Holiday houses in Pleasantville

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Top-rated holiday rentals in Pleasantville

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Guest favourite
The kitchen features classic wooden cabinetry and retro-style appliances, including a pale cream refrigerator. A patterned backsplash complements the checkered floor, while shelves display colorful dinnerware. Natural light fills the space, enhancing the inviting atmosphere for cooking and gathering.
Home in Ankeny
4.97 out of 5 average rating, 202 reviews

Historic Home on 4 Acres - Hot Tub, Pool, Tiki Bar

Our 1948 vacation home is on 4 acres & boasts 3 bedrooms, 3 full baths, 2 half baths, Bridal Suite (4th bedroom), 70s TV/Game Room, Tiki Bar, & Children's Playroom. Outside we have a pool (guaranteed to be open 5/26 - 9/5) & hot tub (year round). Located 15min away from Downtown DSM & a mile away from a grocery store/restaurants. Up to 2 dogs allowed for an additional fee. ***Events/photo shoots are allowed with written permission only and will be an added fee. No events larger than 25 total.***

Top Guest favourite
Cabin in Prole
4.98 out of 5 average rating, 121 reviews

Tranquil Cabin Retreat Near Des Moines

Welcome to Timberlandia! Just south of the Metro, at the border of Madison & Warren counties in the Middle River Valley, the cabin is on 2 acres of shaded lawns with plenty of exploring options on 18 acres of wooded paths & walking trails. Timberlandia is a secluded tranquil getaway, but only 15 minutes from the Airport, 20 minutes from West Des Moines Jordan Creek, and 25 minutes from downtown. Our cabin is great for romantic getaways, family gatherings, festivals, retreats & wedding stays.

Top Guest favourite
Apartment in Knoxville
4.97 out of 5 average rating, 92 reviews

Charming Garden Suite at PineRidge Rose Farm

Experience the quiet beauty of the Iowa countryside at PineRidge Roses. Whether you’re here for the high-octane excitement of the Knoxville Raceway or the Dutch charm of Pella, our suite offers a fragrant, peaceful home base. As a guest, you’re staying on a developing a flower farm. While we are still growing and building our floral dreams, you might see active farm working during the day. The reward is a fresh, hand-picked bouquet waiting in your suite to brighten every morning of your stay.

Top Guest favourite
Home in Pella
4.99 out of 5 average rating, 152 reviews

Historic Dutch Cottage • Walk to Central • Firepit

The Rock House • Historic• Walk to Central College• Fire Pit Stay in a true piece of Pella history. The Rock House was built in 1856 by Dutch homesteaders and has been beautifully restored with modern comforts. This cozy 2-bedroom cottage sits next to Central College and is just minutes from downtown shops, bakeries, and the famous Vermeer Windmill. Perfect for couples, small families, Central College visitors or a cozy Pella getaway, the home blends historic charm with a peaceful retreat.

Guest favourite
A spacious room features a gray sectional sofa positioned on a warm-toned floor. A cozy bed with green bedding is visible in the background, alongside a desk and lamp. Natural light enters through a window adorned with light curtains.
Guest suite in Pleasantville
5 out of 5 average rating, 10 reviews

Cozy Loft South of Pleasantville

Escape to the countryside with a stay in our charming lofted studio, attached to our family home and nestled on a peaceful farm just 10 minutes from Pleasantville, Iowa. This cozy retreat offers a private studio-style space perfect for a quiet getaway We’re just 15-20 minutes from Knoxville and the famous Knoxville Raceway, making this an ideal spot for race fans. A short drive will also take you to Pella for the stunning Tulip Time Festival or to Des Moines for the iconic Iowa State Fair.

Top Guest favourite
A cozy living area features a plush sofa alongside two armchairs positioned around a low table. Soft lighting from a nearby lamp creates a relaxed ambiance. Decorative elements, including a bookshelf and a neatly arranged rug, enhance the inviting atmosphere.
Cabin in Pella
4.96 out of 5 average rating, 181 reviews

The Prayer Cabin

The Prayer Cabin is located at Lake Red Rock outside of Pella, IA. The cabin Is an Earthen/Berm home located on a 1 acre lot in a quiet & clean neighborhood. The lot boasts a wooded valley with many birds and squirrels to watch. The Prayer Cabin was recently remodeled with a brand new kitchen and bathroom. Our first guests asked us if Chip and Joanna were the creators of the design. 💚 Navy Blue cabinets, Tons of white shiplap and open shelving. Peaceful. A place of respite and relaxation.

Top Guest favourite
The exterior of a remodeled house is adorned with warm white lights, highlighting the entrance. A porch with two chairs is visible, alongside decorative plants and stones. The landscape features a welcoming pathway leading to the front door, surrounded by winter foliage.
Cottage in Pella
4.99 out of 5 average rating, 413 reviews

The Strawtown Cottage - in downtown Pella

Completely remodeled 1865 original Strawtown Store of Pella conveniently located in one of the best small towns in Iowa. Three blocks to downtown Pella, 1 1/2 blocks to West Market Park, 2 blocks to Central football, baseball and softball complex. Enjoy the cottage charm with two private bed and bath suites, a family room with dining, full kitchen, front and side porch, laundry and large back yard. Off-street parking in the back. Luxury sheets on queen beds await after your adventures.

Top Guest favourite
A newly remodeled home is showcased, featuring a welcoming facade with a mix of light and dark exterior colors. A concrete driveway leads to the entrance, surrounded by a well-kept lawn and mature trees. A detached garage is visible nearby.
Home in Indianola
4.93 out of 5 average rating, 198 reviews

Charming Home in Indianola

Discover comfort in our newly remodeled 3-bedroom home in the heart of Indianola, Iowa. This charming space boasts modern amenities and stylish decor, providing a cozy retreat for your stay. Enjoy a fully equipped kitchen, spacious living areas, and a modern bathroom. Perfect for families or groups, our home offers a blend of convenience and warmth. Explore nearby attractions or simply relax in our inviting space. Your home away from home awaits in Indianola!

Guest favourite
Two modern A-frame cabins are showcased amid lush greenery, featuring angular rooftops and large glass windows. A well-maintained gravel path leads to the cabins, while the surrounding lawn is spacious and shaded by mature trees, contributing to a serene outdoor setting.
Cabin in Hartford
5 out of 5 average rating, 11 reviews

New A-Frame Cabin by Des Moines (Hackberry theme)!

Escape to one of our three brand-new, fully furnished A-frame cabins at River Oaks RV Park—where modern comfort meets rustic charm. Each A-frame is uniquely designed, stylishly appointed, and perfect for making unforgettable memories. Whether you’re relaxing by the river, roasting s’mores under the stars, or just soaking in the cool, creative vibe of your private space, this family-friendly getaway is anything but ordinary.

Top Guest favourite
The exterior of a single-level bungalow is shown, featuring light-colored siding and blue shutters. A manicured lawn is visible, with flowering shrubs near the front porch. The attached garage is seen on the right, and trees are present in the background under a clear sky.
Home in Knoxville
5 out of 5 average rating, 52 reviews

"Ms. Becky's Bungalow"

Discover Ms. Becky’s Bungalow! A 2-bedroom, fully furnished home for up to 4-6 guests . Features include one queen bed, two twin beds, air mattresses available for more guests, attached garage, laundry, shade tree in front, backyard firepit, and deck. Pet-friendly, non-smoking, and all one level for easy access. Close to great hunting, fishing, and wildlife areas, as well as the Knoxville Raceway.

Top Guest favourite
A cozy living area features a turquoise sofa topped with a patterned throw. A coffee table sits in front, with a small television on a vintage stand. Bright red curtains frame the window, while a decorative globe and record wall accents add a touch of charm.
Apartment in Pella
4.98 out of 5 average rating, 385 reviews

60's Inspired Studio

Our awesome 60's Inspired studio has a mid-century vintage vibe! A quick walk to explore the unique city of Pella. Including the city park, historical buildings, restaurants, bakeries, meat markets, stores, Central College, movie theater and much more to explore. This is a second story walk-up; you will have a flight of steps to enter and exit. Private entrance and parking in driveway.

Guest favourite
A cozy bedroom is highlighted by a spacious bed covered with a floral-patterned quilt. A ceiling fan provides air circulation, while a closet is accessible through a door on the right. Decorative wall art adds interest to the room’s neutral tones.
Apartment in Knoxville
4.95 out of 5 average rating, 22 reviews

Vintage Downtown Loft

Welcome to your cozy retreat in the heart of downtown Knoxville, Iowa. This thoughtfully furnished apartment sits just a flight of stairs above a local business, offering both privacy and convenience in one of the most walkable parts of town. Enjoy original architectural charm with modern updates—perfect for solo travelers, couples, or visiting professionals.

Popular amenities for Pleasantville holiday rentals