Holiday rentals in Oakland

Find and book unique accommodation on Airbnb

Top-rated holiday rentals in Oakland

Guests agree: these stays are highly rated for location, cleanliness and more.

%{current} / %{total}1 / 1
Top guest favourite
A comfortable living area features two upholstered armchairs and a cozy sofa, with a ceiling fan above. A white brick fireplace is central to the space, accompanied by a TV and built-in shelves. Large windows allow natural light and display autumn foliage outside.
Home in Bellevue
4.97 out of 5 average rating, 356 reviews

Cozy Forest Refuge ( Accommodate 1-11) (7 Beds)

With 4 bedrooms, 2 1/2 bathrooms and 7 beds - its great for anyone. With low price you can be an individual, couple, or up to 11 people. Includes a fire pit, washer and dryer, free WiFi, and parking space. It is a 1425 sq home tucked in Fontenelle forest, very peaceful and quiet. It is within 15 minutes of The Old Market, Charles Schwab Field , and 10 minutes to the Henry Doorly Zoo! Great places to hike right in the neighborhood. It is great for individuals, couples, families, and big groups.

Top guest favourite
A spacious bedroom is furnished with a large bed dressed in white linens and a blue throw blanket. Decorative pillows add a touch of color. A vintage-style bench with floral detailing is placed at the foot of the bed, complementing the rustic wooden flooring.
Home in Underwood
5 out of 5 average rating, 67 reviews

The Railhouse in Weston, Iowa

Completely renovated older 1880 home in a quaint little town in Weston, Iowa. Country setting with the view of farm fields, rolling hills, the ambiance of a slow moving train once a day or evening. A short paved walking/ bike trail, that soon will connect to another trail. There is a county highway out front that will have traffic. You can wake up to a beautiful view and enjoy your coffee on the deck or a walk in our back lot and listen to nature. We are across the river from Omaha, Nebraska.

Top guest favourite
The A-frame exterior of the house is showcased against a twilight sky, with warm lights glowing from within. A striking red door stands at the center, flanked by large windows and a sloping roof nestled among trees.
Chalet in Benson
5 out of 5 average rating, 107 reviews

Dahlia House (A-Frame, Sauna, Wood Fired Hot tub)

Dahlia House is a modern A-frame retreat for two in the heart of Omaha’s Benson Creative District. Thoughtfully curated, as featured in Architectural Digest, it features many unique touches and amenities — sauna, wood-burning hot tub, etc. — to help you find what exactly what you need, and to leave rejuvenated. Please note: Each stay is curated with great care, and we have a firm cancellation policy. Dahlia House hosts two registered guests only, and no unapproved visitors are permitted.

Guest favourite
Two repurposed grain bins are situated on a landscaped area, featuring a small patio with seating arrangements. A vibrant flower bed is placed adjacent to the patio, and a gravel pathway leads to the entrance. Lush greenery surrounds the structure, creating a serene environment.
Tiny home in Missouri Valley
4.97 out of 5 average rating, 230 reviews

Grain Bin Getaway

Nestled at the foot of the Loess Hills, this repurposed grain bin is a sight to see. Every inch of the inside has been customized for a relaxing and luxurious experience. Conveniently located just 30 minutes from downtown Omaha, as well as within a quick drive to numerous state parks. There is even an external electrical hook up for campers. Finally, our grain bin includes 20 acres of the Loess Hills to explore. We recommend hiking to the top of the ridge for sunset. It's breath taking.

Top guest favourite
A comfortable living area features a large sectional sofa, accompanied by a patterned coffee table. Two bright windows provide natural light, while decorative curtains frame the views. Various plants add greenery, and a cozy basket is placed nearby, enhancing the inviting space.
Home in Council Bluffs
4.99 out of 5 average rating, 379 reviews

Cheerful two bedroom home in peaceful neighborhood

Relax with the whole family at this peaceful two bedroom home. Beautiful quiet neighborhood close to interstates, sports fields, IWCC, Henry Doorly Zoo, bike/running trails, downtown Omaha, Old Market, CHI Center, Eppley Airfield, and more. Spacious tree filled private backyard, outdoor patio, and grill. Plenty of parking. Great WiFi and Netflix, YouTube TV and Discovery+. Washer/dryer available. Dog friendly but no cats please. No gatherings, events, or parties inside or outdoors.

Top guest favourite
A rustic farmhouse is seen in the distance, surrounded by green fields and a neatly plowed crop area. A large barn and a silo are positioned on the property, with trees lining the background under a clear blue sky.
Farm stay in Glenwood
4.98 out of 5 average rating, 236 reviews

Ellington Place

A rustic farmhouse retreat on a crop producing farm, which means we could be planting or harvesting during your stay. Ellington Place has a furnished kitchen, updated bathroom and washer and dryer. Along with excellent outdoor entertainment, complete with a fire pit, porch for sitting and open area for short walks. The property is located 25 minutes from the Omaha metro area as well as less than 10 minutes from the Wabash Trace, a bike trail that travels through Mills County.

Top guest favourite
A cozy room features a spacious bed with a striped comforter and decorative pillows. A comfortable couch sits beside a bedside table and lamp, creating a welcoming area. A dresser is positioned against the wall, and soft lighting gives the space a warm feel.
Flat in Papillion
4.95 out of 5 average rating, 342 reviews

Coastal Retreat Getaway, Secluded, Off 370/I-80

Step into a private and cozy space. Relax watching TV in bed or on the couch. This place is part of our walk out basement, so you may hear day to day living upstairs. For your safety there is a Ring camera installed at the entrance and will light up the entryway when it’s dark. Parking is on the well lit public street. Easily walk up our dedicated Airbnb sidewalk, no steps, walk around to the back of the house. You’ll be in a serene space that makes you feel right at home.

Top guest favourite
A bright living area presents large windows allowing natural light to fill the space. Comfortable teal sofas and a wooden coffee table create a casual atmosphere. A dark wood TV stand supports a flat-screen television, while a soft rug lies underneath, adding texture to the floor.
Guest house in Blackstone
5 out of 5 average rating, 227 reviews

The Hidden Garden at Blackstone

Newly renovated second floor of a carriage house located on a historic property in the popular Blackstone District. Shares an acre of land with the main house, built in 1892 and occupied by the owners. Although situated in the middle of the city, the unit feels secluded from its urban environment and looks out onto a garden surrounded by trees, shrubs and flowers and is in walking distance to many restaurants and bars in both the Blackstone District and Midtown Crossing.

Top guest favourite
The exterior of the church is highlighted by its distinctive architecture, featuring a combination of white and red details. A large sign displays '150TH' and '1873', marking its historical significance. The tower silhouette rises against a soft evening sky.
Place to stay in Malvern
4.99 out of 5 average rating, 330 reviews

Art Church Iowa

Art Church Iowa is a re-purposed/desanctified 153 year old Presbyterian Church. Its last religious service was in 1969. Artist Zack Jones purchased the building in 2012 from the Historical Society. Zack originally lived in the downstairs while using the upstairs as a studio space. Zack encourages guests to look upstairs during daylight and also night time as the space changes. Disclaimer: Use of the upstairs is not part of the Airbnb rental.

Guest favourite
Home in Omaha
4.96 out of 5 average rating, 136 reviews

Spacious 3-Level Townhome - Dundee, Garage Parking

Your Omaha escape is here! This bright, end-unit townhome features 2 spacious master suites, 3 levels of stylish living, and private garage parking. Perfectly located near UNMC, downtown, and Dundee dining, it’s ideal for travel nurses, professionals, families, or friends. Enjoy a large living room, fully stocked kitchen, and relaxing vibe — all designed for comfort, convenience, and a memorable stay.

Top guest favourite
A serene lake surrounded by trees is captured at sunset, with vibrant hues of orange and yellow reflecting off the still water. Silhouetted branches create a natural frame, enhancing the peaceful ambiance of the waterfront setting.
Loft in Bellevue
4.96 out of 5 average rating, 192 reviews

Beachfront paradise 20 min from Omaha

Stay in paradise on Hanson Lakes, just ten miles south of downtown Omaha. Perfect getaway from the city or magical place to stay while visiting our lovely city. I lived in this loft myself for five months and it's an awesome space. Perfect for someone looking for inspiration or relaxation. We recently added a queen size Murphy bed so it now has two beds.

Guest favourite
A well-equipped kitchen features light wood cabinetry and granite countertops. Stainless steel appliances, including a dishwasher and microwave, are present. Large windows provide natural light, and a dark trash bin is located adjacent to the cabinetry.
Guest suite in Omaha
4.79 out of 5 average rating, 136 reviews

Private & Central 1BR/1 Bath Unit | StayWise

Massive walkout basement apartment in a peaceful and central Omaha neighborhood where you will enjoy: • Off street driveway parking • Private entrance • Enormous 65” TV and spacious living room • Private kitchen • Private bathroom • Private laundry access • Large King bed • Walkout patio access

Popular amenities for Oakland holiday rentals

  1. Airbnb
  2. United States
  3. Iowa
  4. Pottawattamie County
  5. Oakland