Holiday houses in Overland Park

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Top-rated holiday rentals in Overland Park

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Guest favourite

Guesthouse in Westwood

4.99 out of 5 average rating, 544 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.

Guest favourite

Home in Prairie Village

4.97 out of 5 average rating, 191 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.

Guest favourite

Home in Kansas City

4.96 out of 5 average rating, 195 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.

Guest favourite

Home in Olathe

4.93 out of 5 average rating, 209 reviews

The Mulberry House: Cozy Home In Downtown Olathe

- Adorable house on large lot (not a guest house/cottage) -60 ft driveway - Separate bedroom with smart tv, queen size bed (comfy memory foam mattress) - Living room with 55" smart TV, leather sofa and additional seating - Fully equipped kitchen w/ eating area - Full bathroom w/ tub/shower - Washer/dryer - Table with leafs converts to great office area - Deck w/ outdoor seating and grill - 20 min from the Plaza, Westport and Downtown, 30 min from Lawrence, 40 min from the airport - $25 pet fee

Guest favourite

Home in Overland Park

4.94 out of 5 average rating, 101 reviews

Glenwood Getaway - Great Location + Pet Friendly

Discover the charm of Overland Park from the comfort of our cozy, updated ranch. Nestled in a quiet neighborhood within easy walking distance of downtown, this home allows you to experience the local lifestyle at its best. Our cozy home boasts two comfortable bedrooms and a modern bathroom, perfect for your getaway. The interior decor is charming, while still providing all the modern amenities for a comfortable stay. Unwind in the secluded 1/2 acre backyard. Your relaxing, cozy getaway awaits!

Guest favourite

Home in Overland Park

4.94 out of 5 average rating, 433 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.

Guest favourite

Home in Overland Park

4.95 out of 5 average rating, 370 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.

Guest favourite

Loft in Kansas City

4.97 out of 5 average rating, 141 reviews

Truman Loft

Truly one of a kind Historic property converted into a spacious, cozy loft in the heart of South KC. This 100-year-old space(5 min from HS Truman farm. He spoke on this stage on his first political campaign) has been completely rennovated with concrete countertops, beautifully vaulted ceilings, huge bathroom, built in workspace and even a fun kid's room. Let the natural light pour through the massive windows or close the curtains and dim the lights:) We hope you enjoy it as much as us!

Superhost

Guesthouse in Prairie Village

4.85 out of 5 average rating, 144 reviews

Prairie Village Modern Farmhouse! Great Location!

Enjoy your home away from home with style! This separate guest house has 1 bedroom & 1 bathroom that gives you privacy while still being centrally located in Prairie Village of Kansas City. Floor to ceiling shiplap walls, wood floors, black metal railing, & stylish decor you will feel like you're in an episode of Chip and Joanna Gaines' Fixer Upper! The home has its own private entrance, Washer/Dryer in unit and a fully functioning kitchen. High speed GooglFiber internet.

Guest favourite

Holiday home in Overland Park

4.92 out of 5 average rating, 108 reviews

Modern Space - Downtown Overland Park

Come and stay at a comfortable yet modern home that includes all of the amenities you could need. This memorable place is anything but ordinary, and we are always looking to beat expectations and go above and beyond for our guests. Centrally located in Downtown Overland Park - Food, coffee, bars, farmer’s markets, and shops are all within walking distance. 15 minutes from the plaza and downtown Kansas City, 25 minutes from Arrowhead stadium and MCI airport.

Guest favourite

Guest suite in Olathe

4.99 out of 5 average rating, 355 reviews

Secret Garden Short Stay

1 King Bed. 1 Twin roll away (plz req rollaway) Washer/Dryer for your personal use. Fast Wi-Fi Fiber. Sep. fenced off backyard area with Private entry 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 refrig if electricity goes out!!!

Guest favourite

Guest suite in Overland Park

4.98 out of 5 average rating, 129 reviews

Charming Basement Oasis

Pets- Dogs Only. Private basement suite with walk out entry, situated 1 mile from Historical Downtown Overland District. Within walking distance to South Lake Park. Basement suite is part of a single family home. The house is central air with thermostat located upstairs. Main level is occupied by residents & is separate from the basement suite. Suite includes full kitchen & laundry, full bathroom, walk in closet, one queen bed, & fold down sofa.