Oak Bluffs Rentals by Owner
New
House
10.0(42 Reviews)
4 Bedrooms
2 Baths
10 Guests
2500 ft²
Hot Tub
Parking
Ocean View
Balcony/Terrace
US $609/Night
7 Nights - US $4,261
House
10.0(4 Reviews)
2 Bedrooms
2 Baths
4 Guests
1097.92 ft²
Oceanfront- Parking
- Ocean View
View
US $239/Night
7 Nights - US $1,673
Resort
8.2(40 Reviews)
1 Bath
- Parking
Pool- Ocean View
- Balcony/Terrace
US $732/Night
7 Nights - US $5,122
New
House
10.0(33 Reviews)
4 Bedrooms
1 Bath
6 Guests
1800 ft²
- Oceanfront
- Parking
- Ocean View
- Balcony/Terrace
US $321/Night
7 Nights - US $2,247
Apartment
10.0(1 Review)
1 Bedroom
1 Bath
2 Guests
699.65 ft²
- View
Air Conditioner
Internet
Child Friendly
US $490/Night
7 Nights - US $3,428
Apartment
10.0(1 Review)
2 Bedrooms
1 Bath
4 Guests
900 ft²
- Parking
Kitchen- Air Conditioner
- Internet
US $859/Night
7 Nights - US $6,012
Apartment
10.0(1 Review)
1 Bedroom
1 Bath
2 Guests
495.14 ft²
- Balcony/Terrace
- View
- Air Conditioner
- Internet
US $541/Night
7 Nights - US $3,788
New
House
10.0(1 Review)
3 Bedrooms
2 Baths
6 Guests
- Parking
- Ocean View
- Balcony/Terrace
- View
US $801/Night
7 Nights - US $5,604
House
10.0(1 Review)
3 Bedrooms
2 Baths
6 Guests
1001.04 ft²
- Parking
- Balcony/Terrace
- View
- Air Conditioner
US $434/Night
7 Nights - US $3,038
Apartment
10.0(155 Reviews)
2 Bedrooms
1 Bath
5 Guests
800 ft²
- Oceanfront
- Ocean View
- Balcony/Terrace
- View
US $887/Night
7 Nights - US $6,208
House
9.3(3 Reviews)
4 Bedrooms
4 Baths
7 Guests
4897.58 ft²
- Balcony/Terrace
- View
- Air Conditioner
- Internet
US $1,026/Night
7 Nights - US $7,182
Apartment
10.0(59 Reviews)
1 Bedroom
1 Bath
2 Guests
700 ft²
- Parking
- Ocean View
- Balcony/Terrace
- View
US $435/Night
7 Nights - US $3,042
Why Choose Rent By Owner for your Oak Bluffs vacation rental?
What makes our Rentals by Owner special?
Verified Listings
Book with confidence knowing every property meets our quality and safety standards.
Unbeatable Value
Enjoy competitive pricing with no hidden fees, providing exceptional value for every stay.
Diverse Options
From cozy cabins to luxurious villas, find a rental that suits your style and needs.
Best Times to Visit Oak Bluffs
When should you plan your Rentals by Owner stay?
To make the most of your stay, consider planning your vacation during the optimal seasons when the weather and local events enhance your experience here in Oak Bluffs, Massachusetts, USA.
Peak Season Highlights
Summer (June to August)
During the peak summer months, you can enjoy warm weather and lively local events, making it the ideal time to explore this destination. The region experiences high visitor numbers, so booking your rental by owner in advance ensures a seamless stay.
Average Temperature Daytime: 75°F to 85°F - Nighttime: 65°F to 70°F
Fall (September to October)
Early fall offers pleasant weather and beautiful scenery, attracting many visitors who want to experience the area's natural beauty. Secure your rental by owner early to enjoy the region's vibrant autumn atmosphere without last-minute worries.
Average Temperature Daytime: 70°F to 78°F - Nighttime: 55°F to 60°F
Off-Season Highlights
Winter (November to February)
During the colder months, the area is quieter, providing a peaceful retreat for those seeking tranquility. Booking a rental by owner now allows you to enjoy a cozy escape while taking advantage of lower rates.
Average Temperature Daytime: 40°F to 50°F - Nighttime: 30°F to 40°F
Spring (March to May)
In early spring, fewer visitors come to the region, offering a more relaxed experience as blossoms start to bloom. Reserve your rental by owner ahead of time to enjoy an off-peak visit with comfortable weather and fewer crowds.
Average Temperature Daytime: 55°F to 65°F - Nighttime: 45°F to 50°F
Weekly Weather Forecast for Oak Bluffs
How to Book Your Oak Bluffs vacation rental
What's our booking process?
Our platform allows you to browse a curated selection of rentals by owner. 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
Common Rentals by Owner Amenities
What amenities can you expect?
Our Rentals by Owner 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
Outdoor Amenities
- Enjoy a private outdoor patio or balcony perfect for relaxing after exploring the area.
- Take advantage of outdoor dining areas to savor meals al fresco during your stay.
- Make use of lush, well-maintained gardens or landscaped yards to unwind in nature.
- Benifit from access to a swimming pool or hot tub for added relaxation amidst the outdoors.
- Utilize outdoor grilling stations to host barbecues with family and friends.
- Relax on spacious decks or verandas offering scenic views of the surroundings.
- Take advantage of proximity to nearby outdoor activities like biking or walking trails often accessible from rentals in this region.
Top Attractions Around Oak Bluffs
What attractions are nearby?
In this charming destination, you can enjoy a variety of nearby activities such as exploring scenic beaches, strolling through vibrant local shops, or experiencing the region’s unique cultural events—all effortlessly accessible for a memorable stay.
Family Activities
- Flying Horses Carousel: Experience a timeless family activity by riding the historic carousel, a beloved attraction that has been enchanting visitors in this area for generations.
- Main Street Beach: Spend a fun-filled day on the sandy shores, where you can swim, build sandcastles, or simply relax while enjoying the coastal scenery.
- Marthas Vineyard Museum at the Oak Bluffs: Discover local history and culture through engaging exhibits that are perfect for curious children and parents alike.
- Inkwell Beach: Enjoy a peaceful retreat by the water, ideal for families looking to unwind, with calm waves and scenic views right here on this island destination.
Adult Activities
- Visit the Martha's Vineyard Camp meeting Association (CMA) Grounds: Explore this historic site with its colorful Victorian cottages and lush gardens, offering a charming glimpse into the area's rich history.
- Enjoy a scenic walk along the Oak Bluffs Harbor: Take in stunning waterfront views and watch boats sail in and out, making it a perfect spot for relaxing strolls in the region.
- Experience local dining at renowned eateries: Savor fresh seafood and regional cuisine at some of the area's top restaurants, immersing yourself in the culinary scene here.
- Discover the vibrant Arts District: Browse galleries, attend art events, and appreciate creative works that capture the spirit of this destination’s lively cultural scene.
Other Places to Stay in Oak Bluffs, MA
Joseph Sylvia State Beach
Farm Neck Golf Club
Circuit Avenue
Oak Bluffs Public Library
Martha's Vineyard Hospital
Martha's Vineyard Hospital Development
Trinity Park Tabernacle
Cottage Museum
Oak Bluffs Harbor
Ocean Park
Lagoon Heights
East Chop
Oak Bluffs Travel Tips
How Can You Make the Most of Your Stay?
- Explore Local Events and Festivals: Check the area's event calendar to participate in seasonal festivals and community gatherings that showcase the region's vibrant culture and traditions.
- Discover Hidden Gems: Venture beyond popular spots to find charming local cafes, boutique shops, and scenic spots that offer an authentic experience of this destination.
- Plan Outdoor Activities: Take advantage of the region's natural beauty by scheduling outdoor adventures like walking tours, biking, or relaxing on nearby beaches during your stay.
- Choose a Centrally Located Rental: Book a rental by owner that offers easy access to key attractions and transportation options to maximize your time exploring here.
Transportation Options
- Island Transit Bus Service: This convenient public transportation option provides easy connectivity throughout the area, making it simple to explore Oak Bluffs without the need for a rental car.
- Rental Cars: Renting a vehicle offers flexibility and freedom to visit popular attractions around this destination at your own pace.
- Bicycle Rentals: Biking is an eco-friendly and enjoyable way to discover the charming streets and scenic areas of the region.
- Taxi and Ride-Sharing Services: Accessible options like taxis and ride-sharing apps allow you to conveniently get around here, especially if you prefer door-to-door service.
Local Customs Options
- Gathering Traditions: Embrace the local custom of community gatherings and festivals that celebrate the area's rich maritime history and inclusive spirit.
- Architectural Style: Notice the distinctive Victorian architecture prevalent throughout here, reflecting a deep respect for historic preservation and aesthetic elegance.
- Local Artisanship: Support the region's vibrant arts scene by engaging with handcrafted goods and artworks that showcase the creative spirit of this destination.
- Seaside Etiquette: Observe respectful behavior towards the natural environment and fellow visitors while enjoying the scenic oceanfront and outdoor activities.
Oak Bluffs Rentals by Owner Frequently Asked Questions
1. 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:
- Private Meadow View Family Retreat - 4 BR, AC, Large Yard, Tennis, on Bike Path
- ART FILLED BEACH COTTAGE IN THE PRIVATE WATERFRONT COMMUNITY OF WATERVIEW FARMS!
- Close to town, beautifully updated
- Modern, luxury 5-bed, 4.5-bath w/full basement! Now booking for 2026!
- Modern 4 bed/3.5 bath Farmhouse, private HEATED POOL and AC on bike path
- Historic Home in East Chop
- 4+ Bedroom. Great location. Meadow View Rd. Oak Bluffs.
- Glorious Sunsets and Fun on Private Waterfront in Beautiful, Comfortable Home.
- Perfect Home For A Family Vacation With All The Amenities
- The Island Collection MV: Enjoy This 1850s Victorian Home With Ocean Views!
2. How many Vacation Rentals are available in Oak Bluffs?
Currently, the total number of properties listed by RBO in 2026 is over 546 in the Oak Bluffs area, and still counting. By aggregating listings from multiple websites, RBO offers an immense amount of choice of the best Vacation Rentals in Oak Bluffs.
3. What is the cancellation policy for a rental by owner in Oak Bluffs?
The cancellation policy varies depending on the individual listing. You should review the specific terms provided by the host before completing your booking or contact the owner directly for detailed information.
4. How do I confirm the availability of a vacation rental in this area?
Availability details are typically updated in real-time on the listing. To ensure your dates are open, proceed with the booking process or reach out to the property owner for confirmation.
5. Are there any additional fees besides the nightly rate when booking through Rent By Owner?
Additional fees such as cleaning, service charges, or security deposits may apply. These will be detailed in the listing, so review the full fee breakdown before finalizing your reservation.
6. What amenities and features can I expect in a rental by owner here?
Listings usually highlight key amenities like Wi-Fi, parking, and kitchen facilities. For specific features, check the property description or contact the owner directly for any personalized requests.
7. How is the check-in and check-out process managed for rentals in this destination?
Check-in and check-out procedures vary by property. Many owners use keyless entry systems or provide detailed instructions; contact the host in advance to coordinate your arrival and departure times.
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Apartment
10.0(55 Reviews)
2 Bedrooms
1 Bath
5 Guests
- Oceanfront
Breakfast- Parking
- Ocean View
US $1,014/Night
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1 Bedroom
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Apartment
10.0(34 Reviews)
1 Bedroom
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- Parking
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House
10.0(33 Reviews)
1 Bedroom
1 Bath
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- Parking
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- Balcony/Terrace
- View
US $479/Night
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House
10.0(22 Reviews)
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2 Baths
6 Guests
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- Pool
- Ocean View
US $735/Night
7 Nights - US $5,144
Apartment
10.0(22 Reviews)
1 Bedroom
1 Bath
4 Guests
400 ft²
- Oceanfront
- Parking
- Ocean View
- Balcony/Terrace
US $467/Night
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House
10.0(11 Reviews)
2 Bedrooms
1 Bath
6 Guests
1000 ft²
- Oceanfront
- Parking
- Ocean View
- Balcony/Terrace
US $759/Night
7 Nights - US $5,314
House
10.0(8 Reviews)
1 Bedroom
1 Bath
2 Guests
755 ft²
- Oceanfront
- Parking
- Ocean View
- Balcony/Terrace
US $840/Night
7 Nights - US $5,882
Apartment
10.0(7 Reviews)
2 Bedrooms
1 Bath
4 Guests
- Oceanfront
- Parking
- Ocean View
- Balcony/Terrace
US $496/Night
7 Nights - US $3,472
