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
4.82 out of 5 average rating, 179 reviewsWaterview, Private, Walk to Beach, Mile to Town
May 27 – Jun 3
Home in Oak Bluffs
4.94 out of 5 average rating, 116 reviewsThe Lighthouse
Sep 11 – 18
Home in Oak Bluffs
4.78 out of 5 average rating, 217 reviewsCentral location for your vacation
Oct 15 – 22
Home in Oak Bluffs
4.79 out of 5 average rating, 103 reviewsCozy Vacation Getaway On Bike Path
Nov 1 – 8
Home in Edgartown
5.0 out of 5 average rating, 115 reviewsClose to Edgartown Village Center!
Nov 16 – 23
Home in Tisbury
4.98 out of 5 average rating, 247 reviewsVineyard Retreat: Just a mile from Tisbury center
Sep 17 – 24
Home in West Tisbury
4.98 out of 5 average rating, 183 reviewsWest Tisbury Escape, Long Point Beach
Nov 18 – 25
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, 214 reviewsNot Your Great Aunt's Island Cottage
Dec 8 – 15
Cottage in Tisbury
4.98 out of 5 average rating, 313 reviewsMartha's Vineyard Getaway Cottage
Dec 31 – Jan 7
Cottage in Mashpee
4.95 out of 5 average rating, 302 reviews★The Islander | Steps From Water, Fire Pit, AC★
Oct 22 – 29
Cottage in Sandwich
4.95 out of 5 average rating, 157 reviewsWaterfront Lake Cottage, Private Beach, Wow View!
Sep 29 – Oct 6
Cottage in Mashpee
4.9 out of 5 average rating, 183 reviewsWaterfront! Family Beach & Dock
Dec 9 – 16
Cottage in Bourne
4.94 out of 5 average rating, 129 reviewsSeaglass Cottage
Mar 24 – 31
Cottage in Falmouth
4.94 out of 5 average rating, 135 reviews“Cozy Cottage” on Great Bay
Feb 16 – 23
Cottage in Fairhaven
4.79 out of 5 average rating, 277 reviewsOn the Beach Cottage in Fairhaven
Sep 16 – 23
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 7 – 14
Condo in Oak Bluffs
5.0 out of 5 average rating, 20 reviewsFABULOUS OCEAN VIEWS-Oak Bluffs Condo Across Beach
May 5 – 12
Condo in Oak Bluffs
5.0 out of 5 average rating, 6 reviewsOcean View Gem, Walk to it All, No Car Needed!
Oct 21 – 28
Condo in Tisbury
4.91 out of 5 average rating, 45 reviewsSunny 2bedroom condo w pool, walk to town
Mar 8 – 15
Condo in Mattapoisett
4.97 out of 5 average rating, 29 reviewsBrand new! Whole apartment, huge tub, full kitchen
Oct 11 – 18
Condo in Tisbury
4.98 out of 5 average rating, 44 reviewsShort Walk into Town - Nice Comfortable Reasonable
Jun 5 – 12
Condo in Vineyard Haven
5.0 out of 5 average rating, 17 reviewsRelax....You're on Island Time......
Feb 7 – 14
Condo in Tisbury
4.91 out of 5 average rating, 45 reviewsPrivate 3bdrm Condo Tashmoo Woods
Apr 14 – 21
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
€ 9 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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