Discover winter rentals Highland - We found 55 exact matches
About Highland Winter Rental on Vacation Cottage
At Vacation Cottage, we showcase a diverse array of accommodations in Highland, FL perfect for your winter retreat or seasonal escape. Our listings encompass hotels, private vacation homes, cabins, condos, villas, resorts, and pet-friendly apartments, ensuring travelers find their ideal accommodation. Vacation Cottage's winter vacation homes boast premier amenities such as Wi-Fi, heated indoor/outdoor swimming pools, spas, hot tubs, outdoor grills, and cozy fireplaces.
Whether you're seeking to escape the snow or embrace it, Vacation Cottage facilitates your connection to the finest cabins, bungalows, lodges, rent-by-owner homes, and the best accommodations in both sunny retreats and ski resorts. Vacation Cottage ensures your winter getaway becomes an unforgettable experience.
Vacation Cottage presents luxury options for travelers seeking to rent a place in Highland. To access these benefits and book your winter vacation home, simply utilize the Vacation Cottage filter option. Enter your travel dates, refine your search with filters for property type and amenities, then choose from our extensive list of exceptional winter vacation rentals hassle-free. Our interactive map further enhances your experience, allowing you to explore destinations worldwide or within Highland and unlock incredible deals. Life is Better at the Cottage with Vacation Cottage.
Frequently Asked Questions About Highland Winter Rentals
What are the top rated Winter 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 Winter Rentals in Highland:
- Lake House
- Peaceful home away from home at Sebring!
- Minutes away to Sebring Raceway, Golf Course and many great fishing spots.
- cozy cabin on lake placid fishing spot, house with 3 bedrooms, and 2 bathrooms!
- Dreamy Home on Lake Istokpoga w/Dock + Views!
- LAKE VIEW COTTAGE GETAWAY
- Condo w/Screened-in Porch, 1 Mi to Sebring Golf!
- Windy Point Estate - On Lake Istokpoga-5bdr. 5 1/2bath 7 beds. Amazing grounds
- Lanai, Pool & Gas Grill: Sebring Retreat!
- Unique Studio Apartment nWifinKing BednJet Tubn Pooln C/O
How much does it cost to rent a place to stay near Highland in the wintertime?
The average cost for winter rentals in Highland is $379 per night. Vacation Cottage has a wide list of great winter places to stay near Highland that would suit your preferences. There are single and multiple rooms for solo trips or family vacations.
Are there any winter cottages/chalets in Highland that allow pets?
Yes, here are the top cottage/chalet rentals in Highland that allow you to bring your pet or dog:
- Lakefront Sanctuary Near Sebring Private Dock Sunset Views Cozy Retreat
- Lake Francis Lily Pad
- 21-Acre Lakefront Paradise: Pool, Beach, Animals & Fire Pit
- Lake Francis Lily Pad – Entire Lakefront Home w/Hot Tub
See all pet-friendly vacation rentals in Highland on Vacation Cottage
Do you have any winter rentals in Highland that are suitable for families?
Most of our rentals homes are suitable for families. Check out the complete list of places to stay in Highland to find what works for you.
Are there winter accommodations in Highland that have indoor swimming pools?
As of 2025, the data from Vacation Cottage shows that there are over 55 private swimming pools or indoor pools accommodations near Highland along with other great amenities.
Do any winter holiday rentals in Highland have hot tubs?
About 55 holiday rentals in Highland boast of premium hot tubs. Some of the popular winter places to stay with hot tubs include:
Are there luxury winter rentals in Highland?
Yes, there are many luxury places to stay in Highland for the winter season. Find out more luxury, lakefront, winter, & last-minute rental homes near Highland with all the best amenities for your next trip.
