Best Vacation Homes in Oak Bluffs
New
House
5 Bedrooms
4 Baths
12 Guests
2500 ft²
Private Pool
Oceanfront
Hot Tub
Fireplace/Heating
US $2,583/Night
7 Nights - US $18,080
House
10.0(4 Reviews)
2 Bedrooms
2 Baths
4 Guests
1097.92 ft²
- Oceanfront
- Fireplace/Heating
Ocean View
View
US $239/Night
7 Nights - US $1,673
Hotel
9.8(94 Reviews)
1 Bath
- Fireplace/Heating
Air Conditioner
Internet
Child Friendly
US $265/Night
7 Nights - US $1,857
House
12 Bedrooms
7 Baths
20 Guests
- Fireplace/Heating
- Internet
- Child Friendly
Laundry
US $2,486/Night
7 Nights - US $17,403
Apartment
10.0(1 Review)
1 Bedroom
1 Bath
2 Guests
495.14 ft²
- Fireplace/Heating
Balcony/Terrace- Air Conditioner
- Child Friendly
US $624/Night
7 Nights - US $4,366
New
House
3 Bedrooms
3 Baths
6 Guests
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
- View
US $941/Night
7 Nights - US $6,590
New
House
3 Bedrooms
2 Baths
8 Guests
- Fireplace/Heating
- Air Conditioner
- Internet
- Child Friendly
US $858/Night
7 Nights - US $6,009
House
4 Bedrooms
2 Baths
8 Guests
- Ocean View
- Balcony/Terrace
- View
Kitchen
US $773/Night
7 Nights - US $5,412
Oak Bluffs Luxury Rentals
House
9.8(25 Reviews)
6 Bedrooms
2 Baths
12 Guests
2764 ft²
- Oceanfront
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
US $4,729/Night
7 Nights - US $33,100
New
House
5 Bedrooms
4 Baths
17 Guests
- Fireplace/Heating
Pet Friendly- Air Conditioner
- Internet
US $4,709/Night
7 Nights - US $32,965
House
5 Bedrooms
3 Baths
12 Guests
4500 ft²
- Hot Tub
- Fireplace/Heating
Pool- Ocean View
US $4,669/Night
7 Nights - US $32,683
House
9.1(6 Reviews)
3 Bedrooms
2 Baths
6 Guests
8008.35 ft²
- Fireplace/Heating
- View
- Air Conditioner
- Internet
US $3,675/Night
7 Nights - US $25,725
House
10.0(1 Review)
9 Bedrooms
4 Baths
18 Guests
- Fireplace/Heating
- Pet Friendly
- Kitchen
Parking
US $3,507/Night
7 Nights - US $24,552
House
10.0(3 Reviews)
4 Bedrooms
3 Baths
8 Guests
- Oceanfront
- Hot Tub
- Fireplace/Heating
- Ocean View
US $3,435/Night
7 Nights - US $24,046
House
10.0(39 Reviews)
4 Bedrooms
1 Bath
10 Guests
3200 ft²
- Oceanfront
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
US $2,960/Night
7 Nights - US $20,720
House
9.2(7 Reviews)
7 Bedrooms
5 Baths
14 Guests
- Ocean View
- Balcony/Terrace
- View
- Kitchen
US $2,905/Night
7 Nights - US $20,334
Oak Bluffs Pet Friendly Vacation Rentals
Apartment
10.0(155 Reviews)
2 Bedrooms
1 Bath
5 Guests
800 ft²
- Oceanfront
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
US $722/Night
7 Nights - US $5,056
House
10.0(1 Review)
3 Bedrooms
2 Baths
6 Guests
1001.04 ft²
- Fireplace/Heating
- Balcony/Terrace
- View
- Pet Friendly
US $434/Night
7 Nights - US $3,038
Cottage
10.0(98 Reviews)
2 Bedrooms
1 Bath
4 Guests
700 ft²
- Oceanfront
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
US $463/Night
7 Nights - US $3,243
House
9.0(1 Review)
1 Bedroom
2 Baths
10 Guests
936.46 ft²
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Child Friendly
US $816/Night
7 Nights - US $5,712
Apartment
10.0(46 Reviews)
1 Bedroom
1 Bath
4 Guests
- Oceanfront
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
US $814/Night
7 Nights - US $5,696
House
10.0(3 Reviews)
2 Bedrooms
1 Bath
4 Guests
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
- View
US $1,525/Night
7 Nights - US $10,673
Cottage
8.0(1 Review)
1 Bedroom
1 Bath
4 Guests
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $507/Night
7 Nights - US $3,549
Apartment
7.6(4 Reviews)
1 Bedroom
1 Bath
3 Guests
100 ft²
- Oceanfront
- Fireplace/Heating
- Ocean View
- View
US $361/Night
7 Nights - US $2,529
Oak Bluffs Large Vacation Homes
House
10.0(71 Reviews)
5 Bedrooms
4 Baths
12 Guests
3500 ft²
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
- View
US $1,340/Night
7 Nights - US $9,383
House
9.0(3 Reviews)
1 Bedroom
3 Baths
12 Guests
2174.31 ft²
- Fireplace/Heating
- Balcony/Terrace
- Child Friendly
Restaurant
US $834/Night
7 Nights - US $5,838
House
10.0(71 Reviews)
6 Bedrooms
3 Baths
10 Guests
3000 ft²
- Private Pool
- Oceanfront
- Fireplace/Heating
- Pool
US $1,192/Night
7 Nights - US $8,343
House
8.7(102 Reviews)
7 Bedrooms
7 Baths
14 Guests
196.82 ft²
- Oceanfront
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
US $362/Night
7 Nights - US $2,534
House
10.0(44 Reviews)
5 Bedrooms
2 Baths
10 Guests
2800 ft²
- Oceanfront
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
US $614/Night
7 Nights - US $4,300
House
10.0(42 Reviews)
5 Bedrooms
3 Baths
12 Guests
3200 ft²
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
- View
US $1,970/Night
7 Nights - US $13,793
House
10.0(40 Reviews)
4 Bedrooms
4 Baths
13 Guests
2600 ft²
- Oceanfront
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
US $602/Night
7 Nights - US $4,217
House
10.0(39 Reviews)
4 Bedrooms
2 Baths
10 Guests
2500 ft²
- Hot Tub
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
US $517/Night
7 Nights - US $3,616
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:
- In-Town Certified National Historic Oak Bluffs Property -
- 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
2. How many vacation rentals have private pools in Oak Bluffs?
There are 10 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 674 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
House
10.0(22 Reviews)
2 Bedrooms
2 Baths
6 Guests
- Private Pool
- Fireplace/Heating
- Pool
- Ocean View
US $709/Night
7 Nights - US $4,965
House
10.0(7 Reviews)
4 Bedrooms
2 Baths
9 Guests
2500 ft²
- Private Pool
- Oceanfront
- Fireplace/Heating
- Pool
US $1,487/Night
7 Nights - US $10,409
House
10.0(4 Reviews)
5 Bedrooms
7 Baths
12 Guests
5423 ft²
- Private Pool
- Hot Tub
- Fireplace/Heating
- Pool
US $2,729/Night
7 Nights - US $19,102
House
10.0(3 Reviews)
5 Bedrooms
4 Baths
10 Guests
3100 ft²
- Private Pool
- Fireplace/Heating
- Pool
- Ocean View
US $2,446/Night
7 Nights - US $17,120
House
9.4(13 Reviews)
5 Bedrooms
3 Baths
10 Guests
2800 ft²
- Private Pool
- Oceanfront
- Hot Tub
- Fireplace/Heating
US $1,792/Night
7 Nights - US $12,545
House
9.2(9 Reviews)
3 Bedrooms
2 Baths
12 Guests
1864 ft²
- Oceanfront
- Fireplace/Heating
- Pool
- Ocean View
US $484/Night
7 Nights - US $3,385
US $725/Night
7 Nights - US $5,075
House
6.0(2 Reviews)
4 Bedrooms
3 Baths
12 Guests
- Hot Tub
- Fireplace/Heating
- Pool
- Balcony/Terrace
US $1,334/Night
7 Nights - US $9,335
