Leawood Holiday Rentals
Apartment
- Kansas City
- ·
- South Kansas City
- 4.50 mi to center
10.0Exceptional
(10 Reviews)
2 Bedrooms
1 Bath
5 Guests
Parking
Kitchen
Air Conditioner
Internet
US $81/Night
7 Nights - US $568
House
- Kansas City
- ·
- Nall Hills
- 0.43 mi to center
10.0Exceptional
(1 Review)
3 Bedrooms
2 Baths
9 Guests
1302.43 ft²
- Parking
- Air Conditioner
- Internet
Child Friendly
US $236/Night
7 Nights - US $1,650
Apartment
- Kansas City
- ·
- Overland Park
- 4.17 mi to center
9.2Exceptional
(1180 Reviews)
1 Bedroom
1 Bath
2 Guests
- Parking
Balcony/Terrace- Kitchen
- Air Conditioner
US $140/Night
7 Nights - US $979
Apartment
- Kansas City
- ·
- Overland Park
- 7.15 mi to center
10.0Exceptional
(1 Review)
2 Bedrooms
2 Baths
5 Guests
- Child Friendly
US $486/Night
7 Nights - US $3,399
House
- Kansas City
- ·
- South Kansas City
- 5.80 mi to center
3 Bedrooms
3 Baths
6 Guests
3003.13 ft²
Oceanfront- Parking
Pool
Ocean View
US $3,049/Night
7 Nights - US $21,340
Apartment
- Kansas City
- ·
- Overland Park
- 7.15 mi to center
1 Bedroom
1 Bath
2 Guests
614 ft²
- Kitchen
- Air Conditioner
- Internet
- Child Friendly
US $196/Night
7 Nights - US $1,372
Apartment
- Kansas City
- ·
- Overland Park
- 7.15 mi to center
1 Bedroom
1 Bath
2 Guests
850 ft²
- Balcony/Terrace
- Kitchen
- Air Conditioner
- Internet
US $176/Night
7 Nights - US $1,230
Apartment
- Kansas City
- ·
- Overland Park
- 3.50 mi to center
10.0Exceptional
(2 Reviews)
1 Bedroom
1 Bath
4 Guests
- Parking
- Pool
- Kitchen
- Air Conditioner
US $156/Night
7 Nights - US $1,092
Apartment
- Kansas City
- ·
- Overland Park
- 3.55 mi to center
10.0Exceptional
(1 Review)
1 Bedroom
1 Bath
4 Guests
- Parking
- Pool
- Kitchen
- Air Conditioner
US $168/Night
7 Nights - US $1,176
Luxury Holiday Rentals in Leawood
Over 141+ Luxury Holiday Rentals in or Near Leawood
House
- Kansas City
- ·
- Leawood
- 3.06 mi to center
6 Bedrooms
6 Baths
12 Guests
- Air Conditioner
- Internet
- Child Friendly
Laundry
Unlock the Best Price
House
- Kansas City
- ·
- Leawood
- 3.42 mi to center
10.0Exceptional
(5 Reviews)
6 Bedrooms
6 Baths
12 Guests
Private Pool
Hot Tub- Parking
- Pool
US $1,747/Night
7 Nights - US $12,226
House
- Kansas City
- ·
- South Kansas City
- 5.50 mi to center
4 Bedrooms
2 Baths
7 Guests
- Parking
- Kitchen
- Air Conditioner
- Internet
US $753/Night
7 Nights - US $5,273
House
- Kansas City
- ·
- Prairie Village
- 2.43 mi to center
10.0Exceptional
(1 Review)
1 Bedroom
3 Baths
12 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $679/Night
7 Nights - US $4,756
Hotel
- Kansas City
- ·
- Overland Park
- 4.26 mi to center
8.8Fabulous
(1001 Reviews)
1 Bath
Breakfast- Parking
- Balcony/Terrace
- Kitchen
US $627/Night
7 Nights - US $4,391
House
- Kansas City
- ·
- South Kansas City
- 5.80 mi to center
10.0Exceptional
(3 Reviews)
3 Bedrooms
2 Baths
6 Guests
3000 ft²
- Private Pool
- Parking
- Pool
- Ocean View
US $562/Night
7 Nights - US $3,933
House
- Kansas City
- ·
- Leawood
- 4.06 mi to center
4 Bedrooms
3 Baths
8 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $515/Night
7 Nights - US $3,603
New
House
- Kansas City
- ·
- Overland Park
- 3.87 mi to center
10.0Exceptional
(15 Reviews)
4 Bedrooms
2 Baths
8 Guests
- Air Conditioner
- Internet
- Child Friendly
- Laundry
US $477/Night
7 Nights - US $3,340
Apartment
- Kansas City
- ·
- Overland Park
- 7.15 mi to center
3 Bedrooms
2 Baths
6 Guests
1464 ft²
- Balcony/Terrace
- Kitchen
- Air Conditioner
- Internet
US $425/Night
7 Nights - US $2,978
Top-Rated Holiday Rentals with a Pool in Leawood
Over 58+ The Best Private Villas and Holiday Rentals in Leawood with a Pool
Apartment
- Kansas City
- ·
- Overland Park
- 3.65 mi to center
10.0Exceptional
(1 Review)
1 Bedroom
1 Bath
4 Guests
- Parking
- Pool
- Kitchen
- Air Conditioner
US $150/Night
7 Nights - US $1,051
Hotel
- Kansas City
- ·
- Overland Park
- 3.78 mi to center
9.6Exceptional
(1156 Reviews)
1 Bath
- Hot Tub
- Breakfast
- Parking
- Pool
US $151/Night
7 Nights - US $1,060
Hotel
- Kansas City
- ·
- Leawood
- 1.83 mi to center
9.4Exceptional
(344 Reviews)
1 Bath
- Breakfast
- Parking
- Pool
- Balcony/Terrace
US $142/Night
7 Nights - US $992
Hotel
- Kansas City
- ·
- Overland Park
- 3.98 mi to center
9.2Exceptional
(1005 Reviews)
1 Bath
- Hot Tub
- Breakfast
- Parking
- Pool
US $222/Night
7 Nights - US $1,557
Hotel
- Kansas City
- ·
- Prairie Village
- 3.18 mi to center
9.2Exceptional
(697 Reviews)
1 Bath
- Breakfast
- Parking
- Pool
- Kitchen
US $149/Night
7 Nights - US $1,045
Hotel
- Kansas City
- ·
- Overland Park
- 3.76 mi to center
9.2Exceptional
(650 Reviews)
15 Baths
350.9 ft²
- Hot Tub
- Parking
- Pool
- Kitchen
US $121/Night
7 Nights - US $849
Hotel
- Kansas City
- ·
- Leawood
- 1.81 mi to center
9.2Exceptional
(45 Reviews)
8 Baths
450.74 ft²
- Private Pool
- Oceanfront
EV Charge Station- Parking
US $191/Night
7 Nights - US $1,339
Hotel
- Kansas City
- ·
- Prairie Village
- 3.16 mi to center
9.1Exceptional
(92 Reviews)
12 Baths
372.25 ft²
- Private Pool
- Parking
- Pool
- Air Conditioner
US $187/Night
7 Nights - US $1,306
Hotel
- Kansas City
- ·
- Overland Park
- 3.92 mi to center
9.0Exceptional
(1010 Reviews)
1 Bath
- Breakfast
- Parking
- Pool
- Kitchen
US $136/Night
7 Nights - US $953
Pet-Friendly Holiday Rentals in Leawood
Over 54+ Pet-Friendly Holiday Rentals in or Near Leawood
Apartment
- Kansas City
- ·
- Overland Park
- 3.47 mi to center
1 Bedroom
1 Bath
4 Guests
- Parking
- Pool
- Kitchen
- Air Conditioner
US $247/Night
7 Nights - US $1,726
Hotel
- Kansas City
- ·
- Overland Park
- 4.17 mi to center
9.0Exceptional
(473 Reviews)
14 Baths
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $149/Night
7 Nights - US $1,043
Apartment
- Kansas City
- ·
- Overland Park
- 3.46 mi to center
1 Bedroom
1 Bath
6 Guests
- Parking
- Pool
- Kitchen
- Air Conditioner
US $220/Night
7 Nights - US $1,538
Hotel
- Kansas City
- ·
- Overland Park
- 4.25 mi to center
8.6Fabulous
(331 Reviews)
5 Baths
372.43 ft²
- Oceanfront
- Parking
- Pool
- Ocean View
US $149/Night
7 Nights - US $1,044
Apartment
- Kansas City
- ·
- Overland Park
- 3.53 mi to center
1 Bedroom
1 Bath
4 Guests
- Parking
- Pool
- Kitchen
- Air Conditioner
US $179/Night
7 Nights - US $1,256
Apartment
- Kansas City
- ·
- Overland Park
- 3.31 mi to center
1 Bedroom
1 Bath
4 Guests
- Parking
- Pool
- Kitchen
- Air Conditioner
US $150/Night
7 Nights - US $1,051
House
- Kansas City
- ·
- Overland Park
- 4.57 mi to center
9.8Exceptional
(70 Reviews)
4 Bedrooms
3 Baths
8 Guests
4400 ft²
- Parking
- Ocean View
- Balcony/Terrace
View
US $357/Night
7 Nights - US $2,502
House
- Kansas City
- ·
- South Kansas City
- 5.61 mi to center
3 Bedrooms
2 Baths
6 Guests
- Parking
- Kitchen
- Air Conditioner
- Internet
US $147/Night
7 Nights - US $1,027
New
Apartment
- Kansas City
- ·
- Overland Park
- 4.19 mi to center
10.0Exceptional
(3 Reviews)
1 Bedroom
1 Bath
4 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $284/Night
7 Nights - US $1,988
Large Holiday Rentals and Private Villas in Leawood
Over 15+ Large Holiday Rentals and Private Villas in or Near Leawood
House
- Kansas City
- ·
- Leawood
- 5.20 mi to center
4 Bedrooms
3 Baths
10 Guests
2000 ft²
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $186/Night
7 Nights - US $1,302
House
- Kansas City
- ·
- Leawood
- 2.95 mi to center
6 Bedrooms
6 Baths
14 Guests
- Hot Tub
- Air Conditioner
- Internet
- Laundry
Unlock the Best Price
House
- Kansas City
- ·
- Leawood
- 4.15 mi to center
6 Bedrooms
5 Baths
15 Guests
- Air Conditioner
- Internet
- Laundry
Bedding/Linens
US $3,089/Night
7 Nights - US $21,625
Villa
- Kansas City
- ·
- Leawood
- 1.70 mi to center
3 Bedrooms
3 Baths
7 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $1,943/Night
7 Nights - US $13,600
House
- Kansas City
- ·
- South Kansas City
- 4.67 mi to center
5 Bedrooms
3 Baths
14 Guests
- Hot Tub
- Parking
- Pool
- Kitchen
US $1,292/Night
7 Nights - US $9,044
House
- Kansas City
- ·
- Leawood
- 4.98 mi to center
5 Bedrooms
3 Baths
8 Guests
4500 ft²
- Private Pool
- Parking
- Pool
- Balcony/Terrace
US $1,286/Night
7 Nights - US $9,005
House
- Kansas City
- ·
- South Kansas City
- 3.39 mi to center
4 Bedrooms
3 Baths
12 Guests
- Kitchen
- Air Conditioner
- Internet
Pet Friendly
US $969/Night
7 Nights - US $6,785
House
- Kansas City
- ·
- Leawood
- 3.85 mi to center
5 Bedrooms
4 Baths
12 Guests
- Private Pool
- Parking
- Pool
- Kitchen
US $422/Night
7 Nights - US $2,957
House
- Kansas City
- ·
- Leawood
- 3.59 mi to center
5 Bedrooms
7 Baths
15 Guests
- Air Conditioner
- Internet
- Laundry
- Bedding/Linens
US $2,728/Night
7 Nights - US $19,093
Wheelchair Accessible Holiday Homes in Leawood
Over 43+ Wheelchair Accessible Holiday Homes in or Near Leawood
New
Apartment
- Kansas City
- ·
- Prairie Village
- 3.21 mi to center
10.0Exceptional
(2 Reviews)
1 Bedroom
1 Bath
2 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $276/Night
7 Nights - US $1,932
Hotel
- Kansas City
- ·
- Overland Park
- 6.96 mi to center
9.0Exceptional
(76 Reviews)
1 Bath
322.92 ft²
- Parking
- Pool
- Air Conditioner
- Internet
US $98/Night
7 Nights - US $686
Hotel
- Kansas City
- ·
- Overland Park
- 4.04 mi to center
9.0Exceptional
(1009 Reviews)
1 Bath
- Breakfast
- Parking
- Pool
- Balcony/Terrace
US $144/Night
7 Nights - US $1,011
New
Apartment
- Kansas City
- ·
- Prairie Village
- 3.18 mi to center
9.4Exceptional
(6 Reviews)
1 Bedroom
1 Bath
4 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $252/Night
7 Nights - US $1,761
Hotel
- Kansas City
- ·
- Overland Park
- 6.80 mi to center
8.8Fabulous
(235 Reviews)
9 Baths
322.92 ft²
- Private Pool
- Hot Tub
- Breakfast
- Parking
US $98/Night
7 Nights - US $688
Apartment
- Kansas City
- ·
- Prairie Village
- 3.19 mi to center
10.0Exceptional
(2 Reviews)
1 Bedroom
1 Bath
4 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $154/Night
7 Nights - US $1,078
Apartment
- Kansas City
- ·
- Prairie Village
- 3.19 mi to center
5 Bedrooms
5 Baths
16 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $470/Night
7 Nights - US $3,292
House
- Kansas City
- ·
- Overland Park
- 3.93 mi to center
1 Bedroom
2 Baths
3 Guests
- Hot Tub
- Kitchen
- Air Conditioner
- Child Friendly
US $261/Night
7 Nights - US $1,827
House
- Kansas City
- ·
- Overland Park
- 4.31 mi to center
1 Bedroom
1 Bath
3 Guests
291 ft²
- Hot Tub
- Pool
- Air Conditioner
- Internet
US $215/Night
7 Nights - US $1,505
Leawood Private Villas and Holiday Homes Under $200
Over 63+ Leawood Private Villas and Holiday Homes Under $200
House
- Kansas City
- ·
- South Kansas City
- 5.07 mi to center
3 Bedrooms
2 Baths
6 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $192/Night
7 Nights - US $1,342
Hotel
- Kansas City
- ·
- Overland Park
- 5.53 mi to center
8.9Fabulous
(190 Reviews)
9 Baths
409.03 ft²
- Private Pool
- Oceanfront
- Pool
- Ocean View
US $164/Night
7 Nights - US $1,148
Hotel
- Kansas City
- ·
- Overland Park
- 5.53 mi to center
9.0Exceptional
(1005 Reviews)
1 Bath
- Breakfast
- Parking
- Pool
- Balcony/Terrace
US $127/Night
7 Nights - US $887
House
- Kansas City
- ·
- Overland Park
- 3.58 mi to center
3 Bedrooms
2 Baths
5 Guests
- Air Conditioner
- Internet
- Child Friendly
- Laundry
US $147/Night
7 Nights - US $1,029
Hotel
- Kansas City
- ·
- Overland Park
- 4.02 mi to center
8.6Fabulous
(260 Reviews)
8 Baths
398.26 ft²
- Oceanfront
- Breakfast
- Parking
- Pool
US $127/Night
7 Nights - US $889
House
- Kansas City
- ·
- South Kansas City
- 5.64 mi to center
3 Bedrooms
2 Baths
5 Guests
1500 ft²
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $96/Night
7 Nights - US $674
New
Condo
- Kansas City
- ·
- Leawood
- 0.85 mi to center
3 Bedrooms
2 Baths
6 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $131/Night
7 Nights - US $918
Apartment
- Kansas City
- ·
- South Kansas City
- 5.45 mi to center
10.0Exceptional
(8 Reviews)
1 Bedroom
1 Bath
4 Guests
- Kitchen
- Air Conditioner
- Internet
- Laundry
US $147/Night
7 Nights - US $1,030
House
- Kansas City
- ·
- South Kansas City
- 4.65 mi to center
8.6Fabulous
(18 Reviews)
2 Bedrooms
1 Bath
4 Guests
1800 ft²
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $132/Night
7 Nights - US $923
Instantly Bookable Holiday Homes in Leawood
Over 36+ Instantly Bookable Holiday Homes in or Near Leawood
House
- Kansas City
- ·
- Nall Hills
- 0.31 mi to center
10.0Exceptional
(16 Reviews)
3 Bedrooms
2 Baths
9 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $328/Night
7 Nights - US $2,294
US $214/Night
7 Nights - US $1,501
House
- Kansas City
- ·
- Leawood
- 0.33 mi to center
3 Bedrooms
3 Baths
4 Guests
- Air Conditioner
- Child Friendly
- Laundry
- Bedding/Linens
US $300/Night
7 Nights - US $2,097
New
Apartment
- Kansas City
- ·
- Overland Park
- 4.05 mi to center
10.0Exceptional
(1 Review)
1 Bedroom
1 Bath
4 Guests
- Air Conditioner
- Internet
- Pet Friendly
- Child Friendly
US $284/Night
7 Nights - US $1,988
New
Apartment
- Kansas City
- ·
- Overland Park
- 3.93 mi to center
9.4Exceptional
(10 Reviews)
1 Bedroom
1 Bath
2 Guests
- Air Conditioner
- Internet
- Pet Friendly
- Child Friendly
US $268/Night
7 Nights - US $1,875
New
Apartment
- Kansas City
- ·
- Prairie Village
- 2.93 mi to center
9.2Exceptional
(7 Reviews)
1 Bedroom
1 Bath
2 Guests
- Air Conditioner
- Internet
- Pet Friendly
- Child Friendly
US $268/Night
7 Nights - US $1,875
New
Apartment
- Kansas City
- ·
- Overland Park
- 3.99 mi to center
8.8Fabulous
(6 Reviews)
1 Bedroom
1 Bath
4 Guests
- Air Conditioner
- Internet
- Pet Friendly
- Laundry
US $274/Night
7 Nights - US $1,915
New
Apartment
- Kansas City
- ·
- Overland Park
- 3.97 mi to center
8.6Fabulous
(4 Reviews)
1 Bedroom
1 Bath
4 Guests
- Parking
- Kitchen
- Air Conditioner
- Internet
US $276/Night
7 Nights - US $1,932
New
Apartment
- Kansas City
- ·
- Overland Park
- 3.79 mi to center
8.0Excellent
(2 Reviews)
1 Bedroom
1 Bath
4 Guests
- Parking
- Kitchen
- Air Conditioner
- Internet
US $296/Night
7 Nights - US $2,070
Book a Last Minute Place to Stay in Leawood
About Casai's Private Villas and Holiday Rentals in Leawood
Discover more than 150 vacation rentals available in Leawood. These rentals, ranging from vacation rentals to Casai Homes and other short-term private accommodations, offer top-notch amenities with unbeatable value, ensuring both comfort and luxury. Enjoy more space and value when you stay at a Casai property in Leawood.
Seeking last-minute deals or the best available offers for cottages, condos, private villas, and spacious vacation homes? With Casai in Leawood, you can effortlessly compare various deals with just a click. Whether you're looking for a Casai with exceptional swimming pools, hot tubs, pet-friendly options, or large master suite bedrooms equipped with large screen televisions, you'll find a variety of options near Leawood. On average, places to stay near Leawood offer 356.97 ft², with nightly prices averaging US $772.
With Casai, finding and comparing holiday rentals in Leawood is easy and secure, often at a 30-40% discount compared to hotel prices. Simply search for your destination and secure your reservation today.
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Top Accommodation Types in Leawood
| Type | Count |
|---|---|
| Holiday Apartments | 50 |
| Vacation Homes | 50 |
| Villas | 1 |
Use these Quick Filters to Find a Holiday Rental in Leawood
★ Pro Tip: Casai simplifies the process of comparing the finest listings across various online vacation rental platforms, including Booking.com and more. Utilize the Advanced Filter feature located at the top to effortlessly switch between Casai homes, vacation rentals, bed and breakfasts, private Airbnb-style rentals, eco-friendly properties, and different property types. Explore various cancellation policies, prices, and numerous options to find the ideal accommodation for your next vacation in Leawood.
Weather in Leawood, KS
View the weather forecast for Leawood before booking your Leawood Vacation Rentals to confirm your best time to go.
December - February
High 60°F Low 26°F
March - May
High 77°F Low 40°F
June - August
High 91°F Low 64°F
September - November
High 84°F Low 38°F
Top Attractions Around Leawood, KS
Casai offers a large selection of top attractions around Leawood . Research things to do on your vacation before you visit Leawood.
Other Places to Stay in Leawood, KS
Frequently Asked Questions About Leawood?
What are the top holiday rentals in Leawood?
With numerous options available in Leawood, planning to stay in the area? Consider booking a few nights at one of these properties, rated as the Top Holiday Rentals in Leawood:
- Nall Hills Gem! Great location & new interior!
- Newly listed 4 bedroom home with 2 car garage in great location
- Brand NEW Luxury Scandinavian Style Basement Apartment!
- LUXURY GOLF COURSE ESTATE WITH POOL, SAUNA & ENTERTAINMENT SPACE
- Luxe 3000sqft Heated Pool Oasis in Kansas City
- Overland Park Apartment w/Gym King Bed & Parking
- Classic Corner Queen BD No Stairs Fast WiFi Parking
- Spacious King Studio w/Full Kitchen in KS
- Brand New Heated Pool, Family Oasis, Kids Welcome!
- 2BR Apt In OP_Great Location_Pool_Walkable
How many holiday rentals have private pools in Leawood?
Discover a selection of holiday rentals with private pools near Leawood with Casai. Experience the epitome of luxury and relaxation in our top-rated villas and holiday homes, where you can enjoy exclusive access to refreshing swimming pools.
- Its not a house, its a Lifestyle.
- Sheraton Overland Park Hotel at the Convention Center
- Luxurious Poolside Escape on 106th Street: Your Private Oasis in Kansas City
- Private Resort Estate | Pool, Spa, Theater, Game
Which holiday homes in Leawood are best for families?
If you're searching for a family-friendly holiday home in Leawood, consider one of the following properties. Each comes highly recommended, with excellent reviews for families or groups staying in Leawood:
- Life is Suite King Bed Fast WiFi Free Parking Spot Dedicated Work table & chair
- Sheraton Overland Park Hotel at the Convention Center
- Hampton Inn & Suites Overland Park South
How many Casai.com holiday rentals are available in Leawood?
As of 2026, Casai boasts over 150 properties listed in the Leawood area, with more being added continually. By consolidating listings from various websites, Casai provides an extensive selection of the finest Casai properties in Leawood.
Nearby Neighborhood (2)
| Neighborhood | Property Count |
|---|---|
| South Kansas City Vacation Rentals in Kansas City, Kansas | 146 |
| Lea Manor Vacation Rentals in Kansas City, Kansas | 224 |
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