Best Vacation Homes in Pleasant Hill
2 Guests
1 Bedroom
1 Bathroom
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
US $213/Night
For 7 Nights US $1,489
1603.82 ft²
9 Guests
1 Bedroom
2 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
US $225/Night
For 7 Nights US $1,575
1 Bedroom
1 Bathroom
Family Friendly
Bed & Breakfast
- Fireplace/Heating
- Balcony/Terrace
- Breakfast
US $358/Night
For 7 Nights US $2,509
2 Guests
1 Bedroom
1 Bathroom
Family Friendly
Villa
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
US $207/Night
For 7 Nights US $1,446
602.78 ft²
3 Guests
1 Bedroom
1 Bathroom
House
- Fireplace/Heating
- Parking
- Air Conditioner
US $81/Night
For 7 Nights US $567
279 ft²
2 Guests
1 Bedroom
1 Bathroom
Couples Retreat
Cottage
- Fireplace/Heating
- Air Conditioner
- Internet
US $149/Night
For 7 Nights US $1,045
1000 ft²
4 Guests
2 Bedrooms
1 Bathroom
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
US $179/Night
For 7 Nights US $1,250
680 ft²
3 Guests
1 Bedroom
1 Bathroom
Family Friendly
Apartment
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
US $233/Night
For 7 Nights US $1,633
Pleasant Hill Luxury Rentals
12 Guests
4 Bedrooms
4 Bathrooms
Ocean View
House
- Fireplace/Heating
- Ocean View
- View
US $9,809/Night
For 7 Nights US $68,665
8 Guests
2 Bedrooms
2 Bathrooms
Family Friendly
Bed & Breakfast
- Fireplace/Heating
- Pool
- Balcony/Terrace
US $3,003/Night
For 7 Nights US $21,023
3500 ft²
8 Guests
3 Bedrooms
2 Bathrooms
Family Friendly
House
- Hot Tub
- Fireplace/Heating
- Balcony/Terrace
US $2,434/Night
For 7 Nights US $17,038
1399.31 ft²
4 Guests
2 Bedrooms
3 Bathrooms
Free Cancellation
House
- Hot Tub
- Fireplace/Heating
- Pool
US $1,762/Night
For 7 Nights US $12,334
5500 ft²
15 Guests
5 Bedrooms
5 Bathrooms
Pet Friendly
House
- Child Friendly
US $1,639/Night
For 7 Nights US $11,475
10 Guests
5 Bedrooms
5 Bathrooms
Family Friendly
House
- Hot Tub
- Fireplace/Heating
- Pool
US $1,575/Night
For 7 Nights US $11,025
10 Guests
4 Bedrooms
3 Bathrooms
Ocean View
House
- Private Pool
- Hot Tub
- Fireplace/Heating
US $1,480/Night
For 7 Nights US $10,362
12 Guests
5 Bedrooms
4 Bathrooms
Family Friendly
House
- Private Pool
- Hot Tub
- Fireplace/Heating
US $1,351/Night
For 7 Nights US $9,460
Pleasant Hill Pet Friendly Vacation Rentals
500 ft²
4 Guests
1 Bedroom
1 Bathroom
Family Friendly
Apartment
- Fireplace/Heating
- Pet Friendly
- Kitchen
US $139/Night
For 7 Nights US $973
1097.92 ft²
6 Guests
3 Bedrooms
2 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Pet Friendly
- Parking
US $154/Night
For 7 Nights US $1,078
8 Guests
4 Bedrooms
2 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
US $162/Night
For 7 Nights US $1,132
19848.65 ft²
16 Guests
1 Bedroom
3 Bathrooms
Free Cancellation
House
- Hot Tub
- Fireplace/Heating
- Balcony/Terrace
US $1,200/Night
For 7 Nights US $8,400
4000 ft²
20 Guests
6 Bedrooms
5 Bathrooms
Family Friendly
House
- Hot Tub
- Spa
- Fireplace/Heating
US $1,138/Night
For 7 Nights US $7,968
1500 ft²
8 Guests
4 Bedrooms
3 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
US $610/Night
For 7 Nights US $4,267
24 Guests
5 Bedrooms
4 Bathrooms
Ocean View
House
- Hot Tub
- Fireplace/Heating
- Ocean View
US $540/Night
For 7 Nights US $3,782
1500 ft²
10 Guests
2 Bedrooms
1 Bathroom
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
US $174/Night
For 7 Nights US $1,218
Pleasant Hill Large Vacation Homes
3500 ft²
10 Guests
4 Bedrooms
6 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Kitchen
- Parking
US $912/Night
For 7 Nights US $6,382
19848.65 ft²
16 Guests
1 Bedroom
3 Bathrooms
Family Friendly
House
- Hot Tub
- Balcony/Terrace
- View
US $1,080/Night
For 7 Nights US $7,560
10 Guests
3 Bedrooms
2 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
US $401/Night
For 7 Nights US $2,809
2002.09 ft²
8 Guests
3 Bedrooms
2 Bathrooms
Villa
- Pet Friendly
- Parking
- Air Conditioner
US $270/Night
For 7 Nights US $1,890
2002 ft²
13 Guests
4 Bedrooms
2 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
US $568/Night
For 7 Nights US $3,978
13 Guests
4 Bedrooms
3 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
US $668/Night
For 7 Nights US $4,677
8 Guests
5 Bedrooms
2 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
US $786/Night
For 7 Nights US $5,500
10 Guests
4 Bedrooms
2 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
US $484/Night
For 7 Nights US $3,386
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.
Explore and book the perfect rental in Pleasant Hill
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
- Rebecca's Retreat on Katy Trail in beautiful downtown Pleasant Hill MO
- Drew's Den in Historic Downtown Pleasant Hill, MO
- New Conestoga 1843 Wagon
- Great Space! 2 Blocks from Downtown Lee's Summit!
- Anna Lou's Guest House
- Cozy World Cup Hub: Walk to FIFA Fan Fest Shuttle!
- Estate Home Hot Tub Beach view Wi-Fi 8 acres 5000 sqft 4 bd 3.5 bath
- The Cabin at Big Creek
2. How many vacation rentals have private pools in Pleasant Hill?
There are 2 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 161 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
1400 ft²
4 Guests
2 Bedrooms
2 Bathrooms
Family Friendly
House
- Hot Tub
- Spa
- Fireplace/Heating
US $457/Night
For 7 Nights US $3,200
264.79 ft²
15 Guests
107 Bedrooms
1 Bathroom
Hotel
- Private Pool
- Oceanfront
- Fireplace/Heating
US $478/Night
For 7 Nights US $3,349
1 Bedroom
1 Bathroom
Family Friendly
Hotel
- Hot Tub
- Pool
- Breakfast
US $144/Night
For 7 Nights US $1,010
1 Bedroom
1 Bathroom
Family Friendly
Hotel
- Pool
- Breakfast
- Kitchen
US $145/Night
For 7 Nights US $1,017
400.06 ft²
57 Guests
35 Bedrooms
10 Bathrooms
Family Friendly
Hotel
- Private Pool
- Fireplace/Heating
- Pool
US $183/Night
For 7 Nights US $1,281
1 Bedroom
1 Bathroom
Family Friendly
Hotel
- Pool
- Breakfast
- Kitchen
US $127/Night
For 7 Nights US $886
299.24 ft²
21 Guests
56 Bedrooms
5 Bathrooms
Family Friendly
Hotel
- Private Pool
- Fireplace/Heating
- Pool
US $125/Night
For 7 Nights US $876
3229.18 ft²
12 Guests
62 Bedrooms
5 Bathrooms
Hotel
- Private Pool
- Hot Tub
- Pool
US $98/Night
For 7 Nights US $686
