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 a turquoise coverlet, complemented by decorative pillows. Natural light floods through a nearby window covered with light curtains. A wooden dresser and bedside table add warmth to the room, while framed artwork enhances the decor.
Guest house in Westwood
4.99 out of 5 average rating, 675 reviews

Westwood cottage in garden setting

This 400 sq. ft. guesthouse (studio) on a historic property in Westwood, KS 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 kitchenette. 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.

Top guest favourite
A private pool surrounded by a diamond cut concrete patio is visible. Lounge chairs and an umbrella provide shaded seating. The backyard is enclosed by a privacy fence, with the house in the background featuring multiple windows and a deck access.
Home in Overland Park
4.96 out of 5 average rating, 153 reviews

Luxury 4BR Oasis w/ Private Pool – Top Rated

World Cup–ready 4-bedroom home with heated private pool, ideal for families and professionals. Comfortably sleeps up to 10 guests and is a great home base for out-of-town visitors attending World Cup matches or watching the games during downtime. Located in a desirable neighborhood close to dining, shopping, and golf. Features 4 bedrooms (2 en suite), 3.5 baths, a fully equipped kitchen, large laundry room, and two living spaces. Pool open early April–late Sept/early Oct, weather permitting.

Top guest favourite
A bright living room features a comfortable leather sectional couch and two circular coffee tables. Natural light floods in through large windows adorned with dark curtains. Exposed wooden beams add character to the ceiling, while a modern TV is mounted on the wall.
Home in Overland Park
4.94 out of 5 average rating, 161 reviews

Room to Spread Out • Central Overland Park

3 King Size Beds, 1 Bunk Bed (Full & Twin Size) 6 Smart TVs, Driveway Parking, Washer & Dryer, oversized backyard w/ patio, batting cage & swing set. *15 Minutes to Downtown KC, Country Club Plaza, Crown Center! *23 Min to Chiefs & Royals stadiums. *5 Minutes to Downtown Overland Park ft. restaurants, farmers market, bars & more! Main Level: + Open living room + Updated kitchen & dining + 3 bedrooms & full bath Lower Level: + Second living area + 1 bedroom & full bath + Wet bar + mini fridge

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, 500 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 modern sofa adorned with decorative pillows. A flat-screen television is mounted above a sleek fireplace, where flickering flames create a warm ambiance. Light filters through window treatments, enhancing the inviting atmosphere.
Home in Prairie Village
4.91 out of 5 average rating, 100 reviews

Modern Prairie Village Home

Nestled in the heart of Prairie Village, this delightful home was recently remodeled and is equipped with everything you need for the perfect stay. Enjoy luxury mattresses in the two bedrooms which are both equipped with TVs. Cozy up next to the fireplace with your favorite book or watch a movie on the living room tv. Play a round of foosball or shuffle board with the game on while your favorite dish is smoking in the Traeger outside. Walk to the Shops of Prairie Village within minutes.

Top guest favourite
Home in Fairway
5 out of 5 average rating, 120 reviews

Prestige-Stunning Home W/Game Room+ Mins to Plaza

⭐ Fully renovated 3BR home in Fairway, KS — minutes from KC attractions ⭐ Main-level primary suite with spa-style en-suite bath + clawfoot tub ⭐ Open-concept kitchen with quartz counters + full coffee bar ⭐ Cozy living room with gas fireplace + Smart TV ⭐ Upstairs game room with Xbox + lounge space ⭐ Private office, exercise area, and landscaped backyard ⭐Conveniently located less than 5 minutes from The Shops of Prairie Village and roughly 10 minutes from the Country Club Plaza!

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, 214 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
The living area features a vaulted ceiling with natural light streaming through large windows. A cozy sofa sits over a colorful rug, with a modern armchair nearby. A wall-mounted TV is positioned above a stylish fireplace, complemented by dining and seating areas in the background.
Home in Lenexa
4.87 out of 5 average rating, 196 reviews

Vibrant remodeled 3 bedroom townhome

Newly remodeled vibrant and stylish townhome. Featuring 3 bedrooms and 1 bathroom. Fully equipped kitchen, onsite washer/dryer, smart TVs, high speed WiFi with streaming abilities, coffee bar, grill, outdoor patio with seating, and access to 4 neighborhood outdoor pools(seasonal - typically Memorial Day thru Labor Day), tennis courts, and other amenities. Located in a safe and quiet neighborhood in Lenexa with easy access to both interstate I35 and I435.

Top guest favourite
A bright living area features large windows that provide views of greenery and the outdoors. A cozy sofa is positioned across from a small table, with a light-furniture accent chair nearby. Soft lighting enhances the space, creating a relaxed atmosphere.
Guest suite in Downtown Kansas City
4.97 out of 5 average rating, 190 reviews

Warm & Curated Retreat, New Build Carriage House

🪴🛌 Your space: the coizest apartment, thoughtfully designed to be where you want to rest and recharge. 🚶🏡 The neighborhood: Martini Corner is a block away w great food, including new Noka, Japanese farm-to-table spot. Local roasting coffee shops Filling Station & Billies Groceries are short walks. 🚙 🚗 Central location: CROWN CENTER - 3 min drive POWER & LIGHT DISTRICT - 5 min PLAZA - 8 min ARROWHEAD & KAUFFMAN STADIUM - 12 min

Guest favourite
A cozy living area is presented with a blend of textures and colors. A comfortable brown leather sofa and armchairs are arranged around a central rug. A television is mounted on the wall above a fireplace, and a wall art piece adds character.
Townhouse in Crestview
4.91 out of 5 average rating, 117 reviews

Upscale Mission 3BR•Patio•10 Min to Downtown KC

Relax in this stylish 3BR Kansas City townhome, perfect for couples, families, or remote work. Features a King DreamLux King bed, fully equipped kitchen, cozy fireplace, private patio with BBQ, and blazing-fast Gigabit Wi-Fi. Centrally located in a quiet, safe neighborhood, you're just minutes from The Plaza and downtown. Comfortably sleeps 8. Secure, keyless entry and driveway parking spots for 2 cars.

Superhost
A spacious living room is presented with a large smart TV mounted on a wooden entertainment unit. Comfortable leather seating surrounds a stylish coffee table. Sliding glass doors provide natural light and a view of the outdoor deck, enhancing the living area.
Townhouse in Overland Park
4.83 out of 5 average rating, 107 reviews

Comfortable Clean home*central location*

relaxing, clean and nicely decorated. It features 3 bedrooms 2 Full Bathroom with all new mattresses, freshly laundered linens, nicely stocked kitchen, everything you need for a great relaxing stay Conveniently location near highways for easy access to anywhere KC offers! .very close Oak Park Mall. 14min to downtown, P&L district best restaurants, coffee shops and grocery store near by

Guest favourite
A cozy living room showcases a gray sofa complemented by an orange armchair and a checked blue-and-white armchair. Natural light streams through large windows, illuminating a patterned area rug and decorative wall pieces. A flat-screen TV is mounted on the wall opposite the seating.
Home in Overland Park
4.93 out of 5 average rating, 136 reviews

~Great Location | Game Room | Easy Self Check-in~

This beautifully updated and decorated home is perfect for families, couples getaway or business professionals. Complete with 2 living room spaces and a game room, it is sure to entertain the whole family. You will be centrally located just minutes from Overland Park's historic downtown area as well as The Prairie Village Shops with an array of dining options, shopping and activities.

Popular amenities for Overland Park holiday rentals

When is the best time to visit Overland Park?

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Frequently Asked Questions

  • What are the best places to stay in Overland Park?

    Stays in central Overland Park, near green spaces or shopping areas, are often recommended for visitors. Suburban neighborhoods feature spacious accommodations for families and groups, with easy access to parks and local dining.

  • What are the best things to do in Overland Park with kids?

    Kids enjoy exploring the Overland Park Arboretum and Botanical Gardens, interactive museums, and hands-on science centers. Playgrounds, splash parks, and seasonal events around neighborhoods provide family-friendly fun.

  • What are some of the best things to do in Overland Park?

    Stroll gardens at the Overland Park Arboretum and Botanical Gardens, browse local art galleries, and visit suburban parks for outdoor recreation. Historic markets and seasonal festivals add to the city’s cultural scene.

  • How is the weather in Overland Park?

    Overland Park sees cold winters around 20–38°F (-7–4°C) and warm summers near 88°F (31°C), with rainfall peaking in spring and early summer. Layered clothing and rain gear are useful, especially from March to June.

  • When is the best time to visit Overland Park?

    Late spring and early autumn have milder temperatures, blooming gardens, and frequent community events. Summer is often popular for outdoor activities, though afternoons can be warm and humid.

  • What are the best places to visit in Overland Park?

    Explore the Overland Park Arboretum and Botanical Gardens, stroll through downtown galleries, or relax at neighborhood parks. Locally-run restaurants and community markets round out popular spots.

  • What are some hiking trails in Overland Park?

    Wander pathways in the Overland Park Arboretum and Botanical Gardens, stroll through local parks, or follow nature trails along wooded creeks. These spaces have loops and easy walking routes accessible for many visitors.

  • What are some family activities we can do in Overland Park?

    Families frequently explore the Overland Park Arboretum and Botanical Gardens, visit interactive science centers, or enjoy playgrounds in local parks. Seasonal festivals and farmers markets add variety to family outings.

  • What are some of the best day trip ideas from Overland Park?

    Day trips often include exploring Kansas City’s museums or public markets, venturing to state parks for hiking, and visiting nearby historic towns for local shopping and arts. Seasonal outdoor recreation can be found around lakes and trails.

  • Are there any pet friendly accommodations available in Overland Park?

    Many stays near Overland Park's parks and residential neighborhoods welcome pets. The city has dog-friendly outdoor spaces, making it easy to explore with your companion.

  • What are some local tips for visiting Overland Park?

    Locals often suggest visiting parks during weekdays for quieter walks, bringing water on hot summer days, and reserving spots early for busy restaurants. Farmers markets and outdoor events draw crowds, so arrive early to enjoy them.

  • What is Overland Park known for?

    Overland Park is known for its botanical gardens, vibrant arts scene, and family-friendly attractions. The city has extensive green spaces and is recognized for community festivals and local dining.

  • What are the best hidden gems to explore in Overland Park?

    Explore neighborhood art galleries, small coffee shops, and local parks that are tucked away from busy areas. Family-owned restaurants and gardens around suburban sections often surprise visitors with unique experiences.

  • What are the best foods to try in Overland Park?

    Overland Park has a mix of classic barbecue, Kansas City-style steaks, and locally inspired comfort food. International cuisines, fresh baked goods, and seasonal produce are frequently suggested by locals.

  • What should I bring for a trip to Overland Park?

    Pack layers to adapt to variable weather, as temperatures range from 20°F (-7°C) in winter to 88°F (31°C) in summer. Bring comfortable shoes for parks and attractions, plus an umbrella for spring and early summer rain.

  • What is the nightlife in Overland Park like?

    Nightlife in Overland Park blends laid-back lounges, craft breweries, and late-night restaurants, mostly centered around the downtown area. Live music and casual venues are often recommended for an evening out.

  • What are the most popular events or festivals in Overland Park?

    Overland Park frequently hosts art fairs, seasonal farmers markets, and community festivals, particularly in late spring and early autumn. The area is also known for music and food events around downtown and local parks.

  • Are there family friendly vacation rentals in Overland Park?

    Overland Park has many vacation rentals in welcoming neighborhoods, often featuring amenities like multiple bedrooms, kitchens, and outdoor spaces. Areas around parks and near major attractions make it easy to enjoy family activities.

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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