Discover Your Perfect Fairdealing Vacation Homes

Best Vacation Homes in Fairdealing

House
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like-icon10.0
Exceptional
(17 Reviews)
2 Bedrooms 1 Bath 6 Guests
  • Fireplace/Heating
    Fireplace/Heating
  • Kitchen
    Kitchen
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R4,850/Night 7 Nights - R33,958
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House
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like-icon9.2
Exceptional
(5 Reviews)
2 Bedrooms 2 Baths 7 Guests 2561.81 ft²
  • Fireplace/Heating
    Fireplace/Heating
  • Pet Friendly
    Pet Friendly
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R2,328/Night 7 Nights - R16,296
Cabin
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like-icon10.0
Exceptional
(1 Review)
1 Bedroom 1 Bath 4 Guests
  • Fireplace/Heating
    Fireplace/Heating
  • Balcony/Terrace
    Balcony/Terrace
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R2,455/Night 7 Nights - R17,190
Cabin
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like-icon10.0
Exceptional
(16 Reviews)
1 Bedroom 1 Bath 2 Guests 1100 ft²
  • Fireplace/Heating
    Fireplace/Heating
  • Ocean View
    Ocean View
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R3,136/Night 7 Nights - R21,947
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Apartment
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2 Bedrooms 1 Bath 4 Guests 1302.43 ft²
  • Oceanfront
    Oceanfront
  • Fireplace/Heating
    Fireplace/Heating
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R2,800/Night 7 Nights - R19,602
Cottage
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like-icon10.0
Exceptional
(15 Reviews)
1 Bedroom 1 Bath 2 Guests 224 ft²
  • Fireplace/Heating
    Fireplace/Heating
  • Balcony/Terrace
    Balcony/Terrace
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R2,786/Night 7 Nights - R19,501
Apartment
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like-icon10.0
Exceptional
(7 Reviews)
1 Bedroom 1 Bath 4 Guests
  • Hot Tub
    Hot Tub
  • Fireplace/Heating
    Fireplace/Heating
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R3,656/Night 7 Nights - R25,591
House
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like-icon10.0
Exceptional
(3 Reviews)
2 Bedrooms 2 Baths 4 Guests
  • Fireplace/Heating
    Fireplace/Heating
  • Pet Friendly
    Pet Friendly
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R3,141/Night 7 Nights - R21,981

Fairdealing Luxury Rentals

House
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4 Bedrooms 3 Baths 10 Guests 3599 ft²
  • Fireplace/Heating
    Fireplace/Heating
  • Balcony/Terrace
    Balcony/Terrace
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R17,919/Night 7 Nights - R125,440
Cabin
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like-icon9.8
Exceptional
(18 Reviews)
5 Bedrooms 2 Baths 18 Guests 2400 ft²
  • Fireplace/Heating
    Fireplace/Heating
  • Pool
    Pool
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R14,605/Night 7 Nights - R102,245
Cabin
Map-icon
like-icon10.0
Exceptional
(14 Reviews)
3 Bedrooms 2 Baths 9 Guests
  • Oceanfront
    Oceanfront
  • Hot Tub
    Hot Tub
More amenities
R9,856/Night 7 Nights - R68,995
Cabin
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like-icon9.8
Exceptional
(6 Reviews)
4 Bedrooms 3 Baths 9 Guests 2200 ft²
  • Hot Tub
    Hot Tub
  • Fireplace/Heating
    Fireplace/Heating
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R9,667/Night 7 Nights - R67,663
House
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like-icon10.0
Exceptional
(18 Reviews)
7 Bedrooms 3 Baths 14 Guests
  • Fireplace/Heating
    Fireplace/Heating
  • Balcony/Terrace
    Balcony/Terrace
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R9,240/Night 7 Nights - R64,677
Cabin
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like-icon10.0
Exceptional
(8 Reviews)
7 Bedrooms 3 Baths 14 Guests
  • Fireplace/Heating
    Fireplace/Heating
  • Balcony/Terrace
    Balcony/Terrace
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R8,520/Night 7 Nights - R59,633
Cabin
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like-icon10.0
Exceptional
(4 Reviews)
4 Bedrooms 3 Baths 12 Guests
  • Fireplace/Heating
    Fireplace/Heating
  • Kitchen
    Kitchen
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R7,741/Night 7 Nights - R54,184
Cabin
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like-icon8.4
Excellent
(6 Reviews)
3 Bedrooms 2 Baths 11 Guests
  • Fireplace/Heating
    Fireplace/Heating
  • Kitchen
    Kitchen
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R6,697/Night 7 Nights - R46,880

Fairdealing Pet Friendly Vacation Rentals

House
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like-icon9.4
Exceptional
(31 Reviews)
2 Bedrooms 2 Baths 7 Guests 2558 ft²
  • Fireplace/Heating
    Fireplace/Heating
  • Balcony/Terrace
    Balcony/Terrace
More amenities
R3,141/Night 7 Nights - R21,981
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Hotel
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like-icon9.2
Exceptional
(488 Reviews)
7 Baths 342.91 ft²
  • Hot Tub
    Hot Tub
  • Fireplace/Heating
    Fireplace/Heating
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R2,519/Night 7 Nights - R17,628
House
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like-icon9.0
Exceptional
(11 Reviews)
2 Bedrooms 2 Baths 4 Guests 1100 ft²
  • Fireplace/Heating
    Fireplace/Heating
  • Balcony/Terrace
    Balcony/Terrace
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R4,493/Night 7 Nights - R31,444
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Hotel
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like-icon8.7
Fabulous
(259 Reviews)
1 Bath 355.21 ft²
  • Pool
    Pool
  • Pet Friendly
    Pet Friendly
More amenities
R1,879/Night 7 Nights - R13,158
RV Rental
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1 Bedroom 1 Bath 8 Guests
  • Pet Friendly
    Pet Friendly
  • Child Friendly
    Child Friendly
More amenities
R4,952/Night 7 Nights - R34,666
House
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like-icon10.0
Exceptional
(72 Reviews)
4 Bedrooms 2 Baths 8 Guests
  • Fireplace/Heating
    Fireplace/Heating
  • Balcony/Terrace
    Balcony/Terrace
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R3,437/Night 7 Nights - R24,056
House
Map-icon
like-icon10.0
Exceptional
(9 Reviews)
3 Bedrooms 2 Baths 6 Guests
  • Fireplace/Heating
    Fireplace/Heating
  • Balcony/Terrace
    Balcony/Terrace
More amenities
R3,284/Night 7 Nights - R22,993
House
Map-icon
like-icon10.0
Exceptional
(7 Reviews)
3 Bedrooms 2 Baths 6 Guests
  • Fireplace/Heating
    Fireplace/Heating
  • Pet Friendly
    Pet Friendly
More amenities
R3,378/Night 7 Nights - R23,651

Fairdealing Large Vacation Homes

Cabin
Map-icon
like-icon10.0
Exceptional
(63 Reviews)
3 Bedrooms 2 Baths 10 Guests 2200 ft²
  • Fireplace/Heating
    Fireplace/Heating
  • Ocean View
    Ocean View
More amenities
R5,135/Night 7 Nights - R35,948
House
Map-icon
like-icon10.0
Exceptional
(9 Reviews)
4 Bedrooms 2 Baths 10 Guests
  • Fireplace/Heating
    Fireplace/Heating
  • Balcony/Terrace
    Balcony/Terrace
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R6,494/Night 7 Nights - R45,463
Other
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like-icon9.4
Exceptional
(6 Reviews)
3 Bedrooms 2 Baths 16 Guests 2100 ft²
  • Fireplace/Heating
    Fireplace/Heating
  • Kitchen
    Kitchen
More amenities
R6,517/Night 7 Nights - R45,615
House
Map-icon
like-icon9.6
Exceptional
(10 Reviews)
5 Bedrooms 4 Baths 7 Guests
  • Fireplace/Heating
    Fireplace/Heating
  • Balcony/Terrace
    Balcony/Terrace
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R3,526/Night 7 Nights - R24,680
House
Map-icon
like-icon9.8
Exceptional
(48 Reviews)
4 Bedrooms 3 Baths 15 Guests
  • Hot Tub
    Hot Tub
  • Spa
    Spa
More amenities
R6,537/Night 7 Nights - R45,766
House
Map-icon
like-icon9.8
Exceptional
(18 Reviews)
6 Bedrooms 3 Baths 16 Guests
  • Fireplace/Heating
    Fireplace/Heating
  • Ocean View
    Ocean View
More amenities
R9,720/Night 7 Nights - R68,034
Cabin
Map-icon
like-icon5.0
Average
(8 Reviews)
4 Bedrooms 3 Baths 10 Guests
  • Child Friendly
    Child Friendly
R6,225/Night 7 Nights - R43,573
House
Map-icon
like-icon4.8
Average
(20 Reviews)
4 Bedrooms 4 Baths 12 Guests
  • Balcony/Terrace
    Balcony/Terrace
  • Kitchen
    Kitchen
More amenities
R3,290/Night 7 Nights - R23,027

Why Choose Rent By Owner for your Fairdealing 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 Fairdealing

When should you plan your Vacation Rentals stay?

Timing your visit to this destination can significantly enhance your experience, as certain seasons here offer more favorable weather and activities, making it easier to find the perfect vacation rentals in the area.

Peak Season Highlights

spring
Spring (March - May)

During spring, the area experiences mild and comfortable weather, making it ideal for exploring outdoor activities and enjoying the natural beauty of this destination.

Average Temperature Daytime: 65°F to 75°F - Nighttime: 45°F to 55°F
autumn
Fall (September - November)

Autumn offers pleasant temperatures and vibrant foliage, providing a picturesque setting for your stay and outdoor adventures in this region.

Average Temperature Daytime: 60°F to 70°F - Nighttime: 40°F to 50°F

Off-Season Highlights

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Summer (June - August)

The summer months are warmer, with higher temperatures that appeal to travelers seeking sunny weather and outdoor activities.

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

During winter, cooler temperatures and occasional cold fronts create a quieter atmosphere, ideal for those looking for a peaceful retreat away from peak crowds.

Average Temperature Daytime: 40°F to 50°F - Nighttime: 25°F to 35°F

Weekly Weather Forecast for Fairdealing

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 dining areas equipped for family meals and gatherings
  • Relax in private outdoor spaces with comfortable seating and lounge chairs
  • Make the most of spacious yards ideal for play or outdoor activities
  • Take advantage of barbecue grills available for cookouts under the open sky
  • Benefit from well-maintained patios perfect for soaking in the local scenery
  • Explore nearby walking trails or scenic paths accessible directly from your rental
  • Unwind in outdoor fire pits suitable for cozy evenings in the region
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Family Activities

  • Fairdealing Family Fun Park: Enjoy a day of outdoor entertainment with miniature golf, go-karts, and arcade games perfect for all ages.
  • Circle B Recreation Area: Experience outdoor adventures such as hiking, picnicking, and fishing at this scenic spot ideal for family outings.
  • Local Nature Trails: Discover the natural beauty of the region by exploring peaceful walking trails that offer opportunities for wildlife viewing and educational nature walks.
  • Community Events and Festivals: Participate in seasonal festivals and local events that showcase the area's friendly atmosphere and family-friendly activities.
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Adult Activities

  • Exploring local history at the Fairdealing Historical Museum: Discover fascinating stories and artifacts that showcase the region’s rich heritage during your stay.
  • Enjoying outdoor recreation in nearby parks: Take advantage of scenic trails, picnic spots, and tranquil settings perfect for relaxing activities amidst nature.
  • Fishing and boating on the area’s lakes: Spend a peaceful day engaging in water-based activities on the serene lakes close to your vacation rental.
  • Visiting local eateries and cafes: Savor regional flavors and comfort foods by exploring the charming dining options available here.

Fairdealing Travel Tips

How Can You Make the Most of Your Stay?

  • Plan Ahead for Local Attractions: Research the area’s key sights and activities to ensure your stay in this destination aligns with your interests and maximizes your experience.
  • Choose Your Vacation Rentals Wisely: Opt for properties that are centrally located or offer easy access to the region's main spots, enhancing convenience during your visit.
  • Explore Authentic Local Cuisine: Take time to dine at nearby eateries or try cooking local ingredients in your vacation rental to immerse yourself in the regional flavors.
  • Stay Connected with Reliable Internet: Select accommodations with dependable Wi-Fi to enjoy seamless communication and plan your daily excursions efficiently within the area.

Transportation Options

  • Car Rentals: Convenient car rental services are available for exploring the region around your vacation rental in Fairdealing, Missouri, offering flexibility and ease of travel.
  • Public Transit: Local bus services provide an affordable way to navigate this part of Missouri and access nearby attractions from your accommodation.
  • Taxi and Rideshare: Taxis and rideshare options like Uber or Lyft offer a reliable transportation choice for quick trips around the area or to local points of interest.
  • Airport Shuttle Services: Shuttle services connect you directly from the nearest airports to your vacation rental, simplifying your arrival and departure process here.

Local Customs Options

  • Southern Hospitality: Warm welcomes and friendly interactions are a cherished part of local culture, making your stay here feel like visiting family.
  • Participating in or observing this regional social event is a great way to experience the area's community spirit in Fairdealing.
  • Church Community Gatherings: Attending local church services offers insight into the region's close-knit traditions and cultural values.
  • Holiday Celebrations: Festive events during holidays showcase the area's unique way of honoring traditions with parades and community activities.

Frequently Asked Questions About Fairdealing?

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

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

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

Currently, the total number of properties listed by Rent By Owner in 2026 is over 81 in the Fairdealing 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 Fairdealing. 

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

Cancellation policies vary by listing, so it's important to review the specific property's terms before booking. You can find detailed information on the listing page or contact the property owner directly for clarification.

5. How do I ensure my reservation is secured and what payment methods are accepted?

Reservations are typically confirmed once you complete the payment process through the platform. Accepted payment methods often include credit/debit cards, but verify with the specific listing for any additional options or requirements.

6. Are there any specific amenities or features available in these vacation rentals in the region?

Amenities differ across properties, so be sure to check each listing for details on essentials like Wi-Fi, parking, or kitchen facilities. Reach out to the property owner if you have particular needs or questions.

7. What should I know about check-in and check-out procedures when staying here?

Check-in and check-out times are specified in each listing. Contact the host directly if you require special arrangements or need further guidance on the process to ensure a smooth stay.

8. Is there any local regulation or requirement I should be aware of before booking a vacation rental in this destination?

Local regulations may influence your stay, including permits or restrictions. Review the listing details or consult with the property owner to ensure compliance with regional rules during your visit.

Fairdealing Top Rated Vacation Rentals

House
Map-icon
like-icon10.0
Exceptional
(28 Reviews)
3 Bedrooms 1 Bath 6 Guests
  • Fireplace/Heating
    Fireplace/Heating
  • Pool
    Pool
More amenities
R2,395/Night 7 Nights - R16,768
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Hotel
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like-icon9.4
Exceptional
(876 Reviews)
1 Bath
  • Pool
    Pool
  • Balcony/Terrace
    Balcony/Terrace
More amenities
R2,096/Night 7 Nights - R14,676
Hotel
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like-icon9.4
Exceptional
(842 Reviews)
1 Bath
  • Pool
    Pool
  • Breakfast
    Breakfast
More amenities
R1,766/Night 7 Nights - R12,365
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Hotel
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like-icon9.2
Exceptional
(1003 Reviews)
1 Bath
  • Hot Tub
    Hot Tub
  • Pool
    Pool
More amenities
R1,792/Night 7 Nights - R12,534
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Hotel
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like-icon8.8
Fabulous
(740 Reviews)
1 Bath
  • Pool
    Pool
  • Breakfast
    Breakfast
More amenities
R1,696/Night 7 Nights - R11,876
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Hotel
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like-icon8.7
Fabulous
(197 Reviews)
3 Baths 261.92 ft²
  • Private Pool
    Private Pool
  • Oceanfront
    Oceanfront
More amenities
R1,957/Night 7 Nights - R13,698
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Hotel
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like-icon8.6
Fabulous
(158 Reviews)
9 Baths 521.45 ft²
  • Private Pool
    Private Pool
  • Oceanfront
    Oceanfront
More amenities
R1,971/Night 7 Nights - R13,799
Hotel
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like-icon7.8
Very Good
(410 Reviews)
1 Bath
  • Pool
    Pool
  • Breakfast
    Breakfast
More amenities
R1,736/Night 7 Nights - R12,163