Best Vacation Homes in Greenwood
House
10.0(51 Reviews)
1 Bedroom
1 Bath
2 Guests
Fireplace/Heating
Balcony/Terrace
Kitchen
Parking
US $213/Night
7 Nights - US $1,489
House
10.0(1 Review)
1 Bedroom
2 Baths
9 Guests
1603.82 ft²
- Fireplace/Heating
- Balcony/Terrace
Pet Friendly- Parking
US $225/Night
7 Nights - US $1,575
Hotel
7.6(1001 Reviews)
1 Bath
Pool
Breakfast- Kitchen
- Parking
US $109/Night
7 Nights - US $761
Villa
10.0(45 Reviews)
1 Bedroom
1 Bath
2 Guests
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
US $168/Night
7 Nights - US $1,176
House
10.0(1 Review)
1 Bedroom
1 Bath
3 Guests
602.78 ft²
- Fireplace/Heating
- Parking
Air Conditioner
Internet
US $81/Night
7 Nights - US $567
House
10.0(15 Reviews)
2 Bedrooms
1 Bath
4 Guests
1000 ft²
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
US $190/Night
7 Nights - US $1,333
House
10.0(1 Review)
2 Bedrooms
1 Bath
4 Guests
800 ft²
Ocean View- Balcony/Terrace
View- Kitchen
US $170/Night
7 Nights - US $1,192
House
9.4(26 Reviews)
2 Bedrooms
1 Bath
4 Guests
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
US $115/Night
7 Nights - US $805
Greenwood Luxury Rentals
House
4 Bedrooms
4 Baths
12 Guests
- Fireplace/Heating
- Ocean View
- View
- Kitchen
US $9,809/Night
7 Nights - US $68,665
New
House
5 Bedrooms
5 Baths
12 Guests
4500 ft²
- Ocean View
- Balcony/Terrace
- View
- Kitchen
US $5,171/Night
7 Nights - US $36,197
New
House
5 Bedrooms
5 Baths
18 Guests
4251.74 ft²
- Balcony/Terrace
- Parking
- Air Conditioner
- Internet
US $2,500/Night
7 Nights - US $17,500
House
10.0(13 Reviews)
4 Bedrooms
6 Baths
10 Guests
3500 ft²
- Fireplace/Heating
- Kitchen
- Parking
- Air Conditioner
US $1,596/Night
7 Nights - US $11,173
House
5 Bedrooms
6 Baths
14 Guests
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
US $1,409/Night
7 Nights - US $9,860
House
10.0(15 Reviews)
4 Bedrooms
3 Baths
10 Guests
Private Pool
Hot Tub- Fireplace/Heating
- Pool
US $1,361/Night
7 Nights - US $9,528
House
9.6(12 Reviews)
6 Bedrooms
5 Baths
20 Guests
4000 ft²
- Hot Tub
Spa- Fireplace/Heating
- Balcony/Terrace
US $1,303/Night
7 Nights - US $9,121
New
House
5 Bedrooms
6 Baths
14 Guests
5898.62 ft²
- Balcony/Terrace
- Parking
- Air Conditioner
- Internet
US $1,116/Night
7 Nights - US $7,812
Greenwood Pet Friendly Vacation Rentals
House
10.0(10 Reviews)
2 Bedrooms
1 Bath
10 Guests
1500 ft²
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $178/Night
7 Nights - US $1,245
House
1.0(1 Review)
3 Bedrooms
2 Baths
6 Guests
1097.92 ft²
- Fireplace/Heating
- Pet Friendly
- Parking
- Internet
US $154/Night
7 Nights - US $1,078
Apartment
10.0(3 Reviews)
1 Bedroom
1 Bath
3 Guests
- Pet Friendly
- Kitchen
- Parking
- Internet
US $85/Night
7 Nights - US $595
Villa
3 Bedrooms
2 Baths
8 Guests
2002.09 ft²
- Pet Friendly
- Parking
- Air Conditioner
- Internet
US $429/Night
7 Nights - US $3,003
House
10.0(20 Reviews)
3 Bedrooms
2 Baths
10 Guests
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $386/Night
7 Nights - US $2,704
House
10.0(13 Reviews)
4 Bedrooms
2 Baths
13 Guests
2002 ft²
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $595/Night
7 Nights - US $4,162
House
10.0(4 Reviews)
3 Bedrooms
2 Baths
8 Guests
2000 ft²
- Hot Tub
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
US $645/Night
7 Nights - US $4,512
House
9.8(18 Reviews)
3 Bedrooms
2 Baths
8 Guests
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $480/Night
7 Nights - US $3,360
Greenwood Large Vacation Homes
House
8.0(1 Review)
3 Bedrooms
2 Baths
10 Guests
1800 ft²
- Hot Tub
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
US $121/Night
7 Nights - US $844
House
3 Bedrooms
2 Baths
10 Guests
2700 ft²
- Hot Tub
- Spa
- Fireplace/Heating
- Ocean View
US $645/Night
7 Nights - US $4,512
House
4 Bedrooms
2 Baths
12 Guests
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $609/Night
7 Nights - US $4,265
House
5 Bedrooms
3 Baths
12 Guests
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
- View
US $382/Night
7 Nights - US $2,677
Why Choose Rent By Owner for your Greenwood 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 Greenwood
When should you plan your Vacation Rentals stay?
Choosing the optimal time to vacation in Greenwood, Missouri, can enhance your experience by aligning your visit with favorable weather and local events, allowing you to enjoy the region’s unique charm to the fullest when booking your ideal vacation rentals.
Peak Season Highlights
Spring (March to May)
During spring, the region experiences mild and pleasant weather, making it an ideal time for outdoor activities and exploring local attractions.
Average Temperature Daytime: 60-75°F - Nighttime: 40-55°F
Fall (September to November)
In fall, the area boasts vibrant foliage and comfortable temperatures, perfect for enjoying the scenic beauty and outdoor pursuits.
Average Temperature Daytime: 65-70°F - Nighttime: 45-50°F
Off-Season Highlights
Summer (June to August)
Although summer offers warm weather, it is less crowded, providing a quieter experience for those seeking relaxation in this destination.
Average Temperature Daytime: 80-90°F - Nighttime: 60-70°F
Winter (December to February)
Winter tends to bring colder temperatures, with fewer visitors, which can be advantageous if you prefer a peaceful retreat here during the colder months.
Average Temperature Daytime: 30-45°F - Nighttime: 20-30°F
Weekly Weather Forecast for Greenwood
How to Book Your Greenwood 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 Greenwood
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 grilling with a private barbecue area, perfect for entertaining during your stay.
- Relax on spacious patios or decks that offer scenic views of the surrounding landscape.
- Take advantage of outdoor dining spaces to savor meals al fresco in the fresh air.
- Access lush gardens or landscaped yards ideal for leisurely strolls or outdoor activities.
- Make use of refreshing swimming pools or hot tubs available at select properties here.
- Explore nearby hiking or walking trails directly from your rental's outdoor settings.
- Utilize dedicated outdoor fire pits or fireplaces for cozy evenings under the stars.
Top Attractions Around Greenwood
What attractions are nearby?
In this vibrant region, you can enjoy a variety of outdoor activities, local parks, and cultural attractions that make your stay both memorable and engaging.
Family Activities
- Greenwood Community Park: Enjoy outdoor family fun with spacious playgrounds, walking trails, and picnic areas perfect for a relaxing day in this inviting local park.
- Missouri Town 1855: Step back in time at this historic village where your family can experience living history demonstrations and interactive exhibits that bring the region's heritage to life.
- The Greenway Trail System: Explore scenic hiking and biking trails suitable for all ages, offering an active way to discover the natural beauty of the area together.
- Local Farmers Markets: Visit neighborhood farmers markets to enjoy fresh produce, homemade treats, and craft goods, providing a delightful experience for the whole family in the region.
Adult Activities
- Visit Cunningham Park: Enjoy a relaxing day outdoors at this popular park, offering scenic trails, picnic areas, and a peaceful environment perfect for unwinding.
- Explore the Greenwood Community Center: Engage in various recreational activities, fitness classes, or attend community events that foster local culture and wellness.
- Discover local dining options: Savor regional flavors at nearby eateries known for their welcoming atmosphere and delicious menus, ideal for experiencing the area's culinary scene.
- Take part in seasonal festivals and markets: Participate in community celebrations that showcase the region’s vibrant local traditions and artisanal offerings.
Other Places to Stay in Greenwood, MO
Lake Winnebago
Greenwood Travel Tips
How Can You Make the Most of Your Stay?
- Plan Ahead for Local Events: Check the area's event calendar to align your stay with local festivals or community activities, enriching your experience in Greenwood's charming region.
- Explore Nearby Outdoor Spaces: Take advantage of outdoor recreation opportunities close to your vacation rental to fully enjoy the natural beauty that the area offers.
- Discover Authentic Local Cuisine: Visit nearby eateries and markets to sample regional flavors, making your stay memorable through culinary experiences unique to this destination.
- Utilize Convenient Transportation Options: Arrange transportation in advance to navigate easily around the region and access popular attractions from your vacation rental.
Transportation Options
- Greenwood Transit Services: Local bus routes provide convenient transportation within the area, making it easy for you to explore nearby attractions and neighborhoods.
- Personal Vehicle Rental: Renting a car offers flexibility and comfort, allowing you to navigate the region at your own pace and access more remote spots easily.
- Taxi and Rideshare Options: Taxis and rideshare services are readily available here, providing a reliable way to travel without the hassle of parking or driving yourself.
- Public Transportation Infrastructure: The area's well-maintained transit infrastructure ensures smooth and efficient travel connections throughout this destination and beyond.
Local Customs Options
- Community Events and Festivals: Participating in local events and festivals is a cherished tradition here that reflects the area's vibrant community spirit.
- Southern Hospitality: Expect warm welcomes and friendly exchanges, embodying the region's well-known Southern hospitality standard.
- Traditional Southern Cuisine: The region takes pride in its culinary traditions, with local eateries often serving signature Southern dishes.
- Respect for Nature and Outdoors: Outdoor activities and environmental conservation are highly valued, contributing to a harmonious connection with the natural surroundings.
Greenwood Vacation Rental Frequently Asked Questions
1. What are the top vacation rentals in Greenwood?
There are a lot of options in Greenwood. If you plan on staying in the Greenwood area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Vacation Rentals in Greenwood:
- 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
- Great Space! 2 Blocks from Downtown Lee's Summit!
- Cozy Home Sleeps 10!Walk to FIFA Fan Fest Shuttle!
- Estate Home Hot Tub Beach view Wi-Fi 8 acres 5000 sqft 4 bd 3.5 bath
- Charming Missouri Home < 1 Mi to Katy Trail!
- The Cabin at Big Creek
- Sleeps 13 4Bedrooms + Pets OK + Near FIFA
- Large Home Ready For You or Your Family!
2. Which vacation homes in Greenwood are best for families?
If you are looking for a family-friendly vacation home in Greenwood, check out one of the following properties as all are highly-rated places to stay with excellent review for families or groups staying in Greenwood:
3. How many Rentbyowner vacation rentals are available in Greenwood?
Currently, the total number of properties listed by Rent By Owner in 2026 is over 68 in the Greenwood 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 Greenwood.
4. What is the cancellation policy for vacation rentals in Greenwood, Missouri?
Cancellation policies vary depending on the property owner or manager. You should review the specific listing details or contact the host directly to understand the terms and any associated fees before booking.
5. Are there any additional fees I should be aware of when booking a vacation rental in the area?
Additional fees such as cleaning fees, service charges, or local taxes may apply. These will be detailed on each listing, so it's advisable to read the full description or reach out to the host for clarification.
6. How do I secure my reservation at vacation rentals in Greenwood, Missouri?
Reservations are secured through the booking platform by completing the payment process and confirming your stay. Make sure to follow all listing instructions and communicate with the host if needed to ensure your reservation is confirmed.
7. What amenities are typically included with vacation rentals here?
Most properties offer amenities like Wi-Fi, kitchen facilities, parking, and outdoor spaces. However, amenities can differ between listings, so check the individual property details for specific features available during your stay.
8. Can I modify or cancel my booking if my plans change while staying in this region?
Modification and cancellation policies depend on the specific property’s terms. Review these policies carefully in the listing or contact the host directly to discuss any changes or cancellations prior to confirming your reservation.
Greenwood Top Rated Vacation Rentals
Hotel
6.5(298 Reviews)
4 Baths
261.02 ft²
- Private Pool
Oceanfront- Fireplace/Heating
- Pool
US $105/Night
7 Nights - US $735
US $62/Night
7 Nights - US $433
Hotel
6.2(258 Reviews)
5 Baths
269.1 ft²
- Private Pool
- Fireplace/Heating
- Pool
- Air Conditioner
US $587/Night
7 Nights - US $4,106
US $91/Night
7 Nights - US $635
Bed & Breakfast
2 Bedrooms
2 Baths
8 Guests
- Fireplace/Heating
- Pool
- Balcony/Terrace
- Kitchen
US $3,003/Night
7 Nights - US $21,023
