Pinellas County Holiday Rentals
- St. Petersburg - Clearwater
- ·
- Indian Rocks Beach
- 0.34 mi to center
- Oceanfront
- Hot Tub
- Fireplace/Heating
- Pool
- St. Petersburg - Clearwater
- ·
- Bay Esplanade
- 0.44 mi to center
- Pool
- Balcony/Terrace
- Kitchen
- Parking
- Florida
- ·
- St. Petersburg - Clearwater
- 6.59 mi to center
- Fireplace/Heating
- Air Conditioner
- Internet
- Child Friendly
- St. Petersburg - Clearwater
- ·
- Clearwater Beach
- 0.98 mi to center
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
- View
- St. Petersburg - Clearwater
- ·
- Bay Esplanade
- 0.44 mi to center
- Pool
- Balcony/Terrace
- Kitchen
- Parking
- St. Petersburg - Clearwater
- ·
- Indian Shores
- 0.07 mi to center
- Private Pool
- Oceanfront
- Fireplace/Heating
- Pool
- St. Petersburg - Clearwater
- ·
- Belle Vista
- 0.40 mi to center
- Oceanfront
- Hot Tub
- Fireplace/Heating
- Pool
- St. Petersburg - Clearwater
- ·
- Indian Shores
- 0.93 mi to center
- Hot Tub
- Fireplace/Heating
- Pool
- Ocean View
- St. Petersburg - Clearwater
- ·
- Indian Shores
- 0.37 mi to center
- Fireplace/Heating
- Pool
- Ocean View
- Balcony/Terrace
Luxury Holiday Rentals in Pinellas County
- St. Petersburg - Clearwater
- ·
- Indian Rocks Beach
- 0.59 mi to center
- Private Pool
- Oceanfront
- Fireplace/Heating
- Pool
- St. Petersburg - Clearwater
- ·
- Clearwater Beach
- 0.98 mi to center
- Ocean View
- Balcony/Terrace
- View
- Pet Friendly
- St. Petersburg - Clearwater
- ·
- St. Pete Beach
- 1.34 mi to center
- Private Pool
- Fireplace/Heating
- Pool
- Ocean View
- St. Petersburg - Clearwater
- ·
- Seminole
- 2.05 mi to center
- Fireplace/Heating
- Pool
- Balcony/Terrace
- View
- St. Petersburg - Clearwater
- ·
- Seminole
- 2.71 mi to center
- Pool
- Pet Friendly
- Parking
- Air Conditioner
- St. Petersburg - Clearwater
- ·
- Largo
- 1.29 mi to center
- Oceanfront
- Hot Tub
- Fireplace/Heating
- Pool
- St. Petersburg - Clearwater
- ·
- Clearwater Beach
- 0.98 mi to center
- Fireplace/Heating
- Pool
- View
- Pet Friendly
- St. Petersburg - Clearwater
- ·
- Indian Rocks Beach
- 0.53 mi to center
- Private Pool
- Hot Tub
- Spa
- Fireplace/Heating
- St. Petersburg - Clearwater
- ·
- St. Petersburg
- 1.66 mi to center
- Hot Tub
- Fireplace/Heating
- Pool
- Ocean View
Top-Rated Holiday Rentals with a Pool in Pinellas County
- St. Petersburg - Clearwater
- ·
- St. Petersburg
- 5.79 mi to center
- Private Pool
- Oceanfront
- Hot Tub
- Fireplace/Heating
- St. Petersburg - Clearwater
- ·
- Clearwater Beach
- 0.46 mi to center
- Pool
- Balcony/Terrace
- Kitchen
- Parking
- St. Petersburg - Clearwater
- ·
- Clearwater Beach
- 0.81 mi to center
- Pool
- Balcony/Terrace
- Kitchen
- Air Conditioner
- St. Petersburg - Clearwater
- ·
- Clearwater Beach
- 0.87 mi to center
- Oceanfront
- Fireplace/Heating
- Pool
- Ocean View
- St. Petersburg - Clearwater
- ·
- Clearwater Beach
- 0.57 mi to center
- Hot Tub
- Fireplace/Heating
- Pool
- Ocean View
- St. Petersburg - Clearwater
- ·
- Philippe Estates
- 0.23 mi to center
- Private Pool
- Hot Tub
- Fireplace/Heating
- Pool
- St. Petersburg - Clearwater
- ·
- Indian Shores
- 0.54 mi to center
- Private Pool
- Oceanfront
- Fireplace/Heating
- Pool
- St. Petersburg - Clearwater
- ·
- Indian Rocks Beach
- 1.02 mi to center
- Oceanfront
- Fireplace/Heating
- Pool
- Ocean View
- St. Petersburg - Clearwater
- ·
- Indian Rocks Beach
- 0.52 mi to center
- Fireplace/Heating
- Pool
- Ocean View
- Balcony/Terrace
Pet-Friendly Holiday Rentals in Pinellas County
- St. Petersburg - Clearwater
- ·
- Historic Old Northeast
- 0.44 mi to center
- Oceanfront
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
- St. Petersburg - Clearwater
- ·
- Largo
- 1.95 mi to center
- Balcony/Terrace
- Breakfast
- Pet Friendly
- Parking
- St. Petersburg - Clearwater
- ·
- Clearwater Beach
- 0.98 mi to center
- Private Pool
- Oceanfront
- Hot Tub
- Fireplace/Heating
- St. Petersburg - Clearwater
- ·
- Safety Harbor
- 1.47 mi to center
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
- St. Petersburg - Clearwater
- ·
- Treasure Island
- 0.34 mi to center
- Private Beach
- Oceanfront
- Ocean View
- Balcony/Terrace
- St. Petersburg - Clearwater
- ·
- Pass-a-Grille
- 0.45 mi to center
- Oceanfront
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
- St. Petersburg - Clearwater
- ·
- Indian Rocks Beach
- 0.50 mi to center
- Oceanfront
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
- St. Petersburg - Clearwater
- ·
- Indian Rocks Beach
- 0.23 mi to center
- Private Pool
- Oceanfront
- Hot Tub
- Fireplace/Heating
- St. Petersburg - Clearwater
- ·
- Independence Square
- 0.08 mi to center
- Oceanfront
- Pool
- Ocean View
- Balcony/Terrace
Large Holiday Rentals and Private Villas in Pinellas County
- St. Petersburg - Clearwater
- ·
- Bay Esplanade
- 0.61 mi to center
- Oceanfront
- Hot Tub
- Fireplace/Heating
- Ocean View
- St. Petersburg - Clearwater
- ·
- Disston Heights
- 1.13 mi to center
- Balcony/Terrace
- Breakfast
- Kitchen
- Parking
- St. Petersburg - Clearwater
- ·
- Seminole
- 2.20 mi to center
- Oceanfront
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
- St. Petersburg - Clearwater
- ·
- Dunedin
- 1.67 mi to center
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
- St. Petersburg - Clearwater
- ·
- Indian Shores
- 0.71 mi to center
- Private Beach
- Hot Tub
- Pool
- Ocean View
- St. Petersburg - Clearwater
- ·
- Safety Harbor
- 1.17 mi to center
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
- View
- St. Petersburg - Clearwater
- ·
- Bay Esplanade
- 0.34 mi to center
- Private Pool
- Oceanfront
- Fireplace/Heating
- Pool
- St. Petersburg - Clearwater
- ·
- Indian Shores
- 1.21 mi to center
- Oceanfront
- Fireplace/Heating
- Pool
- Ocean View
- St. Petersburg - Clearwater
- ·
- Tarpon Springs
- 1.76 mi to center
- Private Pool
- Oceanfront
- Fireplace/Heating
- Pool
Wheelchair Accessible Holiday Homes in Pinellas County
- St. Petersburg - Clearwater
- ·
- Indian Shores
- 1.24 mi to center
- Fireplace/Heating
- Pool
- Ocean View
- Balcony/Terrace
- St. Petersburg - Clearwater
- ·
- Bay Esplanade
- 0.44 mi to center
- Pool
- Balcony/Terrace
- Kitchen
- Parking
- Florida
- ·
- St. Petersburg - Clearwater
- 8.04 mi to center
- Fireplace/Heating
- Pool
- Ocean View
- View
- St. Petersburg - Clearwater
- ·
- Madeira Beach
- 0.86 mi to center
- Hot Tub
- Fireplace/Heating
- Pool
- Ocean View
- St. Petersburg - Clearwater
- ·
- Bay Esplanade
- 0.44 mi to center
- Pool
- Balcony/Terrace
- Kitchen
- Parking
- St. Petersburg - Clearwater
- ·
- Clearwater Beach
- 0.50 mi to center
- Private Pool
- Oceanfront
- Hot Tub
- Fireplace/Heating
- St. Petersburg - Clearwater
- ·
- Clearwater Beach
- 0.38 mi to center
- Oceanfront
- Hot Tub
- Spa
- Fireplace/Heating
- St. Petersburg - Clearwater
- ·
- Indian Rocks Beach
- 0.86 mi to center
- Fireplace/Heating
- Pool
- Ocean View
- Balcony/Terrace
- St. Petersburg - Clearwater
- ·
- Madeira Beach
- 0.89 mi to center
- Private Pool
- Fireplace/Heating
- Pool
- Ocean View
Pinellas County Private Villas and Holiday Homes Under $200
- St. Petersburg - Clearwater
- ·
- Ozona
- 0.34 mi to center
- Oceanfront
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
- St. Petersburg - Clearwater
- ·
- Bay Esplanade
- 0.44 mi to center
- Pool
- Balcony/Terrace
- Kitchen
- Parking
- St. Petersburg - Clearwater
- ·
- Historic Kenwood
- 0.22 mi to center
- Pool
- Balcony/Terrace
- Breakfast
- Kitchen
- St. Petersburg - Clearwater
- ·
- Sunset Beach
- 0.22 mi to center
- Oceanfront
- Fireplace/Heating
- Pool
- Ocean View
- St. Petersburg - Clearwater
- ·
- Bay Esplanade
- 0.44 mi to center
- Pool
- Balcony/Terrace
- Kitchen
- Parking
- St. Petersburg - Clearwater
- ·
- Seminole
- 2.89 mi to center
- Oceanfront
- Fireplace/Heating
- Pool
- Ocean View
- St. Petersburg - Clearwater
- ·
- St. Petersburg
- 8.04 mi to center
- Oceanfront
- Hot Tub
- Fireplace/Heating
- Pool
- St. Petersburg - Clearwater
- ·
- Madeira Beach
- 0.87 mi to center
- Private Pool
- Oceanfront
- Hot Tub
- Spa
- St. Petersburg - Clearwater
- ·
- Gulfport
- 0.83 mi to center
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
Instantly Bookable Holiday Homes in Pinellas County
- St. Petersburg - Clearwater
- ·
- Independence Square
- 0.06 mi to center
- Oceanfront
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
- St. Petersburg - Clearwater
- ·
- Bay Esplanade
- 0.44 mi to center
- Pool
- Balcony/Terrace
- Kitchen
- Parking
- St. Petersburg - Clearwater
- ·
- Clearwater Beach
- 0.48 mi to center
- Oceanfront
- Fireplace/Heating
- Pool
- Ocean View
- St. Petersburg - Clearwater
- ·
- Treasure Island
- 0.21 mi to center
- Fireplace/Heating
- Pool
- Ocean View
- Balcony/Terrace
- St. Petersburg - Clearwater
- ·
- Bay Esplanade
- 0.44 mi to center
- Pool
- Balcony/Terrace
- Kitchen
- Parking
- Hot Tub
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
- St. Petersburg - Clearwater
- ·
- Clearwater Beach
- 0.21 mi to center
- Oceanfront
- Hot Tub
- Fireplace/Heating
- Pool
- St. Petersburg - Clearwater
- ·
- Indian Rocks Beach
- 0.39 mi to center
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
- View
- St. Petersburg - Clearwater
- ·
- Indian Shores
- 0.07 mi to center
- Fireplace/Heating
- Pool
- Ocean View
- Balcony/Terrace
Book a Last Minute Place to Stay in Pinellas County
About Casai's Private Villas and Holiday Rentals in Pinellas County
Discover more than 22165 vacation rentals available in Pinellas County. These rentals, ranging from vacation rentals to Casai Homes and other short-term private accommodations, offer top-notch amenities with unbeatable value, ensuring both comfort and luxury. Enjoy more space and value when you stay at a Casai property in Pinellas County.
Seeking last-minute deals or the best available offers for cottages, condos, private villas, and spacious vacation homes? With Casai in Pinellas County, you can effortlessly compare various deals with just a click. Whether you're looking for a Casai with exceptional swimming pools, hot tubs, pet-friendly options, or large master suite bedrooms equipped with large screen televisions, you'll find a variety of options near Pinellas County. On average, places to stay near Pinellas County offer 859.06 ft², with nightly prices averaging د.إ.1,404.
With Casai, finding and comparing holiday rentals in Pinellas County is easy and secure, often at a 30-40% discount compared to hotel prices. Simply search for your destination and secure your reservation today.
Top Accommodation Types in Pinellas County
| Type | Count |
|---|---|
| Vacation Homes | 8973 |
| Holiday Apartments | 3789 |
| Cottages | 449 |
| Villas | 248 |
Use these Quick Filters to Find a Holiday Rental in Pinellas County
★ Pro Tip: Casai simplifies the process of comparing the finest listings across various online vacation rental platforms, including Booking.com and more. Utilize the Advanced Filter feature located at the top to effortlessly switch between Casai homes, vacation rentals, bed and breakfasts, private Airbnb-style rentals, eco-friendly properties, and different property types. Explore various cancellation policies, prices, and numerous options to find the ideal accommodation for your next vacation in Pinellas County.
Weather in Pinellas County, FL
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
Casai 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 in Pinellas County, FL
Frequently Asked Questions About Pinellas County?
What are the top holiday rentals in Pinellas County?
With numerous options available in Pinellas County, planning to stay in the area? Consider booking a few nights at one of these properties, rated as the Top Holiday Rentals in Pinellas County:
- Casa Dolphina: 6BR Waterfront Mini-Resort—Pool & Spa, Sunsets, Dock, St. Pete FL
- Ivory Sands Beach Suites
- 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
- Downtown Dunedin Walking District
- You Are Closer to Your Own Private Paradise on Beautiful Tampa Bay!
- Luxurious Oceanfront Home w/MILES of sandy beach & private Inter-Coastal dock!
- Beachfront Condo w/breathtaking full ocean & pool views, Top Flr, Small complex
- 230+ Reviews! Gulf Retreat I: Amazing views, luxury comfort, steps to beach
How many holiday rentals have private pools in Pinellas County?
Discover a selection of holiday rentals with private pools near Pinellas County with Casai. Experience the epitome of luxury and relaxation in our top-rated villas and holiday homes, where you can enjoy exclusive access to refreshing swimming pools.
- "Private Pool Oasis 3-MinnWalk to Crystal Beach nTropical Escape"
- Waterfront Luxury w/Heated Salt Pool & Golf Cart
- All Seasons Vacation Resort by Liberte'
- May 13-July 1 AVAIL-POOL OPEN! BCHFRONT PENTHOUSE MillionView
Which holiday homes in Pinellas County are best for families?
If you're searching for a family-friendly holiday home in Pinellas County, consider one of the following properties. Each comes highly recommended, with excellent reviews for families or groups staying in Pinellas County:
- *BEACH FRONT CONDO* OUTSTANDING LOCATION! AND A BREATH-TAKING VIEW*
- Five Palms Suite 202 - Daily - Weekly - Monthly
- Heated Pool Home Pool Table Spacious Family
How many Casai.ae holiday rentals are available in Pinellas County?
As of 2026, Casai boasts over 22165 properties listed in the Pinellas County area, with more being added continually. By consolidating listings from various websites, Casai provides an extensive selection of the finest Casai properties in Pinellas County.









































































