Overland holiday lettings

We found 1,268 holiday rentals — enter your dates for availability
Discover a selection of 7 homes and other holiday rentals in Overland that are perfect for your trip. Holiday rentals offer the amenities that you expect for you and your friends, family or even pets, such as Wi-Fi and a fireplace. What you'll find is a property to rent that has what everyone needs, including places that are non-smoking or accessible.

Holiday rentals with weekly discounts – Overland

Showing deals for:22 Jan - 29 Jan

Dining
Room
Interior
Interior
Wonderful
(22 reviews)

Downtown Boutique Comfort w/ Style- Otter Suite

St. Charles

7% off
£933
for 7 nights, 1 room
£133 per night
includes taxes & fees
Downtown Boutique Comfort w/ Style- Otter Suite
Property grounds
Room
Exterior detail
Interior
Exceptional
(34 reviews)

Modern Boutique Stay w/ Plush King Bed- Hare Suite

St. Charles

7% off
£645
for 7 nights, 1 room
£92 per night
includes taxes & fees
Modern Boutique Stay w/ Plush King Bed- Hare Suite
Kitchen Island
Living room with a sofa
Master bedroom with luxurious king bed, dresser, and attached bathroom & closet
Living room with a sofa
Exceptional
(17 reviews)

Perfect Getaway @ CWE- Entire Home + Free Parking Near Fox, Universities & More!

St. Louis

8% off
£2,866
for 7 nights, 1 home
£409 per night
includes taxes & fees
Perfect Getaway @ CWE- Entire Home + Free Parking Near Fox, Universities & More!
Private kitchen
Property grounds
Pool
Interior
Wonderful
(28 reviews)

Elegant home with pool, fenced yard, full kitchen & theater.

St. Louis

8% off
£2,541
for 7 nights, 1 home
£363 per night
includes taxes & fees
Elegant home with pool, fenced yard, full kitchen & theater.
Private kitchen
Private kitchen
Exterior
Terrace/patio
Very good
(25 reviews)

Office and 5 BR, Updated Bathrooms, Movie Theater in Creve Coeur

St. Louis

20% off
£2,403
for 7 nights, 1 home
£343 per night
includes taxes & fees
Office and 5 BR, Updated Bathrooms, Movie Theater in Creve Coeur
Room
Living area
Interior
Private kitchen
Exceptional
(9 reviews)

Safe Quiet Neighborhood! Clean and Cozy Family Friendly 2 bd w/ Large Deck!

Webster Groves

8% off
£1,196
for 7 nights, 1 home
£171 per night
includes taxes & fees
Safe Quiet Neighborhood! Clean and Cozy Family Friendly 2 bd w/ Large Deck!
Dining room
basketball court, and side view of property
Front yard connection to backyard area
Front living room
Wonderful
(32 reviews)

Elegant house pool, sports, pizza & boat bar, business center, mini theater.

St. Louis

8% off
£2,541
for 7 nights, 1 home
£363 per night
includes taxes & fees
Elegant house pool, sports, pizza & boat bar, business center, mini theater.
Living area
Living area
Dining
Room
Exceptional
(65 reviews)

Rustic Charm 4BDRM Home| STL Developers

St. Louis

8% off
£1,084
for 7 nights, 1 home
£155 per night
includes taxes & fees
Rustic Charm 4BDRM Home| STL Developers
Private kitchen
Living area
Third Floor bedroom with one queen size bed and one full size bed.
Large dining room table seats eight.
Exceptional
(31 reviews)

Centrally Located Home Perfect for Family Getaway

St. Louis

19% off
£885
for 7 nights, 1 home
£126 per night
includes taxes & fees
Centrally Located Home Perfect for Family Getaway
Room
Exterior
Interior
Living area
Exceptional
(120 reviews)

Cute 2-Bed 2- Bath Cottage in Kirkwood MO

Kirkwood

8% off
£1,146
for 7 nights, 1 home
£164 per night
includes taxes & fees
Cute 2-Bed 2- Bath Cottage in Kirkwood MO
6S8A0192
6S8A0201
6S8A0171
Property grounds
Exceptional
(51 reviews)

The Loft on Main | Steps to Dining & Nightlife

St. Charles

5% off
£1,000
for 7 nights, 1 room
£143 per night
includes taxes & fees
The Loft on Main | Steps to Dining & Nightlife
Interior
Living area
Room
Living area
Exceptional
(24 reviews)

The Luck Dragon Loft

St. Louis

8% off
£5,897
for 7 nights, 1 apartment
£842 per night
includes taxes & fees
The Luck Dragon Loft
Private kitchen
Interior
Living area
Exterior detail
Exceptional
(5 reviews)

Shenandoah Place

St. Louis

8% off
£1,268
for 7 nights, 1 home
£181 per night
includes taxes & fees
Shenandoah Place
Beverage and snack station offering a variety of coffee, tea, cocoa, snacks, etc
Cozy living room with games, multi seating options, wifi, free TV and Movie apps
Full size large shelves fridge/freezer that's kept very clean. Bottled water too
Cutting boards, small appliances, cookware, utensil variety, bar glasses & more
Wonderful
(37 reviews)

Charming 2-bedroom, cozy bungalow with sunroom in fabulous St. Louis with WiFi

St. Louis

7% off
£849
for 7 nights, 1 home
£121 per night
includes taxes & fees
Charming 2-bedroom, cozy bungalow with sunroom in fabulous St. Louis with WiFi
Exterior detail
Private kitchen
Dining
Living area
Wonderful
(38 reviews)

Hidden Gem in the ❤ of STL

St. Louis

7% off
£980
for 7 nights, 1 home
£140 per night
includes taxes & fees
Hidden Gem in the ❤ of STL
Room
Property grounds
Pool
Living area
Very good
(10 reviews)

Unique Home w/Private Pool, Fenced Yard, Projector & 1920's Style Speakeasy!

St. Louis

8% off
£2,547
for 7 nights, 1 home
£364 per night
includes taxes & fees
Unique Home w/Private Pool, Fenced Yard, Projector & 1920's Style Speakeasy!
Front exterior of the house
Living Room with built-in bookcases and stain glass windows
Kitchen looking out onto the deck and yard
Main Bedroom with queen size bed
Exceptional
(110 reviews)

☆ Newly Renovated ☆Yard☆Close to Local Attractions

St. Louis

8% off
£765
for 7 nights, 1 home
£109 per night
includes taxes & fees
☆ Newly Renovated ☆Yard☆Close to Local Attractions
6S8A1389
Exterior
6S8A1385
6S8A1388
Excellent
(24 reviews)

Honky Tonk Hideaway | 2BR Near Historic Main St

St. Charles

7% off
£763
for 7 nights, 1 home
£109 per night
includes taxes & fees
Honky Tonk Hideaway | 2BR Near Historic Main St
Room
Living area
Living area
Private kitchen
Exceptional
(53 reviews)

Remodeled 3br 4ba Home with Secret Speakeasy Basement

St. Louis

11% off
£1,515
for 7 nights, 1 home
£216 per night
includes taxes & fees
Remodeled 3br 4ba Home with Secret Speakeasy Basement
Property grounds
Dining
Exterior
Living area
Very good
(8 reviews)

Spacious 3-bedroom apartment with WiFi, AC in charming St. Louis

St. Louis

8% off
£1,744
for 7 nights, 1 apartment
£249 per night
includes taxes & fees
Spacious 3-bedroom apartment with WiFi, AC in charming St. Louis
Exterior detail
Living area
Interior
Private kitchen
Exceptional
(41 reviews)

Historic, quiet 2 Bdrm/office space Full Condo

St. Louis

8% off
£548
for 7 nights, 1 apartment
£78 per night
includes taxes & fees
Historic, quiet 2 Bdrm/office space Full Condo
Living area
Private kitchen
Exterior
Dining
Exceptional
(31 reviews)

Remodeled Tower Grove Park gem

St. Louis

11% off
£3,100
for 7 nights, 1 home
£443 per night
includes taxes & fees
Remodeled Tower Grove Park gem
Living area
Room
Interior
Exterior
Excellent
(19 reviews)

Charming Home in Cozy Frenchtown

St. Charles

5% off
£1,133
for 7 nights, 1 home
£162 per night
includes taxes & fees
Charming Home in Cozy Frenchtown
Private kitchen
Living area
Room
Interior
Exceptional
(21 reviews)

Cozy Clark Suite in Frenchtown

St. Charles

6% off
£621
for 7 nights, 1 apartment
£89 per night
includes taxes & fees
Cozy Clark Suite in Frenchtown

  • Peace of mind

    Our Book with Confidence Guarantee gives you 24/7 support

  • More quality time

    From booking to staying, the whole process is simple and enjoyable

  • All the privacy of home

    Enjoy full kitchens, pools, gardens and more

  • More for less

    More space, more privacy, more amenities — more value

Lively Overland will entice you

The area's live music and churches are just some of the reasons to come on holiday to Overland. This romantic city attracts visitors thanks to its bars and coffee shops. St. Louis Zoo and St. Louis Union Station are just a couple of the must-see attractions in the area. A holiday rental can help make your stay complete—many rentals come with a full kitchen and laundry facilities.

Sightseeing in and around Overland

Are you searching for top things to see and do while you're in the area? Venture out of your cosy holiday rental and check out everything that makes Overland a one-of-a-kind holiday spot. These are some of the most popular attractions to put on your list, all within 30 miles (48.2 km) of the city centre:

  • St. Louis Zoo (6.2 mi / 9.9 km)
  • St. Louis Aquarium at Union Station (10.1 mi / 16.2 km)
  • Grant's Farm (10.4 mi / 16.7 km)
  • World Wide Technology Raceway (13.1 mi / 21 km)
  • Creve Coeur Golf Club (4.1 mi / 6.7 km)
  • St. Louis Union Station Mini Golf (10 mi / 16.1 km)

Exploring the natural features in Overland

Whether you're an adventurous traveller or just want to take in the scenery, Overland is a great place to spend some time outside. Here are some of the area’s most stunning natural features, all within 30 miles (48.2 km) of the city centre:

  • Forest Park (6.5 mi / 10.5 km)
  • Jewel Box (6.5 mi / 10.5 km)
  • Lou Fusz Soccer Complex (7 mi / 11.2 km)
  • Missouri Botanical Garden (8.5 mi / 13.6 km)
  • Tower Grove Park (8.5 mi / 13.7 km)
  • Katy Trail (8.6 mi / 13.9 km)

Travelling to and around Overland

The nearest airport is in Lambert-St. Louis International Airport (STL), located 2.9 mi (4.7 km) from the city centre. If you can't find a flight that works for your travel itinerary, you could also fly into St. Louis, MO (SUS-Spirit of St. Louis), which is 15.1 mi (24.3 km) away.

Frequently asked questions

What is the best area to stay in Overland when booking a holiday rental?
When considering a holiday rental in Overland, Missouri, a popular area to stay is near the charming neighbourhood of Overland itself. This area offers a friendly, suburban atmosphere that is great for families and those looking to relax. The properties here typically range from cosy family homes to modern apartments, providing a variety of options to suit different tastes and budgets.A top attraction nearby is the beautiful Overland Community Centre, which often hosts events and activities, making it a great spot to engage with locals and enjoy community spirit. Additionally, the scenic parks in the area, such as the popular Overland Park, provide ample opportunities for outdoor activities like walking, picnicking, and enjoying nature.Another appealing neighbourhood is Northwoods, which boasts a quiet, residential feel while still being conveniently close to local shops and restaurants. Here, you can find a selection of holiday rentals that allow you to settle into the local lifestyle. The proximity to attractions like the St. Louis Zoo and the Missouri Botanical Garden, both a short drive away, makes this area particularly desirable for visitors wanting to explore beyond Overland itself.
How much does it cost to rent a holiday home in Overland?
Prices for holiday rentals in Overland vary based on factors like travel dates, length of stay, accommodation type, and location. Simply enter your trip details to explore a wide range of options—whether you're traveling solo, as a couple, with family, or in a group. Vrbo offers something for every taste and budget, from affordable rentals in Overland to more spacious homes. To get the best value, book early and take advantage of Vrbo's free rewards program.
Are there any discounts for Overland holiday house rentals?
You can find great discounts on house rentals in Overland on Vrbo, including special rates on new listings and savings for weekly or monthly stays with top amenities such as a pool or parking. There are several discounts for Last minute bookings, and Early bird bookings too. The best part is, there's no need for a discount code—just enter your travel dates and apply the discount filters to view the top rates.
What is the most popular type of holiday rental accomodation in Overland?
In Overland, holiday houses are the most popular type of holiday rental, with about 18 available throughout the area. These homes offer spacious layouts, typically featuring multiple bedrooms, fully equipped kitchens, and private outdoor spaces for relaxation. Many are situated in quiet neighbourhoods, providing a comfortable and homely atmosphere for families or groups. Additionally, there are several condos available, which often come with amenities such as shared pools and fitness facilities, suiting those looking for a more communal living experience.
Are there any family house rentals in Overland?
In Overland, Missouri, there are several family-friendly house rentals available, making it a great choice for those travelling with children. This suburban area offers a variety of spacious homes, often featuring multiple bedrooms and ample living spaces for family gatherings. Many properties come equipped with full kitchens, allowing families to prepare meals together, as well as outdoor areas where kids can enjoy fresh air and play.Visitors can explore nearby parks such as the scenic Overland Community Park, which provides playgrounds, sports facilities, and picnic areas superb for family outings. Additionally, the locale is conveniently situated near attractions like the St. Louis Zoo and the Missouri Botanical Garden, making it easy to plan day trips filled with family-friendly activities.
Can I find long-stay holiday rentals in Overland?
A long-stay holiday rental in Overland is the best way to experience local living. Plus, you can make the most of long-stay discounts. Long-stay discounts are applied automatically when you enter your travel dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
Are there pet-friendly house rentals in Overland?
In Overland, Missouri, there are several pet-friendly house rentals available for travellers seeking a comfortable stay. These holiday homes typically offer a range of amenities such as spacious living areas, fully equipped kitchens, and outdoor spaces, making them ideal for families or groups travelling with pets. Many properties also include features like fenced yards or nearby parks, ensuring a safe environment for your furry companions.The area is well-connected, allowing easy access to local parks where pets can enjoy walks and playtime.
Are there any remote work holiday rentals in Overland?
In Overland, Missouri, there are numerous remote work holiday rentals available, with around 18 options to choose from. These properties cater well to those needing to balance work and leisure, featuring amenities specifically designed for remote work, such as free Wi-Fi, dedicated desk spaces, and comfortable desk chairs. Many rentals also provide additional conveniences like fully equipped kitchens and spacious living areas, allowing for a productive yet relaxing stay.The neighbourhood offers a friendly suburban atmosphere with easy access to local parks and amenities, making it ideal for those who enjoy outdoor activities during their downtime. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
Are there any Overland holiday rentals with parking?
Vrbo offers a wide selection of holiday rentals in Overland with parking available—perfect for families or travellers who value the convenience of having a car during their stay. To easily find these properties, simply enter your travel details on Vrbo and use the "Parking available" filter under the amenities section. This makes it quick and easy to browse listings that suit your needs, whether you're planning a short city break or a longer stay.
What are popular rental amenities in Overland?
In Overland, popular rental amenities include fully-equipped kitchens, allowing guests to prepare their own meals during their stay. Onsite parking is also a common feature, providing convenience for those travelling with vehicles. Many rentals come with a coffee and tea maker, superb for enjoying a warm beverage at any time of day. Additionally, properties often include a deck or patio, offering outdoor space to relax and enjoy the surroundings. For those needing to work while away, a desk is typically available in the accommodations, making it easier to combine leisure and productivity.
When is the best time to visit Overland for a holiday rental?
The most popular time to visit Overland is during the vibrant summer months, particularly from May to July. This peak season welcomes a variety of travellers eager to enjoy the warm weather and partake in local festivities. With temperatures often reaching the low to mid-30s Celsius, it's an ideal time for outdoor activities, exploring parks, and enjoying community events.July stands out as the peak month, bustling with energy as families and friends gather for summer outings and celebrations. The lively option makes it a fantastic time to experience everything Overland has to offer, from its charming neighbourhoods to local dining spots.If you're looking for a more budget-friendly option, consider planning your visit in November. While this month falls outside the high tourist season, it offers a unique opportunity to explore the area in a quieter setting. Enjoying the crisp autumn air and the beautiful changing colours can greatly enhance your experience without the crowds.Ultimately, the best time to book your holiday rental in Overland will depend on whether you prefer the lively summer atmosphere or the calm beauty of autumn.
How early should I book a Overland holiday rental?
Book your Overland holiday rental at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your holiday rental, the better the price. *Based on analysis of Vrbo booking and occupancy data for 2024 stays.
What are the top attractions in Overland?
In Overland, Missouri, visitors can explore several local attractions that highlight the area's charm. The city is home to the Overland Community Centre, which offers recreational facilities and hosts various events throughout the year. Nearby, the picturesque St. Vincent Park provides a lovely green space for relaxation and outdoor activities, featuring playgrounds and walking trails.For those interested in history, the Overland Historical Society showcases the local heritage and is a great place to learn about the city's past. The neighbourhood also boasts a variety of dining options and small shops, giving visitors a taste of local cuisine and culture.
Can I change or cancel my Overland home rental booking on Vrbo?
To find Overland holiday rentals with free cancellation, just use Vrbo's handy "Free cancellation" search filter. We get that plans can change, so it's easy to filter properties that give you flexibility. If you need to make changes to an existing booking, drop your host a message. Go to "My Trips" in your account, click "Change or Cancel" and then "Message Host". Vrbo makes it easy to book with confidence.
Why should I join Vrbo as a host?
Joining Vrbo as a host opens the door to a global community of travellers seeking unique stays, giving you the opportunity to earn income from your property on your terms. With user-friendly tools, dedicated support, and exposure on major travel sites, Vrbo makes it easy to list, manage, and succeed. Whether it's a cosy cabin or a beach house, you can turn your space into a standout destination, become a host and let Vrbo handle the heavy lifting to help you thrive. Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.
Are all fees included in the Overland holiday rental prices shown on Vrbo?
Vrbo provides upfront pricing from the moment you start your search. There are no hidden fees added during the check-out process. This allows you to compare properties with ease and plan your trip with confidence.
What is VrboCare™ and how does it work?
Vrbo's mission is to help guests relax, reconnect, and enjoy precious time together. With VrboCare™, you can have peace of mind knowing you're protected and that if something goes wrong, we will do our best to make it right as applicable. If a significant issue arises that your host can't resolve, we'll help you address it, find a similar property, or get your reservation refunded if applicable. That's our promise. If a home is significantly different than listed, we'll get you into a new space that meets your needs and makes it right, or if a host cancels before your stay, you have a dedicated support team to get you into a similar home as applicable.
What can I expect from Vrbo customer service and VrboCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, VrboCare™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, Vrbo customer service is available 24/7 to support you every step of the way. Vrbo also offers support via live chat through our Help Centre, where you can find helpful resources on bookings, payments, property management, and safety, making it easy to get instant answers to many common questions.
Can I plan a group trip on Vrbo?
Vrbo's Trip Planner makes organising group trips easy and stress-free. Whether you're planning with friends or coordinating a large group, you can collaborate in one place, save and share properties, vote on favorites, and build the perfect itinerary together.

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