House holiday rentals in Oak Bluffs

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Popular amenities for house rentals in Oak Bluffs

House rentals with a pool

Superhost
Home in New Seabury
5 out of 5 average rating, 7 reviews

Waterfront Home w/ Dock, Heated Pool, Kayaks & A/C

MadisonRating, 5 stars6 months ago
Prescott’s house is such a relaxing place to stay with a big group. The house has a very pretty view and is very clean and peaceful. We are very grateful for such a nice stay at this beautiful house. The BBQ outside didn’t work great but other than that we had a wonderful time! Thank you Prescott.
Superhost
Home in Barnstable
4.8 out of 5 average rating, 20 reviews

Stunning Cape Home - Inground Pool, 5 Min To Beach

KristenRating, 5 stars3 weeks ago
This house and property were charming and beautiful. The location was extremely close to beaches, restaurants, and stores all while being nestled in a quiet neighborhood. Highly recommend!
Guest favourite
Home in Popponesset
5 out of 5 average rating, 12 reviews

18 Menemsha Rd., Popponesset, Pool, 3-Beds, 4 bath

CarolRating, 5 stars2 weeks ago
We loved are family stay at Paul & Katie’s home for Easter Week. It is a dream home . The neighborhood was beautiful and walkable, with a peaceful path to a private beach. We enjoyed the shops and restaurants in Mashpee Commons about an 8 minute drive away.
Top guest favourite
Home in Oak Bluffs
4.94 out of 5 average rating, 194 reviews

Spectacular beach & pool combo; beautiful sunsets!

JillRating, 5 stars1 month ago
The house was beautiful, very comfortable and extremely well equipped. I would highly recommend this home. We had a wonderful stay there!
Superhost
Home in East Falmouth
5 out of 5 average rating, 3 reviews

Spacious home with Pool! Close to Beaches & Town!

michaelRating, 5 stars8 months ago
it is a nice comfy house esp for a family. Swimming pool and game room down in the basement would be alot of fun for kids to keep them busy at day time and night time. Beach, restaurants, grocery stores, liquor stores, etc are all right there esp. only like less than 5 to 15 minutes drive and also less than 25 minutes drive to go to north Falmouth or Wood Hole. They have a nice downtown with many stores, restaurants, bowling ally, etc which that is only less than 15 minutes drive from the house Also taking a walk from the house to the beach is so beautiful esp morning time. i walked every morning, and love every bit of the walk. It rained once during our vacation week and rest were sunny days for the rest of the week. We were lucky to have the good weather. Anyway, the house is approximately about less than a mile and half from the beach. Driving to Chetham is about little a hour drive from the house. To Provincetown, about 1 hour and 45 minutes drive.
Guest favourite
Home in North Falmouth
5 out of 5 average rating, 14 reviews

New Construction Home with Pool in N. Falmouth

TaylorRating, 5 stars6 days ago
This house was stunning! So beautiful and more than enough space for our group of 10. I’d definitely recommend staying here if you’re going to Cape Cod. It was a quick drive for us to bars/ restaurants/ stores, and a great house to stay in and entertain.
Top guest favourite
Home in Cotuit
4.95 out of 5 average rating, 113 reviews

Private Pool, near beaches, 3 BR/3 BA, Central Air

CamilleRating, 5 stars7 months ago
There should be more than 5 stars for this lovely property and its hosts!!! We were three couples vacationing for the first time on the Cape and this charming home was perfect for us. Conveniently located to serve as home base for many excursions we felt immediately at home. We each had our own themed bedroom with en suite bathroom and TV. All common areas including the sun porch and outdoor deck were fantastic places to gather and enjoy our time together. Our hosts were so pleasant and helpful throughout our stay. As only one example, on a rainy day the host proactively contacted us wth suggestions on things to do in the event of rain on the Cape. We so appreciated this thoughtful gesture and there were many more. When I think about it, this really sums up why we had such a wonderful time. Everything about this property speaks to how much these hosts care about their guests! Hope to return one day. Thank you!
Guest favourite
Home in Oak Bluffs
4.96 out of 5 average rating, 47 reviews

Private Heated Pool, Wifi, AC, Grill & Firepit

AriaRating, 5 stars6 months ago
Best airbnb I’ve ever stayed in! Flexible check in and check out, even left snacks, water and a note for us. Would for sure go back

Weekly house rentals

Guest favourite
Home in Centerville
4.88 out of 5 average rating, 111 reviews

#25 Seasonal Cottage is 200 feet from the Beach

RuthRating, 5 stars6 months ago
A minor communication glitch between host and cleaners meant two of the beds had not been made and probably a general cleaning between guests wasn't done. Fortunately the property was already very clean and the guests before me must have been, too. Everything else was in order. When I let the host know, she immediately contacted the cleaners while I went out for groceries. By the time I got back, the place was perfect and the cleaners were gone. I don't think this is a regular occurrence at all. In October this neighborhood was very quiet, which is a priority for me. And I felt very safe, which is also important. I would definitely return and highly recommend.
Top guest favourite
Home in Edgartown
4.96 out of 5 average rating, 68 reviews

Newly constructed home with AC , new furniture.

BillRating, 5 stars6 months ago
Again, we had a wonderful stay. The home was clean and has everything you need. Would definitely book again.
Superhost
Home in Tisbury
4.69 out of 5 average rating, 160 reviews

Carolyn's Vineyard Haven

Nish HinesRating, 5 stars1 week ago
We had a fantastic stay at this home! Our group of eight adults, including two seniors (75 and 85 years old), found the space incredibly comfortable and well-suited to our needs. The host was excellent—communicative, quick to respond, and accommodating, even allowing us to check in early to ensure a smooth arrival for our older guests. The house itself was spacious, well-maintained, and stocked with great amenities. Each bathroom had complimentary toiletries, which was a thoughtful touch, and the kitchen was fully equipped with everything we needed for cooking and dining. We truly felt at home. Beyond the house, the location was ideal. Vineyard Haven, just a short drive or walk away, offered plenty of shops and restaurants to explore, adding to the experience. Overall, this rental exceeded our expectations, and we would highly recommend it to anyone looking for a comfortable and well-appointed place to stay. Thank you to Carolyn for making our visit so seamless and enjoyable.
Top guest favourite
Home in Teaticket
4.84 out of 5 average rating, 74 reviews

Expansive & Renovated Teaticket Cape

AnnieRating, 5 stars1 month ago
Great house for a larger group. It has all the amenities and lots of beds. Very close to the ocean and Brien was easy to communicate with. Thank you for having us at your home!
Guest favourite
Home in Oak Bluffs
4.83 out of 5 average rating, 193 reviews

Waterview, Private, Walk to Beach, Mile to Town

LaurenRating, 5 stars6 months ago
We stayed at Lisa’s place for three nights and it was a 10/10 experience. Lisa was a fantastic host and was very helpful with island recommendations prior to our trip. The property itself is stunning and although we wanted to explore the island, the property also provided a beautiful landscape to just relax. Even given its private, peaceful location, it was still so convenient to town. The house is an adorable converted barn that has incredible, rustic charm and the decor was so beautifully thought out. Before we even left we were talking about booking again in the future. We definitely recommend booking here!
Top guest favourite
Home in Centerville, Barnstable
4.97 out of 5 average rating, 153 reviews

Luxury House 0.25 mi from Craigville Beach

SarahRating, 5 stars1 week ago
Came here for my sisters bachelorette. It was amazing . We felt right at home . It was very spacious and clean . Hosts thought of everything . Definitely would come back. The hosts were very responsive and very flexible. Great place to stay. The games and ping pong and air hockey tables were a hit !!
Guest favourite
Home in Teaticket
4.93 out of 5 average rating, 122 reviews

Cute Single Family Home in Nice Neighborhood

NicoleRating, 5 stars6 months ago
This little beach oasis is such a great value! We thoroughly enjoyed our stay here. As mentioned in the description, Patty & Bruce's spot is legitimately only a few minute walk from multiple beaches and is in such a cute little neighborhood! They have plenty of beach items should you not bring your own, which is great. The space itself is perfect for a quick little weekend getaway.
Superhost
Home in West Tisbury
4.78 out of 5 average rating, 67 reviews

Beautiful Quiet Country Cottage

DevoraRating, 5 stars8 months ago
This is a lovely tiny cottage In the woods. it has everything you might need: a lovely front porch. A perfect kitchen, outside tables, and a clean comfortable. place to stay with a big tv. A great place I would highly recommend!

Private house rentals

Guest favourite
Home in Oak Bluffs
5 out of 5 average rating, 25 reviews

Vineyard Vacation, 3-Bedroom, Hot-tub, Golf course

JayneRating, 5 stars3 weeks ago
The home was clean and cozy. Updated decor and well supplied with everything we would need. I would stay again.
Top guest favourite
Home in Falmouth
4.92 out of 5 average rating, 78 reviews

Private home with walkable freshwater beach access

MatthewRating, 5 stars8 months ago
The house was as advertised. In a nice quiet area. The house was well set up and as advertised. We felt right at home for the weekend.
Guest favourite
Home in Edgartown
4.85 out of 5 average rating, 26 reviews

Classic Edgartown Stunner close to Town and Beach

MeganRating, 5 stars9 months ago
This house was amazing! Beautiful and very clean! Megan had timely responses to messages and was clear in her instructions regarding the check in process. The beds were comfortable. The outdoor shower was maybe our favorite part of the trip, all the ladies enjoyed being outside and also the coolness of the inside of the house. There was tons of room. The overall aesthetic of the house was a calm, beachy vibe and made you feel like you were right beside the water. I wish we had played horseshoes in the back yard! If we need a place to stay in the future for a group trip with the ladies I would try to book here if it was available!
Superhost
Home in New Seabury
4.91 out of 5 average rating, 34 reviews

New Seabury home, private yard, great location

MikeRating, 5 stars6 months ago
Comfortable yet spacious home nestled in the woods of New Seabury. Great location to visit beaches and restaurants. Just minutes from Mashpee Commons and Falmouth for shopping and dining. Beautiful place, Thanks Alex!
Guest favourite
Home in New Seabury
4.83 out of 5 average rating, 109 reviews

New Seabury Retreat. Butchart Gardens' Inspired

ErinRating, 5 stars7 months ago
Vlad’s home was a wonderful place to stay with many people! Really appreciated all the decor and attention to detail. My friends and I stayed for a wedding, and we were so glad all communication was smooth. Would definitely stay again!
Top guest favourite
Home in Oak Bluffs
4.96 out of 5 average rating, 93 reviews

**Vineyard Vacation Retreat** -3 BR

DianeRating, 5 stars7 months ago
We loved staying at Whitney’s house! It was the first time an Airbnb exceeded our expectations! The home was stocked with everything we needed and more. The home is so pretty and cozy and tucked into the neighborhood which was very private. It was about a mile from the Town center so we could easily ride a bike or drive to the beach and there’s so much to do in town. The beds were comfortable and there were plenty of extra pillows and blankets and towels. I have absolutely no complaints. We would definitely stay here again. :)
Top guest favourite
Home in Edgartown
5 out of 5 average rating, 20 reviews

Valentine's Retreat Hot Tub Fire Pit Trails Beach

PaulRating, 5 stars5 days ago
This place is such a gem! Great location if you want a little peace and quiet but also easy to get to Edgartown or OB for some fun, The property has an amazing yard where we played various sports, grilled and definitely enjoyed the hot tub! Inside is just as described in the listing. And the hosts were super communicative and helpful. Would definitely highly recommend!!
Guest favourite
Home in Tisbury
4.86 out of 5 average rating, 69 reviews

Your home away from home

CristinaRating, 5 stars8 months ago
Patricia was very responsive before and during our stay. She was easy to communicate with and gave great suggestions for beaches to visit. The house is about a 10 minute drive from the closest beach. It’s near water but it’s more for fishing or boating. It’s less than 10 minutes from the center of town where there are great places to eat and shop around. The house is beautiful and spacious. Two bedrooms and a full bathroom on the main level and 2 bedrooms and a full bathroom the second level. Highly recommend.

Quick stats about house rentals in Oak Bluffs

  • Total rentals

    440 properties

  • Nightly prices starting at

    £30 before taxes and fees

  • Total number of reviews

    12K reviews

  • Family-friendly rentals

    390 properties are a good fit for families

  • Pet-friendly rentals

    110 properties allow pets

  • Rentals with a pool

    20 properties have a pool

Destinations to explore

  1. Airbnb
  2. United States
  3. Massachusetts
  4. Dukes County
  5. Oak Bluffs
  6. House rentals