Highlands Cottage Rentals
450 ft²
2 Guests
1 Bedroom
1 Bathroom
Ocean View
Cottage
- Private Pool
- Fireplace/Heating
- Pool
US $152/Night
For 7 Nights US $1,061
947.22 ft²
4 Guests
2 Bedrooms
1 Bathroom
Ocean View
House
- Oceanfront
- Fireplace/Heating
- Pool
US $165/Night
For 7 Nights US $1,155
1 Bedroom
1 Bathroom
Family Friendly
Cottage
- Fireplace/Heating
- Kitchen
- Parking
US $405/Night
For 7 Nights US $2,837
3 Guests
1 Bedroom
1 Bathroom
Family Friendly
Cottage
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
US $238/Night
For 7 Nights US $1,667
1302.43 ft²
8 Guests
3 Bedrooms
2 Bathrooms
House
- Oceanfront
- Pool
- Ocean View
US $495/Night
For 7 Nights US $3,465
220 ft²
4 Guests
2 Bedrooms
1 Bathroom
Family Friendly
Cottage
- Fireplace/Heating
- Kitchen
- Parking
US $189/Night
For 7 Nights US $1,326
1001.04 ft²
2 Guests
2 Bedrooms
1 Bathroom
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
US $146/Night
For 7 Nights US $1,022
1 Guest
1 Bedroom
1 Bathroom
Family Friendly
Cottage
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
US $151/Night
For 7 Nights US $1,054
753.47 ft²
4 Guests
1 Bedroom
1 Bathroom
Family Friendly
Apartment
- Fireplace/Heating
- Pool
- View
US $176/Night
For 7 Nights US $1,232
4 Guests
1 Bedroom
1 Bathroom
Family Friendly
Cottage
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
US $145/Night
For 7 Nights US $1,018
US $215/Night
For 7 Nights US $1,505
833 ft²
6 Guests
1 Bedroom
1 Bathroom
Ocean View
Cottage
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
US $191/Night
For 7 Nights US $1,339
Why Choose Rent By Owner for your Highlands 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.
Weekly Weather Forecast for Highlands
How to Book Your Highlands 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
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
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
Other Places to Stay in Highlands, FL
Florida
Shady Hills
Florida Central Atlantic Coast
Whitney Beach
Port Canaveral
Biggar
Trailer Estates
Braden River
Bearss Plaza
Hunt Club
Survey Creek
Ludlam
Highlands Cottage Rentals Frequently Asked Questions
1. What are the top Cottages in Highlands?
There are a lot of options in Highlands. If you plan on staying in the Highlands area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Cottages in Highlands:
- Cleanest & most affordable lakefront cottage! Lots of charm and character!
- Waterfront Cozy Cottage On Cow Creek With Dock, Canoe, Kayaks, Fishing
- Carriage House on 120 acres on Blackwater Bay with Private Pool
- Bikini Top Cottage in the historic village of Longboat Key
- Sarasota, Fl. Wild Orchid Creek
- Cozy, Coastal Cottage in Art District
- NEW-Lakefront/on 5 acres/near Lakewood Ranch/Pool/Pet Friendly
- Par and Away Cottage
- Hidden Gem- Waterfront Guest house
- Lake Escape~Tranquility sleeps 8+ in Tallahassee
2. How many Cottages are available in Highlands?
Currently, the total number of properties listed by RBO in 2026 is over 217 in the Highlands area, and still counting. By aggregating listings from multiple websites, RBO offers an immense amount of choice of the best Cottages in Highlands.
More Rentals You May Like Near Highlands
753.47 ft²
5 Guests
2 Bedrooms
1 Bathroom
Family Friendly
Apartment
- Fireplace/Heating
- Pool
- View
US $241/Night
For 7 Nights US $1,687
2 Guests
1 Bedroom
1 Bathroom
Family Friendly
Cottage
- Kitchen
- Parking
- Air Conditioner
US $123/Night
For 7 Nights US $860
6 Guests
2 Bedrooms
1 Bathroom
Pet Friendly
Cottage
- Pet Friendly
- Air Conditioner
- Internet
US $299/Night
For 7 Nights US $2,092
800 ft²
6 Guests
2 Bedrooms
1 Bathroom
Ocean View
Cottage
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
US $207/Night
For 7 Nights US $1,450
6 Guests
2 Bedrooms
2 Bathrooms
Pet Friendly
Cottage
- Fireplace/Heating
- Pet Friendly
- Air Conditioner
US $242/Night
For 7 Nights US $1,694
4 Guests
2 Bedrooms
1 Bathroom
Couples Retreat
Cottage
- Fireplace/Heating
- Pet Friendly
- Air Conditioner
US $219/Night
For 7 Nights US $1,536
1350 ft²
5 Guests
3 Bedrooms
1 Bathroom
Ocean View
Cottage
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
US $133/Night
For 7 Nights US $928
7 Guests
3 Bedrooms
2 Bathrooms
Family Friendly
Cottage
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
US $154/Night
For 7 Nights US $1,079
1141 ft²
6 Guests
3 Bedrooms
2 Bathrooms
Ocean View
Cottage
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
US $216/Night
For 7 Nights US $1,512
8 Guests
4 Bedrooms
2 Bathrooms
Family Friendly
Cottage
- Fireplace/Heating
- Kitchen
- Parking
US $131/Night
For 7 Nights US $918
4 Guests
2 Bedrooms
2 Bathrooms
Family Friendly
Cottage
- Balcony/Terrace
- Kitchen
- Parking
US $275/Night
For 7 Nights US $1,922
900 ft²
6 Guests
2 Bedrooms
1 Bathroom
Family Friendly
Cottage
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
US $220/Night
For 7 Nights US $1,541
