Discover Your Perfect Olmstead Vacation Homes

Best Vacation Homes in Olmstead

Cabin
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like-icon10.0
Exceptional
(6 Reviews)
1 Bedroom 2 Baths 4 Guests
  • Fireplace/Heating
    Fireplace/Heating
  • Kitchen
    Kitchen
More amenities
£103/Night 7 Nights - £722
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House
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like-icon10.0
Exceptional
(8 Reviews)
4 Bedrooms 3 Baths 8 Guests 3003.13 ft²
  • Hot Tub
    Hot Tub
  • Fireplace/Heating
    Fireplace/Heating
More amenities
£159/Night 7 Nights - £1,111
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Bed & Breakfast
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like-icon10.0
Exceptional
(50 Reviews)
1 Bedroom 1 Bath
  • Balcony/Terrace
    Balcony/Terrace
  • Breakfast
    Breakfast
More amenities
£97/Night 7 Nights - £681
House
Map-icon
like-icon10.0
Exceptional
(2 Reviews)
2 Bedrooms 1 Bath 6 Guests 1200 ft²
  • Fireplace/Heating
    Fireplace/Heating
  • Balcony/Terrace
    Balcony/Terrace
More amenities
£192/Night 7 Nights - £1,342
Bed & Breakfast
Map-icon
like-icon10.0
Exceptional
(3 Reviews)
4 Bedrooms 12 Baths 16 Guests 527.43 ft²
  • Balcony/Terrace
    Balcony/Terrace
  • Breakfast
    Breakfast
More amenities
£74/Night 7 Nights - £519
Cottage
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like-icon10.0
Exceptional
(1 Review)
1 Bedroom 1 Bath 2 Guests 384 ft²
  • Fireplace/Heating
    Fireplace/Heating
  • Balcony/Terrace
    Balcony/Terrace
More amenities
£83/Night 7 Nights - £583
Cabin
Map-icon
like-icon9.8
Exceptional
(14 Reviews)
1 Bedroom 3 Baths 6 Guests 1800 ft²
  • Fireplace/Heating
    Fireplace/Heating
  • Balcony/Terrace
    Balcony/Terrace
More amenities
£170/Night 7 Nights - £1,191
Apartment
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like-icon8.0
Excellent
(1 Review)
1 Bedroom 1 Bath 2 Guests 600 ft²
  • Fireplace/Heating
    Fireplace/Heating
  • Balcony/Terrace
    Balcony/Terrace
More amenities
£94/Night 7 Nights - £658

Olmstead Luxury Rentals

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House
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like-icon9.0
Exceptional
(2 Reviews)
5 Bedrooms 2 Baths 12 Guests 3003.13 ft²
  • Fireplace/Heating
    Fireplace/Heating
  • Balcony/Terrace
    Balcony/Terrace
More amenities
£282/Night 7 Nights - £1,974
House
Map-icon
like-icon9.2
Exceptional
(21 Reviews)
5 Bedrooms 2 Baths 12 Guests 3000 ft²
  • Fireplace/Heating
    Fireplace/Heating
  • Balcony/Terrace
    Balcony/Terrace
More amenities
£236/Night 7 Nights - £1,653
New
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House
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3 Bedrooms 3 Baths 6 Guests 1603.82 ft²
  • Fireplace/Heating
    Fireplace/Heating
  • Balcony/Terrace
    Balcony/Terrace
More amenities
£212/Night 7 Nights - £1,481
House
Map-icon
like-icon10.0
Exceptional
(7 Reviews)
4 Bedrooms 3 Baths 17 Guests 4600 ft²
  • Fireplace/Heating
    Fireplace/Heating
  • Pet Friendly
    Pet Friendly
More amenities
£194/Night 7 Nights - £1,358
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House
Map-icon
1 Bedroom 3 Baths 6 Guests 1797.57 ft²
  • Fireplace/Heating
    Fireplace/Heating
  • Balcony/Terrace
    Balcony/Terrace
More amenities
£191/Night 7 Nights - £1,336
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House
Map-icon
3 Bedrooms 3 Baths 8 Guests 1700.7 ft²
  • Fireplace/Heating
    Fireplace/Heating
  • Pet Friendly
    Pet Friendly
More amenities
£175/Night 7 Nights - £1,226
House
Map-icon
like-icon9.8
Exceptional
(102 Reviews)
5 Bedrooms 3 Baths 20 Guests 4600 ft²
  • Fireplace/Heating
    Fireplace/Heating
  • Balcony/Terrace
    Balcony/Terrace
More amenities
£175/Night 7 Nights - £1,223
House
Map-icon
like-icon8.4
Excellent
(5 Reviews)
3 Bedrooms 2 Baths 8 Guests 1700 ft²
  • Fireplace/Heating
    Fireplace/Heating
  • Balcony/Terrace
    Balcony/Terrace
More amenities
£168/Night 7 Nights - £1,177

Olmstead Pet Friendly Vacation Rentals

House
Map-icon
like-icon10.0
Exceptional
(18 Reviews)
4 Bedrooms 3 Baths 8 Guests
  • Hot Tub
    Hot Tub
  • Fireplace/Heating
    Fireplace/Heating
More amenities
£161/Night 7 Nights - £1,127
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Cabin
Map-icon
like-icon8.5
Fabulous
(101 Reviews)
20 Bedrooms 1 Bath 24 Guests 279.86 ft²
  • Fireplace/Heating
    Fireplace/Heating
  • Pet Friendly
    Pet Friendly
More amenities
£82/Night 7 Nights - £577
House
Map-icon
like-icon10.0
Exceptional
(3 Reviews)
3 Bedrooms 2 Baths 6 Guests
  • Fireplace/Heating
    Fireplace/Heating
  • Pet Friendly
    Pet Friendly
More amenities
£163/Night 7 Nights - £1,142
Bed & Breakfast
Map-icon
4 Bedrooms 4 Baths 12 Guests 419.79 ft²
  • Balcony/Terrace
    Balcony/Terrace
  • Pet Friendly
    Pet Friendly
More amenities
£82/Night 7 Nights - £572
House
Map-icon
4 Bedrooms 2 Baths 8 Guests
  • Fireplace/Heating
    Fireplace/Heating
  • Pet Friendly
    Pet Friendly
More amenities
£153/Night 7 Nights - £1,069
House
Map-icon
like-icon9.4
Exceptional
(13 Reviews)
5 Bedrooms 6 Baths 20 Guests 4000 ft²
  • Private Pool
    Private Pool
  • Hot Tub
    Hot Tub
More amenities
£593/Night 7 Nights - £4,148
House
Map-icon
6 Bedrooms 7 Baths 14 Guests
  • Hot Tub
    Hot Tub
  • Spa
    Spa
More amenities
£375/Night 7 Nights - £2,623
Other
Map-icon
3 Bedrooms 2 Baths 6 Guests
  • Hot Tub
    Hot Tub
  • Fireplace/Heating
    Fireplace/Heating
More amenities
£88/Night 7 Nights - £614

Olmstead Large Vacation Homes

Cabin
Map-icon
like-icon10.0
Exceptional
(42 Reviews)
4 Bedrooms 3 Baths 12 Guests 2200 ft²
  • Hot Tub
    Hot Tub
  • Spa
    Spa
More amenities
£199/Night 7 Nights - £1,394
House
Map-icon
6 Bedrooms 6 Baths 16 Guests 5000 ft²
  • Fireplace/Heating
    Fireplace/Heating
  • Balcony/Terrace
    Balcony/Terrace
More amenities
£639/Night 7 Nights - £4,470
Bed & Breakfast
Map-icon
6 Bedrooms 7 Baths 14 Guests
  • Hot Tub
    Hot Tub
  • Spa
    Spa
More amenities
£359/Night 7 Nights - £2,513
Other
Map-icon
like-icon5.0
Average
(2 Reviews)
3 Bedrooms 3 Baths 10 Guests
  • Kitchen
    Kitchen
  • Air Conditioner
    Air Conditioner
More amenities
£281/Night 7 Nights - £1,968

Why Choose Rent By Owner for your Olmstead 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 Olmstead

When should you plan your Vacation Rentals stay?

Choosing the optimal time to vacation here ensures you experience the region’s natural beauty and pleasant weather, making your stay in Olmstead, Kentucky, USA, truly memorable.

Peak Season Highlights

spring
Spring (March to May)

During this time, the region experiences mild and pleasant weather, making it ideal for exploring the outdoors and enjoying the scenic surroundings of the area.

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

Autumn brings beautiful foliage and comfortable temperatures, offering a perfect backdrop for relaxing stays and outdoor activities around here.

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

Off-Season Highlights

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Summer (June to August)

Although summer offers warm weather, it can be quite hot and humid, which may impact your outdoor plans while visiting here.

Average Temperature Daytime: 85°F to 90°F - Nighttime: 65°F to 70°F
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Winter (December to February)

During winter, expect colder temperatures and possible snowfall, providing a quieter experience for those seeking solitude in the region.

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

Weekly Weather Forecast for Olmstead

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 a private outdoor space with a spacious patio or deck for relaxing and entertaining.
  • Take advantage of scenic views with access to nearby fishing or boating opportunities in the area.
  • Benefit from outdoor grilling facilities perfect for preparing meals amidst natural surroundings.
  • Explore walking trails or nature paths directly from your rental, ideal for outdoor enthusiasts.
  • Make use of a swimming pool or hot tub to unwind after a day of exploring the region.
  • Utilize outdoor sports amenities such as basketball courts or volleyball setups if available.
  • Experience the tranquility of well-maintained gardens or landscaped yards that enhance your stay here.
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Family Activities

  • Olmstead River Walk: Take a leisurely stroll along the scenic river walk perfect for families to enjoy nature and local scenery in the region.
  • Heritage Park: Visit this family-friendly park featuring open spaces, playgrounds, and picnic areas ideal for relaxing days with children.
  • Local Farm Tours: Experience the charm of nearby farms offering educational tours and hands-on activities that engage kids and teach about regional agriculture.
  • Community Events: Participate in seasonal festivals and outdoor concerts hosted regularly here, creating memorable family moments in this destination.
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Adult Activities

  • Fishing at Lake Malone State Park: Spend a relaxing day casting your line in the tranquil waters of Lake Malone, a popular spot near here for both novice and experienced anglers.
  • Exploring Lake Malone State Park Trails: Discover scenic hiking and biking trails that wind through the area’s natural beauty, offering an ideal outdoor adventure for active visitors.
  • Bird Watching and Wildlife Viewing: Enjoy observing diverse bird species and local wildlife in their natural habitat within the region's protected areas.
  • Picnic and Leisure Activities: Take advantage of picnic areas in the vicinity to unwind and enjoy a peaceful meal surrounded by the area's scenic landscapes.

Olmstead Travel Tips

How Can You Make the Most of Your Stay?

  • Explore Local Attractions: Discover nearby scenic spots and cultural sites to enrich your stay in this region.
  • Plan Ahead for Activities: Book outdoor adventures or tours in advance to make the most of your time here.
  • Choose the Right Rental: Select a vacation rental that offers convenient access to key destinations around the area.
  • Embrace the Local Cuisine: Try regional specialties at local eateries to experience the authentic flavor of this destination.

Transportation Options

  • Interstate Highway Access: Major highways connect this destination to nearby cities, making road trips convenient and straightforward for visitors staying here.
  • Regional Bus Services: Local bus routes provide affordable and reliable transportation options within the area, ideal for exploring without a vehicle.
  • Private Car Rentals: Renting a car here offers flexibility and ease of travel, enabling you to discover all that this region has to offer at your own pace.
  • Nearby Airports: The closest airports serve as convenient gateways, ensuring seamless travel connections for those arriving from farther destinations.

Local Customs Options

  • Southern Hospitality: You will notice a warm and welcoming attitude toward visitors, reflecting the region's tradition of genuine friendliness.
  • Local Festivals: Participating in or observing community festivals offers insight into the area's cultural heritage and local pride.
  • Traditional Cuisine: Expect to enjoy regional dishes that highlight the area's culinary history, often shared during family gatherings and community events.
  • Respect for Nature: The community values outdoor activities and conservation, making it common for locals to prioritize environmental preservation during your stay.

Frequently Asked Questions About Olmstead?

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

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

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

Currently, the total number of properties listed by Rent By Owner in 2026 is over 39 in the Olmstead 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 Olmstead. 

4. What is the cancellation policy for vacation rentals in Olmstead, Kentucky?

Cancellation policies vary by property, so it’s important to review the specific listing details or contact the property owner directly to understand the terms and possible fees associated with cancellations.

5. Are pets allowed in vacation rentals here?

Pet policies differ among properties, so please check each listing for specific pet restrictions or contact the host to confirm if bringing your pet is permitted during your stay.

6. How do I find out about the amenities included in a vacation rental in this region?

Details about amenities are listed on the property page; however, reaching out to the owner can provide additional information or clarify any special features you’re interested in.

7. What is the check-in and check-out process at these vacation rentals?

Check-in and check-out procedures are detailed on the listing, but contacting the owner beforehand ensures a smooth arrival and departure experience tailored to your schedule.

8. How do I confirm the availability of a property I want to book?

Availability calendars are updated regularly on the listing, but confirming with the property owner guarantees that your selected dates are open and reserved for your stay.