Best Vacation Homes in Oak Bluffs
2500 ft²
12 Guests
5 Bedrooms
4 Bathrooms
Ocean View
House
- Private Pool
- Oceanfront
- Hot Tub
US $1,440/Night
For 7 Nights US $10,079
1097.92 ft²
4 Guests
2 Bedrooms
2 Bathrooms
Apartment
- Oceanfront
- Fireplace/Heating
- Ocean View
US $239/Night
For 7 Nights US $1,673
US $265/Night
For 7 Nights US $1,857
6 Guests
3 Bedrooms
3 Bathrooms
Ocean View
House
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
US $941/Night
For 7 Nights US $6,590
2497.23 ft²
9 Guests
4 Bedrooms
3 Bathrooms
Family Friendly
House
- Spa
- Fireplace/Heating
- View
US $583/Night
For 7 Nights US $4,081
8 Guests
4 Bedrooms
2 Bathrooms
Ocean View
House
- Ocean View
- Balcony/Terrace
- View
US $879/Night
For 7 Nights US $6,155
8 Guests
3 Bedrooms
2 Bathrooms
Group Friendly
House
- Fireplace/Heating
- Air Conditioner
- Internet
US $824/Night
For 7 Nights US $5,770
6 Guests
3 Bedrooms
3 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
US $621/Night
For 7 Nights US $4,350
Oak Bluffs Luxury Rentals
4500 ft²
12 Guests
5 Bedrooms
3 Bathrooms
Ocean View
House
- Hot Tub
- Fireplace/Heating
- Pool
US $4,911/Night
For 7 Nights US $34,378
2764 ft²
12 Guests
6 Bedrooms
2 Bathrooms
Ocean View
House
- Oceanfront
- Fireplace/Heating
- Ocean View
US $4,133/Night
For 7 Nights US $28,930
2500 ft²
6 Guests
3 Bedrooms
2 Bathrooms
Family Friendly
House
- Private Pool
- Pool
- Balcony/Terrace
US $3,725/Night
For 7 Nights US $26,076
8008.35 ft²
6 Guests
3 Bedrooms
2 Bathrooms
House
- Fireplace/Heating
- View
- Air Conditioner
US $3,675/Night
For 7 Nights US $25,725
18 Guests
9 Bedrooms
4 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Pet Friendly
- Kitchen
US $3,483/Night
For 7 Nights US $24,384
8 Guests
4 Bedrooms
3 Bathrooms
Ocean View
House
- Oceanfront
- Hot Tub
- Fireplace/Heating
US $3,249/Night
For 7 Nights US $22,740
3200 ft²
10 Guests
4 Bedrooms
1 Bathroom
Ocean View
House
- Oceanfront
- Fireplace/Heating
- Ocean View
US $2,960/Night
For 7 Nights US $20,720
14 Guests
7 Bedrooms
5 Bathrooms
Ocean View
House
- Ocean View
- Balcony/Terrace
- View
US $2,905/Night
For 7 Nights US $20,334
Oak Bluffs Pet Friendly Vacation Rentals
700 ft²
4 Guests
2 Bedrooms
1 Bathroom
Ocean View
Cottage
- Oceanfront
- Fireplace/Heating
- Ocean View
US $454/Night
For 7 Nights US $3,177
1001.04 ft²
6 Guests
3 Bedrooms
2 Bathrooms
House
- Fireplace/Heating
- Balcony/Terrace
- View
US $434/Night
For 7 Nights US $3,038
4 Guests
1 Bedroom
1 Bathroom
Ocean View
Apartment
- Oceanfront
- Fireplace/Heating
- Ocean View
US $713/Night
For 7 Nights US $4,992
936.46 ft²
10 Guests
1 Bedroom
2 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
US $816/Night
For 7 Nights US $5,712
700 ft²
4 Guests
2 Bedrooms
1 Bathroom
Ocean View
Apartment
- Oceanfront
- Hot Tub
- Fireplace/Heating
US $757/Night
For 7 Nights US $5,296
5 Guests
1 Bedroom
1 Bathroom
Family Friendly
House
- Fireplace/Heating
- Pet Friendly
- Kitchen
US $651/Night
For 7 Nights US $4,559
4 Guests
2 Bedrooms
1 Bathroom
Ocean View
House
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
US $1,525/Night
For 7 Nights US $10,673
3872 ft²
10 Guests
2 Bedrooms
2 Bathrooms
Ocean View
House
- Oceanfront
- Fireplace/Heating
- Ocean View
US $745/Night
For 7 Nights US $5,212
Oak Bluffs Large Vacation Homes
3500 ft²
12 Guests
5 Bedrooms
4 Bathrooms
Ocean View
House
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
US $1,303/Night
For 7 Nights US $9,120
2174.31 ft²
12 Guests
1 Bedroom
3 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- Child Friendly
US $834/Night
For 7 Nights US $5,838
3000 ft²
10 Guests
6 Bedrooms
3 Bathrooms
Ocean View
House
- Private Pool
- Oceanfront
- Fireplace/Heating
US $1,206/Night
For 7 Nights US $8,445
196.82 ft²
14 Guests
7 Bedrooms
7 Bathrooms
House
- Oceanfront
- Fireplace/Heating
- Ocean View
US $362/Night
For 7 Nights US $2,534
2800 ft²
10 Guests
5 Bedrooms
2 Bathrooms
Ocean View
House
- Oceanfront
- Fireplace/Heating
- Ocean View
US $746/Night
For 7 Nights US $5,223
3200 ft²
12 Guests
5 Bedrooms
3 Bathrooms
Ocean View
House
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
US $2,290/Night
For 7 Nights US $16,029
2600 ft²
13 Guests
4 Bedrooms
4 Bathrooms
Ocean View
House
- Oceanfront
- Fireplace/Heating
- Ocean View
US $602/Night
For 7 Nights US $4,217
2500 ft²
10 Guests
4 Bedrooms
2 Bathrooms
Ocean View
House
- Hot Tub
- Fireplace/Heating
- Ocean View
US $483/Night
For 7 Nights US $3,382
Why Choose Rent By Owner for your Oak Bluffs Vacation Rental Homes?
What makes our Vacation Rentals 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 Vacation Rentals stay?
Choosing the optimal time to visit ensures you can enjoy the area's pleasant weather and vibrant local atmosphere, making your stay in Oak Bluffs memorable and well-suited to your preferences.
Peak Season Highlights
Summer (June to August)
This is the most popular time to visit, when the region's lively atmosphere and warm weather attract many travelers seeking vibrant outdoor activities.
Average Temperature Daytime: 75°F to 85°F - Nighttime: 65°F to 70°F
Early Fall (September to October)
Enjoy pleasant weather and fewer crowds as the area transitions into autumn, perfect for exploring at a relaxed pace and experiencing the changing foliage.
Average Temperature Daytime: 68°F to 75°F - Nighttime: 55°F to 60°F
Off-Season Highlights
Late Fall to Winter (November to February)
During this quieter period, you can experience the region with fewer visitors, ideal for peaceful getaways and enjoying the off-peak tranquility.
Average Temperature Daytime: 45°F to 55°F - Nighttime: 35°F to 45°F
Early Spring (March to May)
As the area awakens from winter, it offers mild weather and blooming scenery, making it a good shoulder season for those preferring smaller crowds.
Average Temperature Daytime: 50°F to 60°F - Nighttime: 40°F to 50°F
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
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
Outdoor Amenities
- Enjoy a spacious outdoor patio or deck for relaxing and al fresco dining amid the region’s scenic views.
- Take advantage of beautifully landscaped gardens or yard spaces to unwind or entertain guests outdoors.
- Make the most of private or shared outdoor pools, perfect for cooling off during your stay in this destination.
- Utilize outdoor grilling areas or BBQ stations to host memorable cookouts with family and friends.
- Benefit from on-site outdoor parking facilities, ensuring convenience while exploring the area.
- Relish in outdoor seating areas designed for socializing and enjoying the region’s pleasant weather.
- Explore nearby walking trails or pathways if your rental includes access to outdoor recreation spaces in the region.
Top Attractions Around Oak Bluffs
What attractions are nearby?
Here, you can explore a variety of outdoor activities and local attractions that showcase the charm and natural beauty of the region, making your stay truly memorable.
Family Activities
- Flying Horses Carousel: You can enjoy a nostalgic ride on this historic carousel, perfect for creating lasting memories with your family here in Oak Bluffs.
- Inkwell Beach: Spend a relaxing day at the sandy shores where your family can swim, play, or simply unwind while taking in the scenic views of the region.
- Ocean Park Playground: The area's popular playground offers a fun space for children to play and interact, making it an ideal stop for families staying in local vacation rentals.
- Main Street Shopping and Dining: Explore the local shops and family-friendly eateries along this vibrant street, allowing you to experience the area's welcoming community atmosphere.
Adult Activities
- Exploring the Martha's Vineyard Campground: You can enjoy a peaceful walk or a relaxing picnic at the historic campground, a must-visit spot in this popular vacation destination.
- Strolling through the Arts and Crafts Colony: Discover unique local art and handmade crafts along the region’s vibrant arts community in the area.
- Visiting Ocean Park: Relax by the water and take in scenic views while strolling through this picturesque beachfront park in the region.
- Taking a Sunset Harbor Cruise: Experience breathtaking views of the coastline as you unwind on a boat tour departing from the area’s harbor.
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?
- Plan Ahead for the Peak Season: Secure your stay early to take advantage of the popular vacation rentals and avoid missing out during busy times in this sought-after destination.
- Explore Local Dining and Markets: Delight in the region’s culinary scene by visiting local markets and eateries to enjoy authentic flavors and fresh regional produce.
- Take Advantage of Waterfront Activities: Make the most of the nearby shoreline by engaging in water-based activities, which are a highlight of this coastal area.
- Discover Unique Neighborhoods: Wander through the charming neighborhoods to experience the distinct character and vibrant atmosphere that make this destination special.
Transportation Options
- Public Ferry Services: You can easily access ferry services here, which provide scenic and convenient transportation to nearby islands and mainland destinations.
- Local Bus System: The regional bus network offers affordable and reliable transit options around the area, making it simple to explore without a car.
- Rental Cars: Renting a car allows you the flexibility to visit more secluded spots and explore the region at your own pace during your stay.
- Taxis and Ride-Sharing: Taxis and ride-sharing services are readily available for quick trips within this destination, ensuring you reach your vacation rentals comfortably and efficiently.
Local Customs Options
- Clamming and Seafood Festivals: Participating in local clamming activities and enjoying seasonal seafood festivals are cherished customs that highlight the region's rich maritime heritage.
- Historic Gingerbread Cottages: Appreciating the charming, gingerbread-style cottages is a beloved tradition, reflecting the area's unique architectural history during your stay.
- Harbor Celebrations: Attending boat parades and harbor celebrations offers an authentic glimpse into the community’s close relationship with its maritime roots.
- Art and Craft Fairs: Visiting local art and craft fairs allows you to experience the creative spirit of those who call this destination home.
Oak Bluffs Vacation Rental 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:
- Arrowsmith Cottage - Oak Bluffs - 1 mi to Eastville Point Beach via bike path.
- Private Meadow View Family Retreat - 4 BR, AC, Large Yard, Tennis, on Bike Path
- Multiple Ensuites, Central Air, Perfect Location
- ART FILLED BEACH COTTAGE IN THE PRIVATE WATERFRONT COMMUNITY OF WATERVIEW FARMS!
- Close to town, beautifully updated
- Martha's Vineyard Beachfront Condo in Oak Bluffs
- 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
- Discover the magic of Martha’s Vineyard! NEW ! Build in 2020 !
2. How many vacation rentals have private pools in Oak Bluffs?
There are 9 vacation rentals with private pools near Oak Bluffs. Top-rated RBO homes that have access to a swimming pool include:
3. 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:
4. How many Rentbyowner vacation rentals are available in Oak Bluffs?
Currently, the total number of properties listed by Rent By Owner in 2026 is over 629 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.
5. What is the cancellation policy for vacation rentals in Oak Bluffs?
Cancellation policies vary depending on the specific property owner. You should review the listing details or contact the host directly to understand the terms and any applicable fees.
6. Are there any specific check-in and check-out times I should be aware of when booking in this area?
Check-in and check-out times are set by each property owner. It’s recommended to confirm these details during your booking process or by communicating with the host to ensure a smooth arrival and departure.
7. What amenities are typically included in vacation rentals in Oak Bluffs?
Amenities can differ between properties, but many renters find that common features such as Wi-Fi, parking, and fully equipped kitchens are available. To get exact information, review the property listing or inquire with the owner directly.
8. How do I ensure my reservation is secure and reliable in this region?
Booking through a trusted platform ensures a secure transaction. Always read reviews and communicate directly with the property owner to verify details and build confidence before finalizing your reservation.
9. Is there a minimum stay requirement for vacation rentals here?
Minimum stay requirements vary by property. To avoid surprises, check the specific listing details or ask the host about any minimum night policies before confirming your booking.
Oak Bluffs Top Rated Vacation Rentals
6 Guests
2 Bedrooms
2 Bathrooms
Ocean View
House
- Private Pool
- Fireplace/Heating
- Pool
US $709/Night
For 7 Nights US $4,965
9 Guests
4 Bedrooms
2 Bathrooms
Ocean View
House
- Private Pool
- Oceanfront
- Fireplace/Heating
US $1,327/Night
For 7 Nights US $9,289
5423 ft²
12 Guests
5 Bedrooms
7 Bathrooms
Family Friendly
House
- Private Pool
- Hot Tub
- Fireplace/Heating
US $2,316/Night
For 7 Nights US $16,211
3100 ft²
10 Guests
5 Bedrooms
4 Bathrooms
Ocean View
House
- Private Pool
- Fireplace/Heating
- Pool
US $2,479/Night
For 7 Nights US $17,355
750 ft²
5 Guests
2 Bedrooms
1 Bathroom
Ocean View
House
- Fireplace/Heating
- Pool
- Ocean View
US $922/Night
For 7 Nights US $6,451
2800 ft²
10 Guests
5 Bedrooms
3 Bathrooms
Ocean View
House
- Private Pool
- Oceanfront
- Hot Tub
US $1,585/Night
For 7 Nights US $11,095
1864 ft²
12 Guests
3 Bedrooms
2 Bathrooms
Ocean View
House
- Oceanfront
- Fireplace/Heating
- Pool
US $484/Night
For 7 Nights US $3,385
US $725/Night
For 7 Nights US $5,075
