Pinellas County Cottage Rentals & Holiday Homes
Find the best cottages in Pinellas County - We found 526 exact matches
About Pinellas County Luxury Rental on Top Winter Vacations
Searching for cottages to rent near Pinellas County? Top Winter Vacations features more than 526 cottages that are perfect for your next trip. Discover luxury cottage rentals that are a few miles away from the lake or beach. These cottage rentals in Pinellas County have hot baths, are kid-friendly & family-friendly, and are near top local attraction spots, to give guests the best travel experience they could ever wish for. Top Winter Vacations’s cottage listings come in all shapes and sizes for large groups, friends, or couples in Pinellas County.
Are you planning to travel to the lakeside, beach, or mountain area? Top Winter Vacations’s cottage rentals offers a wide selection, giving you direct access to the owners of these cottage rentals, and offering you the best opportunity to find a good price.
Top Winter Vacations boasts of 526 holiday cottages and places to stay in Pinellas County. The site provides unique Airbnb, VRBO, Top Winter Vacations-style cottages to fit your trip or get away with your friends and family. This can be a weekend getaway, spring break, summer vacation, or annual holiday -- all fitting within your budget.
Frequently Asked Questions About Pinellas County Cottage Rentals
What are the top rated Cottage Rentals in Pinellas County?
There are a lot of options in Pinellas County. If you plan on staying in the Pinellas County area, consider making a reservation for a few nights at one of these properties as these have been rated the top Cottage Rentals in Pinellas County:
- OLD FLORIDA CHARM- DIRECT BEACH FRONT COTTAGE - STEP RIGHT INTO THE SAND!
- 1BR/1BA NEW Coastal Boutique Cottage. HGTV Worthy! Sleeps 4. Steps to Beach!
- Cottage on Beach Side of Gulf Blvd!
- Family and dog friendly beach cottage w/pool & grill in quaint seaside village
- Beautiful Beach Cottage w/Private Heated Pool & Spa - Heart of Sunset Beach
- Professional cottage on 1/2 acre lot in quiet country setting
- Historic, sunny cottage - Walk to parks by the sea and downtown!
- Your Beach Cottage Getaway! 'Come and enjoy our sand and sunsets '
- "Old Florida" Beach Cottage-Beachfront!
- Barefoot House.A Haven for Nurturing Well-being
How much does it cost to rent a cottage in Pinellas County?
The average cost for a cottage rental in Pinellas County is $327 per night. Topwintervacations has a wide list of great cottages near Pinellas County that would suit your needs. There are single and multiple rooms for solo trips or family vacations.
Are there any cottages in Pinellas County that allow pets?
Yes, here are the top cottage rentals in Pinellas County that allow you to bring your pet:
- Beachfront, Chic a si Cottage, original vintage Florida charm right on the Gulf
- Coastal Cottage
- Cozy St Pete Home ~ 2 Mi to Madeira Beach!
- Historic Old Northeast! Walk to Water & Downtown! KING BED!
See all pet-friendly vacation rentals in Pinellas County on Topwintervacations
Do you have any rental cottages in Pinellas County that are suitable for families?
Most of our listed cottages are suitable for families. Check out the complete list of cottages in Pinellas County to find one that works for you.
Are there quality cottages in Pinellas County that have indoor swimming pools?
As of 2026, the data from Topwintervacations shows that there are Over 526 private swimming pools or cottages with indoor pools in the Pinellas County area along with other great amenities.
