Highland Cottage Rentals By Owner

Highland Cottage Rentals

Cottage

Beautiful cottage on lake istokpoga with lake view!

4.0

Average

(3 Reviews)

1 Bedroom 1 Bath 2 Guests

US $123/Night 7 Nights - US $860

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Cottage

The Lake Loft at Redwater

2 Bedrooms 1 Bath 6 Guests

US $299/Night 7 Nights - US $2,092

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Cottage

Lake Front Oasis. Amazing Sunsets-12 min from Sebring Raceway

9.0

Exceptional

(4 Reviews)

3 Bedrooms 2 Baths 6 Guests 1141 ft²

US $218/Night 7 Nights - US $1,528

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Cottage

Relaxing Winter Retreat, w/dock. Fishing, wildlife, hunting, SNOWBIRDS WELCOMED.

4 Bedrooms 2 Baths 8 Guests

US $131/Night 7 Nights - US $918

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Cottage

Cozy cottage in Welcoming Sebring

1 Bedroom 1 Bath 2 Guests

US $56/Night 7 Nights - US $394

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Cottage

Peaceful Cottage Located in a Small Farm

9.6

Exceptional

(25 Reviews)

1 Bedroom 1 Bath 4 Guests

US $144/Night 7 Nights - US $1,006

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Cottage

Relax/Watch Sunsets & Birds Over Lake Between Lk Placid & Sebring at LoonCottage

5.0

Average

(5 Reviews)

3 Bedrooms 2 Baths 2 Guests 900 ft²

US $144/Night 7 Nights - US $1,008

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Cottage

The Lake Loft at Redwater

2 Bedrooms 1 Bath 6 Guests

US $299/Night 7 Nights - US $2,092

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Screened Patio & Grill at Sebring Resort Community

Frequently Viewed

Villa

Screened Patio & Grill at Sebring Resort Community

10.0

Exceptional

(14 Reviews)

2 Bedrooms 2 Baths 4 Guests 1054 ft²

US $136/Night 7 Nights - US $954

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Lanai, Pool & Gas Grill: Sebring Retreat!

House

Lanai, Pool & Gas Grill: Sebring Retreat!

10.0

Exceptional

(3 Reviews)

4 Bedrooms 3 Baths 8 Guests 2335.77 ft²

US $317/Night 7 Nights - US $2,217

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House

21-Acre Lakefront Paradise: Pool, Beach, Animals & Fire Pit

5 Bedrooms 3 Baths 12 Guests 4700 ft²

US $532/Night 7 Nights - US $3,721

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Villa

Elegant Villa Retreat

10.0

Exceptional

(7 Reviews)

2 Bedrooms 2 Baths 8 Guests

US $210/Night 7 Nights - US $1,470

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More Top-Rated Cottage Rentals in Highland Area

Why Choose Rent By Owner for your Highland Cottage Rentals?

What makes our Cottage 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 Cottage Rentals stay?

To ensure an optimal vacation experience, consider planning your stay during the most pleasant weather months in this destination, when the region's natural beauty and tranquility are at their peak, making it ideal for relaxing in your chosen cottages.

Peak Season Highlights

Winter (December to February)

During the winter months, this destination experiences its peak season as visitors seek refuge from colder climates elsewhere. This is an ideal time to enjoy the region's mild temperatures and vibrant local events.

Average Temperature Daytime: 75°F - Nighttime: 55°F

Spring (March to May)

Spring marks another peak period when the area blooms with activity and pleasant weather. It’s a perfect time to explore the outdoors while staying in cozy cottages that offer comfort and convenience.

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

Off-Season Highlights

Summer (June to August)

The summer months tend to be quieter, providing a more relaxed atmosphere for those seeking tranquility. The warm weather offers excellent conditions for outdoor leisure at your cottage retreat.

Average Temperature Daytime: 88°F - Nighttime: 70°F

Fall (September to November)

Fall is a less busy season, ideal for enjoying the scenic beauty and fewer crowds. The region’s moderate temperatures make it a comfortable time to stay in cottages without the peak season rush.

Average Temperature Daytime: 78°F - Nighttime: 58°F

Weekly Weather Forecast for Highland

How to Book Your Highland Cottage Rentals

What's our booking process?

Our platform allows you to browse a curated selection of cottage rentals. Once you find the ideal property, you’ll be redirected to a trusted booking partner to complete your reservation securely.

Booking Steps

Search Properties

Use our filters to find the right property that fits your needs.

Select a Rental

Click on your preferred listing to view details, amenities, and pricing.

Book Online

Follow the link to finalize your reservation directly on the partner’s website.

Explore and book the perfect rental in Highland

More Top-Rated Cottage Rentals in Highland Area

Common Cottage Rentals Amenities

What amenities can you expect?

Our Cottage 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 outdoor seating areas such as patios or verandas to relax while taking in the scenic surroundings.
Take advantage of private or shared swimming pools that provide a refreshing escape during your stay.
Utilize landscaped gardens or yard spaces perfect for outdoor activities or family gatherings.
Benefit from picnic areas or barbecue grills to easily host outdoor meals with loved ones.
Make use of outdoor lighting features that enhance safety and ambiance during evening hours.
Experience the convenience of parking spaces surrounded by lush greenery, adding to the regional charm.
Explore nearby walking trails or access points to nature, ideal for outdoor adventures in this area.

Top Attractions Around Highland

What attractions are nearby?

In this charming destination, you can enjoy a variety of outdoor activities and scenic excursions just minutes from your cottages, making it an ideal spot for exploring nearby parks, nature trails, and recreational sites that highlight the beauty of Highland, Florida.

Family Activities

Highland Hammock State Park Experience the great outdoors with a family-friendly day exploring scenic trails, wildlife viewing, and picnicking in this beautiful natural area.
Lake Istokpoga Enjoy a relaxing day of fishing, boating, or simply soaking in the peaceful lakeside views in this well-known regional destination.
Florida Nature Adventures Embark on guided eco-tours that highlight the region's diverse flora and fauna, perfect for an educational and entertaining family outing.
Highland City Park Play together on playgrounds, enjoy open green spaces, and partake in family-friendly events hosted regularly at this local community park.

Adult Activities

Lake Highland Park Relax and enjoy a leisurely day by the water at this scenic park, perfect for picnics and birdwatching in the region.
Highland Reserve Golf Club Improve your swing on the lush fairways of this well-maintained golf course, offering a challenging experience for enthusiasts.
Nature Trails Explore the area's natural beauty through various walking or biking trails that showcase the local flora and fauna.
Local Dining Experiences Savor regional flavors at nearby restaurants renowned for their fresh ingredients and welcoming atmosphere, ideal for adult outings.

Highland Travel Tips

How Can You Make the Most of Your Stay?

Plan Your Activities in Advance: To make the most of your stay, research local events and outdoor activities available nearby to fully immerse yourself in the region's natural beauty.
Choose a Prime Location: Selecting a cottage close to key attractions or scenic areas ensures easy access and maximizes your leisure time in this destination.
Experience Local Cuisine: Take advantage of nearby restaurants or consider preparing meals in your cottage to enjoy authentic flavors and save on dining expenses.
Respect the Environment: Help preserve the area's natural charm by following eco-friendly practices during your visit, ensuring the region remains pristine for future travelers.

Transportation Options

Rental Cars Renting a car offers you the flexibility to explore Highland and its surrounding areas at your own pace, ensuring convenient access to local attractions and amenities.
Public Transit Bus services and regional transit options available here provide an economical and eco-friendly way to move around without the need for personal transportation.
Taxis and Ride-Sharing Taxis and ride-sharing services such as Uber or Lyft are widely accessible, allowing you to quickly reach your cottage and nearby destinations with ease.
Bike Rentals Cycling is an excellent way to experience the scenic views and tranquil surroundings of this region, with bike rental services readily available for your convenience.

Local Customs Options

Respect for Nature Locals in the area prioritize environmental conservation, so you’ll notice an emphasis on preserving the natural beauty of the region during your stay.
Community Gatherings Participating in or observing local community events is common, reflecting a tight-knit atmosphere that welcomes visitors with warmth and hospitality.
Traditional Crafts The region takes pride in its handmade crafts, which are often showcased at local markets, offering authentic souvenirs and insights into the area's heritage.
Festivals and Celebrations Seasonal festivals celebrating regional customs are vibrant occasions where you can experience the local culture firsthand and enjoy communal festivities.

Frequently Asked Questions About Highland Rental Cottages

1. What are the top Cottages 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 Cottages in Highland:

2. How many Cottages are available in Highland?

Currently, the total number of properties listed by RBO in 2026 is over 8 in the Highland area, and still counting. By aggregating listings from multiple websites, RBO offers an immense amount of choice of the best Cottages in Highland. 

3. What is the cancellation policy for my Highland cottage reservation?

The cancellation policy varies depending on the specific listing. It’s best to review the terms listed on the property page or contact the owner directly for detailed information.

4. Are there any amenities included with cottages in this region?

Amenities differ by property, but common features include Wi-Fi, parking, and kitchen facilities. Check the individual listing to see what amenities are offered for your stay.

5. How do I know if a cottage is available for my travel dates?

Availability is shown in real-time on the booking page of each listing. If your preferred dates are unavailable, consider reaching out directly to the property owner or checking for alternative dates.

6. What should I do if I need to modify or cancel my booking?

Modification and cancellation policies depend on the property's terms. You can usually manage your booking through the site or contact the owner for assistance.

7. Are pets allowed in cottages around Highland, FL?

Pet policies vary from one property to another. Please review the pet allowance details on the listing or contact the owner to confirm if your pet can stay.