Trippy Mates - Vacation Rentals in Pinellas County
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Luxury Places to Stay in Pinellas County
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Top-Rated Vacation Rentals with a Pool in Pinellas County
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Pet-Friendly Vacation Rentals in Pinellas County
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Large Vacation Homes & Villas in Pinellas County
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Wheelchair Accessible Vacation Homes in Pinellas County
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Pinellas County Vacation Rentals and Airbnb Places to Stay Under $200
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Instantly Bookable Vacation Homes in Pinellas County
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About Pinellas County Vacation Rentals
With more than 21280 Pinellas County vacation rentals, we can help you find a place to stay. These rentals, including vacation rentals, Trippymates and other short-term private accommodations, have top-notch amenities with the best value, providing you with comfort and luxury at the same time. Get more value and more room when you stay at a rental property in Pinellas County.
Looking for last-minute deals, or finding the best deals available for cottages, condos, private villas, and large vacation homes? With Trippymates Pinellas County, you have the flexibility of comparing different options of various deals with a single click. Looking for a rental by owner with the best swimming pools, hot tubs, allows pets, or even those with huge master suite bedrooms and have large screen televisions? You can find vacation rentals by owner, and other popular Airbnb-style properties in Pinellas County. Places to stay near Pinellas County are 839.79 ft² on average, with prices averaging $396 a night.
Trippymates makes it easy and safe to find and compare vacation rentals in Pinellas County with prices often at a 30-40% discount versus the price of a hotel. Just search for your destination and secure your reservation today.
Top Rental Accommodation Types in Pinellas County
| Type | Count |
|---|---|
| Vacation Homes | 8461 |
| Holiday Apartments | 3666 |
| Hotels with Suites | 825 |
| Cottages | 441 |
| Resorts | 278 |
| Villas | 242 |
| B&B | 81 |
| Cabin Rentals | 22 |
| Others | 9 |
| Hostels | 3 |
| Ski Chalet Rentals | 2 |
Use these Quick Filters to Find a Vacation Rental in Pinellas County
★ Pro Tip: Trippymates makes it easy to compare the best listings on Trippymates homes from online vacation rental OTAs, including Booking.com and more. Use the Advanced Filter feature at the top to easily flip between Trippymates homes, vacation rentals, bed and breakfasts, private Airbnb-style rentals availability, eco-friendly properties, property type, cancellation policies, prices, and several different options. All these make it easier to find the perfect accommodation for your next vacation in Pinellas County.
Weather in Pinellas County
View the weather forecast for Pinellas County before booking your Pinellas County Vacation Rentals to confirm your best time to go.
Top Attractions Around Pinellas County, FL
Trippymates offers a large selection of top attractions around Pinellas County. Research things to do on your vacation before you visit Pinellas County.
Other Places to Stay Near Pinellas County, FL
Complexes around Pinellas County, FL
Pinellas County Vacation Rental Frequently Asked Questions
What are the top vacation 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 Vacation Rentals in Pinellas County:
- Casa Dolphina: 6BR Waterfront Mini-Resort—Pool & Spa, Sunsets, Dock, St. Pete FL
- Breathtaking Gulf Facing Condo Hotel Suite
- Updated condo just steps to the white sand beaches of Clearwater Beach
- 1 Bedroom Penthouse Suite located within the Sandpearl Resort & Spa
- Ivory Sands Beach Suites
- You Are Closer to Your Own Private Paradise on Beautiful Tampa Bay!
- Downtown Dunedin Walking District
- Luxurious Oceanfront Home w/MILES of sandy beach & private Inter-Coastal dock!
- Beachfront Condo w/breathtaking full ocean & pool views, Top Flr, Small complex
- 200+ Reviews! Gulf Retreat I: Amazing views, luxury comfort, steps to beach
How many vacation rentals have private pools in Pinellas County?
There are 3162 vacation rentals with private pools near Pinellas County. Top-rated homes that have access to a swimming pool include:
Which vacation homes in Pinellas County are best for families?
If you are looking for a family-friendly vacation home in Pinellas County, check out one of the following properties as all are highly-rated places to stay with excellent review for families or groups staying in Pinellas County:
How many vacation rentals are available in Pinellas County?
Currently, the total number of properties listed in 2026 is over 21280 in the Pinellas County area, and still counting. By aggregating listings from multiple websites, offers an immense amount of choice of the best properties in Pinellas County.
