Apartment
10.0(157 Reviews)
2 Bedrooms
5 Guests
Oceanfront
Ocean View
Balcony/Terrace
View
US $798/Night
7 Nights - US $5,589
Oak Bluffs Villa Rentals
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Compare Villas, Resorts, & Rentals in Oak Bluffs
10.0
House
10.0(4 Reviews)
2 Bedrooms
4 Guests
- Oceanfront
Parking- Ocean View
- View
US $636/Night
7 Nights - US $4,452
US $183/Night
7 Nights - US $1,281
Cottage
10.0(104 Reviews)
2 Bedrooms
4 Guests
- Oceanfront
- Parking
- Ocean View
- Balcony/Terrace
US $464/Night
7 Nights - US $3,249
Apartment
10.0(2 Reviews)
1 Bedroom
2 Guests
- Balcony/Terrace
- View
Air Conditioner
Internet
US $541/Night
7 Nights - US $3,788
Condo
10.0(93 Reviews)
2 Bedrooms
6 Guests
- Parking
- Ocean View
- Balcony/Terrace
- View
US $549/Night
7 Nights - US $3,843
Condo
10.0(63 Reviews)
2 Bedrooms
4 Guests
- Oceanfront
- Parking
- Ocean View
- Balcony/Terrace
US $986/Night
7 Nights - US $6,902
Apartment
10.0(62 Reviews)
1 Bedroom
2 Guests
- Oceanfront
- Parking
- Ocean View
- Balcony/Terrace
US $156/Night
7 Nights - US $1,093
Cottage
10.0(51 Reviews)
2 Bedrooms
4 Guests
- Parking
- Ocean View
- Balcony/Terrace
- View
US $712/Night
7 Nights - US $4,981
Luxury Places to Stay in Oak Bluffs
Over 640+ Luxury Places to Stay in or Near Oak Bluffs
House
10.0(5 Reviews)
5 Bedrooms
10 Guests
- Oceanfront
- Parking
- Ocean View
- Balcony/Terrace
US $4,498/Night
7 Nights - US $31,483
House
10.0(3 Reviews)
5 Bedrooms
12 Guests
Hot Tub- Parking
Pool- Ocean View
US $4,442/Night
7 Nights - US $31,096
House
10.0(1 Review)
9 Bedrooms
18 Guests
- Parking
Kitchen- Air Conditioner
- Internet
US $4,388/Night
7 Nights - US $30,717
Apartment
6 Bedrooms
18 Guests
- Oceanfront
- Ocean View
- Balcony/Terrace
- View
US $3,735/Night
7 Nights - US $26,147
Condo
10.0(1 Review)
4 Bedrooms
9 Guests
- Air Conditioner
- Internet
Child Friendly
Laundry
US $3,732/Night
7 Nights - US $26,123
House
10.0(3 Reviews)
4 Bedrooms
8 Guests
- Oceanfront
- Hot Tub
- Parking
- Ocean View
US $3,704/Night
7 Nights - US $25,928
House
9.8(28 Reviews)
6 Bedrooms
12 Guests
- Oceanfront
- Parking
- Ocean View
- Balcony/Terrace
US $3,694/Night
7 Nights - US $25,861
House
10.0(43 Reviews)
5 Bedrooms
12 Guests
- Parking
- Ocean View
- Balcony/Terrace
- View
US $3,305/Night
7 Nights - US $23,138
Condo
2 Bedrooms
5 Guests
- Air Conditioner
- Internet
- Child Friendly
- Laundry
US $3,281/Night
7 Nights - US $22,967
Top-Rated Villas with a Pool in Oak Bluffs
Over 126+ Top-Rated Private Villas with a Pool in or Near Oak Bluffs
House
10.0(75 Reviews)
4 Bedrooms
10 Guests
Private Pool- Oceanfront
- Parking
- Pool
US $1,385/Night
7 Nights - US $9,692
House
10.0(26 Reviews)
2 Bedrooms
6 Guests
- Private Pool
- Parking
- Pool
- Balcony/Terrace
US $702/Night
7 Nights - US $4,911
House
10.0(15 Reviews)
3 Bedrooms
6 Guests
- Private Pool
- Parking
- Pool
- Balcony/Terrace
US $3,229/Night
7 Nights - US $22,603
House
10.0(4 Reviews)
5 Bedrooms
12 Guests
- Private Pool
- Hot Tub
- Parking
- Pool
US $2,532/Night
7 Nights - US $17,726
New
House
9.8(63 Reviews)
2 Bedrooms
5 Guests
Breakfast- Parking
- Pool
- Balcony/Terrace
US $509/Night
7 Nights - US $3,566
House
9.6(18 Reviews)
5 Bedrooms
10 Guests
- Private Pool
- Oceanfront
- Hot Tub
- Parking
US $1,340/Night
7 Nights - US $9,381
House
9.2(9 Reviews)
3 Bedrooms
12 Guests
- Parking
- Pool
- Ocean View
- Balcony/Terrace
US $594/Night
7 Nights - US $4,155
House
9.0(2 Reviews)
3 Bedrooms
8 Guests
- Parking
- Pool
- Kitchen
- Air Conditioner
US $1,467/Night
7 Nights - US $10,270
House
8.8(3 Reviews)
5 Bedrooms
10 Guests
- Private Pool
- Pool
- Balcony/Terrace
- Kitchen
US $1,216/Night
7 Nights - US $8,514
Pet-Friendly Villas in Oak Bluffs
Over 137+ Pet-Friendly Private Villas in or Near Oak Bluffs
Apartment
10.0(47 Reviews)
1 Bedroom
4 Guests
- Ocean View
- Balcony/Terrace
- View
- Kitchen
US $309/Night
7 Nights - US $2,166
House
10.0(1 Review)
3 Bedrooms
6 Guests
- Parking
- Balcony/Terrace
- View
- Air Conditioner
US $434/Night
7 Nights - US $3,038
Apartment
10.0(43 Reviews)
2 Bedrooms
4 Guests
- Oceanfront
- Hot Tub
- Parking
- Ocean View
US $526/Night
7 Nights - US $3,679
House
9.0(1 Review)
4 Bedrooms
10 Guests
- Balcony/Terrace
- View
- Air Conditioner
- Internet
US $532/Night
7 Nights - US $3,722
House
10.0(11 Reviews)
2 Bedrooms
6 Guests
- Oceanfront
- Parking
- Ocean View
- Balcony/Terrace
US $693/Night
7 Nights - US $4,848
House
10.0(3 Reviews)
2 Bedrooms
4 Guests
- Parking
- Ocean View
- Balcony/Terrace
- View
US $1,376/Night
7 Nights - US $9,632
Cottage
10.0(2 Reviews)
1 Bedroom
2 Guests
- Oceanfront
- Parking
- Ocean View
- View
US $510/Night
7 Nights - US $3,573
House
9.8(9 Reviews)
2 Bedrooms
10 Guests
- Oceanfront
- Ocean View
- Balcony/Terrace
- View
US $1,069/Night
7 Nights - US $7,481
House
8.8(9 Reviews)
2 Bedrooms
6 Guests
- Oceanfront
- Parking
- Ocean View
- Balcony/Terrace
US $838/Night
7 Nights - US $5,864
Large Private Villas in Oak Bluffs
Over 134+ Large Villas in or Near Oak Bluffs for Groups and Families
House
10.0(76 Reviews)
5 Bedrooms
12 Guests
- Parking
- Ocean View
- Balcony/Terrace
- View
US $1,572/Night
7 Nights - US $11,001
House
9.0(3 Reviews)
6 Bedrooms
12 Guests
- Balcony/Terrace
- View
- Air Conditioner
- Internet
US $834/Night
7 Nights - US $5,838
House
10.0(4 Reviews)
5 Bedrooms
10 Guests
- Parking
- Kitchen
- Air Conditioner
- Internet
US $719/Night
7 Nights - US $5,033
House
10.0(41 Reviews)
4 Bedrooms
13 Guests
- Parking
- Ocean View
- Balcony/Terrace
- View
US $688/Night
7 Nights - US $4,815
House
8.9(166 Reviews)
7 Bedrooms
14 Guests
- Oceanfront
- Ocean View
- Balcony/Terrace
- View
US $362/Night
7 Nights - US $2,534
House
10.0(37 Reviews)
7 Bedrooms
14 Guests
- Oceanfront
- Parking
- Ocean View
- Balcony/Terrace
US $2,049/Night
7 Nights - US $14,344
House
10.0(21 Reviews)
6 Bedrooms
12 Guests
- Parking
- Ocean View
- Balcony/Terrace
- View
US $1,063/Night
7 Nights - US $7,441
House
10.0(17 Reviews)
5 Bedrooms
10 Guests
- Oceanfront
- Parking
- Ocean View
- Balcony/Terrace
US $978/Night
7 Nights - US $6,847
House
10.0(14 Reviews)
5 Bedrooms
13 Guests
- Oceanfront
- Parking
- Ocean View
- Balcony/Terrace
US $921/Night
7 Nights - US $6,450
Wheelchair Accessible Holiday Homes in Oak Bluffs
Over 4+ Wheelchair Accessible Villas and Holiday Homes in or Near Oak Bluffs
Condo
10.0(36 Reviews)
2 Bedrooms
4 Guests
- Parking
- Ocean View
- Balcony/Terrace
- View
US $627/Night
7 Nights - US $4,389
US $348/Night
7 Nights - US $2,434
Condo
10.0(18 Reviews)
2 Bedrooms
4 Guests
- Parking
- Ocean View
- Balcony/Terrace
- View
US $874/Night
7 Nights - US $6,117
House
5 Bedrooms
10 Guests
- Balcony/Terrace
- Kitchen
- Air Conditioner
- Internet
US $1,285/Night
7 Nights - US $8,995
Oak Bluffs Villas, Airbnb and Holiday Homes Under $200
Over 3+ Oak Bluffs Private Villas, Airbnb and Holiday Homes Under $200
Apartment
7.2(12 Reviews)
1 Bedroom
2 Guests
- Oceanfront
- Parking
- Ocean View
- Balcony/Terrace
US $180/Night
7 Nights - US $1,261
House
7.6(6 Reviews)
3 Bedrooms
6 Guests
- Balcony/Terrace
- View
- Air Conditioner
- Internet
US $153/Night
7 Nights - US $1,071
House
1.0(3 Reviews)
1 Bedroom
4 Guests
- Balcony/Terrace
- View
- Air Conditioner
- Internet
US $154/Night
7 Nights - US $1,078
Instantly Bookable Villa Rentals in Oak Bluffs
Over 324+ Instantly Bookable Private Villas in or Near Oak Bluffs
Condo
10.0(14 Reviews)
2 Bedrooms
6 Guests
- Oceanfront
- Ocean View
- Balcony/Terrace
- View
US $836/Night
7 Nights - US $5,851
Apartment
10.0(8 Reviews)
2 Bedrooms
4 Guests
- Oceanfront
- Parking
- Ocean View
- Balcony/Terrace
US $750/Night
7 Nights - US $5,247
House
10.0(8 Reviews)
1 Bedroom
2 Guests
- Oceanfront
- Parking
- Ocean View
- Balcony/Terrace
US $714/Night
7 Nights - US $5,000
Apartment
10.0(6 Reviews)
2 Bedrooms
5 Guests
- Parking
- Kitchen
- Air Conditioner
- Internet
US $957/Night
7 Nights - US $6,701
House
10.0(4 Reviews)
1 Bedroom
4 Guests
- Hot Tub
- Parking
- Ocean View
- Balcony/Terrace
US $543/Night
7 Nights - US $3,801
Apartment
10.0(3 Reviews)
1 Bedroom
2 Guests
- Oceanfront
- Ocean View
- Balcony/Terrace
- View
US $611/Night
7 Nights - US $4,274
House
10.0(2 Reviews)
2 Bedrooms
4 Guests
- Oceanfront
- Ocean View
- Balcony/Terrace
- View
US $789/Night
7 Nights - US $5,522
House
10.0(2 Reviews)
2 Bedrooms
6 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $430/Night
7 Nights - US $3,008
Cottage
9.8(65 Reviews)
2 Bedrooms
3 Guests
- Oceanfront
- Parking
- Ocean View
- Balcony/Terrace
US $431/Night
7 Nights - US $3,014
Book a Last Minute Place to Stay in Oak Bluffs
About Oak Bluffs Vacation Rentals
There are more than 649 incredible getaway rentals that are available in Oak Bluffs. These choices include villas, hotels, and other rental options. Browse from a massive selection of luxury amenities at great prices, providing you with the dream spot to base your next vacation. Relax with BedroomVillas and uncover great stays in Oak Bluffs.
BedroomVillas features numerous last-minute deals on villas, hotels, and rentals, in locations near you or across the globe. If you need a place for a group or event, be it a hotel or vacation rental (as well as cabins and private luxury villas), let us help. With BedroomVillas in Oak Bluffs, you can compare options from multiple suppliers with a single click to find the price point, amenities, and style of stay that works for you. Group deals, private pools, hot tubs, allows pets, or even huge master suite bedrooms with open-air showers? You can find it all with the BedroomVillas vacation rentals, resorts, and Airbnb-style properties in Oak Bluffs. Places to stay near Oak Bluffs are 887.09 ft² on average, with prices averaging US $936 a night.
BedroomVillas helps you find the ideal holiday rental to create lifetime travel memories in Oak Bluffs. Prices listed are often found to be discounted versus the rack rates. Just search for your destination and secure your perfect place to stay today.
Find Hotels, Resorts, and Rentals Nearby in these Cities & Neighborhoods Oak Bluffs, MA
There are 10 hotels in Oak Bluffs 1 resorts, and 531 rentals
- Prices for a holiday home in Oak Bluffs start at US $153
- Top rated vacation home in Oak Bluffs is In-Town Certified National Historic Oak Bluffs Property -
- Most popular short term in Oak Bluffs is Summercamp
- Cheapest place to stay in Oak Bluffs is Oak Bluffs Cottage
- Most expensive holiday rental in Oak Bluffs is Waterfront House On Oak Bluffs Harbor
Recently Booked Hotels, Resorts, or Rentals in Oak Bluffs
Frequently Asked Questions About Oak Bluffs?
What are the top hotels or resorts in Oak Bluffs?
We provide an array of great vacation destinations in Oak Bluffs. If you are looking to stay in or around the Oak Bluffs area, make sure to browse our options to find a premium rental location in a top vacation destination. Whether it is a few nights, a week, or more, we've got the luxury stays that rank among the Top Vacation Rentals in Oak Bluffs:
- In-Town Certified National Historic Oak Bluffs Property -
- Arrowsmith Cottage - Oak Bluffs Near Eastville Beach; Steps to bike path.
- Private Meadow View Family Retreat - 4 BR, AC, Large Yard, Tennis, on Bike Path
- Martha's Vineyard Beachfront Condo in Oak Bluffs
- Modern, luxury 5-bed, 4.5-bath w/full basement! Now booking for 2026!
- Modern 4 bed/3.5 bath Farmhouse, private HEATED POOL and AC on bike path
- Beautiful Beachfront “Oasis by the Sea” in the Heart of Oak Bluffs!
- Historic Home in East Chop
- Discover the magic of Martha’s Vineyard! NEW ! Build in 2020 !
- The Island Collection MV: Charming Cottage Located In Heart Of Oak Bluffs
How many vacation rentals have private pools in Oak Bluffs?
We have 9 luxury villas and vacation rentals featuriung a private pool in and near Oak Bluffs. Some of the best destinations to stay that feature or have access to a swimming pool are:
Which hotel or resort in Oak Bluffs is best for families?
Searching for a family-friendly getaway in Oak Bluffs? We've got you covered. Check out one of these luxurious getaways that are highly-rated and perfect fits for families of all sizes.
How many hotels, resorts, or rentals are available in Oak Bluffs?
BedroomVillas offers a consistent supply of new options, combined with established great stays in top areas. Currently, the number of properties listed by BedroomVillas in 2026 is over 649 in the Oak Bluffs area, and that number rises every day. By combining listings from multiple websites and travel providers, BedroomVillas can provide you with a diverse amount of choices of the best luxury stays in Oak Bluffs.
