Discover Your Perfect Overland Vacation Homes

Best Vacation Homes in Overland

House
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like-icon10.0
Exceptional
(5 Reviews)
1 Bedroom 1 Bath 2 Guests
  • Air Conditioner
    Air Conditioner
  • Internet
    Internet
More amenities
£225/Night 7 Nights - £1,576
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House
Map-icon
like-icon9.3
Exceptional
(3 Reviews)
2 Bedrooms 1 Bath 5 Guests 1248.61 ft²
  • Parking
    Parking
  • Balcony/Terrace
    Balcony/Terrace
More amenities
£161/Night 7 Nights - £1,124
Hotel
Map-icon
like-icon9.2
Exceptional
(3113 Reviews)
1 Bath
  • Breakfast
    Breakfast
  • Parking
    Parking
More amenities
£79/Night 7 Nights - £550
House
Map-icon
like-icon10.0
Exceptional
(4 Reviews)
2 Bedrooms 1 Bath 6 Guests
  • Parking
    Parking
  • Balcony/Terrace
    Balcony/Terrace
More amenities
£124/Night 7 Nights - £865
House
Map-icon
like-icon8.8
Fabulous
(161 Reviews)
3 Bedrooms 5 Baths 6 Guests 233.22 ft²
  • Parking
    Parking
  • Balcony/Terrace
    Balcony/Terrace
More amenities
£115/Night 7 Nights - £805
House
Map-icon
like-icon10.0
Exceptional
(2 Reviews)
2 Bedrooms 1 Bath 4 Guests
  • Balcony/Terrace
    Balcony/Terrace
  • Kitchen
    Kitchen
More amenities
£209/Night 7 Nights - £1,464
House
Map-icon
like-icon10.0
Exceptional
(2 Reviews)
2 Bedrooms 1 Bath 4 Guests
  • Kitchen
    Kitchen
  • Air Conditioner
    Air Conditioner
More amenities
£108/Night 7 Nights - £758
New
House
Map-icon
like-icon10.0
Exceptional
(1 Review)
2 Bedrooms 1 Bath 6 Guests
  • Air Conditioner
    Air Conditioner
  • Pet Friendly
    Pet Friendly
More amenities
£150/Night 7 Nights - £1,051

Overland Luxury Rentals

House
Map-icon
like-icon10.0
Exceptional
(8 Reviews)
3 Bedrooms 2 Baths 6 Guests 1800 ft²
  • Hot Tub
    Hot Tub
  • Parking
    Parking
More amenities
£280/Night 7 Nights - £1,961
House
Map-icon
like-icon9.6
Exceptional
(24 Reviews)
5 Bedrooms 3 Baths 11 Guests 2300 ft²
  • Parking
    Parking
  • Balcony/Terrace
    Balcony/Terrace
More amenities
£278/Night 7 Nights - £1,948
House
Map-icon
like-icon8.2
Excellent
(32 Reviews)
4 Bedrooms 2 Baths 10 Guests
  • Parking
    Parking
  • Balcony/Terrace
    Balcony/Terrace
More amenities
£263/Night 7 Nights - £1,840
House
Map-icon
like-icon9.6
Exceptional
(11 Reviews)
2 Bedrooms 1 Bath 8 Guests 800 ft²
  • Parking
    Parking
  • Balcony/Terrace
    Balcony/Terrace
More amenities
£259/Night 7 Nights - £1,812
House
Map-icon
3 Bedrooms 1 Bath 8 Guests 1395 ft²
  • Parking
    Parking
  • Balcony/Terrace
    Balcony/Terrace
More amenities
£247/Night 7 Nights - £1,728
House
Map-icon
like-icon10.0
Exceptional
(16 Reviews)
3 Bedrooms 2 Baths 6 Guests 1675 ft²
  • Parking
    Parking
  • Balcony/Terrace
    Balcony/Terrace
More amenities
£237/Night 7 Nights - £1,656
House
Map-icon
like-icon9.2
Exceptional
(5 Reviews)
2 Bedrooms 1 Bath 4 Guests 1400 ft²
  • Hot Tub
    Hot Tub
  • Parking
    Parking
More amenities
£236/Night 7 Nights - £1,649
House
Map-icon
like-icon8.0
Excellent
(4 Reviews)
2 Bedrooms 1 Bath 9 Guests
  • Parking
    Parking
  • Balcony/Terrace
    Balcony/Terrace
More amenities
£229/Night 7 Nights - £1,606

Overland Pet Friendly Vacation Rentals

House
Map-icon
like-icon9.8
Exceptional
(49 Reviews)
2 Bedrooms 1 Bath 4 Guests 900 ft²
  • Parking
    Parking
  • Kitchen
    Kitchen
More amenities
£218/Night 7 Nights - £1,527
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House
Map-icon
5 Bedrooms 3 Baths 11 Guests 2325 ft²
  • Breakfast
    Breakfast
  • Parking
    Parking
More amenities
£197/Night 7 Nights - £1,379
Apartment
Map-icon
like-icon9.8
Exceptional
(13 Reviews)
2 Bedrooms 1 Bath 5 Guests
  • Parking
    Parking
  • Balcony/Terrace
    Balcony/Terrace
More amenities
£209/Night 7 Nights - £1,466
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House
Map-icon
2 Bedrooms 1 Bath 5 Guests 1194.79 ft²
  • Parking
    Parking
  • Internet
    Internet
More amenities
£99/Night 7 Nights - £696
House
Map-icon
like-icon9.4
Exceptional
(22 Reviews)
2 Bedrooms 1 Bath 4 Guests
  • Kitchen
    Kitchen
  • Air Conditioner
    Air Conditioner
More amenities
£146/Night 7 Nights - £1,019
House
Map-icon
like-icon9.4
Exceptional
(16 Reviews)
2 Bedrooms 1 Bath 4 Guests
  • Kitchen
    Kitchen
  • Air Conditioner
    Air Conditioner
More amenities
£136/Night 7 Nights - £952
House
Map-icon
like-icon8.0
Excellent
(2 Reviews)
2 Bedrooms 1 Bath 6 Guests
  • Parking
    Parking
  • Balcony/Terrace
    Balcony/Terrace
More amenities
£160/Night 7 Nights - £1,122
House
Map-icon
like-icon7.6
Very Good
(14 Reviews)
2 Bedrooms 1 Bath 6 Guests
  • Parking
    Parking
  • Balcony/Terrace
    Balcony/Terrace
More amenities
£192/Night 7 Nights - £1,344

Overland Large Vacation Homes

House
Map-icon
like-icon10.0
Exceptional
(1 Review)
3 Bedrooms 1 Bath 10 Guests
  • Hot Tub
    Hot Tub
  • Parking
    Parking
More amenities
£183/Night 7 Nights - £1,280
House
Map-icon
like-icon10.0
Exceptional
(1 Review)
4 Bedrooms 2 Baths 10 Guests
  • Parking
    Parking
  • Kitchen
    Kitchen
More amenities
£292/Night 7 Nights - £2,045
House
Map-icon
like-icon7.4
Very Good
(10 Reviews)
4 Bedrooms 2 Baths 10 Guests 1913 ft²
  • Parking
    Parking
  • Balcony/Terrace
    Balcony/Terrace
More amenities
£192/Night 7 Nights - £1,342
House
Map-icon
like-icon7.6
Very Good
(4 Reviews)
6 Bedrooms 4 Baths 13 Guests
  • Hot Tub
    Hot Tub
  • Breakfast
    Breakfast
More amenities
£768/Night 7 Nights - £5,379
House
Map-icon
4 Bedrooms 3 Baths 11 Guests
  • Child Friendly
    Child Friendly
£259/Night 7 Nights - £1,811

Why Choose Rent By Owner for your Overland Vacation Rental Homes?

What makes our Vacation Rentals special?

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Verified Listings
Book with confidence knowing every property meets our quality and safety standards.
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Unbeatable Value
Enjoy competitive pricing with no hidden fees, providing exceptional value for every stay.
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Diverse Options
From cozy cabins to luxurious villas, find a rental that suits your style and needs.

Best Times to Visit Overland

When should you plan your Vacation Rentals stay?

Choosing the right time to vacation here can enhance your experience by aligning your plans with the area's seasonal attractions and local climate, ensuring a memorable stay in this destination.

Peak Season Highlights

summer
Late Spring to Early Summer (May to June)

During this time, you can enjoy the pleasant weather with warm daytime temperatures, making it ideal for outdoor activities in the area.

Average Temperature Daytime: 75°F to 85°F - Nighttime: 55°F to 65°F
autumn
Early Fall (September to October)

This period offers comfortable temperatures and fewer crowds, providing a relaxed atmosphere for exploring the region's local attractions.

Average Temperature Daytime: 70°F to 80°F - Nighttime: 50°F to 60°F

Off-Season Highlights

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Winter (December to February)

Here, cooler temperatures mean fewer visitors, offering a quieter experience while enjoying cozy accommodations in the region.

Average Temperature Daytime: 40°F to 50°F - Nighttime: 25°F to 35°F
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Late Fall to Early Winter (November)

As the region transitions into colder months, you can find more affordable vacation rentals and a peaceful ambiance perfect for relaxation.

Average Temperature Daytime: 50°F to 60°F - Nighttime: 30°F to 40°F

Weekly Weather Forecast for Overland

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 Overland

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 a private outdoor patio or deck to relax and unwind amidst the natural surroundings.
  • Take advantage of a spacious backyard ideal for outdoor activities and family gatherings.
  • Experience outdoor dining options with a barbecue grill available for your use.
  • Make the most of a community pool or nearby swimming facilities for refreshing swims during your stay.
  • Benefit from well-maintained walking trails or nature paths in the vicinity for scenic strolls.
  • Relax in a charming garden area that adds to the tranquil ambiance of your accommodation.
  • Utilize outdoor recreational amenities such as volleyball nets or court access, perfect for active vacations.
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Family Activities

  • St. Louis Zoo: Spend a day exploring one of the top family-friendly attractions near you, home to a wide variety of animals and engaging exhibits suitable for all ages.
  • Hidden Valley Ski Resort: Enjoy outdoor adventures with skiing, snowboarding, or tubing during winter months, offering fun activities close to your Overland vacation rental.
  • Tierre Verde Park: Relax outdoors at this scenic park featuring playgrounds, picnic areas, and walking trails, perfect for family outings in the region.
  • Center of creating memories at St. Louis Science Center: Ignite curiosity with interactive exhibits, planetarium shows, and educational programs that make learning fun for children and adults alike.
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Adult Activities

  • Ozark Greenways Trail: Explore this scenic trail for cycling and walking, offering a peaceful way to enjoy the natural beauty of the region.
  • St. Louis County Library-Overland Branch: Visit the library for community events, literary activities, and a cozy atmosphere perfect for relaxing afternoons.
  • Bigfoot Hill: Discover local folklore by hiking around this intriguing site, which offers a blend of outdoor activity and regional history.
  • Mid Rivers Mall: Shop at this popular shopping destination featuring a variety of stores, dining options, and entertainment for an enjoyable day out.

Other Places to Stay in Overland, MO

Overland Travel Tips

How Can You Make the Most of Your Stay?

  • Plan Your Arrival Times: Coordinate your check-in times to coincide with local business hours, ensuring a smooth transition into your vacation rental here.
  • Explore Local Dining Options: Take advantage of nearby restaurants and eateries to enjoy authentic flavors unique to this area.
  • Discover Nearby Attractions: Use your vacation rentals as a comfortable base to explore the region’s must-see sites and hidden gems.
  • Utilize Local Transportation: Familiarize yourself with available transit options or car rental services to easily navigate around here and maximize your stay.

Transportation Options

  • St. Louis Lambert International Airport: This major airport offers convenient domestic and international flights, making arrivals and departures straightforward for travelers staying nearby.
  • Public Transit (MetroBus): The local bus system provides an affordable and accessible way to explore the area without the need for a rental car.
  • Taxi and Rideshare Services: Taxis and rideshare options like Uber and Lyft are widely available, providing flexible transportation throughout this region.
  • Car Rentals: Numerous rental agencies operating in the area make it easy to secure a vehicle for exploring the broader region at your own pace.

Local Customs Options

  • Community Festivals and Parades: Participating in local festivals and parades is a cherished tradition here, reflecting the area's vibrant community spirit.
  • Food and Dining Etiquette: Respect for regional culinary customs, such as polite tipping and appreciation of local flavors, enhances your experience in this region's eateries.
  • Respect for Local History: Showing reverence for historical landmarks and participating in heritage events can deepen your connection with the area's rich past.
  • Environmental Awareness: Embracing practices like recycling and conservation aligns with the community's values of preserving the region’s natural beauty.

Frequently Asked Questions About Overland?

2. How many vacation rentals have private pools in Overland?

There are 5 vacation rentals with private pools near Overland. Top-rated RBO homes that have access to a swimming pool include:

3. Which vacation homes in Overland are best for families?

If you are looking for a family-friendly vacation home in Overland, check out one of the following properties as all are highly-rated places to stay with excellent review for families or groups staying in Overland:

4. How many Rentbyowner vacation rentals are available in Overland?

Currently, the total number of properties listed by Rent By Owner in 2026 is over 149 in the Overland 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 Overland. 

5. What is the cancellation policy for vacation rentals in Overland, Missouri?

Cancellation policies for properties in this area vary depending on the host. To ensure you understand the specific terms, please review the cancellation details listed on the property page or contact the host directly before booking.

6. Are there any additional fees I should be aware of when booking a stay here?

Additional fees such as cleaning, service charges, or security deposits are specified in each listing. Be sure to read the entire description or contact the host for clarification on all applicable fees before confirming your reservation.

7. What amenities are typically included in vacation rentals in this region?

Most properties in the area offer essential amenities like Wi-Fi, parking, and fully equipped kitchens. For specific features like pools or pet-friendly options, check the individual listing details or ask the host directly.

8. How do I find the most suitable vacation rental for my stay?

Start by filtering listings based on your preferred dates, number of guests, and desired amenities. Reading reviews and viewing multiple listings can help you select the best property that fits your needs in this destination.

9. Is it possible to get in touch with the property owner before booking?

Yes, most hosts in the region are available to answer your questions. Use the messaging feature on the listing page to communicate directly with the owner and clarify any specifics about the vacation rental before booking.

Overland Top Rated Vacation Rentals

star-icons-3
Hotel
Map-icon
like-icon9.2
Exceptional
(1712 Reviews)
1 Bath
  • Breakfast
    Breakfast
  • Parking
    Parking
More amenities
£104/Night 7 Nights - £726
star-icons-3
Hotel
Map-icon
like-icon9.2
Exceptional
(1327 Reviews)
1 Bath
  • Hot Tub
    Hot Tub
  • Breakfast
    Breakfast
More amenities
£117/Night 7 Nights - £823
Hotel
Map-icon
like-icon9.2
Exceptional
(1010 Reviews)
1 Bath
  • Breakfast
    Breakfast
  • Parking
    Parking
More amenities
£100/Night 7 Nights - £702
Hotel
Map-icon
like-icon9.0
Exceptional
(2074 Reviews)
5 Baths 301.39 ft²
  • Parking
    Parking
  • Pool
    Pool
More amenities
£67/Night 7 Nights - £467
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Hotel
Map-icon
like-icon8.8
Fabulous
(591 Reviews)
8 Baths 339.06 ft²
  • Private Pool
    Private Pool
  • Breakfast
    Breakfast
More amenities
£97/Night 7 Nights - £679
Hotel
Map-icon
like-icon8.8
Fabulous
(190 Reviews)
1 Bath
  • Breakfast
    Breakfast
  • Parking
    Parking
More amenities
£116/Night 7 Nights - £813
star-icons-3
Hotel
Map-icon
like-icon8.7
Fabulous
(573 Reviews)
7 Baths 322.92 ft²
  • Oceanfront
    Oceanfront
  • Parking
    Parking
More amenities
£73/Night 7 Nights - £509
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Hotel
Map-icon
like-icon8.6
Fabulous
(784 Reviews)
12 Baths 309.46 ft²
  • Hot Tub
    Hot Tub
  • Parking
    Parking
More amenities
£98/Night 7 Nights - £687