Discover winter rentals Big Pine Key - We found 109 exact matches
About Big Pine Key Winter Rental on Vacation Cottage
At Vacation Cottage, we showcase a diverse array of accommodations in Big Pine Key, 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 Big Pine Key. 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 Big Pine Key and unlock incredible deals. Life is Better at the Cottage with Vacation Cottage.
Frequently Asked Questions About Big Pine Key Winter Rentals
What are the top rated Winter Rentals in Big Pine Key?
There are a lot of options in Big Pine Key. If you plan on staying in the Big Pine Key area, consider making a reservation for a few nights at one of these properties as these have been rated the top Winter Rentals in Big Pine Key:
- Captain D's Hideout - Beautiful waterfront home in the heart of a deer preserve
- Island Sunrise Resort- 3 acre estate with open water sunrises.
- Awesome Open Water View at Blue Heron Estate
- Big Pine Key Waterfront Home: Boating, Sunrises, Sunsets; Relax in Paradise!
- Gorgeous Beachfront Home with a pool. Water views from every direction.
- Fisherman’s Paradise - Ocean & Gulf Access! Key Deer Preserve. TIME TO FISH!
- "Canal-Front Paradise in Big Pine Key-Relax &Explore the keys"
- Incredible~Ocean Views~ramp-dock-hot tub. Stay 14 days get up to 14 more FREE!
- Mickey and Lynn's House of Windows
- Tropical Oasis with Beautiful Home, Pool, Dock and Tiki Hut
How much does it cost to rent a place to stay near Big Pine Key in the wintertime?
The average cost for winter rentals in Big Pine Key is $363 per night. Vacation Cottage has a wide list of great winter places to stay near Big Pine Key that would suit your preferences. There are single and multiple rooms for solo trips or family vacations.
Are there any winter cottages/chalets in Big Pine Key that allow pets?
Yes, here are the top cottage/chalet rentals in Big Pine Key that allow you to bring your pet or dog:
- Frigate Landing - Beautiful Waterfront home,60ft seawall,Tiki Hut, Pet Friendly,
- Old Wooden Bridge Resort & Marina
- Sunshine Key RV Resort & Marina
- Open water view, boat dockage, 4 bedroom Home in Big Pine Key
See all pet-friendly vacation rentals in Big Pine Key on Vacation Cottage
Do you have any winter rentals in Big Pine Key that are suitable for families?
Most of our rentals homes are suitable for families. Check out the complete list of places to stay in Big Pine Key to find what works for you.
Are there winter accommodations in Big Pine Key that have indoor swimming pools?
As of 2026, the data from Vacation Cottage shows that there are over 109 private swimming pools or indoor pools accommodations near Big Pine Key along with other great amenities.
Do any winter holiday rentals in Big Pine Key have hot tubs?
About 109 holiday rentals in Big Pine Key boast of premium hot tubs. Some of the popular winter places to stay with hot tubs include:
Are there luxury winter rentals in Big Pine Key?
Yes, there are many luxury places to stay in Big Pine Key for the winter season. Find out more luxury, lakefront, winter, & last-minute rental homes near Big Pine Key with all the best amenities for your next trip.
