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.

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Top guest favourite
A spacious sleeping area features a queen-size bed dressed in soft linens and a blue sofa, along with a coffee table. A smart TV is mounted on the wall, and a desk is positioned in the adjacent office area, illuminated by natural light from nearby windows.
Home in Mission
4.93 out of 5 average rating, 384 reviews

The Little House: Cozy Home in Overland Park

- Adorable house on large lot (not a guest house/cottage) - 110 ft Driveway - Sleeping quarters with queen size bed (comfy memory foam mattress) - Living room with 40" smart TV, sofa-sleeper and additional seating - Fully equipped kitchen w/ eating area - Full bathroom w/ clawfoot tub/shower - Sunroom w/ seating area and daybed - Washer/dryer - Office area w/ desk - Deck w/ outdoor seating and grill - 10 min from the Plaza, 15 min from Westport and Downtown, 25 min from the airport - $25 pet fee

Guest favourite
A cozy living room is showcased with two brown leather sofas, a coffee table, and lamps on either side. A television is mounted on the wall opposite the seating. Natural light enters through two windows, while decorative items and plants add a welcoming touch.
Home in Olathe
4.83 out of 5 average rating, 105 reviews

Newly renovated - all amenities

Come and stay in our spacious & beautiful 1k sq ft apartment in the private, lower level of our home (we live upstairs). This space has been recently remodeled and has many sunny windows and great amenities for you. Our home is nestled in a popular Olathe neighborhood on a culture de sac that's known for safety and home town feeling. Guest have entire lower level to themselves. Host highly focused on great customer service and will always respond in a timely fashion to comments and questions

Guest favourite
A cozy living area showcases a comfortable armchair and a stylish ottoman atop a patterned rug. A modern kitchen with gray cabinetry and marble accents is visible in the background, enhancing the open layout. Natural light brightens the space through adjacent windows.
Flat in Overland Park
4.88 out of 5 average rating, 121 reviews

Stylish 1 bedroom, 1 bath custom apartment home

Completely remodeled, stylish apartment home in the heart of downtown Overland Park. Conveniently located 4 blocks from downtown Overland Park's entertainment district with many unique shops & restaurants. Walk across the street to Burg & Barrell for great food or a craft beer. Short walking distance to CVS Pharmacy, Hawaiian Bros, Dollar Tree, Metcalf Liquors & Price Chopper. Centrally located and only 15 minutes from The Country Club Plaza or Downtown Kansas City. *This is an upstairs unit.

Top guest favourite
A cozy sleeping area features a spacious bed with striped bedding and layers of soft blankets. A dark upholstered bench with textured throws sits at the foot of the bed. A bedside lamp provides soft lighting, and a decorative cabinet stands nearby.
Guest suite in Olathe
4.98 out of 5 average rating, 483 reviews

Secret Garden Short Stay

1 King Bed. 1 Twin air mattress rollaway (plz req rollaway) Washer/Dryer for your use. Wi-Fi Fiber. Sep. fenced backyard area with Priv. entry into your basemnt area that is located around the back of our main house. Parking space on prop. Dog park, walking trails. Pet fee is charged. Close to highwy, & shopping. We also have Solar panels that provide some back up for the heat/air and refrig. Entire daylight basement is separate from us upstairs with locked door. Does have couple of steps.

Guest favourite
A cozy living area is highlighted by a large wall mural featuring trees and soft light. A sectional sofa and an armchair provide comfortable seating. A small coffee table sits on a patterned area rug, while a television and a work desk are positioned nearby.
Home in Overland Park
4.94 out of 5 average rating, 539 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.

Top guest favourite
A dining area is featured with a wooden table surrounded by four chairs. A colorful piece of wall art adds interest to the room. Opposite, a wooden sideboard displays dinnerware, while an open doorway leads to a comfortable living area with a sofa.
Home in Overland Park
4.97 out of 5 average rating, 203 reviews

Glenwood Getaway - Great Location!

Experience the best of Overland Park from our charming, updated ranch. Nestled in a quiet neighborhood near downtown, this home allows you to experience the local lifestyle at its best. With two bedrooms, a modern bathroom and all the comforts of home, you will never want to leave! The interior blends cozy charm with contemporary amenities, while the secluded half-acre backyard is perfect for unwinding. Whether you’re here for a weekend escape or a longer stay, your perfect getaway awaits!

Guest favourite
A serene bedroom space is presented with soft, neutral tones. A spacious bed is dressed with white linens, accompanied by decorative pillows. Natural light filters through sheer curtains, with a floral pendant light hanging above. A cozy blanket is casually draped over the bed.
Home in Prairie Village
4.96 out of 5 average rating, 134 reviews

modern x charming 1930s farmhouse! 10 min plaza!

Step into our fully renovated 1930s farmhouse and be welcomed by natural light and an inviting open concept. The kitchen features beautiful marble countertops and all the essentials. Relax in the stunning black freestanding bathtub or dine al fresco on the spacious outdoor patio. With three cozy bedrooms, including two queen-size beds and one full-size bed, this home can accommodate up to six guests. Experience the perfect blend of old-world charm and modern convenience during your stay.

Top guest favourite
The spacious basement living area features wood-paneled ceilings and soft carpeting. A round dining table with wooden chairs is positioned beside a cozy seating area that includes a couch and an armchair. A TV is mounted on the wall, offering entertainment options.
Home in Overland Park
4.95 out of 5 average rating, 441 reviews

Entire Private Basement with Walkout Entrance

Private basement with two queen 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 will 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.

Top guest favourite
A living area features exposed brick walls complemented by wooden shelving. A dark leather sectional sofa is paired with a light-colored throw, while a contemporary coffee table occupies the center. Natural light filters in through large windows, illuminating potted plants.
Flat in Westside North
4.98 out of 5 average rating, 228 reviews

Historic, Industrial Flat in KC

Live the true Kansas-Citian lifestyle in this sparkling clean, and completely renovated 120-year-old brick beauty! Gorgeous hardwood floors, exposed brick walls, 10' island in the gorgeous chef's kitchen featuring gas cooktop and built-in oven/microwave. Spa-like bathroom with heated floors and rain shower head in the frameless glass shower. Spacious master bedroom with desk. Private rear deck and shared backyard. Walk minutes to KC's highlights: Crossroads, Street Car & Ferris Wheel!

Top guest favourite
The exterior of a charming studio guesthouse is presented, featuring a white façade with decorative white trim. Two large windows and a door with a small wreath add to the inviting look. A black vehicle is parked in front, surrounded by greenery.
Guest house in Overland Park
4.99 out of 5 average rating, 200 reviews

Studio Guest House

Enjoy Southern OP in this quiet neighborhood. Our studio guesthouse has a full kitchen, TV, a new a/c/heater, and google fiber internet. In case you get lonely, we have 2 friendly dogs always looking for attention. We are about 45 minutes away from the Kansas City airport, Kauffman Stadium, Arrowhead Stadium, the KU main campus, and the Harry S Truman sports complex. We are 10-15 minutes from the Scheels soccer complex. Overland Park has plenty of Kansas barbecue and shopping.

Guest favourite
A bright living area features a modern couch adorned with colorful cushions. A small chair and table occupy one corner, and large windows provide natural light, offering views outside. A patterned area rug adds warmth to the space, enhancing the minimalist decor.
Home in Kansas City
4.95 out of 5 average rating, 989 reviews

Minimalist Modern Strawberry Hill Get-Away Home

Entire, separate entry, second floor studio. Minimalist modern decor, nice clean small space with everything you need. We aim to have your stay be an enjoyable experience, greeting you with a clean home, ensuring you have what you need during the stay, and being available as needed. Approximately 5-10 from downtown KCMO, Power and Light, City Market. Within walking distance of a few local family owned restaurants and bars.

Top guest favourite
The main living space displays an open-concept layout with a modern farmhouse style. A cozy seating area features a rich brown sofa, while a dining table made of natural materials is surrounded by six chairs. The kitchen area is equipped with dark cabinetry and stainless-steel appliances.
Guest house in Shawnee
4.99 out of 5 average rating, 174 reviews

Vine & Petal - A Cottage Retreat

IG Handle: @vine_and_petal Ready to escape the hustle and bustle of the city without compromising on amenities? Join us at the Vine & Petal cottage retreat where we invite you to relax and unwind. We are conveniently located 3 minutes from I-435, 8 minutes from I-70, and 10 minutes from Legends Shopping Center including the Kansas Speedway and Sporting KC. Photographers send inquiries only.

Popular amenities for Overland Park holiday rentals

When is the best time to visit Overland Park?

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Frequently Asked Questions

  • Where should I stay in Overland Park?

    Make yourself at home in Overland Park by choosing from our most frequently booked neighborhoods. We have over 180 vacation rentals in Nottingham Forest, over 2,090 vacation rentals in Shawnee Mission, and over 300 vacation rentals in Oak Park.

  • Are there vacation rentals with a dedicated workspace in Overland Park?

    Yes! Work meets play with ease at over 420 vacation rentals in Overland Park featuring dedicated workspaces. Stay connected and productive in your home away from home.

  • Are there pet-friendly vacation rentals in Overland Park?

    Four-legged friends are welcome in Overland Park. Choose from more than 270 vacation rentals for guests traveling with pets.

  • Are there Overland Park vacation rentals on Airbnb with pools?

    Yes! Dive into the perfect getaway at one of over 60 vacation homes with pools in Overland Park, available on Airbnb. Make a splash and soak up the sun in style!

  • Do condo rentals in Overland Park have wifi?

    Absolutely! We offer over 10 condo rentals with wifi in Overland Park. Enjoy a tailored experience with all the comforts you desire.

  • Do house rentals in Overland Park have a bbq area?

    Absolutely! We offer over 110 house rentals with a bbq area in Overland Park. Enjoy a tailored experience with all the comforts you desire.

  • Do apartment rentals in Overland Park have a gym?

    Absolutely! We offer over 20 apartment rentals with a gym in Overland Park. Enjoy a tailored experience with all the comforts you desire.

  • How much does it cost to stay in townhouse rentals in Overland Park?

    Experience the best of Overland Park with our townhouse rentals, starting at about $40 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.

  • Are there family-friendly townhouse rentals in Overland Park?

    Overland Park has more than 40 family-friendly townhouse rentals. Amenities on the property may include high chairs, travel cribs, or strollers.

  • Do guesthouse rentals in Overland Park have air conditioning?

    Absolutely! We offer over 10 guesthouse rentals with air conditioning in Overland Park. Enjoy a tailored experience with all the comforts you desire.

Quick stats about holiday rentals in Overland Park

  • Total holiday rentals

    Explore 780 holiday rentals in Overland Park

  • Nightly prices starting at

    Overland Park holiday rentals start at £15 per night before taxes and fees

  • Verified guest reviews

    Over 47,940 verified reviews to help you choose

  • Family-friendly holiday rentals

    540 properties offer extra space & child-friendly amenities

  • Pet-friendly holiday rentals

    Find 300 rentals that welcome pets

  • Holiday rentals with a pool

    70 properties feature pools

  • Rentals with dedicated workspaces

    470 properties have a dedicated workspace

  • Wifi availability

    770 of Overland Park holiday rentals include wifi access

  • Popular amenities for guests

    Guests love Gym, BBQ grill and Laptop-friendly workspace across Overland Park rentals

  • 4.8 Average rating

    Overland Park stays are highly rated by guests – averaging 4.8 out of 5!

Destinations to explore

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