House holiday rentals in Oakland

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Popular amenities for Oakland house rentals

House rentals with a pool

Superhost

Home in Turner

4.84 out of 5 average rating, 70 reviews

The Getaway- River Paradise

DavidRating, 5 stars3 months ago
every thing was great. I had to get in touch with David when we first arrived and he got back to me immediately. Everybody like it. We will certainly get in touch with David when we come back to Maine. The only thing I would do If I were David is put the house numbers on the mailbox, we were concerned we were going to the right house but really no problem
Superhost

Home in Liberty

4.88 out of 5 average rating, 58 reviews

Luxe Liberty: Getaway with Heated Indoor Pool!

HeatherRating, 5 stars3 weeks ago
Perfect spot for family and friends to do everything needed to relax and have fun. Huge swimming pool, relaxing hot tub, board games, and tons of space to sleep many guests. We will bring more next time!
Superhost

Home in Carrabassett Valley

4.69 out of 5 average rating, 16 reviews

*New to Market* 410 Snowflower

SeanRating, 5 stars1 week ago
This place was a great location walking/skiing distance to the village lift to take you to the main base of Sugarloaf. Chris was really responsive through messaging offering advice and sharing the skiing conditions. The house had everything we needed for cooking with a panini press and external flat top grill. There was a little community hot tub in the area but we were alittle unsure if we had access. However, the fitness club is open to everyone if you are willing to pay 15 or so dollars for a hot tub/sauna/steam room. Overall, this place was great and we would stay again!
Guest favourite

Home in Mechanic Falls

5 out of 5 average rating, 19 reviews

Lovely home with hot tub and pool

AngelicaRating, 5 stars3 months ago
Beautiful Airbnb! Everything in the Airbnb was very well thought out. The host was super nice and always quick to respond. My only regret was not spending more time here!
Guest favourite

Home in Standish

4.94 out of 5 average rating, 50 reviews

6BR+ Retreat on 3 Acres Near Lake w/AC +Pets OK

ZachRating, 5 stars5 months ago
Perfect place for a group or big family! Was much larger than expected, very private, and had so many cute touches and details that made our stay unforgettable. I could not recommend this place enough!
Guest favourite

Home in Rockport

4.96 out of 5 average rating, 52 reviews

Dog Friendly Midcoast Cape

SarahRating, 5 stars3 months ago
BEAUTIFUL Home!! Tons of space to relax and spread out with our family! The beds were very comfortable! We really appreciated all of the bathrooms for our group! The kitchen was huge and so handy for preparing meals! I absolutely loved the style and atmosphere of this wonderful home! We also loved being able to bring our dogs!! We had a lovely time and we would most definitely come back!!! 🥰
Superhost

Home in Windham

4.73 out of 5 average rating, 11 reviews

Gorgeous Maine House Close to Sebago Lake

AmyRating, 5 stars5 months ago
This was our second stay at Craig's place. It is a perfect home for our two families which include a 2, 4, and 14 year olds. there is plenty of space and the pool area and indoor basketball gym are such an amazing treat! We were happily surprised to find a new mini split in the large game room which cooled the whole downstairs.
Superhost

Home in Raymond

4.8 out of 5 average rating, 10 reviews

Turtle Cove Sebago Lake Private Waterfront & Pool

VirgenRating, 5 stars2 months ago
Beautiful property! Great Lake view! We had a wonderful time!

Weekly house rentals

Superhost

Home in Bethel

4.86 out of 5 average rating, 167 reviews

Sunday River - English Woods Chalet

ChrisRating, 5 stars2 weeks ago
Stayed for a long weekend to snowboard and felt right at home! Really enjoyed our stay and highly recommend this place if you’re heading to Sunday River
Guest favourite

Home in Rangeley

4.8 out of 5 average rating, 56 reviews

Snowmobile SKi ATV in Rangeley 3 bedroom home

HongshengRating, 5 stars1 month ago
We had wonderful time when staying at this place like home. My kids loved it and they said this is the best Airbnb in recent years. Strongly recommended!
Superhost

Home in Rangeley

5 out of 5 average rating, 3 reviews

Russell Cove 18 | Shared Access to Rangeley Lake

KathyRating, 5 stars1 month ago
The whole process was easy and communication was great. The house was perfect for our family of 8. We’ll definitely be back. Thank you!!
Guest favourite

Home in Ocean Point

4.93 out of 5 average rating, 45 reviews

137 Shore Road Ocean Point view now with WiFi

ThomasRating, 5 stars3 months ago
Jerry's house was a great location with terrific views. The house was tastefully decorated and immaculate. A perfect Maine getaway that we cannot wait to go back to in the future.
Guest favourite

Home in Brunswick

4.98 out of 5 average rating, 50 reviews

Oceanfront, Mere Point year round home Brunswick

E ThomasRating, 5 stars4 months ago
Loved the layout of the house. Great kitchen and master bedroom. Master bath a little cramped. Enjoyed the view and outdoor seating.
Superhost

Home in Naples

4.69 out of 5 average rating, 13 reviews

Pinecrest Lakefront, Private 1 Bedroom

AndrewRating, 5 stars1 month ago
Very peaceful and quiet during winter time. Great space nice touches with Xmas tree and small details throughout the house. Very comfortable! They take great care of the property.
Guest favourite

Home in Camden

4.93 out of 5 average rating, 130 reviews

Cozy Cottage With River View

ChristineRating, 5 stars3 months ago
We really enjoyed our stay at Jeremy's cottage! The home is charming, cozy, and very well-appointed, with everything we needed – plenty of linens, kitchen supplies, cutlery, and more. The back porch overlooking the river or the breakfast nook were perfect spots for morning coffee, and the kitchen made it easy to cook meals with lots of space. The bedrooms were comfortable and made for a restful night's sleep. The location is fantastic too! Short walk into Camden for great food or shops but also centrally located to visit nearby by towns like Lincolnville, Rockport, and Rockland. Jeremy was a terrific host – friendly, responsive, and helpful. I left my yoga mat behind and he was kind enough to offer to ship back to me. We thoroughly enjoyed our time in Camden and would definitely recommend this cottage!
Superhost

Home in Rockland

4.64 out of 5 average rating, 50 reviews

Downtown "NamaStay"

SunitaRating, 5 stars5 months ago
Annie's place is a clean, well kept older home. We really appreciated her accommodating our early check in, so we could be on time for our tour. The home is well stocked with linens and towels and in a great location. We were able to walk to downtown with delicious restaurants and shops. Our family was happy to each have a bedroom to sleep comfortably, and having air conditioning as an amenity was very helpful in our decision to stay here. Thank you Annie for your suggestions and hospitality for our stay in Rockland :)

Private house rentals

Guest favourite

Home in Northport

4.93 out of 5 average rating, 28 reviews

Close to the Beach, Hiking, Golf course, and Town!

ValerieRating, 5 stars1 month ago
Our family and I had a wonderful stay at Jackies, we are all originally from maine, and her home gives you everything great about maine. We really felt at home, it snowed christmas eve which made it even more beautiful ( The driveway was plowed out early as well). I brought a small christmas tree with us on our trip up, and when we walked in, the place was decorated for christmas, which was just amazing and so thoughtful. We definitly plan on staying again, the next time we are back in maine. Thank you again Jackie!
Guest favourite

Home in Belfast

4.96 out of 5 average rating, 138 reviews

Cove House

SusanRating, 5 stars3 months ago
We have been going to this area of Maine for over fifty years. I found this gem several years ago and haven’t stayed anywhere since. I find it to be peaceful, walkable to the center via footbridge, it’s all that we want. Kathy is a great host, quickly responds to any questions or needs you may have. We always know we will have a great experience staying here.
Guest favourite

Home in Liberty

4.98 out of 5 average rating, 86 reviews

Kirby Island Road Retreat

KellyRating, 5 stars2 months ago
We had a wonderful time. It was so peaceful. We would definitely stay there again.
Superhost

Home in Harpswell

5 out of 5 average rating, 36 reviews

Oceanfront Luxury Estate in Mid-Coast Maine

SharonRating, 5 stars4 months ago
This was such a wonderful property for my family -- beautiful and peaceful with lovely views. We loved spending our days out in the spacious yard, playing lawn games, sitting around the fire pit, and fishing, and eating all our meals out on the patio. Everyone left feeling very relaxed and happy. Thank you Pam and David for sharing your home!
Guest favourite

Home in Belfast

5 out of 5 average rating, 12 reviews

4bed Full House on Private Dr. w/ Large Yard

ChristinaRating, 5 stars1 month ago
Our family was able to come together to relax, cook, enjoy Belfast and celebrate our own little Christmas. We were super comfortable and really enjoyed the space. The house had everything we needed!
Guest favourite

Home in Naples

4.99 out of 5 average rating, 106 reviews

LUX Designer Private Waterfront

ChristopherRating, 5 stars2 weeks ago
The wife and I came here for a weekend getaway. Overall it was a great experience!
Guest favourite

Home in Yarmouth

4.92 out of 5 average rating, 522 reviews

Beautiful Coastal Maine Getaway

KarenRating, 5 stars2 weeks ago
We enjoyed our stay at Randy’s house. The setting was private and peaceful but a short drive to everything you need. The house was beautifully decorated with lots of amenities. We especially enjoyed the fireplace and the large kitchen. We had a couple of questions and Randy was quick to respond. Overall a fabulous stay! We will definitely return.
Guest favourite

Home in Northport

4.98 out of 5 average rating, 42 reviews

Cliff House - Ocean Views! Architectural designed.

Jeff & StephRating, 5 stars1 month ago
By far the best home away from home that any of us have ever stayed at. Better than the photos. Cleanest Airbnb I’ve ever stayed at. Can’t say enough. I am so glad we booked Mark’s place for our Christmas vacation, it was definitely one to be remembered.

Quick stats about house rentals in Oakland

  • Total rentals

    20 properties

  • Nightly prices starting at

    $80 AUD before taxes and fees

  • Total number of reviews

    1.1K reviews

  • Family-friendly rentals

    10 properties are a good fit for families

  • Rentals with dedicated workspaces

    10 properties have a dedicated workspace

  • Wi-Fi availability

    20 properties include access to Wi-Fi

Destinations to explore

  1. Airbnb
  2. United States
  3. Maine
  4. Kennebec County
  5. Oakland
  6. House rentals