Discover Your Perfect Annapolis Vacation Homes

Annapolis Luxury Rentals

10.0 (2 Reviews)
Cabin
RIVER and SKY Cabin; Hot Tub
  • Air Conditioner
  • Balcony/Terrace
  • Security/Safety
View Availability
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Why Choose Rent By Owner for your Annapolis 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 Annapolis

When should you plan your Vacation Rentals stay?

Choosing the optimal time to visit here ensures you experience the region’s unique charm at its best, whether you're seeking pleasant weather or avoiding peak tourist seasons, making it easier to find the perfect vacation rentals and enjoy a memorable getaway.

Peak Season Highlights

spring
Spring (March to May)

This is the time when the region experiences mild temperatures and blooming scenery, making it ideal for outdoor activities and exploring local attractions.

Average Temperature Daytime: 60-75°F - Nighttime: 40-55°F
autumn
Fall (September to November)

During the fall, the area becomes vibrant with colorful foliage, attracting visitors who appreciate scenic drives and outdoor adventures in comfortable weather.

Average Temperature Daytime: 65-70°F - Nighttime: 45-50°F

Off-Season Highlights

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Summer (June to August)

While summer can be warm, it remains a popular time for those seeking to enjoy outdoor activities, although accommodations tend to fill quickly during these months.

Average Temperature Daytime: 80-90°F - Nighttime: 60-70°F
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Winter (December to February)

The winter months are quieter, offering a peaceful retreat for visitors who prefer cooler weather and fewer crowds during their stay in this destination.

Average Temperature Daytime: 35-50°F - Nighttime: 20-30°F

Weekly Weather Forecast for Annapolis

How to Book Your Annapolis 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 Annapolis

More Top-Rated Vacation Rentals in Annapolis Area

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

  • You can enjoy a spacious outdoor area perfect for relaxing or outdoor dining amidst the scenic surroundings.
  • Many rentals feature private patios or decks where you can unwind and take in the fresh air.
  • Expect to find barbecue grills available, making it easy to host cookouts during your stay.
  • Some properties include fire pits ideal for cozy evenings with family or friends.
  • Look for outdoor seating options that provide comfortable spots to enjoy the natural beauty of this region.
  • Many rentals are equipped with lush gardens or landscaped yards to enhance your outdoor experience.
  • Access to nearby outdoor recreational areas such as parks or waterfronts is often available for a day of adventure.

Top Attractions Around Annapolis

What attractions are nearby?

Nearby, you can explore scenic outdoor activities, local attractions, and charming spots that showcase the best of this destination, making it an ideal choice for your next getaway.

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Family Activities

  • Annapolis Riverwalk: Stroll along this scenic pathway to enjoy beautiful views and family-friendly spots perfect for relaxing and taking photos.
  • Lakeview Park: Spend quality time outdoors at this local park, where you can picnic, play, and explore nature close to your vacation rental.
  • Historic Downtown Annapolis: Discover charming shops and eateries while walking through the area’s rich history, ideal for a leisurely family day out.
  • Local Nature Trails: Explore nearby trails that offer easy hikes suitable for all ages, providing an engaging way for your family to connect with nature here.
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Adult Activities

  • Explore the Historic Downtown Area: Stroll through charming streets filled with unique shops, local eateries, and historic architecture that showcase the area's rich heritage.
  • Visit the Local Art Galleries: Discover vibrant artworks and cultural exhibits that highlight the creative spirit of this destination’s artistic community.
  • Enjoy Riverfront Activities: Engage in relaxing walks or boat rides along the scenic waterways that define the region's natural beauty.
  • Participate in Community Events: Experience the lively atmosphere by attending seasonal festivals and outdoor gatherings that bring the area’s residents together.

Other Places to Stay in Annapolis, MO

K Bridge Recreation Area
K Bridge Recreation Area Vacation Rentals
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Walnut Hollow Lake Vacation Rentals
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Annapolis Travel Tips

How Can You Make the Most of Your Stay?

  • Explore local dining options: Savor authentic regional flavors at nearby eateries to enhance your experience in this scenic destination.
  • Plan outdoor activities: Take advantage of the area's natural beauty by engaging in outdoor pursuits like hiking or fishing during your stay.
  • Visit during off-peak seasons: Enjoy quieter surroundings and better deals by scheduling your visit during less busy times of the year.
  • Connect with the community: Engage with local events or markets to gain a deeper appreciation for the region's culture and hospitality.

Transportation Options

  • Personal Vehicles: Renting or using your own car offers the most flexibility for exploring this region at your own pace.
  • Regional Bus Services: Local bus networks provide an affordable way to navigate around and enjoy the scenic views of the area.
  • Shuttle Services: Convenient shuttle options are available for direct transportation to popular spots within the destination.
  • Taxi and Rideshare Apps: Taxis and services like Uber or Lyft offer quick, reliable transportation around the region for short trips and errands.

Local Customs Options

  • Southern Hospitality: You’ll notice the warm and welcoming attitude of locals, a hallmark of the region’s friendly customs.
  • Local Cuisine Traditions: Enjoy savoring regional specialties that reflect the area's culinary heritage, often shared during community gatherings.
  • Respect for Nature: Here, community members emphasize conservation and outdoor etiquette, preserving the area's natural beauty for visitors.
  • Historical Celebrations: Participate in annual festivities that honor the region’s history and foster a sense of community pride.

Annapolis Vacation Rental Frequently Asked Questions

1. What are the top vacation rentals in Annapolis?

There are a lot of options in Annapolis. If you plan on staying in the Annapolis area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Vacation Rentals in Annapolis:

2. Which vacation homes in Annapolis are best for families?

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

3. How many Rentbyowner vacation rentals are available in Annapolis?

Currently, the total number of properties listed by Rent By Owner in 2025 is over 42 in the Annapolis 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 Annapolis. 

4. What is the cancellation policy for vacation rentals in Annapolis, Missouri?

The cancellation policy varies depending on the property listing. You should review the specific terms and conditions outlined in the rental agreement or contact the property owner directly to understand the cancellation options available.

5. How do I secure my reservation for a vacation rental here?

Reservations are typically secured by submitting a booking request through the listing platform and completing any required payment. For detailed steps, refer to the booking instructions provided in the listing or reach out to the property owner for assistance.

6. Are there any additional fees or charges I should be aware of when booking in this region?

Additional fees such as cleaning fees, service charges, or taxes may apply depending on the property. It’s best to review the detailed cost breakdown in the listing or contact the owner to clarify any extra charges before finalizing your reservation.

7. What amenities are commonly available in vacation rentals within this destination?

Many rentals here offer amenities like Wi-Fi, parking, full kitchens, and outdoor spaces. To confirm the specific amenities included, please check the property's listing details or consult with the owner directly.

8. Is it possible to modify or extend my stay in these vacation rentals?

Modifications or extensions depend on the property's availability and the owner's policies. Contact the property owner as early as possible to discuss any changes to your booking and ensure they can accommodate your requests.