, offer top-notch amenities with unbeatable value, ensuring both comfort and luxury. Enjoy more space and value when you stay at a Casai property in Oak Bluffs.

Seeking last-minute deals or the best available offers for cottages, condos, private villas, and spacious vacation homes? With Casai in Oak Bluffs, you can effortlessly compare various deals with just a click. Whether you're looking for a Casai with exceptional swimming pools, hot tubs, pet-friendly options, or large master suite bedrooms equipped with large screen televisions, you'll find a variety of options near Oak Bluffs. On average, places to stay near Oak Bluffs offer 954.81 ft², with nightly prices averaging GB £618.

With Casai, finding and comparing holiday rentals in Oak Bluffs is easy and secure, often at a 30-40% discount compared to hotel prices. Simply search for your destination and secure your reservation today.

Show more
Show less

Top Accommodation Types in Oak Bluffs

Type Count
Vacation Homes 396
Holiday Apartments 76
Cottages 41
Villas 2

Use these Quick Filters to Find a Holiday Rental in Oak Bluffs

★ Pro Tip: Casai simplifies the process of comparing the finest listings across various online vacation rental platforms, including Booking.com and more. Utilize the Advanced Filter feature located at the top to effortlessly switch between Casai homes, vacation rentals, bed and breakfasts, private Airbnb-style rentals, eco-friendly properties, and different property types. Explore various cancellation policies, prices, and numerous options to find the ideal accommodation for your next vacation in Oak Bluffs.

Weather in Oak Bluffs, MA

View the weather forecast for Oak Bluffs before booking your Oak Bluffs Vacation Rentals to confirm your best time to go.

December - February
High 60°F       Low 26°F
March - May
High 77°F       Low 40°F
June - August
High 91°F       Low 64°F
September - November
High 84°F       Low 38°F

Top Attractions Around Oak Bluffs, MA

Casai offers a large selection of top attractions around Oak Bluffs . Research things to do on your vacation before you visit Oak Bluffs.


Oak Bluffs Harbor
Inkwell Beach
Oak Bluffs Town Beach
Flying Horses Carousel
East Chop Light
Trinity Park Tabernacle
Ocean Park
Cottage Museum
Oak Bluffs Public Library
Joseph Sylvia State Beach
Farm Neck Golf Club
Chappaquiddick Graveyard
Seaview Beach
Martha's Vineyard Hospital Development
Martha's Vineyard Hospital
Cape Codder Water Park
Hyannis Harbor
Old Silver Beach
Hyannis Port Beach
Falmouth Heights Beach

Other Places to Stay in Oak Bluffs, MA


Joseph Sylvia State Beach 1,198 Properties
Farm Neck Golf Club 1,197 Properties
Oak Bluffs Public Library 1,091 Properties
Martha's Vineyard Hospital 1,077 Properties
Martha's Vineyard Hospital Development 1,064 Properties
Trinity Park Tabernacle 1,054 Properties
Cottage Museum 1,052 Properties
Circuit Avenue 1,045 Properties
Oak Bluffs Harbor 1,036 Properties
Ocean Park 1,028 Properties
East Chop 59 Properties
Lagoon Heights 44 Properties

Frequently Asked Questions About Oak Bluffs?

What are the top holiday rentals in Oak Bluffs?

With numerous options available in Oak Bluffs, planning to stay in the area? Consider booking a few nights at one of these properties, rated as the Top Holiday Rentals in Oak Bluffs:

How many holiday rentals have private pools in Oak Bluffs?

Discover a selection of holiday rentals with private pools near Oak Bluffs with Casai. Experience the epitome of luxury and relaxation in our top-rated villas and holiday homes, where you can enjoy exclusive access to refreshing swimming pools.

Which holiday homes in Oak Bluffs are best for families?

If you're searching for a family-friendly holiday home in Oak Bluffs, consider one of the following properties. Each comes highly recommended, with excellent reviews for families or groups staying in Oak Bluffs:

How many Casai.uk holiday rentals are available in Oak Bluffs?

As of 2025, Casai boasts over 589 properties listed in the Oak Bluffs area, with more being added continually. By consolidating listings from various websites, Casai provides an extensive selection of the finest Casai properties in Oak Bluffs.


People Also Ask

There are 589 Oak Bluffs, MA Holiday Rentals

Recently Booked Holiday Rentals in Oak Bluffs