Best Vacation Homes in Highland
New
RV Rental
1 Bedroom
1 Bath
6 Guests
Balcony/Terrace
Kitchen
Air Conditioner
Pet Friendly
US $293/Night
7 Nights - US $2,052
House
10.0(3 Reviews)
4 Bedrooms
3 Baths
8 Guests
2335.77 ft²
Parking
Pool- Balcony/Terrace
Internet
US $293/Night
7 Nights - US $2,049
House
5 Bedrooms
3 Baths
12 Guests
4700 ft²
- Parking
- Pool
Ocean View- Balcony/Terrace
US $532/Night
7 Nights - US $3,721
Villa
10.0(7 Reviews)
2 Bedrooms
2 Baths
8 Guests
- Parking
- Pool
- Ocean View
- Balcony/Terrace
US $220/Night
7 Nights - US $1,541
House
10.0(2 Reviews)
2 Bedrooms
2 Baths
7 Guests
1560.77 ft²
- Parking
- Balcony/Terrace
- Air Conditioner
- Internet
US $175/Night
7 Nights - US $1,225
Villa
10.0(7 Reviews)
2 Bedrooms
2 Baths
4 Guests
1100 ft²
- Parking
- Pool
- Ocean View
- Balcony/Terrace
US $218/Night
7 Nights - US $1,529
House
10.0(3 Reviews)
1 Bedroom
1 Bath
4 Guests
- Air Conditioner
- Internet
- Pet Friendly
Child Friendly
US $233/Night
7 Nights - US $1,632
House
10.0(3 Reviews)
2 Bedrooms
1 Bath
3 Guests
- Parking
- Kitchen
- Air Conditioner
- Internet
US $166/Night
7 Nights - US $1,161
Highland Luxury Rentals
New
House
3 Bedrooms
2 Baths
9 Guests
- Air Conditioner
- Internet
- Child Friendly
Laundry
Unlock the Best Price
House
9.8(17 Reviews)
2 Bedrooms
2 Baths
4 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $3,136/Night
7 Nights - US $21,950
Other
10.0(12 Reviews)
6 Bedrooms
7 Baths
14 Guests
3245 ft²
Private Pool- Pool
- Balcony/Terrace
- Kitchen
US $2,020/Night
7 Nights - US $14,137
House
10.0(7 Reviews)
5 Bedrooms
5 Baths
16 Guests
4995 ft²
Hot Tub- Parking
- Kitchen
- Air Conditioner
US $1,083/Night
7 Nights - US $7,581
House
9.6(4 Reviews)
5 Bedrooms
5 Baths
12 Guests
- Hot Tub
- Parking
- Pool
- Kitchen
US $1,060/Night
7 Nights - US $7,422
House
10.0(16 Reviews)
5 Bedrooms
3 Baths
14 Guests
5000 ft²
- Parking
- Pool
- Ocean View
- Balcony/Terrace
US $710/Night
7 Nights - US $4,972
Apartment
10.0(1 Review)
1 Bedroom
1 Bath
4 Guests
- Parking
- Pool
- Kitchen
- Air Conditioner
US $552/Night
7 Nights - US $3,864
House
9.6(4 Reviews)
3 Bedrooms
2 Baths
6 Guests
- Hot Tub
- Parking
- Balcony/Terrace
- Kitchen
US $486/Night
7 Nights - US $3,405
Highland Pet Friendly Vacation Rentals
Condo
9.8(8 Reviews)
2 Bedrooms
2 Baths
4 Guests
1150 ft²
- Pool
- Balcony/Terrace
- Kitchen
- Pet Friendly
US $265/Night
7 Nights - US $1,855
House
10.0(1 Review)
2 Bedrooms
2 Baths
4 Guests
1496.18 ft²
- Parking
- Balcony/Terrace
View- Air Conditioner
US $106/Night
7 Nights - US $744
Villa
9.4(10 Reviews)
2 Bedrooms
2 Baths
6 Guests
1000 ft²
- Parking
- Pool
- Kitchen
- Air Conditioner
US $187/Night
7 Nights - US $1,309
House
10.0(1 Review)
2 Bedrooms
2 Baths
4 Guests
1151.74 ft²
- Parking
- Pool
Spa- Balcony/Terrace
US $208/Night
7 Nights - US $1,456
Cottage
2 Bedrooms
1 Bath
6 Guests
- Air Conditioner
- Internet
- Pet Friendly
- Child Friendly
US $364/Night
7 Nights - US $2,550
Apartment
1 Bedroom
2 Baths
4 Guests
- Air Conditioner
- Internet
- Pet Friendly
- Child Friendly
US $203/Night
7 Nights - US $1,423
Villa
2 Bedrooms
2 Baths
4 Guests
- Air Conditioner
- Internet
- Pet Friendly
- Child Friendly
US $194/Night
7 Nights - US $1,359
House
10.0(46 Reviews)
3 Bedrooms
2 Baths
6 Guests
2656 ft²
- Private Pool
- Parking
- Pool
- Balcony/Terrace
US $365/Night
7 Nights - US $2,558
Highland Large Vacation Homes
Villa
2 Bedrooms
2 Baths
4 Guests
1150 ft²
- Parking
- Pool
- Balcony/Terrace
- Kitchen
US $236/Night
7 Nights - US $1,650
House
7.9(9 Reviews)
6 Bedrooms
6 Baths
12 Guests
328.3 ft²
- Parking
- Balcony/Terrace
- Air Conditioner
- Internet
US $85/Night
7 Nights - US $595
House
10.0(9 Reviews)
4 Bedrooms
3 Baths
10 Guests
2000 ft²
- Kitchen
- Air Conditioner
- Internet
- Pet Friendly
US $398/Night
7 Nights - US $2,789
Villa
2 Bedrooms
2 Baths
6 Guests
1001.04 ft²
Oceanfront- Parking
- Spa
- Ocean View
US $201/Night
7 Nights - US $1,409
House
10.0(3 Reviews)
4 Bedrooms
2 Baths
10 Guests
2000 ft²
- Hot Tub
- Parking
- Balcony/Terrace
- Kitchen
US $459/Night
7 Nights - US $3,211
Villa
10.0(1 Review)
3 Bedrooms
2 Baths
6 Guests
- Parking
- Kitchen
- Air Conditioner
- Internet
US $177/Night
7 Nights - US $1,237
New
House
3 Bedrooms
2 Baths
10 Guests
- Balcony/Terrace
- Kitchen
- Air Conditioner
- Internet
US $403/Night
7 Nights - US $2,820
Villa
10.0(15 Reviews)
2 Bedrooms
2 Baths
4 Guests
1054 ft²
- Parking
- Pool
- Kitchen
- Air Conditioner
US $130/Night
7 Nights - US $907
Why Choose Rent By Owner for your Highland 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 Highland
When should you plan your Vacation Rentals stay?
Choosing the right time to visit here can enhance your experience, as seasonal weather patterns and local events in Highland, Florida influence the best periods for booking your vacation rentals in this charming destination.
Peak Season Highlights
Winter (December to February)
During the winter months, you can enjoy the region's mild and pleasant weather, making it ideal for outdoor activities and exploring the local scenery.
Average Temperature Daytime: high 70s°F to low 80s°F - Nighttime: mid 50s°F to low 60s°F
Spring (March to May)
Spring marks the peak season when the area's natural beauty flourishes, attracting visitors who want to experience the region's vibrant landscapes and comfortable temperatures.
Average Temperature Daytime: mid 70s°F to mid 80s°F - Nighttime: mid 50s°F to low 60s°F
Off-Season Highlights
Summer (June to August)
The summer months see fewer visitors, offering a quieter experience with warm temperatures perfect for relaxing indoors or enjoying water-based activities.
Average Temperature Daytime: high 80s°F to low 90s°F - Nighttime: mid 70s°F
Fall (September to November)
Falling outside the busy season, fall provides cooler weather and fewer crowds, making it a peaceful time to explore the scenic surroundings at your own pace.
Average Temperature Daytime: mid 70s°F to mid 80s°F - Nighttime: mid 50s°F to low 60s°F
Weekly Weather Forecast for Highland
How to Book Your Highland 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.
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 and unwind under the Florida sun.
- Take advantage of spacious patio areas perfect for outdoor dining and entertaining.
- Make the most of well-maintained gardens or landscaped yards that add to the area's natural beauty.
- Benefit from access to outdoor grilling stations for preparing delicious meals during your stay.
- Experience outdoor recreation with nearby walking trails or scenic viewpoints in the region.
- Utilize outdoor lounge furniture to enjoy the pleasant weather and peaceful surroundings.
- Explore available sports facilities like tennis courts or basketball hoops often found at desirable properties here.
Top Attractions Around Highland
What attractions are nearby?
Here, you can enjoy a variety of outdoor activities and local attractions that make this destination an ideal place for your next getaway.
Family Activities
- Lovingston Park: You can enjoy a family picnic or a leisurely walk along scenic trails at this popular park in the area.
- Highland Community Center: This community hub offers engaging activities and events suitable for kids and adults alike, making it a great family outing.
- Local Wildlife Viewing Spots: Explore nearby natural areas where your family can observe local flora and fauna, perfect for outdoor enthusiasts staying in Highland.
- Nearby Water Activities: Take advantage of the region’s lakes and rivers with calm boat rides or fishing excursions ideal for family adventures here.
Adult Activities
- Lake Istokpoga Boat Tours: Explore the tranquil waters of Lake Istokpoga with guided boat tours that showcase the region’s natural beauty and diverse wildlife.
- Highland Hammock State Park: Discover scenic hiking trails, historical exhibits, and lush landscapes perfect for outdoor adventures in this expansive state park.
- Local Art Galleries and Studios: Enjoy browsing through unique art collections and engaging with local artists to experience the creative spirit of the area.
- Wildlife Viewing at Farm Parks: Visit regional farms where you can observe native animals and learn about sustainable agriculture practices in this inviting community setting.
Highland Travel Tips
How Can You Make the Most of Your Stay?
- Explore Local Attractions: Take the time to discover the nearby attractions and scenic spots to fully experience what this destination has to offer.
- Plan Ahead for Activities: Booking outdoor excursions or local tours in advance ensures you make the most of your stay here without missing out on popular experiences.
- Choose the Perfect Vacation Rental: Select a well-located vacation rental that provides comfort and easy access to the region’s key attractions and amenities.
- Immerse Yourself in the Area’s Culture: Engage with local events or try regional cuisine to deepen your connection to this destination during your visit.
Transportation Options
- Personal Vehicle: Having a car offers you the most flexibility to explore the area and access your vacation rental with ease.
- Public Transportation: Local bus services provide an affordable way to navigate here, connecting you to key destinations within the region.
- Taxis and Rideshare Services: Convenient ride options like taxis and rideshare apps are readily available for quick trips around this destination.
- Rental Cars: Renting a vehicle provides comfort and independence, making it simple to discover all that the area has to offer at your own pace.
Local Customs Options
- Southern Hospitality: You will likely notice the warm and welcoming attitude of locals, reflecting the area's rich tradition of Southern hospitality.
Participating in local festivals provides a glimpse into the region’s vibrant community spirit and cultural pride. - Fishing Traditions: The region’s deep-rooted fishing customs offer a unique insight into the area’s relationship with its natural surroundings.
- Local Cuisine: Sampling traditional dishes highlights the regional flavors that are cherished by residents here and are often shared during community gatherings.
Highland Vacation Rental Frequently Asked Questions
1. What are the top vacation rentals in Highland?
There are a lot of options in Highland. If you plan on staying in the Highland area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Vacation Rentals in Highland:
- Welcome, enjoy your own PRIVATE POOL and LAKEFRONT Dock. Fish & Kayak
- 21-Acre Lakefront Paradise: Heated Pool, Private Beach, Animals, Fishing-Boating
- Enjoy this Natural Preserve.
- Lakehouse on lake Istokpoga. Separate inlaws quarters, 10 minutes from Raceway
- “Premier Host ⭐ Lakefront 3BR Private Dock Stunning Sebring Escape, Golf & Races
- Lakehouse on Lake Francis with Huge Game Room next to Boat Ramp
- Lake House
- Elegant Villa Retreat
- Racetrack-Ready Villa Pools Modern Comfort
- Lake Francis Lily Pad – Entire Lakefront Home w/Hot Tub
2. How many vacation rentals have private pools in Highland?
There are 3 vacation rentals with private pools near Highland. Top-rated RBO homes that have access to a swimming pool include:
3. Which vacation homes in Highland are best for families?
If you are looking for a family-friendly vacation home in Highland, check out one of the following properties as all are highly-rated places to stay with excellent review for families or groups staying in Highland:
4. How many Rentbyowner vacation rentals are available in Highland?
Currently, the total number of properties listed by Rent By Owner in 2026 is over 117 in the Highland 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 Highland.
5. What is the cancellation policy for vacation rentals in Highland, Florida?
Cancellation policies vary by property. You should review the specific listing details or contact the owner directly to understand the terms and any potential fees associated with cancelling your reservation here.
6. Are there any house rules I should be aware of before booking a vacation rental in this region?
Each property may have its own set of house rules, such as pet policies, noise restrictions, or check-in procedures. It’s recommended to read the listing carefully or reach out to the host for clarification before finalizing your reservation.
7. How do I modify or cancel my reservation for a Highland vacation rental?
Modifications or cancellations can typically be managed through your booking platform account. For specific instructions or if you encounter issues, contacting the property owner or customer support will ensure your request is handled smoothly.
8. Is there a minimum stay requirement for booking vacation rentals here?
Minimum stay requirements depend on the individual property. Details are listed during the booking process; if not clear, contacting the host directly can provide confirmation.
9. What amenities are usually included in Highland vacation rentals?
Amenities vary between properties but often include essentials like Wi-Fi, kitchen facilities, and parking. To see what’s available at a particular property, review the listing details or ask the host for additional information.
Highland Top Rated Vacation Rentals
House
10.0(1 Review)
2 Bedrooms
2 Baths
4 Guests
957.99 ft²
- Parking
- Pool
- Balcony/Terrace
- Internet
US $137/Night
7 Nights - US $959
Condo
9.8(14 Reviews)
2 Bedrooms
2 Baths
4 Guests
1188 ft²
- Parking
- Pool
- Kitchen
- Air Conditioner
US $197/Night
7 Nights - US $1,379
House
9.3(3 Reviews)
2 Bedrooms
2 Baths
4 Guests
1184.03 ft²
- Parking
- Pool
- Balcony/Terrace
- Internet
US $159/Night
7 Nights - US $1,115
New
House
9.2(49 Reviews)
2 Bedrooms
2 Baths
8 Guests
1671 ft²
- Private Pool
- Parking
- Pool
- Ocean View
US $344/Night
7 Nights - US $2,411
Apartment
9.0(2 Reviews)
2 Bedrooms
2 Baths
4 Guests
1151.74 ft²
Breakfast- Parking
- Pool
- Balcony/Terrace
US $138/Night
7 Nights - US $966
Resort
1 Bath
12 Guests
161.46 ft²
- Oceanfront
- Hot Tub
EV Charge Station- Parking
US $454/Night
7 Nights - US $3,177
New
Condo
2 Bedrooms
2 Baths
4 Guests
- Parking
- Pool
- Kitchen
- Air Conditioner
US $224/Night
7 Nights - US $1,565
New
Condo
2 Bedrooms
2 Baths
4 Guests
1010 ft²
- Parking
- Pool
- Ocean View
- Balcony/Terrace
US $203/Night
7 Nights - US $1,418
