
Holiday rentals in Oakland
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Top-rated holiday rentals in Oakland
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Private Lakefront Retreat| Pool•Hot tub •Sauna•SPA
Private Lakefront Walk-out basement is perfect for families & business travelers Your own resort in the city. No parties allowed! Newly remodeled space with Pool, Hot tub & Sauna Spacious living room with foosball & pool table, sleeper sofas Full kitchen Cozy bedroom with king-size bed & TV 2 bathrooms Breathtaking backyard, various patio options, BBQ, dock for meditation & fishing Close to Dodge & Interstate, Topgolf, grocery stores & Costco, restaurants 15min to the Zoo, Airport & Downtow🏡

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.

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.

Historic Second Floor Apartment near Downtown CB
Upper floor apartment in a tree lined historic neighborhood. Walking distance to our vibrant downtown and several parks. A short drive to airport, IWCC, sports fields, downtown Omaha. 10 minutes to CHI and the NCAA Men’s Basketball Championships. Includes bedroom, living room, kitchen, bathroom and a seasonal sun porch. Use of outdoor spaces such as front porch and back patio shared with main floor guests. It is a historic home so will have your usual quirks that come with an older home.

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.

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.

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.

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.

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.

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.

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.

Private basement apartment w/ separate entrance
My place is close to I-680. 15 minutes to downtown, 10 minutes to Benson and 17 minutes to airport..Close to Immanuel Hospital and Omaha Country Club. You’ll love my place because of Private entrance, nice quiet country feel on the edge of town. You enjoy the screened in patio, your own bath and kitchen.. My place is good for couples, solo adventurers, and business travelers.
Popular amenities for Oakland holiday rentals
Other great holiday rentals in Oakland

Victorian Cottage steps from historic downtown

Beautifully updated quiet oasis

Rockbrook Oasis - Centrally Located - Sleeps 12

Rainwood Cottage in the trees near the lake.

Hangar 1 with a river view

Spacious & Modern Studio. 20 min from DT Omaha

La Casita, Garage and Snow Removal Included

Vintage Vibe Apartment - The Suite
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