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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Superhost
A cozy living room space features a modern electric fireplace set within a wooden feature wall. Above, a flat-screen television is mounted, displaying an image. A dark coffee table is positioned centrally, with a remote placed on its surface. The room leads to a kitchen area in the background.
Flat in Midtown
4.83 out of 5 average rating, 118 reviews

The Winter House Vintage Apt {2} Midtown/Downtown

Charming, beautifully updated historic home, converted into apartments in the 1930s, vintage charm with modern touches. 1st floor apartment. 10 minute drive to Downtown, UNMC, CWS, Henry Doorly Zoo, Blackstone District, CHI Health Center, and Creighton. Fully equipped kitchen with everything for cooking, modern appliances, cookware, Keurig. Cozy bedroom with small closet, Comfy living room/dining area with smart TV and fireplace. Bathroom with vintage tub/shower & walk in closet. On site laundry

Top guest favourite
Home in Council Bluffs
5 out of 5 average rating, 40 reviews

Mae & Mia’s Sweet Escape

Escape to this sweet, cozy cottage bursting with charm in the heart of Council Bluffs. Walking distance to two hospitals and historic downtown (100 Block) provides easy access to food, entertainment, and business. A 10-minute drive will get you to downtown Omaha for more amenities. The single bedroom and living room with pull-out bed will accommodate 4 travelers with room to spare if pets are traveling too! Fully fenced yard will keep them safe while offering ample space to run, fetch or relax.

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, 388 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 cozy room features a spacious bed with a striped comforter and decorative pillows. A comfortable couch sits beside a bedside table and lamp, creating a welcoming area. A dresser is positioned against the wall, and soft lighting gives the space a warm feel.
Flat in Papillion
4.94 out of 5 average rating, 356 reviews

Coastal Retreat Getaway, Secluded, Off 370/I-80

Step into a private and cozy space. Relax watching TV in bed or on the couch. This place is part of our walk out basement, so you may hear day to day living upstairs. For your safety there is a Ring camera installed at the entrance and will light up the entryway when it’s dark. Parking is on the well lit public street. Easily walk up our dedicated Airbnb sidewalk, no steps, walk around to the back of the house. You’ll be in a serene space that makes you feel right at home.

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, 228 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
The exterior of the church is highlighted by its distinctive architecture, featuring a combination of white and red details. A large sign displays '150TH' and '1873', marking its historical significance. The tower silhouette rises against a soft evening sky.
Place to stay in Malvern
4.99 out of 5 average rating, 331 reviews

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.

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.

Guest favourite
The exterior of a two-story shotgun style home features a light yellow facade with white trim. A blue front door is framed by large windows, providing ample natural light. Stone steps lead up to the entrance, bordered by green grass on either side.
Home in Little Italy
4.93 out of 5 average rating, 157 reviews

The Shotgun House - Little Italy - Pets Welcome!

A little taste of South Louisiana in South Omaha - this Shotgun style home is situated in a quiet neighborhood located close to the Old Market and the revived 13th St Corridor AKA Little Bohemia. In addition to having 2bd/2ba, this charming abode has a fully equipped kitchen, full-size washer/dryer, wifi, and a fenced in backyard making this the perfect location for you and your companions! Pets welcome - no fees

Superhost
Flat in Omaha
4.83 out of 5 average rating, 6 reviews

Aksarben Haven, Near Entertainment & I-80

- Centrally located, offering easy access to roadways and essential spots. - Features a private entrance ensuring guests' comfort and convenience. - Enjoy nearby Aksarben Village for entertainment, dining, and shopping. - Fully equipped kitchen and dedicated workspace for long-term stays. - Book now for a comfortable stay in a convenient location!

Guest favourite
A two-car garage is featured in a brick structure topped with a tiled roof. Two large garage doors with rectangular windows are visible. The building's upper section includes a window, providing a glimpse of natural light into the loft interior.
Guest house in Council Bluffs
4.82 out of 5 average rating, 304 reviews

Private Victorian Guest House Loft

Unique and tranquil getaway. Exclusive to guest and very private. Central to Council Bluffs area with a 5-10 minute drive to most of Council Bluffs and 10 minute Drive to Omaha. Small Turn Staircase is not steep as tread height is 7 1/2" USA standard. Spacious sleeping room/Living Room, Kitchen and small bathroom with new shower.

Guest favourite
The exterior of a one-bedroom house is displayed, featuring a brown brick facade and a simple gabled roof. A concrete path leads to the front door, framed by two large windows on each side, alongside a well-maintained grassy area.
Home in Atlantic
4.9 out of 5 average rating, 172 reviews

Cozy Home Away from Home

Cozy one bedroom house with fully equipped kitchen. Pots and pans, dishes, stove, microwave and coffee pot & coffee all available to guests. Roku TV, WiFi, washer and dryer as well. Bedroom with Queen size bed and full size pull out couch in living room. Entry has no steps and convenient on street parking near front door.

Popular amenities for Oakland holiday rentals

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