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
Home in Bellevue
4.99 out of 5 average rating, 206 reviews

Arts & Crafts Bungalow—easy to CWS/Zoo/Omaha

Retreat to this 2 bedroom bungalow with modern amenities & century old charm, located in a semi-secluded neighborhood with easy driving access to the zoo, downtown Omaha, CWS, Bellevue & Offutt. Walk 2 blks to Fontenelle Forest. The sunroom has a fold down sofa, desk, & original French doors for an additional living/working/chill area. Relax on the back deck & admire the sunset, hang out inside & prepare a meal in the fantastic kitchen, or chill on the leather couch with the 55” smart TV w cable

Guest favourite
Guest house in Benson
4.92 out of 5 average rating, 141 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
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
4.98 out of 5 average rating, 242 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 Council Bluffs
4.98 out of 5 average rating, 416 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, 247 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 favourite
A modern kitchen features sleek black cabinetry and stainless-steel appliances, highlighted by a stylish patterned backsplash. A large island with seating for four is accented by pendant lights, and natural light fills the space through nearby windows, enhancing the open concept design.
Apartment in Atlantic
4.97 out of 5 average rating, 174 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.

Guest favourite
A charming two-story home is presented with a welcoming porch, featuring two rocking chairs. The exterior showcases a light-colored facade with dark trim and large windows, framed by a flower box. The roofline includes a prominent gable, set against a colorful sunset sky.
Home in Council Bluffs
4.92 out of 5 average rating, 117 reviews

Casa Verde: Charming Retreat

Welcome to Casa Verde, a charming retreat mere minutes from downtown Omaha, where the pulse of the College World Series and CHI Health Center beats. Just a 10-minute drive lands you amidst the captivating wonders of the Henry Doorly Zoo. Ready for a thrill? Venture to the nearby casinos or Old Market for an electrifying night out. Whether you're exploring the city's vibrant energy or unwinding in tranquility, Casa Verde provides the ideal escape for your stay.

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!

Top guest favourite
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 spacious living area is highlighted by a beautifully decorated Christmas tree adorned with lights. Expansive windows frame a view of the outdoors, while dark wood flooring adds warmth to the scene. A foosball table is visible in the background, enhancing the recreational appeal.
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.

Top guest favourite
The exterior of the historic Union JunKtion building is showcased with a green facade and large windows. A welcoming 'OPEN' sign is visible, and various vintage items, including chairs and decorative elements, are displayed outside, inviting exploration of the eclectic antique store.
Place to stay in Union
4.96 out of 5 average rating, 251 reviews

Shop & Stay @ InnJunKtion: Cozy, fun & vintage!

The InnJunKtion is a guest suite within the Union JunKtion, an eclectic vintage/antique/junk store! Have the comforts of a more traditional suite with en suite bathroom, memory foam queen bed, microwave, mini fridge/freezer, water cooler, washer/dryer, etc. PLUS an entire 2,000 square foot historic building (with amazing decor that is ALL available for sale) to browse & shop to your heart’s content!

Popular amenities for Oakland holiday rentals

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