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 Papillion
4.94 out of 5 average rating, 101 reviews

Private Upstairs, 4 beds, 3 rooms, own entrance!

Quaint & cozy abode that has 3 bedrooms, 4 beds. Fans in every room. You control the heat and a/c. 2 queen beds, 1 full, 1 twin. Large comfy couch that could sleep 2. The kitchen has everything you need to make a full meal. Shampoo/conditioner/soap/laundry detergent provided! There is a small front yard and side patio. There is a large back yard not fenced in but your dogs are welcome to run in it. No parties. Quiet neighborhood. Smoking outside only. Come check out this clean and fun place!!!!!

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, 362 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
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, 114 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
4.97 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, 237 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, 234 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 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
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 .

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, 167 reviews

Cozy Art Deco 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.

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.

Popular amenities for Oakland holiday rentals

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