Holiday rentals in Oakland

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Top-rated holiday rentals in Oakland

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Top guest favourite
A comfortable living area features two upholstered armchairs and a cozy sofa, with a ceiling fan above. A white brick fireplace is central to the space, accompanied by a TV and built-in shelves. Large windows allow natural light and display autumn foliage outside.
Home in Bellevue
4.97 out of 5 average rating, 363 reviews

Cozy Forest Refuge ( Accommodate 1-11) (7 Beds)

With 4 bedrooms, 2 1/2 bathrooms and 7 beds - its great for anyone. With low price you can be an individual, couple, or up to 11 people. Includes a fire pit, washer and dryer, free WiFi, and parking space. It is a 1425 sq home tucked in Fontenelle forest, very peaceful and quiet. It is within 15 minutes of The Old Market, Charles Schwab Field , and 10 minutes to the Henry Doorly Zoo! Great places to hike right in the neighborhood. It is great for individuals, couples, families, and big groups.

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, 231 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, 392 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
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, 236 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
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.
Flat in Glenwood
4.92 out of 5 average rating, 167 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 favourite
The rustic exterior of a cottage is showcased, with a wood-paneled facade and a front porch featuring two white chairs. Large windows allow natural light to enter, while an air conditioning unit is seen on the side. Lush greenery surrounds the property, illuminated by soft sunlight.
Cabin in Coon Rapids
4.98 out of 5 average rating, 319 reviews

The Rookery Cottage - Access scenic hiking trails

This rustic cottage is a quiet retreat in the heart of the Middle Raccoon River Valley. Situated on a private acreage within Whiterock Conservancy, guests can easily access 40mi+ of scenic hiking and mountain biking trails, float the nearby river, or enjoy dark sky viewing. A "rookery" is a nesting site for herons, a bird that prefers quiet, undisturbed habitat near water. And so the Rookery Cottage seeks to provide a natural escape from the daily grind.

Top guest favourite
A cozy seating area features floral-patterned cushions on a built-in bench, complemented by an ornate coffee table. Natural light enters through a nearby window, and decorative wall hangings provide charm to the space. A polished wooden cabinet enhances the warm atmosphere.
Guest suite in Omaha
4.98 out of 5 average rating, 197 reviews

2000 sq ft-2 car garage-dog friendly-private entry

2000 sq ft. Private Floor. Bedroom has California king, second king bed with privacy curtains, queen pull out. All beds have TVs. Washer/dryer, Kitchenette, 2 car garage. WIFI, Cable. Gym with Treadmill, Bike, Weights, Foosball, Key board, record player, TV, etc. Enjoy greenhouse and outdoor eating area. Walkable neighborhood facing Happy Hollow Club, 2 minutes from I80. Continental breakfast included. Dogs enjoy run of fully fenced yard .

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
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
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 serene lake surrounded by trees is captured at sunset, with vibrant hues of orange and yellow reflecting off the still water. Silhouetted branches create a natural frame, enhancing the peaceful ambiance of the waterfront setting.
Loft in Bellevue
4.96 out of 5 average rating, 198 reviews

Beachfront paradise 20 min from Omaha

Stay in paradise on Hanson Lakes, just ten miles south of downtown Omaha. Perfect getaway from the city or magical place to stay while visiting our lovely city. I lived in this loft myself for five months and it's an awesome space. Perfect for someone looking for inspiration or relaxation. We recently added a queen size Murphy bed so it now has two beds.

Popular amenities for Oakland holiday rentals

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