Best Vacation Homes in Highlands County
House
10.0(74 Reviews)
2 Bedrooms
1 Bath
7 Guests
1400 ft²
Fireplace/Heating
Balcony/Terrace
Pet Friendly
Kitchen
R2,467/Night
7 Nights - R17,274
House
10.0(8 Reviews)
3 Bedrooms
3 Baths
7 Guests
236.81 ft²
- Balcony/Terrace
View
Parking
Air Conditioner
R5,623/Night
7 Nights - R39,356
Villa
10.0(1 Review)
1 Bedroom
1 Bath
- Fireplace/Heating
Pool
Ocean View- Balcony/Terrace
R7,654/Night
7 Nights - R53,577
House
10.0(37 Reviews)
2 Bedrooms
2 Baths
6 Guests
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
- View
R5,352/Night
7 Nights - R37,467
House
10.0(4 Reviews)
3 Bedrooms
2 Baths
10 Guests
2002.09 ft²
- Balcony/Terrace
- Parking
- Air Conditioner
Internet
R4,309/Night
7 Nights - R30,162
House
10.0(33 Reviews)
2 Bedrooms
2 Baths
5 Guests
1400 ft²
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
R1,781/Night
7 Nights - R12,466
House
10.0(32 Reviews)
2 Bedrooms
2 Baths
4 Guests
931 ft²
Hot Tub- Balcony/Terrace
- Pet Friendly
- Kitchen
R2,124/Night
7 Nights - R14,862
House
10.0(27 Reviews)
2 Bedrooms
2 Baths
6 Guests
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
R2,394/Night
7 Nights - R16,751
Highlands County Luxury Rentals
House
10.0(20 Reviews)
8 Bedrooms
4 Baths
22 Guests
6250 ft²
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
- View
R78,623/Night
7 Nights - R550,361
House
3 Bedrooms
2 Baths
10 Guests
- Fireplace/Heating
- Pool
- Kitchen
- Parking
R39,221/Night
7 Nights - R274,548
House
4 Bedrooms
3 Baths
10 Guests
- Fireplace/Heating
- Kitchen
- Parking
- Air Conditioner
R34,838/Night
7 Nights - R243,863
House
10.0(1 Review)
4 Bedrooms
2 Baths
8 Guests
- Hot Tub
- Fireplace/Heating
- Pool
- Balcony/Terrace
R34,160/Night
7 Nights - R239,122
House
10.0(6 Reviews)
5 Bedrooms
3 Baths
8 Guests
7000 ft²
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
- View
R31,558/Night
7 Nights - R220,903
House
1 Bedroom
4 Baths
16 Guests
4499.31 ft²
- Fireplace/Heating
- Pool
- View
- Pet Friendly
R26,991/Night
7 Nights - R188,936
House
4 Bedrooms
5 Baths
8 Guests
Private Pool- Fireplace/Heating
- Pool
- Ocean View
R26,298/Night
7 Nights - R184,078
House
4 Bedrooms
3 Baths
11 Guests
3056.95 ft²
Oceanfront- Fireplace/Heating
- Pool
- Ocean View
R24,845/Night
7 Nights - R173,906
Highlands County Pet Friendly Vacation Rentals
House
10.0(24 Reviews)
2 Bedrooms
2 Baths
6 Guests
- Hot Tub
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
R2,495/Night
7 Nights - R17,460
R3,340/Night
7 Nights - R23,381
Cottage
8.0(1 Review)
1 Bedroom
1 Bath
- Oceanfront
- Fireplace/Heating
- Pool
- Ocean View
R8,349/Night
7 Nights - R58,452
House
10.0(16 Reviews)
2 Bedrooms
2 Baths
6 Guests
1300 ft²
- Hot Tub
- Fireplace/Heating
- Ocean View
- View
R7,511/Night
7 Nights - R52,582
House
10.0(2 Reviews)
1 Bedroom
2 Baths
15 Guests
904.17 ft²
- Hot Tub
- Fireplace/Heating
- Pool
- Balcony/Terrace
R2,338/Night
7 Nights - R16,363
House
10.0(15 Reviews)
2 Bedrooms
1 Bath
6 Guests
- Hot Tub
- Ocean View
- Balcony/Terrace
- View
R3,704/Night
7 Nights - R25,928
House
10.0(13 Reviews)
2 Bedrooms
2 Baths
5 Guests
- Hot Tub
- Fireplace/Heating
- Pet Friendly
- Kitchen
R2,759/Night
7 Nights - R19,315
House
10.0(12 Reviews)
2 Bedrooms
1 Bath
6 Guests
1399 ft²
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
R2,635/Night
7 Nights - R18,438
Highlands County Large Vacation Homes
Villa
10.0(8 Reviews)
2 Bedrooms
2 Baths
4 Guests
1000 ft²
- Fireplace/Heating
- Pool
- Ocean View
- Balcony/Terrace
R3,446/Night
7 Nights - R24,123
House
10.0(1 Review)
3 Bedrooms
2 Baths
10 Guests
2185.07 ft²
- Balcony/Terrace
- Kitchen
- Parking
- Air Conditioner
R4,976/Night
7 Nights - R34,835
Villa
10.0(2 Reviews)
2 Bedrooms
2 Baths
6 Guests
- Fireplace/Heating
- Pool
- Balcony/Terrace
- Kitchen
R9,312/Night
7 Nights - R65,183
Villa
10.0(1 Review)
2 Bedrooms
2 Baths
5 Guests
1313.2 ft²
- Fireplace/Heating
- Pool
- Pet Friendly
- Parking
R4,572/Night
7 Nights - R32,001
Villa
10.0(2 Reviews)
1 Bedroom
1 Bath
2 Guests
- Fireplace/Heating
- Air Conditioner
- Internet
Child Friendly
R1,310/Night
7 Nights - R9,160
House
10.0(1 Review)
2 Bedrooms
1 Bath
10 Guests
- Hot Tub
- Fireplace/Heating
- Pet Friendly
- Kitchen
R6,453/Night
7 Nights - R45,176
Villa
10.0(1 Review)
2 Bedrooms
2 Baths
4 Guests
- Fireplace/Heating
- Air Conditioner
- Internet
- Child Friendly
R1,783/Night
7 Nights - R12,483
Villa
9.8(8 Reviews)
2 Bedrooms
2 Baths
5 Guests
- Fireplace/Heating
- Kitchen
- Air Conditioner
- Internet
R5,329/Night
7 Nights - R37,298
Why Choose Rent By Owner for your Highlands County Vacation Rental Homes?
What makes our Vacation Rentals special?
Verified Listings
Book with confidence knowing every property meets our quality and safety standards.
Unbeatable Value
Enjoy competitive pricing with no hidden fees, providing exceptional value for every stay.
Diverse Options
From cozy cabins to luxurious villas, find a rental that suits your style and needs.
Best Times to Visit Highlands County
When should you plan your Vacation Rentals stay?
Choosing the optimal time to vacation in Highlands County ensures you experience the region’s best weather and activities, making it a perfect destination for your next getaway.
Peak Season Highlights
Winter (December to February)
During the winter months, you can enjoy mild temperatures and less humidity, making it an ideal time to explore this region's outdoor activities and local scenery.
Average Temperature Daytime: 70°F - Nighttime: 50°F
Spring (March to May)
Springtime brings pleasant weather and blooming landscapes, perfect for experiencing the outdoors and appreciating the natural beauty here.
Average Temperature Daytime: 78°F - Nighttime: 55°F
Off-Season Highlights
Summer (June to August)
In the summer, the area experiences higher temperatures and increased humidity, which might be less comfortable but ideal for water-based activities and outdoor adventures.
Average Temperature Daytime: 90°F - Nighttime: 72°F
Fall (September to November)
Autumn sees cooler temperatures and fewer tourists, offering a quieter experience while still enjoying warm days and scenic views.
Average Temperature Daytime: 82°F - Nighttime: 60°F
Weekly Weather Forecast for Highlands County
How to Book Your Highlands County 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 Highlands County
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
- Enjoy a private outdoor swimming pool to relax under the Florida sun.
- Take advantage of spacious patios or decks perfect for outdoor dining and gatherings.
- Benefit from lush, well-maintained gardens that add to your outdoor comfort and privacy.
- Make use of outdoor grilling areas for delicious barbecues with family and friends.
- Explore nearby lakes or ponds with access to fishing or kayaking opportunities.
- Relax in shaded pergolas or gazebos designed for leisure and outdoor enjoyment.
- Utilize extensive backyard spaces for outdoor sports or activities, ideal for all ages.
Top Attractions Around Highlands County
What attractions are nearby?
During your stay, you'll find a variety of outdoor activities and scenic spots nearby to explore, making it easy to enjoy the natural beauty and recreational opportunities that this destination offers in Highlands County, Florida.
Family Activities
- Lake Istokpoga Boat Tours: Discover the region's natural beauty by exploring one of its largest lakes through guided boat tours, perfect for family adventures.
- Fishermen’s Village at Lake Placid: Enjoy a day of fishing and waterfront dining in this charming village that offers a relaxing atmosphere for all ages.
- Highlands County Sports Complex: Engage in sports and outdoor activities with features like baseball fields and playgrounds, making it ideal for family fun.
- Heritage Park:** Visit this scenic park to explore walking trails, picnic areas, and interactive exhibits that showcase local history and culture.
Adult Activities
- Fishing at Lake Istokpoga: Experience some of the best freshwater fishing in the region, with abundant opportunities to catch bass and catfish just steps from your Highlands County accommodation.
- Enjoying Lake Placid's Historic Downtown: Stroll through this charming area filled with quaint shops, local eateries, and cultural landmarks that showcase the area's rich history and vibrant community spirit.
- Exploring the Highlands Hammock State Park: Discover scenic hiking trails, lush landscapes, and diverse wildlife right here in one of Florida’s oldest and most beautiful state parks.
- Birdwatching in the Region: Bring your binoculars and observe various bird species in their natural habitat, especially around the lakes and wetlands that surround your Highlands County stay.
Other Places to Stay in Highlands County, FL
Heartland
Avon Park
Lake Istokpoga
Lake Placid
Sebring
Sebring Shores
Lake Jackson
Lorida
Sun 'N Lake
Placid Lakes
Sylvan Shores
Highlands County Travel Tips
How Can You Make the Most of Your Stay?
- Explore Local Nature: Take advantage of the region's scenic parks and lakes to enjoy outdoor activities like fishing, boating, or birdwatching during your stay.
- Discover Regional Cuisine: Savor authentic flavors by visiting nearby eateries that showcase the area’s fresh seafood and local specialties.
- Plan Flexible Activities: Build in time for spontaneous adventures around this destination to truly immerse yourself in the unique atmosphere of here.
- Choose Well-Located Rentals: Select a vacation rental that offers easy access to key attractions and outdoor pursuits in this part of Florida for a more convenient experience.
Transportation Options
- Highlands County Airport: You can conveniently access the region through this local airport, which offers essential flights for travelers arriving from various locations.
- Rental Car Services: Multiple rental agencies operate in the area, providing a flexible way to explore Highlands County and its scenic surroundings at your own pace.
- Taxi and Rideshare Services: Taxis and rideshare options like Uber and Lyft are readily available here, offering convenient transportation within the region and to nearby attractions.
- Public Transit: The local bus system provides an affordable and reliable mode of transportation, helping you easily reach key spots around the destination.
Local Customs Options
- Southern Hospitality: In this region, you’ll experience warm welcomes and friendly interactions that reflect the area's inviting community spirit.
- Local Fishing Traditions: Engaging in or observing the region’s fishing customs offers a glimpse into its heritage and appreciation for water-based recreation.
- Florida Gator Pride: Celebrating regional sports culture with a focus on college football showcases the local enthusiasm and community pride.
- Respect for Nature and Wildlife: The area's customs emphasize conservation and appreciation of the natural surroundings, making outdoor activities particularly meaningful.
Frequently Asked Questions About Highlands County?
1. What are the top vacation rentals in Highlands County?
There are a lot of options in Highlands County. If you plan on staying in the Highlands County area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Vacation Rentals in Highlands County:
- Spacious pool home on corner canal lot to Lake June
- On "The" Lake Placid! Lakefront, Hot Tub, Beach, Large Dock!
- Lake June Escape House
- Newer Home on Lake June with Beach, Dock, Screened Patio and Hot Tub!
- Sitting on the Dock of the Lake Clay Rental Home For the perfect “country” vacat
- Bass Fishing Vacation Rental - Lake Istokpoga - Fisherman Welcome!
- Enjoy Lake June This Spring & Summer with Family Boating, Tubing, Fishing, etc.!
- Waterfront Lake June in Winter Family Fun and Relaxation
- Waterfront Lake Placid Home w/Dock & Fire Pit
- Escape 2 the lake - Oversized pool, private lake access & dock for canal fishing
2. How many vacation rentals have private pools in Highlands County?
There are 56 vacation rentals with private pools near Highlands County. Top-rated RBO homes that have access to a swimming pool include:
3. Which vacation homes in Highlands County are best for families?
If you are looking for a family-friendly vacation home in Highlands 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 Highlands County:
4. How many Rentbyowner vacation rentals are available in Highlands County?
Currently, the total number of properties listed by Rent By Owner in 2026 is over 698 in the Highlands 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 Highlands County.
5. What is the cancellation policy for vacation rentals in Highlands County, Florida?
Cancellation policies vary depending on the specific property listing. You should carefully review the cancellation terms outlined in the rental agreement or contact the property owner directly to understand the options available and any potential fees.
6. How do I verify the safety and cleanliness standards of a vacation rental in Highlands County?
Details regarding safety measures and cleanliness protocols are typically provided in the property listing. It's recommended to read the description thoroughly or reach out to the host for additional information to ensure your standards are met.
7. Are there any specific rules or restrictions I should be aware of when booking a vacation rental in this regional area?
Each vacation rental has its own set of house rules and restrictions, which are listed on the property page. Contact the owner if you have questions or need clarification before booking.
8. What amenities are usually included in vacation rentals here in Highlands County?
Amenities vary by property but often include essentials like Wi-Fi, air conditioning, and fully equipped kitchens. To confirm specific amenities, review the property details or contact the host directly.
9. How can I ensure my reservation for a vacation rental in Highlands County is secure and protected?
Reservations made through a trusted platform generally include secure payment options and support. For additional protection, read reviews and confirm the host’s profile before completing your booking.
Highlands County Top Rated Vacation Rentals
House
10.0(130 Reviews)
4 Bedrooms
2 Baths
10 Guests
2600 ft²
- Private Pool
- Hot Tub
- Fireplace/Heating
- Pool
R3,600/Night
7 Nights - R25,203
House
10.0(25 Reviews)
3 Bedrooms
2 Baths
6 Guests
1908 ft²
- Hot Tub
- Fireplace/Heating
- Pool
- Balcony/Terrace
R4,089/Night
7 Nights - R28,627
House
10.0(18 Reviews)
1 Bedroom
1 Bath
3 Guests
- Fireplace/Heating
- Pool
- Balcony/Terrace
- Kitchen
R1,423/Night
7 Nights - R9,970
House
10.0(15 Reviews)
4 Bedrooms
4 Baths
12 Guests
3268 ft²
- Private Pool
- Hot Tub
- Pool
- Ocean View
R12,140/Night
7 Nights - R84,971
House
10.0(11 Reviews)
2 Bedrooms
2 Baths
4 Guests
- Oceanfront
- Fireplace/Heating
- Pool
- Ocean View
R3,076/Night
7 Nights - R21,525
Condo
10.0(10 Reviews)
2 Bedrooms
2 Baths
4 Guests
1158 ft²
- Fireplace/Heating
- Pool
- Ocean View
- Balcony/Terrace
R3,538/Night
7 Nights - R24,764
House
10.0(9 Reviews)
3 Bedrooms
2 Baths
6 Guests
2000 ft²
- Hot Tub
- Fireplace/Heating
- Pool
- Balcony/Terrace
R4,346/Night
7 Nights - R30,415
House
10.0(8 Reviews)
5 Bedrooms
4 Baths
15 Guests
4200 ft²
- Private Pool
- Hot Tub
- Fireplace/Heating
- Pool
R15,353/Night
7 Nights - R107,474
