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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Guest favourite
The exterior of a ranch-style house is featured, showcasing a well-maintained lawn with green grass and shrubs. A single-car garage is visible, alongside a spacious driveway. Large windows brighten the home's front, and a fenced yard is seen in the background.
Home in Benson
4.85 out of 5 average rating, 579 reviews

Midtown Ranch Close to Everything

The best of what Omaha has to offer-a one level hardwood floor midtown house with fenced yard located between 2 coveted neighborhoods, Dundee and Benson, in a safe and quiet area. One mile to Memorial Park, UNO, Dundee, Benson and a few miles from the interstate, downtown, and zoo, yet situated in a quiet and safe alcove. Newly remodeled kitchen and bathroom and hosted by a professional. Large flat driveway, garage access, 3 bedrooms with king sized bed in master, fenced yard, low cleaning fee.

Top guest favourite
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, 146 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.

Guest favourite
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.
Guest house in Benson
4.91 out of 5 average rating, 115 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 favourite
The living area features rich purple walls and a mix of seating options, including a cozy sofa and armchairs. Natural light filters through the windows, illuminating decorative plants and artwork. A dining area is visible in the adjoining room, enhancing the open layout.
Home in Council Bluffs
4.86 out of 5 average rating, 452 reviews

Apartment in Historic Neighborhood

Main floor apartment in a quiet tree lined neighborhood full of character & charm. Relaxing front porch and back patio. Art sourced from our travels & a fully stocked kitchen. Only two blocks to Downtown Council Bluffs where you can grab a meal, drinks, or shop. Downtown Omaha, airport, Iowa Western Community College, Stir Cove, the Omaha zoo are all within 15 minutes. It is a historic home so will have quirks that come with an older home. The bathroom is a hand held shower/bath only.

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, 233 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
Home in Benson
4.96 out of 5 average rating, 105 reviews

Parker's Place

Welcome to Parker's Place! Conveniently located in Benson just under 1 mile from the Benson Strip filled with nightlife and restaurants. This hideaway for 6 offers a quiet retreat, but still centrally located with everything minutes away. **PARTIES WILL BE SHUT DOWN QUICK** What's close by? -1 mile to USPS Post office -2 miles to Target -5 miles to TD Ameritrade Park/CHI Event Center -5.5 miles to a Walmart Supercenter -8 miles to Henry Doorly Zoo -9 Miles to Lauritzen Gardens

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, 239 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 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, 243 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, 332 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 favourite
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 favourite
A vibrant living area features contemporary furniture, including a leather sofa and multicolored chairs around a glass dining table. A striking abstract painting adds color to the wall, while natural light streams in from two window panes framed by light curtains.
Tiny home in Keystone
4.94 out of 5 average rating, 232 reviews

Contemporary Furnished Home

A cozy place with contemporary furnishing. A home away from home of your own with gated concrete driveway. Tennis court area welcomes you each day for your daily exercise. Full kitchen and laundry are among the amenities provided for your additional comfort. Grocery stores and restaurants are just minutes away to satisfy your cravings early morning or late nights. Multiple gas stations & churches are are just around the corner.

Guest favourite
A cozy living area features a gray sectional couch positioned beside a decorative table with a vintage record player. Green plants are placed throughout, complementing the deep blue wall adorned with framed artwork. Natural light illuminates the space, enhancing the inviting atmosphere.
Flat in Midtown
4.91 out of 5 average rating, 181 reviews

Art Deco Cozy Condo in Midtown Omaha with view!

Secure condo overlooking beautifully decorated Turner Park in the heart of Midtown Omaha. Close to downtown, hospitals, the interstate, and the Blackstone District with great walkable restaurants. Includes a full kitchen with utensils, coffee and creamer, workspace, books, bike access, pull-out couch, and air mattress. Guests must provide an email or phone number to receive Key Café entry code as required by building security.

Popular amenities for Oakland holiday rentals

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