Oak Bluffs vacation rentals
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Top-rated vacation rentals in Oak Bluffs
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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
Sep 14 – 21
Home in Edgartown
4.96 out of 5 average rating, 187 reviewsBrand new gorgeous 2 bedroom guest house.
Feb 2 – 9
Home in Oak Bluffs
4.78 out of 5 average rating, 217 reviewsCentral location for your vacation
Oct 22 – 29
Home in Edgartown
5.0 out of 5 average rating, 116 reviewsClose to Edgartown Village Center!
Nov 6 – 13
Home in Oak Bluffs
4.79 out of 5 average rating, 103 reviewsCozy Vacation Getaway On Bike Path
Nov 16 – 23
Home in Tisbury
4.98 out of 5 average rating, 247 reviewsVineyard Retreat: Ferry Tickets 8/17-8/24
Sep 19 – 26
Home in West Tisbury
4.98 out of 5 average rating, 183 reviewsWest Tisbury Escape, Long Point Beach
Nov 3 – 10
Home in West Tisbury
4.98 out of 5 average rating, 121 reviewsSecluded Up Island Cottage
Feb 18 – 25
Oak Bluffs cottage rentals
Cottage in Tisbury
4.96 out of 5 average rating, 215 reviewsNot Your Great Aunt's Island Cottage
Dec 8 – 15
Cottage in Tisbury
4.98 out of 5 average rating, 314 reviewsMartha's Vineyard Getaway Cottage
Dec 8 – 15
Cottage in Mashpee
4.95 out of 5 average rating, 303 reviews★The Islander | Steps From Water, Fire Pit, AC★
Oct 22 – 29
Cottage in Sandwich
4.95 out of 5 average rating, 158 reviewsWaterfront Lake Cottage, Private Beach, Wow View!
Apr 4 – 11
Cottage in Mashpee
4.9 out of 5 average rating, 184 reviewsWaterfront! Family Beach & Dock
Mar 26 – Apr 2
Cottage in Falmouth
4.94 out of 5 average rating, 135 reviews“Cozy Cottage” on Great Bay
Sep 26 – Oct 3
Cottage in Fairhaven
4.79 out of 5 average rating, 278 reviewsOn the Beach Cottage in Fairhaven
Oct 27 – Nov 3
Cottage in Barnstable
4.99 out of 5 average rating, 122 reviewsBeach Glass Cottage - Pond Front
Jan 3 – 10
Oak Bluffs condo rentals
Condo in Mashpee
4.97 out of 5 average rating, 101 reviewsSleep 6 @ New Seabury w/ Pool Access, All Seasons!
Mar 8 – 15
Condo in Oak Bluffs
4.95 out of 5 average rating, 21 reviewsLOCATION LOCATION!! Ocean- View TOP Floor Condo
Sep 22 – 29
Condo in Oak Bluffs
5.0 out of 5 average rating, 6 reviewsOcean View Gem, Walk to it All, No Car Needed!
Oct 18 – 25
Condo in Tisbury
4.91 out of 5 average rating, 45 reviewsSunny 2bedroom condo w pool, walk to town
Oct 22 – 29
Condo in Tisbury
4.98 out of 5 average rating, 44 reviewsShort Walk into Town - Nice Comfortable Reasonable
Sep 18 – 25
Condo in Mattapoisett
4.97 out of 5 average rating, 30 reviewsBrand new! Whole apartment, huge tub, full kitchen
Aug 13 – 20
Condo in Vineyard Haven
5.0 out of 5 average rating, 17 reviewsRelax....You're on Island Time......
Feb 23 – Mar 2
Condo in Tisbury
4.91 out of 5 average rating, 45 reviewsPrivate 3bdrm Condo Tashmoo Woods
Apr 17 – 24
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
R190 ZAR 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 420 house rentals, over 40 cottage rentals to over 30 condo 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 West Chop, over 640 vacation rentals in East Chop, and over 640 vacation rentals in Eastville.
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.
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.
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 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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