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.
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 East Falmouth
4.93 out of 5 average rating, 129 reviewsSummer House Close To Beaches
Home in Woods Hole
4.92 out of 5 average rating, 117 reviewsJuniper Point Cottage With Ocean View
Home in East Falmouth
4.84 out of 5 average rating, 125 reviewsCozy three bedroom ranch
Home in Tisbury
4.98 out of 5 average rating, 265 reviewsSunny, Spacious Vineyard Retreat
Home in Oak Bluffs
4.83 out of 5 average rating, 193 reviewsWaterview, Private, Walk to Beach, Mile to Town
Home in New Seabury
4.83 out of 5 average rating, 109 reviewsNew Seabury Retreat. Butchart Gardens' Inspired
Home in Teaticket
4.93 out of 5 average rating, 122 reviewsCute Single Family Home in Nice Neighborhood
Home in Oak Bluffs
4.97 out of 5 average rating, 239 reviewsSweet little post and beam
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
4.94 out of 5 average rating, 116 reviewsSeaside cottage
Cottage in East Falmouth
4.93 out of 5 average rating, 158 reviews“Cozy Cottage” on Great Bay
Cottage in Tisbury
4.98 out of 5 average rating, 326 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 Pocasset
4.81 out of 5 average rating, 108 reviews* Rustic Cape Cod Captain's Quarters Cottage
Cottage in Sandwich
4.95 out of 5 average rating, 204 reviewsLakefront cottage, private Beachfront, Wow View!
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
Condo in West Falmouth
4.95 out of 5 average rating, 21 reviewsHistoric W Falmouth Home steps to bikeway & more!
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 50 cottage rentals, over 460 house 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 710 vacation rentals in West Chop, over 710 vacation rentals in Eastville, and over 710 vacation rentals in East Chop.
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.
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.
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!
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