Holiday rentals in Oakland

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Top-rated holiday rentals in Oakland

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

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Top guest favourite
A welcoming entrance features multiple pink Adirondack chairs, each adorned with patterned cushions. A small chair stands beside larger ones, creating an inviting seating area. Above the door, an American flag hangs, while large windows allow natural light to brighten the façade.
Flat in Elk Horn
4.92 out of 5 average rating, 52 reviews

The Review Airbnb

Enjoy a memorable stay right on Elk Horn's charming Main St. in a full one-bedroom apartment, previously The Review Newspaper Office in mid 1900's. Steps from restaurants/pubs, shops, convenience store, museums & iconic Danish Windmill which brings thousands of tourists off Interstate 80 to taste Danish Culture that simply isn't available anywhere in the US. Minutes drive to Danish Winery tucked in picturesque plains of Iowa or to neighboring Kimballton where you will find The Little Mermaid!

Top guest favourite
Flat in Exira
5 out of 5 average rating, 19 reviews

Exira 107 - Cozy 2BR Above Coffee & Goods Shop

Welcome to Exira 107, a cozy 2-bedroom, 1.5-bath stay in the heart of Exira! Brand new and fully furnished, located above Goldie’s Coffee & Goods. Perfect for family visits, weddings, work trips, or a peaceful getaway. Enjoy a full kitchen, in-unit laundry, and a 55" Smart TV. Guests receive a free coffee or tea with every stay. Arriving late or want breakfast taken care of? Optional grocery service from downstairs is available for $5 plus cost of groceries - just request details upon booking.

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
4.98 out of 5 average rating, 417 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 two-story home with a stone facade sits on a gentle slope, surrounded by greenery. A wide driveway leads to a garage, while a small lawn in front adds a touch of nature. The entrance is framed by a set of steps and a porch with seating.
Guest house in Bellevue
4.98 out of 5 average rating, 64 reviews

2 story, In-law suite, rear of house. Near Offutt

Enjoy the home away from home with an in-law suite located in the rear of the main home. The back yard has a fire pit just off the spacious patio and deck. Enjoy the charcoal grill and bistro style seating. Plenty of outdoor seating with rocking chairs and a hammock that you can relax in. There is a play-sets and enjoy the security of a 6-foot privacy fence. We are just outside Offutt’s back gate. Within 20 minutes to Henry Doorly Zoo, Charles Schwab & Werner Park ball fields.

Top guest favourite
The living area is adorned with exposed brick walls and features a comfortable gray sofa with accent pillows. A circular glass table rests on a patterned area rug, surrounded by potted plants. A small beverage fridge and bar are visible, creating a cozy setting.
Apartment in Omaha
4.95 out of 5 average rating, 282 reviews

Cozy downtown Omaha condo - walk to Old Market!

Charming two-bedroom condo in the heart of downtown Omaha. Cozy, comfortable, & fully equipped. Fully stocked kitchen, 2 bedrooms with queen beds, comfortable living room with beverage fridge & cocktail bar. Cozy sunroom with fully supplied coffee bar to sit & enjoy a morning coffee, or turn on the twinkle lights at night & enjoy the view! Just a 5 minute walk from some of Omaha’s best locations: CWS, Gene Leahy Park, & the Old Market! Comes with 1 free gated parking spot.

Top guest favourite
Home in Council Bluffs
5 out of 5 average rating, 78 reviews

Mae & Mia’s Sweet Escape

Escape to this sweet, cozy cottage bursting with charm in the heart of Council Bluffs. Walking distance to historic downtown (100 Block) provides easy access to food, entertainment, and business. A 10-minute drive will get you to downtown Omaha for more amenities. The single bedroom and living room with pull-out bed will accommodate 4 travelers with room to spare if pets are traveling too! Fully fenced yard will keep them safe while offering ample space to run, fetch or relax.

Top guest favourite
Guest house in Blair
5 out of 5 average rating, 22 reviews

The Rendezvous - A Cozy Cottage Escape

This newly built carriage house features a spacious upstairs studio apartment in a quiet, wooded neighborhood. It is perfect for peaceful getaways or business travel. You will enjoy a comfy king sized bed, efficient work space, full kitchen with modern appliances, and a laundry room. This gem sits on its own lot and is surrounded by trees. It is conveniently located just one mile south of Blair with easy access to highway 75 and a short scenic drive into downtown Omaha.

Top guest favourite
The exterior of a charming two-story home is presented, featuring a light brown facade and a covered front porch. A neatly paved walkway leads to the entrance, framed by lush green grass and minimal landscaping. The house showcases several windows allowing for ample natural light.
Home in Atlantic
4.88 out of 5 average rating, 75 reviews

Large Family Home

Enjoy our fully loaded home for holiday gatherings, working on the road, or just traveling by town. Includes a fully equipped kitchen, tvs with streaming, and washer/dryer. This is a four bedroom home. Three of the rooms have a queen bed, and the fourth room has a twin bed. Every room has a tv. The living room has a hide-a-bed sofa for extra places to sleep. We guarantee comforter and all are fresh when you arrive. Bathrooms and kitchen are fully sanitized as well. ❤️

Top guest favourite
An inviting outdoor space features a hot tub surrounded by decorative lighting. A covered seating area provides ample space for relaxation, alongside a dining table set against a backdrop of a mural. Nearby greenery adds a touch of nature to the cozy atmosphere.
Home in Benson
4.97 out of 5 average rating, 121 reviews

Hot tub in beautiful backyard!

Search no more! This cozy home has it all! Charming boho style, well equipped kitchen, comfy beds, plenty of space to relax in the 2 indoor living spaces. But the BEST part of all is the inviting patio space with hot tub, plenty of seating & fire pit! Walking distance to downtown Benson with plentiful options for dining & nightlife. Another unique feature of this home is the dedicated workspace & workout room! This gem is truly your home away from home!

Superhost
A spacious studio is presented with a rustic wood accent wall and warm lighting. A cozy couch is positioned in the foreground, while a sizable bed is located against the back wall. A desk and chair are visible in a designated work area, enhancing the functionality of the space.
Loft in Glenwood
4.77 out of 5 average rating, 196 reviews

Spacious & Modern Studio. 20 min from DT Omaha

This newly remodeled studio is in the heart of downtown Glenwood, IA and only 25 minutes from the Omaha Airport and the old Market. While close to the big city, Glenwood also offers its own character with unique boutiques, coffee shop and vineyards. Home to Keg Creek Brewery, Parea Cocktail Lounge and Adrianos Brick Oven Pizza (rated #1 in the Nation), you will find this studio in a picturesque town square, situated above a quaint smoothie shop.

Top guest favourite
An expansive living area features large windows that provide a view of the surrounding landscape. High ceilings are complemented by wooden beams. A comfortable seating area includes a dark sofa, and a foosball table is visible in the space, enhancing the recreational atmosphere.
Home in Omaha
4.96 out of 5 average rating, 105 reviews

Hangar 1 with a river view

Large secluded home with a private drive and an amazing view! This three bedroom, three full bath home with an aviation theme, has plenty of space with a view of the Missouri River and a hot tub off of the master. Three queen beds, a twin with a twin trundle, and a pull out couch can sleep up to 10. Foosball and air hockey tables. There is a bike path at the end of the driveway and only a 7 min drive to Eppley Airfield.

Guest favourite
Home in Omaha
4.95 out of 5 average rating, 319 reviews

*Romantic* Rose Cottage with Hot Tub in Benson

Romantic Rose Cottage, north Benson. Minutes from UNMC, Downtown, CWS, CHI Center, Zoo, Dundee & Benson Restaurants. Beautifully designed space, perfect for short getaways and comfortable for long term stays . Wood floors, Essential cooking items, Breakfast nook with table for dining/work space. Large off street parking for 2 cars. Washer & Dryer in basement. Furry family members welcome. Fully fenced back yard.

Popular amenities for Oakland holiday rentals

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