Best Vacation Homes in Pleasant Hill
House
10.0(101 Reviews)
2 Bedrooms
2 Baths
6 Guests
1750 ft²
Hot Tub
Parking
Balcony/Terrace
Kitchen
US $241/Night
7 Nights - US $1,688
House
10.0(1 Review)
1 Bedroom
2 Baths
9 Guests
1603.82 ft²
- Parking
- Balcony/Terrace
Air Conditioner
Internet
US $225/Night
7 Nights - US $1,575
Bed & Breakfast
10.0(10 Reviews)
1 Bedroom
1 Bath
Breakfast- Parking
- Balcony/Terrace
- Kitchen
US $295/Night
7 Nights - US $2,063
Apartment
10.0(43 Reviews)
2 Bedrooms
1 Bath
6 Guests
- Air Conditioner
- Internet
Child Friendly
Laundry
US $162/Night
7 Nights - US $1,132
House
10.0(1 Review)
4 Bedrooms
3 Baths
16 Guests
19848.65 ft²
- Hot Tub
- Parking
- Balcony/Terrace
View
US $1,200/Night
7 Nights - US $8,400
House
10.0(13 Reviews)
2 Bedrooms
1 Bath
4 Guests
- Parking
- Kitchen
- Air Conditioner
- Internet
US $152/Night
7 Nights - US $1,061
Apartment
10.0(3 Reviews)
1 Bedroom
1 Bath
3 Guests
- Parking
- Kitchen
- Internet
Pet Friendly
US $91/Night
7 Nights - US $638
House
10.0(2 Reviews)
2 Bedrooms
1 Bath
6 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $208/Night
7 Nights - US $1,457
Pleasant Hill Luxury Rentals
House
3 Bedrooms
2 Baths
6 Guests
- Hot Tub
- Parking
- Balcony/Terrace
- Kitchen
US $1,527/Night
7 Nights - US $10,691
Apartment
1 Bedroom
1 Bath
- Parking
- Kitchen
- Air Conditioner
- Internet
US $1,466/Night
7 Nights - US $10,259
New
House
10.0(1 Review)
2 Bedrooms
2 Baths
4 Guests
1299 ft²
- Parking
- Kitchen
- Air Conditioner
- Internet
US $1,437/Night
7 Nights - US $10,060
House
5 Bedrooms
5 Baths
15 Guests
5500 ft²
Private Pool- Hot Tub
- Parking
Pool
US $1,354/Night
7 Nights - US $9,478
House
9.6(13 Reviews)
5 Bedrooms
4 Baths
20 Guests
4000 ft²
- Hot Tub
- Parking
Spa- Balcony/Terrace
US $1,243/Night
7 Nights - US $8,698
New
House
3 Bedrooms
3 Baths
8 Guests
- Parking
- Pool
- Kitchen
- Air Conditioner
US $1,147/Night
7 Nights - US $8,029
New
House
4 Bedrooms
3 Baths
8 Guests
- Air Conditioner
- Internet
- Child Friendly
- Laundry
US $1,137/Night
7 Nights - US $7,956
House
9.0(4 Reviews)
4 Bedrooms
3 Baths
10 Guests
1844 ft²
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $1,135/Night
7 Nights - US $7,944
Pleasant Hill Pet Friendly Vacation Rentals
House
10.0(1 Review)
2 Bedrooms
1 Bath
4 Guests
- Parking
- Kitchen
- Air Conditioner
- Internet
US $99/Night
7 Nights - US $695
House
1.0(1 Review)
3 Bedrooms
2 Baths
6 Guests
1097.92 ft²
- Parking
- Internet
- Pet Friendly
- Child Friendly
US $154/Night
7 Nights - US $1,078
Cabin
9.6(38 Reviews)
2 Bedrooms
1 Bath
4 Guests
- Hot Tub
- Parking
- Balcony/Terrace
- Kitchen
US $252/Night
7 Nights - US $1,764
New
House
3 Bedrooms
2 Baths
4 Guests
1496.18 ft²
- Parking
- Balcony/Terrace
- Pet Friendly
- Child Friendly
US $249/Night
7 Nights - US $1,741
Cabin
9.0(7 Reviews)
1 Bedroom
1 Bath
2 Guests
- Air Conditioner
- Internet
- Pet Friendly
- Child Friendly
US $239/Night
7 Nights - US $1,676
New
House
2 Bedrooms
1 Bath
4 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $531/Night
7 Nights - US $3,719
New
House
1 Bedroom
1 Bath
4 Guests
- Air Conditioner
- Internet
- Pet Friendly
Bedding/Linens
US $392/Night
7 Nights - US $2,744
House
10.0(2 Reviews)
4 Bedrooms
2 Baths
8 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $179/Night
7 Nights - US $1,254
Pleasant Hill Large Vacation Homes
Villa
10.0(47 Reviews)
1 Bedroom
1 Bath
2 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $147/Night
7 Nights - US $1,029
House
5 Bedrooms
6 Baths
14 Guests
5898.62 ft²
- Parking
- Balcony/Terrace
- Air Conditioner
- Internet
US $1,116/Night
7 Nights - US $7,812
House
5 Bedrooms
4 Baths
24 Guests
- Hot Tub
- Parking
Ocean View- Balcony/Terrace
US $534/Night
7 Nights - US $3,740
House
3 Bedrooms
2 Baths
10 Guests
2701.74 ft²
- Hot Tub
- Parking
- Balcony/Terrace
- Air Conditioner
US $531/Night
7 Nights - US $3,715
House
10.0(26 Reviews)
3 Bedrooms
2 Baths
10 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $329/Night
7 Nights - US $2,306
House
10.0(18 Reviews)
4 Bedrooms
3 Baths
10 Guests
- Private Pool
- Hot Tub
- Pool
- Ocean View
US $919/Night
7 Nights - US $6,434
House
10.0(5 Reviews)
5 Bedrooms
4 Baths
12 Guests
- Private Pool
- Hot Tub
- Parking
- Pool
US $1,133/Night
7 Nights - US $7,933
House
10.0(5 Reviews)
4 Bedrooms
3 Baths
13 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $477/Night
7 Nights - US $3,338
Why Choose Rent By Owner for your Pleasant Hill Vacation Rental Homes?
What makes our Vacation Rentals special?
Verified Listings
Book with confidence knowing every property meets our quality and safety standards.
Unbeatable Value
Enjoy competitive pricing with no hidden fees, providing exceptional value for every stay.
Diverse Options
From cozy cabins to luxurious villas, find a rental that suits your style and needs.
Best Times to Visit Pleasant Hill
When should you plan your Vacation Rentals stay?
Choosing the optimal time to visit here ensures you can fully enjoy the relaxed atmosphere and local charm that make this destination a perfect getaway, especially when selecting the ideal season for vacation rentals in the region.
Peak Season Highlights
Spring (March to May)
During spring, the area witnesses pleasant weather and blooming scenery, making it an ideal time for outdoor activities and exploring local attractions.
Average Temperature Daytime: 60-75°F - Nighttime: 45-55°F
Fall (September to November)
In the fall, the region offers vibrant foliage and comfortable temperatures, perfect for enjoying outdoor leisure and scenic drives.
Average Temperature Daytime: 65-70°F - Nighttime: 50-55°F
Off-Season Highlights
Summer (June to August)
Summers can be hot and humid, which may reduce the appeal for some travelers, but it's a great time for indoor activities and enjoying local events.
Average Temperature Daytime: 85-90°F - Nighttime: 65-70°F
Winter (December to February)
Winter months tend to be cooler with occasional snowfall, offering a quiet atmosphere and fewer crowds for those seeking tranquility.
Average Temperature Daytime: 40-50°F - Nighttime: 25-35°F
Weekly Weather Forecast for Pleasant Hill
How to Book Your Pleasant Hill Vacation Rental Home
What's our booking process?
Our platform allows you to browse a curated selection of vacation rentals. Once you find the ideal property, you’ll be redirected to a trusted booking partner to complete your reservation securely.
Booking Steps
01
Search Properties
Use our filters to find the right property that fits your needs.
02
Select a Rental
Click on your preferred listing to view details, amenities, and pricing.
03
Book Online
Follow the link to finalize your reservation directly on the partner’s website.
Common Vacation Rentals Amenities
What amenities can you expect?
Our Vacation Rentals are designed to offer all the comforts of home, often with added perks to make your stay unforgettable. Here’s some common amenities to look forward to:
Indoor Features
- Fully-equipped kitchens with modern appliances
- Comfortable living areas with flat-screen TVs
- Free Wi-Fi for staying connected
- Air conditioning and heating for year-round comfort
- In-unit washers and dryers for convenience
- Luxurious bedrooms with premium bedding
- Spa-like bathrooms with soaking tubs or walk-in showers
Outdoor Amenities
- Enjoy outdoor dining with a private patio or veranda available at many vacation rentals in the area.
- Take advantage of spacious yards perfect for family games or relaxing in the fresh air.
- Relax by a charming outdoor fire pit, ideal for evening gatherings under the stars.
- Make use of a backyard barbecue grill to prepare delicious meals during your stay here.
- Explore nearby walking trails and scenic spots directly from your rental property’s doorstep.
- Unwind in a private swimming pool, available at select vacation rentals in this region.
- Appreciate beautiful landscaped gardens that enhance the outdoor ambiance of your accommodation.
Top Attractions Around Pleasant Hill
What attractions are nearby?
Nearby, you can enjoy a variety of outdoor activities, explore local parks, or experience the regional charm that makes this destination a perfect spot for a relaxing getaway.
Family Activities
- Pleasant Hill Historic Downtown Tour: Stroll through the charming downtown area to explore local shops, historic landmarks, and enjoy a family-friendly atmosphere.
- Pleasant Hill Park: Spend quality time outdoors at the scenic park, featuring playgrounds, picnic areas, and walking trails suitable for all ages.
- Local Family-Friendly Events: Participate in seasonal festivals and community events that showcase the region's vibrant culture and provide entertainment for children and adults alike.
- Nearby Lake Activities: Discover nearby lakes offering fishing, kayaking, and relaxing boat rides that make for enjoyable day trips with the family.
Adult Activities
- Golfing at Pleasant Hill Golf Course: Enjoy a round of golf amidst scenic views and well-maintained greens at this popular course in the region.
- Shopping and Dining Downtown: Explore charming local shops and indulge in diverse dining options that capture the culinary spirit of the area.
- Exploring Historic Sites: Discover the rich history of this destination through its preserved landmarks and engaging museums.
- Parks and Outdoor Recreation: Relax or partake in outdoor activities at nearby parks, offering trails, picnicking spots, and peaceful natural scenery for adults seeking leisure and adventure.
Other Places to Stay in Pleasant Hill, MO
Baldwin Park
Wingate
Pleasant Hill Travel Tips
How Can You Make the Most of Your Stay?
- Plan Your Arrival Time: Coordinate your check-in to ensure a smooth start and make the most of your time exploring this charming area.
- Explore Local Dining Options: Take advantage of nearby restaurants to sample regional flavors and support local businesses during your stay.
- Utilize Nearby Outdoor Spaces: Maximize your outdoor experience by visiting local parks and trails, perfect for relaxing and enjoying the area's natural beauty.
- Connect with Local Events: Check for community events or markets happening during your visit to immerse yourself in the region’s vibrant culture.
Transportation Options
- Car Rentals: You can easily explore the area with local car rental services, offering convenient transportation to nearby attractions and amenities.
- Public Transit: The regional transit system provides an affordable and reliable way to navigate this destination without the need for a personal vehicle.
- Taxi and Rideshare Services: Taxis and rideshare options like Uber and Lyft are readily available here, ensuring quick and comfortable transportation around the region.
- Bicycle Rentals: For a more scenic and active experience, consider renting a bicycle to travel through the charming streets of this destination.
Local Customs Options
- Southern Hospitality: Expect friendly greetings and warm welcomes that reflect the region’s renowned Southern hospitality here in Pleasant Hill.
- Local Festivals: Participating in or observing local festivals offers a glimpse into the area's cultural traditions and community spirit.
- Historic Respect: Appreciating the preservation of historic sites and customs is a common practice among residents and visitors alike.
- Community Gatherings: Engaging in neighborhood events demonstrates the close-knit nature of this destination’s community life.
Pleasant Hill Vacation Rental Frequently Asked Questions
1. What are the top vacation rentals in Pleasant Hill?
There are a lot of options in Pleasant Hill. If you plan on staying in the Pleasant Hill area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Vacation Rentals in Pleasant Hill:
- Lovely home, peaceful country setting. Short drive to all KC area offers
- Relaxing 3 bedroom home w/full kitchen & WiFi; walking distance to restauraunts
- Drew's Den in Historic Downtown Pleasant Hill, MO
- Great Space! 2 Blocks from Downtown Lee's Summit!
- Fun & Convenient Sleeps 10! Putting green and BBQ Grill.
- Anna Lou's Guest House
- Estate Home Hot Tub Beach view Wi-Fi 8 acres 5000 sqft 4 bd 3.5 bath
- Lee's Summit Loft-near downtown
- Relaxing Retreat in Lee's Summit - NO Cleaning FEE
- Peaceful bunkhouse getaway on quiet farm in KCMO
2. How many vacation rentals have private pools in Pleasant Hill?
There are 4 vacation rentals with private pools near Pleasant Hill. Top-rated RBO homes that have access to a swimming pool include:
3. Which vacation homes in Pleasant Hill are best for families?
If you are looking for a family-friendly vacation home in Pleasant Hill, check out one of the following properties as all are highly-rated places to stay with excellent review for families or groups staying in Pleasant Hill:
4. How many Rentbyowner vacation rentals are available in Pleasant Hill?
Currently, the total number of properties listed by Rent By Owner in 2026 is over 195 in the Pleasant Hill area, and still counting. By aggregating listings from multiple websites, Rent By Owner offers an immense amount of choice of the best RBO properties in Pleasant Hill.
5. What is the cancellation policy for vacation rentals in Pleasant Hill, Missouri?
Cancellation policies vary by listing, so it's important to review the specific terms outlined in the property description or contact the owner directly before booking.
6. How do I find available vacation rentals with flexible booking options in the area?
You can filter search results by flexible booking options on the website, and details about each property's cancellation and refund policies are provided in the listing.
7. Are there any additional fees I should be aware of when booking a vacation rental here?
Additional fees such as cleaning fees, service charges, or security deposits are specified within each listing, so reviewing the detailed property information will help clarify the total cost.
8. What amenities are typically included in vacation rentals near this destination?
Most properties offer essential amenities like Wi-Fi, parking, and full kitchens, but it’s best to check the individual listing for specific features and comforts offered.
9. How can I contact the property owner if I have questions before booking?
Contact details are usually provided on the listing page, allowing you to communicate directly with the owner to inquire about the property or clarify any concerns.
Pleasant Hill Top Rated Vacation Rentals
House
10.0(1 Review)
4 Bedrooms
3 Baths
10 Guests
2000 ft²
- Private Pool
- Hot Tub
- Parking
- Pool
US $756/Night
7 Nights - US $5,289
House
10.0(1 Review)
2 Bedrooms
2 Baths
4 Guests
1400 ft²
- Hot Tub
- Parking
- Pool
- Spa
US $296/Night
7 Nights - US $2,072
US $148/Night
7 Nights - US $1,036
Hotel
9.2(600 Reviews)
1 Bath
- Breakfast
- Parking
- Pool
- Kitchen
US $141/Night
7 Nights - US $985
Hotel
9.1(136 Reviews)
10 Baths
400.06 ft²
- Private Pool
- Breakfast
- Parking
- Pool
US $183/Night
7 Nights - US $1,281
Hotel
9.1(106 Reviews)
1 Bath
264.79 ft²
- Private Pool
Oceanfront- Parking
- Pool
US $159/Night
7 Nights - US $1,115
Hotel
8.4(463 Reviews)
1 Bath
- Breakfast
- Parking
- Pool
- Kitchen
US $117/Night
7 Nights - US $822
Hotel
8.3(156 Reviews)
5 Baths
3229.18 ft²
- Private Pool
- Hot Tub
- Breakfast
- Parking
US $108/Night
7 Nights - US $758
