Discover Your Perfect Calloway County Vacation Homes

Best Vacation Homes in Calloway County

Cabin
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like-icon10.0
Exceptional
(50 Reviews)
2 Bedrooms 1 Bath 6 Guests 1400 ft²
  • Fireplace/Heating
    Fireplace/Heating
  • Balcony/Terrace
    Balcony/Terrace
More amenities
£122/Night 7 Nights - £852
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House
Map-icon
like-icon10.0
Exceptional
(6 Reviews)
2 Bedrooms 1 Bath 6 Guests 1205.56 ft²
  • Pet Friendly
    Pet Friendly
  • Parking
    Parking
More amenities
£141/Night 7 Nights - £989
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Apartment
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1 Bedroom 1 Bath
  • Oceanfront
    Oceanfront
  • Fireplace/Heating
    Fireplace/Heating
More amenities
£354/Night 7 Nights - £2,481
Cabin
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like-icon10.0
Exceptional
(42 Reviews)
2 Bedrooms 1 Bath 6 Guests 1300 ft²
  • Hot Tub
    Hot Tub
  • Fireplace/Heating
    Fireplace/Heating
More amenities
£146/Night 7 Nights - £1,025
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House
Map-icon
like-icon10.0
Exceptional
(4 Reviews)
4 Bedrooms 2 Baths 8 Guests 1399.31 ft²
  • Fireplace/Heating
    Fireplace/Heating
  • Parking
    Parking
More amenities
£307/Night 7 Nights - £2,147
House
Map-icon
like-icon10.0
Exceptional
(31 Reviews)
2 Bedrooms 2 Baths 11 Guests 1900 ft²
  • Fireplace/Heating
    Fireplace/Heating
  • Balcony/Terrace
    Balcony/Terrace
More amenities
£223/Night 7 Nights - £1,560
New
House
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like-icon10.0
Exceptional
(24 Reviews)
2 Bedrooms 2 Baths 5 Guests 1550 ft²
  • Fireplace/Heating
    Fireplace/Heating
  • Balcony/Terrace
    Balcony/Terrace
More amenities
£117/Night 7 Nights - £816
Apartment
Map-icon
like-icon10.0
Exceptional
(22 Reviews)
2 Bedrooms 2 Baths 6 Guests 950 ft²
  • Fireplace/Heating
    Fireplace/Heating
  • Balcony/Terrace
    Balcony/Terrace
More amenities
£159/Night 7 Nights - £1,113

Calloway County Luxury Rentals

House
Map-icon
1 Bedroom 2 Baths 8 Guests 1603.82 ft²
  • Fireplace/Heating
    Fireplace/Heating
  • Air Conditioner
    Air Conditioner
More amenities
£881/Night 7 Nights - £6,164
House
Map-icon
like-icon10.0
Exceptional
(3 Reviews)
7 Bedrooms 6 Baths 24 Guests 4000 ft²
  • Hot Tub
    Hot Tub
  • Fireplace/Heating
    Fireplace/Heating
More amenities
£844/Night 7 Nights - £5,907
House
Map-icon
like-icon8.8
Fabulous
(6 Reviews)
4 Bedrooms 4 Baths 14 Guests 3200 ft²
  • Fireplace/Heating
    Fireplace/Heating
  • Balcony/Terrace
    Balcony/Terrace
More amenities
£717/Night 7 Nights - £5,022
House
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4 Bedrooms 4 Baths 7 Guests 3000 ft²
  • Hot Tub
    Hot Tub
  • Fireplace/Heating
    Fireplace/Heating
More amenities
£447/Night 7 Nights - £3,126
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House
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like-icon10.0
Exceptional
(1 Review)
4 Bedrooms 3 Baths 10 Guests 2012.85 ft²
  • Fireplace/Heating
    Fireplace/Heating
  • Pet Friendly
    Pet Friendly
More amenities
£382/Night 7 Nights - £2,676
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House
Map-icon
like-icon6.0
Good
(1 Review)
4 Bedrooms 4 Baths 14 Guests 3196.88 ft²
  • Fireplace/Heating
    Fireplace/Heating
  • Parking
    Parking
More amenities
£364/Night 7 Nights - £2,550
House
Map-icon
like-icon10.0
Exceptional
(175 Reviews)
4 Bedrooms 3 Baths 10 Guests 3400 ft²
  • Hot Tub
    Hot Tub
  • Fireplace/Heating
    Fireplace/Heating
More amenities
£350/Night 7 Nights - £2,448
Ski Chalet
Map-icon
like-icon10.0
Exceptional
(83 Reviews)
3 Bedrooms 3 Baths 14 Guests 2500 ft²
  • Hot Tub
    Hot Tub
  • Fireplace/Heating
    Fireplace/Heating
More amenities
£333/Night 7 Nights - £2,328

Calloway County Pet Friendly Vacation Rentals

Cabin
Map-icon
like-icon10.0
Exceptional
(1 Review)
2 Bedrooms 2 Baths 8 Guests 1500 ft²
  • Hot Tub
    Hot Tub
  • Fireplace/Heating
    Fireplace/Heating
More amenities
£218/Night 7 Nights - £1,528
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House
Map-icon
like-icon10.0
Exceptional
(3 Reviews)
3 Bedrooms 2 Baths 8 Guests 2002.09 ft²
  • Fireplace/Heating
    Fireplace/Heating
  • Balcony/Terrace
    Balcony/Terrace
More amenities
£272/Night 7 Nights - £1,901
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Hotel
Map-icon
like-icon6.6
Good
(622 Reviews)
1 Bath
  • Fireplace/Heating
    Fireplace/Heating
  • Balcony/Terrace
    Balcony/Terrace
More amenities
£48/Night 7 Nights - £334
Cabin
Map-icon
like-icon9.8
Exceptional
(76 Reviews)
2 Bedrooms 2 Baths 6 Guests 1500 ft²
  • Balcony/Terrace
    Balcony/Terrace
  • Pet Friendly
    Pet Friendly
More amenities
£125/Night 7 Nights - £874
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House
Map-icon
like-icon10.0
Exceptional
(2 Reviews)
1 Bedroom 2 Baths 4 Guests 1076.39 ft²
  • Pet Friendly
    Pet Friendly
  • Parking
    Parking
More amenities
£113/Night 7 Nights - £789
Cabin
Map-icon
like-icon9.8
Exceptional
(58 Reviews)
2 Bedrooms 1 Bath 6 Guests 1200 ft²
  • Balcony/Terrace
    Balcony/Terrace
  • Pet Friendly
    Pet Friendly
More amenities
£118/Night 7 Nights - £825
Cabin
Map-icon
like-icon9.4
Exceptional
(48 Reviews)
2 Bedrooms 2 Baths 6 Guests 2000 ft²
  • Fireplace/Heating
    Fireplace/Heating
  • Balcony/Terrace
    Balcony/Terrace
More amenities
£244/Night 7 Nights - £1,707
Cottage
Map-icon
like-icon9.2
Exceptional
(58 Reviews)
2 Bedrooms 1 Bath 5 Guests 750 ft²
  • Fireplace/Heating
    Fireplace/Heating
  • Balcony/Terrace
    Balcony/Terrace
More amenities
£131/Night 7 Nights - £919

Calloway County Large Vacation Homes

Cabin
Map-icon
like-icon10.0
Exceptional
(1 Review)
4 Bedrooms 3 Baths 10 Guests 2016 ft²
  • Fireplace/Heating
    Fireplace/Heating
  • Balcony/Terrace
    Balcony/Terrace
More amenities
£254/Night 7 Nights - £1,776
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House
Map-icon
like-icon10.0
Exceptional
(1 Review)
4 Bedrooms 3 Baths 10 Guests 1840.63 ft²
  • Fireplace/Heating
    Fireplace/Heating
  • Pet Friendly
    Pet Friendly
More amenities
£192/Night 7 Nights - £1,344
House
Map-icon
like-icon10.0
Exceptional
(1 Review)
5 Bedrooms 3 Baths 14 Guests 2691 ft²
  • Fireplace/Heating
    Fireplace/Heating
  • Balcony/Terrace
    Balcony/Terrace
More amenities
£226/Night 7 Nights - £1,585
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House
Map-icon
like-icon10.0
Exceptional
(1 Review)
2 Bedrooms 2 Baths 11 Guests 1905.21 ft²
  • Oceanfront
    Oceanfront
  • Fireplace/Heating
    Fireplace/Heating
More amenities
£181/Night 7 Nights - £1,269
House
Map-icon
like-icon9.8
Exceptional
(11 Reviews)
4 Bedrooms 3 Baths 10 Guests 1840 ft²
  • Fireplace/Heating
    Fireplace/Heating
  • Balcony/Terrace
    Balcony/Terrace
More amenities
£150/Night 7 Nights - £1,052
House
Map-icon
like-icon9.4
Exceptional
(18 Reviews)
5 Bedrooms 2 Baths 10 Guests 2800 ft²
  • Fireplace/Heating
    Fireplace/Heating
  • Balcony/Terrace
    Balcony/Terrace
More amenities
£323/Night 7 Nights - £2,262
Cabin
Map-icon
4 Bedrooms 2 Baths 10 Guests
  • Fireplace/Heating
    Fireplace/Heating
  • Kitchen
    Kitchen
More amenities
£177/Night 7 Nights - £1,238
Cottage
Map-icon
like-icon10.0
Exceptional
(31 Reviews)
4 Bedrooms 2 Baths 12 Guests 1600 ft²
  • Fireplace/Heating
    Fireplace/Heating
  • Balcony/Terrace
    Balcony/Terrace
More amenities
£505/Night 7 Nights - £3,537

Why Choose Rent By Owner for your Calloway County 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 Calloway County

When should you plan your Vacation Rentals stay?

Choosing the ideal time to vacation here ensures you experience the best of what this destination has to offer, allowing you to enjoy the region’s amenities and natural beauty at their peak whenever you decide to visit.

Peak Season Highlights

summer
Late Spring to Early Summer (May to June)

During this time, the area experiences warm weather and vibrant outdoor activities, making it an ideal period for exploring and enjoying your stay.

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

The region offers pleasant temperatures and beautiful fall foliage, providing a picturesque setting for your vacation rental experience.

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

Off-Season Highlights

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Winter (December to February)

You’ll find fewer visitors during this season, with cooler temperatures offering a peaceful and quiet retreat within the area.

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

This is a less busy period, perfect for those seeking solitude and lower rates in the region’s vacation rentals.

Average Temperature Daytime: 50-60°F - Nighttime: 35-45°F

Weekly Weather Forecast for Calloway County

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.

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 seating areas such as patios or decks to relax and take in the scenic views.
  • Take advantage of private or shared pools available at some properties in the region.
  • Make the most of outdoor dining spaces perfect for gatherings and barbecues.
  • Benefit from access to well-maintained gardens or landscaped yards for outdoor activities.
  • Explore recreational options like fire pits or outdoor fireplaces for cozy evenings.
  • Utilize boat docks or water access points if staying near lakes or waterways in the area.
  • Participate in outdoor sports amenities such as volleyball courts or tennis facilities, if available.
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Family Activities

  • Kentucky Lake Boat Tours: Explore the scenic waters with your family on a boat tour that offers stunning views and a fun outdoor experience here in the region.
  • Wildlife Viewing at Land Between the Lakes National Recreation Area: Discover local wildlife and enjoy nature walks in this expansive area, perfect for family adventures and learning about the region’s flora and fauna.
  • Visit the Kentucky Lake State Park: Relax with picnics, swimming, or fishing at this popular destination, providing plenty of outdoor activities suitable for all ages.
  • Explore local museums and cultural sites: Engage your family in the area's history and culture with visits to museums that highlight the region’s heritage and entertainment options for kids.
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Adult Activities

  • Bird Watching at Kentucky Lake: Experience the tranquility of nature while observing diverse bird species around this renowned lake in the region.
  • Fishing on Kentucky Lake: Enjoy a relaxing day casting your line, as one of the area's top freshwater fishing spots offers abundant opportunities for anglers.
  • Hiking along the Land Between the Lakes: Explore scenic trails that wind through the surrounding wilderness, perfect for outdoor enthusiasts seeking adventure.
  • Golfing at local courses: Play a round at nearby golf courses that showcase the area's lush landscapes and challenging fairways tailored for all skill levels.

Calloway County Travel Tips

How Can You Make the Most of Your Stay?

  • Explore Local Weather Patterns: Check the seasonal weather forecast to plan your activities and pack appropriately for a comfortable stay in this destination.
  • Discover Nearby Outdoor Activities: Take advantage of the region's scenic landscapes by engaging in outdoor pursuits available near your vacation rentals here.
  • Plan Your Dining Experience: Research local eateries and dining options around the property to enjoy authentic regional cuisine during your visit.
  • Utilize Local Resources: Familiarize yourself with community maps, visitor centers, or online guides to maximize your exploration of the area's attractions and amenities.

Transportation Options

  • Calloway County Transit System: Provides convenient bus services that connect key areas within the region, making it easy to explore locally without a car.
  • Private Shuttle Services: Offers door-to-door transportation tailored for visitors seeking hassle-free travel experiences around the area and nearby attractions.
  • Car Rentals: Several national and local rental agencies operate here, giving you flexible options to explore the region at your own pace.
  • Taxis and Ride-Sharing Apps: Available throughout the destination, offering quick and reliable transportation options for short trips or when traveling in groups.

Local Customs Options

  • Southern Hospitality: You will notice that welcoming manners and friendliness are deeply rooted in the local culture here, making your stay in this area truly inviting.
  • Embracing traditional musical styles, locals often gather for events celebrating regional folk music that reflect the area's rich cultural heritage.
  • Farmers' Markets and Local Produce: Visiting the region's farmers' markets offers you a chance to enjoy fresh, locally grown products and experience the community’s agricultural roots.
  • Historical Preservation: Respect for history is evident in the region’s preservation efforts, which maintain the charm of historic sites and architecture for visitors like you to explore.

Frequently Asked Questions About Calloway County?

2. Which vacation homes in Calloway County are best for families?

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

3. How many Rentbyowner vacation rentals are available in Calloway County?

Currently, the total number of properties listed by Rent By Owner in 2026 is over 131 in the Calloway County 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 Calloway County. 

4. What is the cancellation policy for vacation rentals in this area?

Cancellation policies vary by property owner, so you should review the specific listing's terms and conditions carefully or contact the host directly for detailed information.

5. How do I find out about the amenities included in my rental in this region?

The amenities offered are listed on each property’s page. For additional details or special requests, reaching out to the property owner can ensure your needs are met before booking.

6. Are there any house rules I should be aware of before booking?

House rules are typically outlined in the listing description. To avoid misunderstandings, it's advisable to read these rules thoroughly or discuss them with the host prior to confirming your reservation.

7. What is the check-in and check-out process for vacation accommodations here?

Check-in and check-out procedures are specified in each listing, often including self-check-in options. Contact the host if you need clarification or have special timing requests.

8. Is it possible to modify or cancel my reservation after booking?

Changes and cancellations depend on the property's policy. Review the specific listing’s cancellation and modification terms, or contact the owner directly to discuss your options.

Calloway County Top Rated Vacation Rentals

House
Map-icon
like-icon10.0
Exceptional
(34 Reviews)
3 Bedrooms 2 Baths 6 Guests 1500 ft²
  • Fireplace/Heating
    Fireplace/Heating
  • Pool
    Pool
More amenities
£202/Night 7 Nights - £1,410
House
Map-icon
like-icon9.8
Exceptional
(47 Reviews)
4 Bedrooms 2 Baths 8 Guests 1400 ft²
  • Fireplace/Heating
    Fireplace/Heating
  • Pool
    Pool
More amenities
£238/Night 7 Nights - £1,663
Hotel
Map-icon
like-icon9.2
Exceptional
(513 Reviews)
1 Bath
  • Pool
    Pool
  • Breakfast
    Breakfast
More amenities
£97/Night 7 Nights - £681
Hotel
Map-icon
like-icon9.1
Exceptional
(150 Reviews)
6 Baths 322.92 ft²
  • Private Pool
    Private Pool
  • Oceanfront
    Oceanfront
More amenities
£83/Night 7 Nights - £579
star-icons-3
Hotel
Map-icon
like-icon8.7
Fabulous
(104 Reviews)
2 Baths 339.06 ft²
  • Private Pool
    Private Pool
  • Pool
    Pool
More amenities
£91/Night 7 Nights - £637
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Hotel
Map-icon
like-icon8.5
Fabulous
(70 Reviews)
1 Bath 322.92 ft²
  • Private Pool
    Private Pool
  • Fireplace/Heating
    Fireplace/Heating
More amenities
£101/Night 7 Nights - £707
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Hotel
Map-icon
like-icon7.9
Very Good
(188 Reviews)
1 Bath 247.57 ft²
  • Fireplace/Heating
    Fireplace/Heating
  • Pool
    Pool
More amenities
£72/Night 7 Nights - £501
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Hotel
Map-icon
like-icon7.3
Very Good
(52 Reviews)
1 Bath 301.39 ft²
  • Private Pool
    Private Pool
  • Pool
    Pool
More amenities
£61/Night 7 Nights - £428