Top Winter Vacations - Vacation Rentals in Pinellas County

122 · Self Check-in Free Parking Kitchen Pool From US $218
         

Luxury Places to Stay in Pinellas County

Over 10000+ Luxury Places to Stay in or Near Pinellas County

Top-Rated Vacation Rentals with a Pool in Pinellas County

Over 10000+ Top-Rated Vacation Rentals with a Pool in or Near Pinellas County
Ivory Sands Beach Suites From US $191
         

10.0 (266 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pool

Pet-Friendly Vacation Rentals in Pinellas County

Over 5429+ Pet-Friendly Vacation Rentals in or Near Pinellas County
A Great house Close to Clearwater and Belleair Beach From US $84
         

Large Vacation Homes & Villas in Pinellas County

Over 2469+ Large Vacation Homes & Villas in or Near Pinellas County
Coastal Cottage From US $88
         

|
10.0 (65 Reviews)
Villa
  • Air Conditioner
  • Parking
  • Balcony/Terrace
The Gemma by Brightwild From US $1,830
         

|
10.0 (2 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
Villa Italia "Villas by Christine" From US $257
         

10.0 (125 Reviews)
Villa
  • Air Conditioner
  • Parking
  • Pet Friendly

Wheelchair Accessible Vacation Homes in Pinellas County

Over 5360+ Wheelchair Accessible Vacation Homes in or Near Pinellas County

Pinellas County Varoom and Airbnb Places to Stay Under $200

Over 5448+ Pinellas County Varoom and Airbnb Places to Stay Under $200
Sea Sunsets and Sunrises From US $162
         

10.0 (49 Reviews)
Condo
  • Air Conditioner
  • Parking
  • Pool
The Blue Room Bungalow with Saltwater Pool From US $146
         

Cozy Condo in Indian Shores Beach From US $163
         

Instantly Bookable Vacation Homes in Pinellas County

Over 13367+ Instantly Bookable Vacation Homes in or Near Pinellas County

About Pinellas County Vacation Rentals

With more than 20603 Pinellas County vacation rentals, we can help you find a place to stay. These rentals, including vacation rentals, Topwintervacations 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 Topwintervacations 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 828.22 ft² on average, with prices averaging $387 a night.

Topwintervacations 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 7977
Holiday Apartments 3672
Hotels with Suites 817
Cottages 428
Resorts 268
Villas 229
B&B 58
Cabin Rentals 21
Others 7
Hostels 4
Ski Chalet Rentals 2

Use these Quick Filters to Find a Vacation Rental in Pinellas County

Pro Tip: Topwintervacations makes it easy to compare the best listings on Topwintervacations homes from online vacation rental OTAs, including Booking.com and more. Use the Advanced Filter feature at the top to easily flip between Topwintervacations 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.

December - February
High 75°F       Low 58°F
March - May
High 86°F       Low 61°F
June - August
High 91°F       Low 76°F
September - November
High 89°F       Low 63°F