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Oak Bluffs Vacation Rentals

Find 1,926 available home rentals from 10 partners
Anytime
1 guest
Anytime
1 guest

Top 15 Recommended vacation rentals in Oak Bluffs

Find your perfect vacation rental in Oak Bluffs from just $239 per night!

House Oak Bluffs
House ∙ 10 guests ∙ 5 bedrooms

House

Oak Bluffs, Dukes County, Massachusetts, United States
from $1,366
per night
Outstanding(4 ratings)
from $1,366
per night
View deal
House Oak Bluffs
Sept 20 - Sept 27
House ∙ 8 guests ∙ 4 bedrooms

372 m² House

Oak Bluffs, Dukes County, Massachusetts, United States
$1,760
per night
Outstanding(29 ratings)
$1,760
per night
View deal
House Oak Bluffs
House ∙ 15 guests ∙ 5 bedrooms

390 m² House

Oak Bluffs, Dukes County, Massachusetts, United States
from $1,428
per night
Outstanding(41 ratings)
from $1,428
per night
View deal
House Oak Bluffs
House ∙ 8 guests ∙ 4 bedrooms

157 m² House

Oak Bluffs, Dukes County, Massachusetts, United States
from $953
per night
Outstanding(29 ratings)
from $953
per night
View deal
House Oak Bluffs
House ∙ 9 guests ∙ 4 bedrooms

204 m² House

Oak Bluffs, Dukes County, Massachusetts, United States
from $1,050
per night
Outstanding(30 ratings)
from $1,050
per night
View deal
House Oak Bluffs
House ∙ 10 guests ∙ 4 bedrooms

186 m² House

Oak Bluffs, Dukes County, Massachusetts, United States
from $752
per night
Outstanding(32 ratings)
from $752
per night
View deal
House Oak Bluffs
House ∙ 10 guests ∙ 5 bedrooms

House

Oak Bluffs, Dukes County, Massachusetts, United States
from $1,633
per night
Outstanding(25 ratings)
from $1,633
per night
View deal
House Oak Bluffs
House ∙ 13 guests ∙ 6 bedrooms

511 m² House

Oak Bluffs, Dukes County, Massachusetts, United States
from $1,476
per night
Outstanding(51 ratings)
from $1,476
per night
View deal
House Oak Bluffs
Sept 20 - Sept 27
House ∙ 8 guests ∙ 4 bedrooms

163 m² House

Oak Bluffs, Dukes County, Massachusetts, United States
$1,040
per night
Outstanding(49 ratings)
$1,040
per night
View deal
House Oak Bluffs
Sept 20 - Sept 27
House ∙ 8 guests ∙ 4 bedrooms

167 m² House

Oak Bluffs, Dukes County, Massachusetts, United States
$631
per night
Outstanding(31 ratings)
$631
per night
View deal
House Oak Bluffs
Sept 20 - Sept 27
House ∙ 8 guests ∙ 4 bedrooms

186 m² House

Oak Bluffs, Dukes County, Massachusetts, United States
$980
per night
Outstanding(36 ratings)
$980
per night
View deal
House Oak Bluffs
Sept 20 - Sept 27
House ∙ 8 guests ∙ 4 bedrooms

279 m² House

Oak Bluffs, Dukes County, Massachusetts, United States
$2,490
per night
Outstanding(18 ratings)
$2,490
per night
View deal
House Oak Bluffs
-8%
Sept 20 - Sept 27
House ∙ 7 guests ∙ 4 bedrooms

153 m² House

Oak Bluffs, Dukes County, Massachusetts, United States
$1,180$1,087
per night
Outstanding(44 ratings)
$1,180$1,087
per night
View deal
House Oak Bluffs
Sept 20 - Sept 27
House ∙ 10 guests ∙ 5 bedrooms

House

Oak Bluffs, Dukes County, Massachusetts, United States
$3,556
per night
Outstanding(91 ratings)
$3,556
per night
View deal
House Oak Bluffs
Sept 20 - Sept 27
House ∙ 6 guests ∙ 3 bedrooms

143 m² House

Oak Bluffs, Dukes County, Massachusetts, United States
$933
per night
Outstanding(38 ratings)
$933
per night
View deal

Dog-Friendly vacation rentals

House  Oak Bluffs
May 31 - Jun 7
-16%
$921
$850 per night
House ∙ 6 guests ∙ 3 bedrooms
5.0
Outstanding(25 ratings)
Oak Bluffs, Dukes County, Massachusetts, United States
Pet-friendly
View deal
House  Oak Bluffs
Dec 21 - Dec 28
-57%
$1,654
$794 per night
House ∙ 8 guests ∙ 4 bedrooms
Oak Bluffs, Dukes County, Massachusetts, United States
Pet-friendly
View deal
House  Oak Bluffs
Jan 25 - Feb 1
-55%
$1,373
$799 per night
House ∙ 8 guests ∙ 4 bedrooms
5.0
Outstanding(13 ratings)
Oak Bluffs, Dukes County, Massachusetts, United States
Pet-friendly
View deal
See all offers

Best vacation rentals with a balcony

House  Oak Bluffs
Jun 15 - Jun 22
-52%
$3,467
$1,726 per night
House ∙ 9 guests ∙ 4 bedrooms
5.0
Outstanding(21 ratings)
Oak Bluffs, Dukes County, Massachusetts, United States
Balcony
View deal
House  Oak Bluffs
Jun 14 - Jun 21
-18%
$1,005
$881 per night
House ∙ 7 guests ∙ 3 bedrooms
5.0
Outstanding(8 ratings)
Oak Bluffs, Dukes County, Massachusetts, United States
Balcony
View deal
House  Oak Bluffs
May 3 - May 10
-38%
$3,359
$2,130 per night
House ∙ 12 guests ∙ 6 bedrooms
Oak Bluffs, Dukes County, Massachusetts, United States
Balcony
View deal
See all offers

Vacation Houses with pools

House  Oak Bluffs
Nov 30 - Dec 7
-69%
$1,332
$410 per night
House ∙ 6 guests ∙ 3 bedrooms
5.0
Outstanding(1 rating)
Oak Bluffs, Dukes County, Massachusetts, United States
Pool
View deal
House  Oak Bluffs
Jun 7 - Jun 14
-40%
$5,295
$3,247 per night
House ∙ 10 guests ∙ 5 bedrooms
Oak Bluffs, Dukes County, Massachusetts, United States
Pool
View deal
House  Oak Bluffs
Jun 21 - Jun 28
$6,324 per night
House ∙ 12 guests ∙ 5 bedrooms
Oak Bluffs, Dukes County, Massachusetts, United States
Pool
View deal
See all offers

Best Vacation Home Deals in Oak Bluffs

Save up to 49%

House Oak Bluffs
May 15 - May 22
-49%
$831
$421 per night
House ∙ 6 guests ∙ 3 bedrooms
5.0
Outstanding(1 rating)
Oak Bluffs, Dukes County, Massachusetts, United States
Free cancellation
View deal
House Oak Bluffs
Sept 20 - Sept 27
-8%
$667
$616 per night
House ∙ 6 guests ∙ 3 bedrooms
4.9
Outstanding(56 ratings)
Oak Bluffs, Dukes County, Massachusetts, United States
View deal

Search and compare the 1,926 vacation rentals listed in Oak Bluffs and discover a welcoming spot for your getaway. By comparing these vacation homes, HomeToGo highlights the lowest prices and the most popular properties in Oak Bluffs.

Budget-friendly Rentals in Oak Bluffs

Find Fantastic yet Inexpensive Rentals

House Oak Bluffs
from $436 per night
House ∙ 6 guests ∙ 4 bedrooms
4.5
Excellent(31 ratings)
Oak Bluffs, Dukes County, Massachusetts, United States
View deal
House Oak Bluffs
from $564 per night
House ∙ 8 guests ∙ 4 bedrooms
4.7
Excellent(40 ratings)
Oak Bluffs, Dukes County, Massachusetts, United States
View deal
House Oak Bluffs
from $382 per night
House ∙ 6 guests ∙ 4 bedrooms
4.7
Excellent(52 ratings)
Oak Bluffs, Dukes County, Massachusetts, United States
View deal

Top-Rated Offers and Accommodations in Oak Bluffs

Book Vacation Rentals with the Highest User Rating

House Oak Bluffs
Jan 4 - Jan 11
-21%
$576
$492 per night
House ∙ 8 guests ∙ 3 bedrooms
5.0
Outstanding(16 ratings)
Oak Bluffs, Dukes County, Massachusetts, United States
View deal
House Oak Bluffs
Sept 21 - Sept 28
-70%
$2,110
$472 per night
House ∙ 10 guests ∙ 6 bedrooms
4.9
Outstanding(7 ratings)
Oak Bluffs, Dukes County, Massachusetts, United States
View deal
House Oak Bluffs
Jun 28 - Jul 5
$656 per night
House ∙ 6 guests ∙ 3 bedrooms
5.0
Outstanding(3 ratings)
Oak Bluffs, Dukes County, Massachusetts, United States
View deal

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Find your dream stay

Find your dream stay

Explore 15 million+ rentals, the world’s biggest selection of vacation homes.

Popular Rental Amenities in Oak Bluffs

  • Air conditioning (1,749)
  • Pool (227)
  • WiFi (1,893)
  • Kitchen (1,555)
  • Pet-friendly (328)
  • TV (1,752)
  • Washing machine (1,010)
  • Parking (77)
  • Balcony/patio (659)
  • Grill (978)
  • Dishwasher (932)
  • Microwave (1,440)

Filters are available to help you personalize your search to find the ideal vacation home in Oak Bluffs. HomeToGo's data shows that "Air conditioning" and "Pool" turn out to be the most commonly provided amenities in Oak Bluffs. Not as many vacation homes in Oak Bluffs are available if you need a crib for your baby or if you need a crib for your baby as "Crib" and "Wheelchair accessible" are not very common amenities in Oak Bluffs.

Information about vacation rentals in Oak Bluffs

🏡 Vacation rentals available 1,926 rentals
💳 Possible discounts up to 39%
🌙 Nightly prices starting at $239
⭐ Popular amenities Air conditioning, Pool and Internet
🐾 Pet friendly homes 325 homes
🏊 Vacation rentals with pools 224 homes
36,101 reviews
Oak Bluffs vacation rentals have an average rating of 4.7/5 on 36,101 reviews left by travelers.

Frequently Asked Questions

What is the typical availability of vacation rentals in Oak Bluffs?

We found 1,926 vacation homes in Oak Bluffs available for your next trip.

What are the most popular vacation home amenities in Oak Bluffs?

Many travellers are searching for Air conditioning, Pool, and Internet when booking a vacation home in Oak Bluffs.

Are there pet-friendly vacation rentals in Oak Bluffs?

Finding a vacation rental in Oak Bluffs that allows dogs is definitely possible, with 325 pet-friendly homes on offfer.

What's the best month to visit Oak Bluffs?

The warmest time of year in Oak Bluffs is July and August, with the nightly price of a vacation home starting at $239.

Top vacation destinations in Oak Bluffs

Top cities to visit

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