Holiday rentals 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.

Guest favourite

Guest house in Westwood

4.99 out of 5 average rating, 477 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.

20–27 Jul

$125 SGD per night
Guest favourite

Guest suite in Lenexa

4.91 out of 5 average rating, 118 reviews

Styled and cozy mid-century modern suite

Enjoy a stylish experience at this centrally-located place. This studio suite is a perfect launching point for your next adventure in the Kansas City area! Enjoy the local art on the walls and the cute kitchenette in our tucked away neighborhood. Since we live upstairs, you may hear us moving around; on weekdays we are often moving about between 6am-7am to get ready for school/ work. This space (12ft x 19ft) is simple yet elegant, everything you need kind of place. We can’t wait to host you!

20–27 May

$111 SGD per night
Guest favourite

Home in Kansas City

4.97 out of 5 average rating, 153 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.

8–15 Jul

$164 SGD per night

Popular amenities for Overland Park holiday rentals

Stay near Overland Park's top sights

Oak Park Mall66 locals recommend
Overland Park Convention Center3 locals recommend
Overland Park Arboretum & Botanical Gardens45 locals recommend
Prairiefire11 locals recommend
Topgolf33 locals recommend
Deanna Rose Children's Farmstead59 locals recommend

Other great holiday rentals in Overland Park

Guest favourite

Guest suite in Grandview

4.95 out of 5 average rating, 684 reviews

Luxury Suite » Rainfall Shower » Superior Mattress

7–12 Apr

$115 SGD per night
Guest favourite

Home in Lenexa

4.87 out of 5 average rating, 107 reviews

Vibrant remodeled 3 bedroom townhome

9–16 Sep

$183 SGD per night
Guest favourite

Apartment in Overland Park

4.9 out of 5 average rating, 134 reviews

The perfect destination in Kansas City!

15–22 Aug

$161 SGD per night
Guest favourite

Guest house in Kansas City

5.0 out of 5 average rating, 113 reviews

Coho (Cozy Boho) Carriage House, Near Plaza

14–21 Jun

$136 SGD per night
Guest favourite

Flat in Olathe

4.87 out of 5 average rating, 129 reviews

Olathe Friendly Airbnb

29 Aug – 5 Sep

$125 SGD per night
Guest favourite

Home in Liberty

4.95 out of 5 average rating, 259 reviews

Location! Upscale Historic home w/Chef’s Kitchen

29 Dec – 5 Jan

$140 SGD per night
Guest favourite

Bungalow in Westwood

4.95 out of 5 average rating, 395 reviews

Bungalow for Two or Three or Four or...

7–14 Aug

$144 SGD per night
Guest favourite

Guest suite in Overland Park

4.93 out of 5 average rating, 72 reviews

Private DayLight Basement, Own Entrance, 1800 s/f

8–15 Aug

$111 SGD per night
Guest favourite

Treehouse in Lenexa

4.94 out of 5 average rating, 70 reviews

Seven Oaks - Treehouse with deck

23–30 Nov

$187 SGD per night
Guest favourite

Guest house in Overland Park

4.9 out of 5 average rating, 10 reviews

Overland Park Poolside Guest House

12–19 Apr

$128 SGD per night
Guest favourite

Serviced apartment in Overland Park

4.94 out of 5 average rating, 96 reviews

1-bedroom 2nd floor suite— w/private entrance!

5–12 Jun

$90 SGD per night
Guest favourite

Flat in Lenexa

5.0 out of 5 average rating, 40 reviews

Home Away

19–26 Aug

$200 SGD per night

Quick stats about holiday rentals in Overland Park

Total rentals

660 properties

Rentals with dedicated workspaces

400 properties have a dedicated workspace

Rentals with a pool

60 properties have a pool

Pet-friendly rentals

250 properties allow pets

Family-friendly rentals

440 properties are a good fit for families

Total number of reviews

31K reviews

Destinations to explore

  1. Airbnb
  2. United States
  3. Kansas
  4. Johnson County
  5. Overland Park