Oak Bluffs vacation rentals
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Top-rated vacation rentals in Oak Bluffs
Guests agree: these vacation rentals are highly rated for location, cleanliness, and more.
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Popular amenities for Oak Bluffs vacation rentals
Other great vacation rentals in Oak Bluffs
Home in Oak Bluffs
4.94 out of 5 average rating, 116 reviewsThe Lighthouse
Home in Tisbury
4.98 out of 5 average rating, 249 reviewsSunny, Spacious Vineyard Retreat
Home in Edgartown
4.96 out of 5 average rating, 188 reviewsBrand new gorgeous 2 bedroom guest house.
Home in Oak Bluffs
4.78 out of 5 average rating, 219 reviewsCentral location for your vacation
Home in Edgartown
5.0 out of 5 average rating, 116 reviewsClose to Edgartown Village Center!
Home in West Tisbury
4.98 out of 5 average rating, 184 reviewsWest Tisbury Escape, Long Point Beach
Home in Edgartown
4.92 out of 5 average rating, 140 reviews✅Beach ✅Downtown ✅Restaurants/Bars ✅Bike Path
Home in West Tisbury
4.98 out of 5 average rating, 123 reviewsSecluded Up Island Cottage
Oak Bluffs cottage rentals
Cottage in Tisbury
4.96 out of 5 average rating, 217 reviewsNot Your Great Aunt's Island Cottage
Cottage in Tisbury
4.98 out of 5 average rating, 317 reviewsMartha's Vineyard Getaway Cottage
Cottage in Sandwich
4.95 out of 5 average rating, 162 reviewsWaterfront Lake Cottage, Private Beach, Wow View!
Cottage in Mashpee
4.95 out of 5 average rating, 304 reviews★The Islander | Steps From Water, Fire Pit, AC★
Cottage in Mashpee
4.9 out of 5 average rating, 188 reviewsWaterfront! Family Beach & Dock
Cottage in Falmouth
4.93 out of 5 average rating, 136 reviews“Cozy Cottage” on Great Bay
Cottage in Fairhaven
4.8 out of 5 average rating, 280 reviewsOn the Beach Cottage in Fairhaven
Cottage in Barnstable
4.89 out of 5 average rating, 119 reviewsOsterville Charming Cottage in the Heart of Wianno
Oak Bluffs condo rentals
Condo in Mashpee
4.97 out of 5 average rating, 102 reviewsSleep 6 @ New Seabury w/ Pool Access, All Seasons!
Condo in Oak Bluffs
5.0 out of 5 average rating, 20 reviewsFABULOUS OCEAN VIEWS-Oak Bluffs Condo Across Beach
Condo in Oak Bluffs
5.0 out of 5 average rating, 6 reviewsOcean View Gem, Walk to it All, No Car Needed!
Condo in Tisbury
4.98 out of 5 average rating, 44 reviewsShort Walk into Town - Nice Comfortable Reasonable
Condo in Tisbury
4.76 out of 5 average rating, 17 reviewsLovely studio above garage
Condo in Tisbury
4.91 out of 5 average rating, 45 reviewsSunny 2bedroom condo w pool, walk to town
Condo in Tisbury
4.91 out of 5 average rating, 45 reviewsPrivate 3bdrm Condo Tashmoo Woods
Condo in Vineyard Haven
5.0 out of 5 average rating, 17 reviewsRelax....You're on Island Time......
Quick stats about vacation rentals in Oak Bluffs
Total rentals
690 properties
Rentals with a pool
80 properties have a pool
Pet-friendly rentals
160 properties allow pets
Family-friendly rentals
480 properties are a good fit for families
Total number of reviews
22K reviews
Nightly prices starting at
$10 before taxes and fees
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 40 cottage rentals, over 30 condo rentals to over 420 house 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 640 vacation rentals in Eastville, over 640 vacation rentals in West Chop, and over 640 vacation rentals in East Chop.
Are there vacation rentals with a dedicated workspace in Oak Bluffs?
Yes! Work meets play with ease at over 340 vacation rentals in Oak Bluffs featuring dedicated workspaces. Stay connected and productive 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 160 vacation rentals for guests traveling with pets.
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 $10 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.
Are there Oak Bluffs house rentals on Airbnb with pools?
Yes! Dive into the perfect getaway at one of over 10 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 a bbq area?
Absolutely! We offer over 260 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 170 house rentals with self check-in in Oak Bluffs. Enjoy a tailored experience with all the comforts you desire.
Do house rentals in Oak Bluffs have wifi?
Absolutely! We offer over 420 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.
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