Vacation rentals in Oakland

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Top-rated vacation rentals in Oakland

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

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Top guest favorite
A dark sofa is positioned against a light wall, accented by colorful throw pillows. A patterned area rug lies beneath, and a small table with a lamp stands nearby. Shelves on the wall display framed pictures and decorative items, adding a personal touch to the space.
Guest suite in Imogene
4.96 out of 5 average rating, 149 reviews

Imogene Farmhouse/SunnySide Saloon

Lounge outside in the hammock and watch the cornstalks swaying in the breeze or the cattle grazing. Boardgames, cards, records, & fiber-optic wi-fi to keep you entertained when inside. A kitchenette/bar area to relax & rehash the day's adventures. Located one mile from Imogene, a small but mighty Irish community. Book a tour of the stunning St. Patrick Catholic Church on the hill, wet your whistle at the Emerald Isle Bar & Grill, or bike/walk through the tree-lined Wabash Trace Nature Trail.

Top guest favorite
A tranquil outdoor space features a decorative pond surrounded by a stone border, with colorful pots containing flowers and plants. Two green chairs with patterned cushions are positioned nearby. The background displays a cozy guest house and vibrant greenery, providing a peaceful retreat.
Guesthouse in Benson
4.92 out of 5 average rating, 129 reviews

Urban Oasis Studio

Escape to our Charming Guesthouse a perfect blend of comfort and relaxation. Step outside to enjoy a peaceful patio with a soothing waterfall. Stay comfortable A/C and heating, and cozy up next to the beautiful fireplace. High-speed Wi-Fi and a large TV are provided for your entertainment. On a fenced 3/4 acre lot, access to an outdoor firepit perfect for evening relaxation. Located in the heart of Omaha, you’ll enjoy full city access while still retreating to a peaceful, private setting.

Guest favorite
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, 238 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 favorite
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, 408 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 favorite
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, 244 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.

Guest favorite
A modern living area features a spacious gray sectional sofa and a round coffee table, with two blue accent chairs nearby. Large windows with black blinds allow natural light to illuminate the room. A ceiling fan adds comfort to the open layout.
Condo in Atlantic
4.97 out of 5 average rating, 172 reviews

2-bedroom, 1-bathroom whole apartment Atlantic, IA

Take in the sights and explore all that Atlantic, Iowa, has to offer when you stay in this brand-new, fully renovated 2-bedroom, 1-bathroom apartment located in the heart of downtown. It is on the second story of an iconic building called The Telegraph. You will have your own private entrance and access to the space with on-street parking available. The space comes with wi-fi, a roku, washer/dryer, top of the line kitchen appliances and an open concept great for entertaining.

Top guest favorite
A spacious living area is presented, featuring a large sectional sofa positioned for comfort. Tall windows allow natural light to fill the room, revealing views of the outdoors. A stone fireplace adds structure, while a dining table and additional seating create an inviting atmosphere for gatherings.
Home in Dunlap
4.96 out of 5 average rating, 140 reviews

Hilltop Hospitality House

Remodeled split-entry "Hilltop Hospitality House" was my childhood home. One hour from Omaha in the lovely Loess Hills, with beautiful lake and valley views, (sleeps ten). Three queen beds, one double bed, one sofa sleeper, full kitchen, two full baths, laundry, a spacious open floor plan for large groups, and a large deck overlooking my friendly hometown, this is a great space for groups and family gatherings. Nice studio apartment above the garage rents separately.

Top guest favorite
A view of a charming town square is presented, featuring a red-brick building with large windows and decorative elements. Green trees and manicured grass enhance the scene, while parked vehicles line the street, capturing the lively atmosphere of the area.
Apartment in Glenwood
4.92 out of 5 average rating, 173 reviews

Glenwood Loft on Town Square Upstairs

A beautiful old town style apartment in the heart of Glenwood town square. Walking distance to plenty of places. Very up-to-date style. Easy to get to. North windows give view of the town square. Quiet location. Fully furnished. Absolutely no use of any kind of smoking or chewing material is allowed in the apartment or outside the door. And 27 steps to get up to the apartment. The only people that are allowed to stay overnight are the people listed on the reservations.

Top guest favorite
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, 335 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.

Top guest favorite
A welcoming guest house is framed by lush greenery and a well-maintained lawn. A sign displays 'Wildwood Farms Iowa Guest House Est. 2021', while a porch with an American flag is visible, echoing a sense of home and tranquility.
Farm stay in Lewis
4.98 out of 5 average rating, 171 reviews

Wildwood Farms Iowa Guesthouse, Bed and Breakfast

Tucked deep in the rolling hills of the Nishna Valley, get away from the hustle and bustle of the city and enjoy the peaceful sounds of nature in our charming 105 year old, 3 bedroom farmhouse! A star gazers dream! We are located in rural Lewis, IA, 15 minutes south of Interstate 80- just off Historic Hwy 6 - Historic White Pole Road, 12 miles to 'Antique City', Walnut, IA, 45 minutes to Downtown Omaha and 90 minutes to downtown Des Moines.

Top guest favorite
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, 102 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 favorite
Home in Omaha
4.95 out of 5 average rating, 304 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 vacation rentals

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