Oak Bluffs vacation rentals
Book unique vacation rentals, houses, and more on Airbnb
Top-rated vacation rentals in Oak Bluffs
Guests agree: these vacation rentals are highly rated for location, cleanliness, and more.
Vacation rentals for every style
Get the amount of space that is right for you
Popular amenities for Oak Bluffs vacation rentals
Oak Bluffs house rentals
Home in Edgartown
4.96 out of 5 average rating, 67 reviewsNewly constructed Edgartown home with A/C .
Home in Edgartown
4.97 out of 5 average rating, 226 reviewsBrand new gorgeous 2 bedroom guest house.
Home in Edgartown
4.88 out of 5 average rating, 26 reviewsSpacious Contemporary home Game room Central AC
Home in Barnstable
4.92 out of 5 average rating, 104 reviewsCozy 1-level fenced yard Craigville Beach 2000sqft
Home in Oak Bluffs
4.94 out of 5 average rating, 131 reviewsThe Lighthouse
Home in Oak Bluffs
4.83 out of 5 average rating, 193 reviewsWaterview, Private, Walk to Beach, Mile to Town
Home in East Falmouth
5 out of 5 average rating, 36 reviewsSpacious and immaculate custom home.
Home in Mashpee
4.83 out of 5 average rating, 153 reviewsNew Seabury & South Cape Beach State Park
Oak Bluffs cottage rentals
Cottage in Falmouth
4.86 out of 5 average rating, 106 reviewsSpectacular Beach front lake house, includes linen
Cottage in Woods Hole
4.97 out of 5 average rating, 90 reviewsCape Cod Cottage Getaway!
Cottage in Fairhaven
5 out of 5 average rating, 61 reviewsShell Cottage at West Island
Cottage in Oak Bluffs
5 out of 5 average rating, 8 reviewsThe Island Collection MV: Sandy Shores
Cottage in East Falmouth
4.93 out of 5 average rating, 160 reviews“Cozy Cottage” on Great Bay
Cottage in Tisbury
4.98 out of 5 average rating, 330 reviewsMartha's Vineyard Getaway Cottage
Cottage in Barnstable
4.88 out of 5 average rating, 134 reviewsOsterville Charming Cottage in the Heart of Wianno
Cottage in New Seabury
4.96 out of 5 average rating, 92 reviewsCozy Cape Cod Cottage W/ Beach Access
Oak Bluffs condo rentals
Condo in Tisbury
4.98 out of 5 average rating, 50 reviewsShort Walk into Town - Nice Comfortable Reasonable
Condo in Vineyard Haven
5 out of 5 average rating, 21 reviewsRelax....You're on Island Time......
Condo in Tisbury
4.91 out of 5 average rating, 47 reviewsPrivate 3bdrm Condo Tashmoo Woods
Condo in Tisbury
4.9 out of 5 average rating, 72 reviewsSunny 2bedroom condo w pool, walk to town
Condo in Oak Bluffs
4.96 out of 5 average rating, 27 reviewsLOCATION LOCATION!! Ocean- View TOP Floor Condo
Condo in Tisbury
4.77 out of 5 average rating, 13 reviewsMartha’s Vineyard Ground Floor Condo * Near Ferry
Condo in New Seabury
4.94 out of 5 average rating, 72 reviewsSerenity By The Sea, Mashpee/New Seabury, MA
Quick stats about vacation rentals in Oak Bluffs
Total rentals
760 properties
Nightly prices starting at
$40 before taxes and fees
Total number of reviews
26K reviews
Family-friendly rentals
510 properties are a good fit for families
Pet-friendly rentals
170 properties allow pets
Rentals with a pool
80 properties have a pool
Frequently Asked Questions
What types of vacation rentals are available in Oak Bluffs?
Uncover the perfect home-away-from-home with our diverse selection of vacation rentals in Oak Bluffs. From over 460 house rentals, over 30 condo rentals to over 50 cottage rentals, we've got you covered. For even more variety, explore our Airbnb Categories to find the ideal space for your getaway.
Where should I stay in Oak Bluffs?
Make yourself at home in Oak Bluffs by choosing from our most frequently booked neighborhoods. We have over 710 vacation rentals in East Chop, over 710 vacation rentals in West Chop, and over 710 vacation rentals in Eastville.
Are there vacation rentals with a dedicated workspace in Oak Bluffs?
Yes! Work meets play with ease at over 350 vacation rentals in Oak Bluffs featuring dedicated workspaces. Stay connected and productive in your home away from home.
How much does it cost to stay in house rentals in Oak Bluffs?
Experience the best of Oak Bluffs with our house rentals, starting at about $40 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.
Are there pet-friendly vacation rentals in Oak Bluffs?
Four-legged friends are welcome in Oak Bluffs. Choose from more than 170 vacation rentals for guests traveling with pets.
Do house rentals in Oak Bluffs have a bbq area?
Absolutely! We offer over 250 house rentals with a bbq area in Oak Bluffs. Enjoy a tailored experience with all the comforts you desire.
Do house rentals in Oak Bluffs have self check-in?
Absolutely! We offer over 160 house rentals with self check-in in Oak Bluffs. Enjoy a tailored experience with all the comforts you desire.
Are there Oak Bluffs house rentals on Airbnb with pools?
Yes! Dive into the perfect getaway at one of over 20 house rentals with pools in Oak Bluffs, available on Airbnb. Make a splash and soak up the sun in style!
Do house rentals in Oak Bluffs have wifi?
Absolutely! We offer over 460 house rentals with wifi in Oak Bluffs. Enjoy a tailored experience with all the comforts you desire.
Do house rentals in Oak Bluffs have a gym?
Absolutely! We offer over 30 house rentals with a gym in Oak Bluffs. Enjoy a tailored experience with all the comforts you desire.
Destinations to explore
- Martha's Vineyard Vacation rentals
- Cambridge Vacation rentals
- Nantucket Vacation rentals
- Montauk Vacation rentals
- Salem Vacation rentals
- Newport Vacation rentals
- Philadelphia Vacation rentals
- Jersey City Vacation rentals
- New York Vacation rentals
- The Hamptons Vacation rentals
- Boston Vacation rentals
- Cape Cod Vacation rentals
- Rentals with a patio Oak Bluffs
- Rentals with a hot tub Oak Bluffs
- Pet-friendly rentals Oak Bluffs
- Rentals with breakfast Oak Bluffs
- Beachfront rentals Oak Bluffs
- Condo rentals Oak Bluffs
- Hotel rentals Oak Bluffs
- Kid-friendly rentals Oak Bluffs
- Private suite rentals Oak Bluffs
- Monthly Rentals Oak Bluffs
- Rentals with beach access Oak Bluffs
- Rentals with outdoor seating Oak Bluffs
- Rentals with a fireplace Oak Bluffs
- House rentals Oak Bluffs
- Rentals with pools Oak Bluffs
- Family-friendly rentals Oak Bluffs
- Bed and breakfasts Oak Bluffs
- Waterfront rentals Oak Bluffs
- Rentals with a washer and dryer Oak Bluffs
- Rentals with a kayak Oak Bluffs
- Rentals with lake access Oak Bluffs
- Boutique hotel rentals Oak Bluffs
- Apartment rentals Oak Bluffs
- Rentals with a fire pit Oak Bluffs
- Cabins United States
- Treehouses United States
- Glamping United States
- Tiny Houses United States
- Beach Houses United States
- Campers and RVs United States
- Lakehouses United States
- Yurt Rentals United States
- Yurt Rentals United Kingdom
- Castle Rentals United States
- Houseboats United States
- Holiday Caravans United Kingdom
- Private Island Rentals United States
- Farm Houses United States
- Farm Cottages United Kingdom
- Cabin Rentals Australia
- Luxury Cabins United Kingdom
- Luxury Cabins United States
- Holiday Chalets United Kingdom
- Cottage Rentals United States
- Holiday Cottages United Kingdom
- Mansion Rentals United States
- Villa Rentals United Kingdom
- Holiday Bungalows United Kingdom
- Bungalow Rentals United States
- Condo Rentals United States
- Holiday Apartments Australia
- Holiday Houses United States
- Holiday Houses United Kingdom
- Private Holiday Rentals United Kingdom
- Big House Rentals United States
- Big Cottages Australia
- Large Villas United Kingdom
- House Rentals with a Pool United States
- Cabin Rentals with a Pool United States
- Villas with a Pool United Kingdom
- Apartments with a Hot Tub United States
- Holiday Cottages with a Hot Tub United Kingdom
- Beach Cabins United States
- Beach Condos United States
- Beachfront Rentals United States
- Beach Houses United Kingdom
- Beach Villas United Kingdom
- Coastal Cottages United Kingdom
- Pet-Friendly Vacation Rentals United States
- Pet-Friendly Beach Rentals United States
- Pet-Friendly Cabin Rentals United States
- Dog-Friendly Cottages United Kingdom
- Luxury Dog-Friendly Cottages United Kingdom
- Family travel hub Tips and inspiration
- Family budget travel Get there for less
- Vacation ideas for any budget Make it special without making it spendy
- Travel Europe on a budget How to take the kids to Europe for less
- Outdoor adventure Explore nature with the family
- Bucket list national parks Must-see parks for family travel
- Kid-friendly state parks Check out these family-friendly hikes