Holiday houses in Overland Park

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Top-rated holiday rentals in Overland Park

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

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Guest favourite

Guesthouse in Westwood

4.99 out of 5 average rating, 484 reviews

Westwood cottage in garden setting

This 400 sq. ft. guesthouse (studio) on a historic property in Westwood, Kansas has recently been fully renovated and furnished. It has a completely equipped kitchenette, comfortable living area, along with a queen-size bed. The guesthouse also includes a washer/dryer off the kitchen. The guesthouse is a separate dwelling located on a half an acre property which includes the original farmhouse built in 1889 - the guesthouse added in 1920. Westwood, Kansas is 2 miles from the Country Club Plaza.

9–16 Feb

$173 NZD per night

Guest favourite

Home in Prairie Village

4.98 out of 5 average rating, 153 reviews

Prairie Village - 3 bed 2 bath - Dogs Welcome

Enjoy the clean, cozy, cute, and quaint style of this three bedroom two bath home just minutes from the best of Kansas City. The home is fully outfitted and ready for your stay. A few courtesies you may appreciate are 1 gig fiber internet, 42” TV, kitchen utensils, pots, pans, other kitchen supplies, coffee, ironing board, iron, basic over the counter meds, basic toiletries, bottles of water, first aid kit, phone chargers, a few snacks, and even a small sample of libations made in Kansas City.

30 Aug – 6 Sep

$305 NZD per night

Guest favourite

Home in Kansas City

4.97 out of 5 average rating, 159 reviews

Charming Waldo Reader's Retreat

When my husband & I first saw this house, I knew it was the perfect place to escape to do my favorite thing - read. I designed it with that in mind. I could see myself reading in front of the wood-burning stove. Reading on the martini deck with coffee in hand. Reading in the afternoon light in the loft or outside on the deck. Located in the heart of Waldo, walking distance to restaurants, bakeries and bars. Brookside/Plaza are minutes away. I hope you love it as much as I do, I know you will.

28 Sep – 5 Oct

$238 NZD per night

Guest favourite

Home in Overland Park

4.94 out of 5 average rating, 384 reviews

Convenient Overland Park cottage on quiet street

Come relax in this 2 bed/2 bath cottage and enjoy the privacy of an 800 sq foot single family home. Master has queen bed and it's own private bath. 2nd bedroom has a queen bed. A queen size aerobed mattress is provided for extra sleeping room. Has a 50" flat screen TV equipped with Netflix/DVD player. Kitchen has granite counters and is fully stocked to make any great meal. Dining table seats 4 and kitchen seats another 3. Backyard with fire-pit. Pets welcome. Yard is only partially fenced.

26 Aug – 2 Sep

$338 NZD per night

Guest favourite

Home in Overland Park

4.95 out of 5 average rating, 342 reviews

Entire Private Basement with Walkout Entrance

Private basement with two beds, couch, memory foam cot or air mattress (upon request), full bathroom, washer/dryer, coffee maker, toaster, microwave, snacks, mini fridge (no freezer), table, WiFi, and a TV (Roku and antenna). We will be upstairs during your stay. We are not loud but you may be able to hear us walk around upstairs. There is a walkout door to backyard. You will be able to park in the driveway. Walkway to gate located on east side of house. Walkway to backyard is well lit.

12–19 Oct

$156 NZD per night

Superhost

Home in Mission

4.9 out of 5 average rating, 435 reviews

Charming Vintage Bungalow. Business Ready!

You will feel right at home in this cozy bungalow. This is a 2 Bedroom, 1 Bath with fully equipped kitchen, dining and living area, mudroom with coffee station and laundry area. 1 Bedroom located upstairs. Centrally Located convenient to the Plaza/Midtown area, Power and Light District or enjoy the Quaint downtown Overland Park area. Ikea is only a short 5 min drive, we are close to everything! Nice, Safe Neighborhood. Park like setting backyard with walking trail next to house.

18–25 Jul

$236 NZD per night

Guest favourite

Guesthouse in Kansas City

5.0 out of 5 average rating, 118 reviews

Coho (Cozy Boho) Carriage House, Near Plaza

Come experience this century old, newly renovated carriage house right in the heart of Kansas City! With extremely close proximity to the city’s favorite destinations, this historic abode will help make your stay convenient and cozy. Locations and their distances from where you'll be: - The Nelson-Atkins Museum - 1.6 Miles - The Plaza - 1.7 Miles - Kansas City Zoo - 4 Miles - Union Station - 4.6 Miles - Downtown - 5.1 Miles - Chiefs & Royals Stadiums - 5.6 Miles

12–19 Jun

$207 NZD per night

Guest favourite

Guest suite in Olathe

5.0 out of 5 average rating, 275 reviews

Secret Garden’s Short Stay

1 King Bed. 1 Twin roll away (plz req rollaway) Washer/Dryer for your personal use. Fast Wi-Fi Fiber. Separate fenced off backyard area with Private entrance into your Basement area that is located around the back of the main house. Parking space on property. Dog park, walking trails. Restaurants close by. Close to highwy, gas stations and shopping. We also have Solar panels that provide some back up for the heat/air and refrigerator if electricity goes out!!!

6–13 Mar

$199 NZD per night

Guest favourite

Apartment in Westwood

4.99 out of 5 average rating, 183 reviews

Perfectly Located Carriage House Apartment

1 BR loft apartment in centrally located Westwood. Walk to restaurants, groceries, and shops, including Joe's KC BBQ and LuLu's. Close to Plaza, Westport, and downtown/crossroads. Pets ONLY considered for week long stays and longer. As always, the apartment will be spotlessly clean using disinfectant and bleach-based cleaners. We will block 24 hours between stays to ensure the apartment has fully circulated. Virus-grade HVAC filters have also been installed.

23–30 Sep

$160 NZD per night

Guest favourite

Home in Grandview

4.99 out of 5 average rating, 218 reviews

Midcentury LUXE—Firepit, Garage, Spa-like Bathroom

Come & enjoy this luxurious, mid-century modern home, complete with your favorite amenities. The home is a ranch-styled duplex, nestled in a quiet neighborhood 20 minutes from downtown Kansas City. Your space includes a private entrance to 3 bedrooms, a modernized walk-in shower, living room, fully equipped kitchen, dining area, and garage parking. You'll also get a spacious, fenced backyard oasis with a fire pit!

$166 NZD per night

Guest favourite

Cottage in Kansas City

4.97 out of 5 average rating, 329 reviews

Cheerful 2-bedroom cottage

Cheerful 2-bedroom cottage four miles from stadiums with free parking on premises. Family friendly with country feeling close to the city. Newly remodeled bathroom with walk in shower. Large kitchen with separate dinning area. New refrigerator with ice and water through the door. New dishwasher plus new countertops and sink. Just installed recently.

3–10 Feb

$206 NZD per night

Guest favourite

Home in Overland Park

4.89 out of 5 average rating, 369 reviews

Marty's Retreat 1 block to downtown Overland Park

Another Quality Home Spot Retreat! Completely updated ranch home in an established tree-lined neighborhood. Short walk to the local Farmers Market, restaurants, sports bars, bakeries, coffee shop, liquor store & more. Many delivery choices. Just park at the front door and walk inside.

1–8 Oct

$300 NZD per night