Vacation rentals in Oakland

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Top-rated vacation rentals in Oakland

Guests agree: these stays are highly rated for location, cleanliness, and more.

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Top guest favourite
A spacious bedroom is furnished with a large bed dressed in white linens and a blue throw blanket. Decorative pillows add a touch of color. A vintage-style bench with floral detailing is placed at the foot of the bed, complementing the rustic wooden flooring.
Home in Underwood
4.99 out of 5 average rating, 73 reviews

The Railhouse in Weston, Iowa

Completely renovated older 1880 home in a quaint little town in Weston, Iowa. Country setting with the view of farm fields, rolling hills, the ambiance of a slow moving train once a day or evening. A short paved walking/ bike trail, that soon will connect to another trail. There is a county highway out front that will have traffic. You can wake up to a beautiful view and enjoy your coffee on the deck or a walk in our back lot and listen to nature. We are across the river from Omaha, Nebraska.

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.
Guesthouse in Benson
4.92 out of 5 average rating, 141 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 homes in Missouri Valley
4.98 out of 5 average rating, 242 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
Shipping container in Stuart
5 out of 5 average rating, 58 reviews

Cozy Country Container Stay w/ Hot Tub & Fire Pit!

Cozy 1-bed shipping container home in rural Stuart, IA. Perfect for couples or solo travelers. •Sleeps 2 • Queen bed • Full kitchen & Bath •Hot tub • Fire pit • Grill •Shared pond for fishing & scenic views. •Friendly horses & dogs on site (winter months may vary) (guests can interact) please treat them with kindness. •Peaceful country setting—. perfect for relaxing & stargazing •You may see a critter or two—. true country living!

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, 416 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.

Guest favourite
A serene sandy beach is bordered by a calm lake, with a few dark wooden chairs arranged for relaxation. The sun sets on the horizon, casting a warm glow over the water. Trees provide a natural frame to this peaceful setting.
Cabin in Cedar Creek
5 out of 5 average rating, 30 reviews

C.C. Lake House - no wake lake 37 minutes to cws

Relax at this peaceful property located on a private tree lined lot and no wake lake in Cedar Creek, NE. Your stay includes exclusive use of the main house (2 bed/1 bath), separate studio house (1 bed/1 bath), the lake toys (lily pad/kayak/paddleboard), sandy beach and dock. Spend your days swimming & your nights eating smores by 1 of the 2 fire pits (portable fire pit by house or fire ring on the beach) (complimentary fire wood provided). Note: No unapproved guests/parties.

Top guest favourite
Home in Council Bluffs
5 out of 5 average rating, 77 reviews

Mae & Mia’s Sweet Escape

Escape to this sweet, cozy cottage bursting with charm in the heart of Council Bluffs. Walking distance to 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
The exterior of a charming two-story home is presented, featuring a light brown facade and a covered front porch. A neatly paved walkway leads to the entrance, framed by lush green grass and minimal landscaping. The house showcases several windows allowing for ample natural light.
Home in Atlantic
4.89 out of 5 average rating, 73 reviews

Large Family Home

Enjoy our fully loaded home for holiday gatherings, working on the road, or just traveling by town. Includes a fully equipped kitchen, tvs with streaming, and washer/dryer. This is a four bedroom home. Three of the rooms have a queen bed, and the fourth room has a twin bed. Every room has a tv. The living room has a hide-a-bed sofa for extra places to sleep. We guarantee comforter and all are fresh when you arrive. Bathrooms and kitchen are fully sanitized as well. ❤️

Top guest favourite
A light-filled living area features a cozy seating arrangement with two modern armchairs and a stylish sofa. A coffee table sits at the center, surrounded by a plush rug. Seasonal decor includes a Christmas tree, and large windows provide ample natural light.
Farm stay in Harlan
4.96 out of 5 average rating, 57 reviews

Boots, Class, come spread out and relax!

Come feel a slice of heaven nestled in the private surroundings of a historical farming backdrop. Watch the sunset from the barns, see the squirrels jumping in the trees and welcome the unforgettable sunrises right from your bedroom window. When you’re ready to live a day in the life… get dirty, pull up your boots, splash in the mud, play in the corn crib, use your imagination in the forests, dance in the rain, and most importantly, take pictures and make memories!

Top guest favourite
An inviting outdoor space features a hot tub surrounded by decorative lighting. A covered seating area provides ample space for relaxation, alongside a dining table set against a backdrop of a mural. Nearby greenery adds a touch of nature to the cozy atmosphere.
Home in Benson
4.97 out of 5 average rating, 121 reviews

Hot tub in beautiful backyard!

Search no more! This cozy home has it all! Charming boho style, well equipped kitchen, comfy beds, plenty of space to relax in the 2 indoor living spaces. But the BEST part of all is the inviting patio space with hot tub, plenty of seating & fire pit! Walking distance to downtown Benson with plentiful options for dining & nightlife. Another unique feature of this home is the dedicated workspace & workout room! This gem is truly your home away from home!

Top guest favourite
An expansive living area features large windows that provide a view of the surrounding landscape. High ceilings are complemented by wooden beams. A comfortable seating area includes a dark sofa, and a foosball table is visible in the space, enhancing the recreational atmosphere.
Home in Omaha
4.96 out of 5 average rating, 105 reviews

Hangar 1 with a river view

Large secluded home with a private drive and an amazing view! This three bedroom, three full bath home with an aviation theme, has plenty of space with a view of the Missouri River and a hot tub off of the master. Three queen beds, a twin with a twin trundle, and a pull out couch can sleep up to 10. Foosball and air hockey tables. There is a bike path at the end of the driveway and only a 7 min drive to Eppley Airfield.

Guest favourite
Home in Omaha
4.95 out of 5 average rating, 319 reviews

*Romantic* Rose Cottage with Hot Tub in Benson

Romantic Rose Cottage, north Benson. Minutes from UNMC, Downtown, CWS, CHI Center, Zoo, Dundee & Benson Restaurants. Beautifully designed space, perfect for short getaways and comfortable for long term stays . Wood floors, Essential cooking items, Breakfast nook with table for dining/work space. Large off street parking for 2 cars. Washer & Dryer in basement. Furry family members welcome. Fully fenced back yard.

Popular amenities for Oakland vacation rentals

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