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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 charming white house with black shutters is shown. The porch is adorned with a wooden railing and a pink door. A well-maintained lawn and pathway lead to the entrance, enhancing the home's inviting appearance.
Home in Coon Rapids
4.95 out of 5 average rating, 241 reviews

1875 House, 316 Sumpter Ave, Coon Rapids IA

Small home built in 1875 close to Middle Raccoon River. It is six blocks to downtown shops, grocery and restaurants. New, updated walking and biking trails; river access in the park for canoes/kayaks within 300 yards from front door. Access to White Rock Conservancy trails. Coon Rapids also has a 9-hole golf course and a large city park with ball fields and pool. We offer off street parking. Garage available for bicycles. Contact host. Large back yard with small deck area and charcoal grill.

Top guest favourite
A cozy living space features a plush sofa facing a decorative mantel with a fireplace. In the background, a kitchen with modern appliances is visible, complemented by bar seating for three. Soft lighting overhead enhances the inviting atmosphere.
Flat in Keystone
4.92 out of 5 average rating, 728 reviews

Comfortable Apartment in North/Central Omaha

Our place is 15 min. from Omaha's zoo; 10 min from the Old Market; 5 min. from shopping/restaurants; 15 min. from the airport, and for nurses 3-10 min. from several hospitals. The 1000 sq. ft. apartment occupies the lower level of our house with a separate entrance and patio. SANITATION PLEDGE: We are taking extra measures to make sure your rented space is safe. At each cleaning, we use disinfectant to wipe down all surfaces, handles, railings, light switches, remote controls and appliances.

Guest favourite
A spacious two-story house is showcased, featuring a mix of wood and stone exterior. Large windows provide natural light to the inviting entrance area. A wide driveway offers ample parking space, surrounded by landscaped grounds and traces of greenery.
Flat in Logan
4.89 out of 5 average rating, 76 reviews

Hunters Outpost 2 bedroom apt.

Loess Hills Hunting Area, Deer Hunter's Goose & Duck or Uplanders stay with us. Family Friendly, Dog kennel available, Horses welcome Large Barn for turn out or Riding Arena Located on the Loess Hill Senick Byway Close to Restaurants, 25 minutes north of Metro Omaha area, Riding Trails, Golf Cart Trails. Enjoy cool fall evenings around the fire pit or ride in the lighted arena, rest up & relax or up early get out to shoot that trophy Whitetail this area is famous for Big Bucks & Desoto Flyway

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, 232 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
4.98 out of 5 average rating, 393 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, 238 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
The exterior of a charming bungalow is surrounded by lush landscaping. Colorful flowers and greenery frame the entrance, which features a welcoming porch with a mailbox. Sunlight filters through the trees, highlighting the inviting facade of the home.
Home in Omaha
5 out of 5 average rating, 213 reviews

Donna's Midcentury Bungalow

Quiet and comfortable Midcentury themed bungalow. Furnished in Broyhill Brasilia and Woodard Sculptura furniture. Newly remodeled full kitchen with vintage Frigidaire Flair Oven and Range. Large covered deck with gas grill and charcoal grill. Off-street parking and beautifully landscaped grounds. Enjoy festive mid-century decor during the holidays. Near Benson, Dundee, Downtown, Blackstone, Med Center, CHI health center convention center, Creighton, and Charles Schwab field.

Top guest favourite
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, 136 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 favourite
Flat in Ralston
4.98 out of 5 average rating, 330 reviews

Highland Hideaway

Cozy apartment with fireplace; Enjoy a morning cup of coffee or an evening glass of wine on the patio. Located in the lower level of my home--Private entrance with key code entry and off-street parking. Easy access to I-80. The perfect setting for a romantic getaway, family visit, fun-filled girls' weekend, or business trip. Whoever you are and whatever your needs may be, I invite you to come enjoy my Highland Hideaway!

Guest favourite
A charming blue cottage exterior features a welcoming front porch with wooden railings and steps. Two large front windows allow natural light to brighten the entrance. The well-maintained landscape includes mulch and decorative elements that enhance the home’s curb appeal.
Home in Omaha
4.94 out of 5 average rating, 163 reviews

Kathy's Cottage

STOP and enjoy this charming yet spacious little home on a pet friendly large corner lot. Enjoy a peaceful evening on the patio listening to the water feature and birds, or start the grill with everything needed on site to cook your meals. Plenty of beautiful flowers on this well landscaped property as well. Also enjoy the Benson night life for live music and restaurants nearby if you care to step out.

Guest favourite
The exterior of the Malvern Depot bunkhouse is shown, featuring a light-colored facade with green shutters and a welcoming red door. A bench sits outside, and a bicycle leans against the building. The paved Wabash Trace pathway runs alongside a grassy area.
Cabin in Malvern
4.89 out of 5 average rating, 272 reviews

Malvern Depot

A railroad depot renovated into a bunkhouse located midway on the Wabash Trace Nature Trail. It includes 2 bedrooms, kitchenette, and bathroom with shower. A/C & heat, coffee maker, dorm fridge, microwave, and toaster oven. Linens and towels provided. One queen bed, the other twin bunk beds. The Futon in the living area folds out. Conveniently located 2 blocks from downtown. No pets please.

Top guest favourite
A well-lit bedroom is furnished with a spacious bed featuring a geometric patterned coverlet. A dresser is positioned against one wall, while a bedside lamp is placed next to the bed. Two windows with light curtains allow natural light to fill the room.
Townhouse in Bellevue
4.98 out of 5 average rating, 149 reviews

Cheerful 2Bed/1Bath/1 Garage

Completely renovated 2bed/1bath/1car garage with full laundry. 2 miles from HWY 75S. Easy access to anywhere in Omaha. Less than 15 minutes from UNMC, CUMC Bergan, VA and Methodist. 10 minutes from Zoo, Old Market & Midtown. We tried to think of everything, if you need anything, just ask! PLEASE READ 2 night minimum 3 months max Message for monthly rate Sorry no pets

Popular amenities for Oakland holiday rentals

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