Pinellas County Winter Rental
New
House
8.0(1 Review)
6 Bedrooms
3 Baths
16 Guests
Fireplace/Heating
Balcony/Terrace
Pet Friendly
Kitchen
US $771/Night
7 Nights - US $5,395
House
10.0(14 Reviews)
3 Bedrooms
2 Baths
8 Guests
1991.32 ft²
Oceanfront- Fireplace/Heating
Ocean View- Balcony/Terrace
US $346/Night
7 Nights - US $2,422
House
10.0(2 Reviews)
6 Bedrooms
7 Baths
16 Guests
Private Pool- Oceanfront
Hot Tub- Fireplace/Heating
US $1,695/Night
7 Nights - US $11,867
New
House
3 Bedrooms
3 Baths
10 Guests
- Private Pool
- Hot Tub
- Fireplace/Heating
Pool
US $1,370/Night
7 Nights - US $9,591
House
10.0(10 Reviews)
1 Bedroom
1 Bath
2 Guests
365.97 ft²
- Oceanfront
- Hot Tub
- Fireplace/Heating
- Ocean View
US $228/Night
7 Nights - US $1,596
New
House
2 Bedrooms
4 Baths
6 Guests
4800 ft²
- Oceanfront
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
US $765/Night
7 Nights - US $5,358
House
10.0(10 Reviews)
6 Bedrooms
4 Baths
12 Guests
10763.91 ft²
- Oceanfront
- Pool
- Ocean View
View
US $1,058/Night
7 Nights - US $7,406
New
Condo
3 Bedrooms
3 Baths
8 Guests
1800 ft²
- Hot Tub
- Fireplace/Heating
- Pool
- Ocean View
US $710/Night
7 Nights - US $4,970
House
10.0(6 Reviews)
4 Bedrooms
4 Baths
10 Guests
1463.89 ft²
- Hot Tub
- Fireplace/Heating
- Pool
- View
US $409/Night
7 Nights - US $2,863
New
House
3 Bedrooms
3 Baths
6 Guests
1852 ft²
- Private Pool
- Fireplace/Heating
- Pool
- Balcony/Terrace
US $640/Night
7 Nights - US $4,483
Apartment
10.0(5 Reviews)
3 Bedrooms
2 Baths
8 Guests
1851.39 ft²
Private Beach- Oceanfront
- Hot Tub
- Fireplace/Heating
US $407/Night
7 Nights - US $2,849
House
4 Bedrooms
4 Baths
22 Guests
- Private Pool
- Oceanfront
- Hot Tub
- Fireplace/Heating
US $614/Night
7 Nights - US $4,299
Why Choose Rent By Owner for your Pinellas County Winter Rental?
What makes our Winter Rental special?
Verified Listings
Book with confidence knowing every property meets our quality and safety standards.
Unbeatable Value
Enjoy competitive pricing with no hidden fees, providing exceptional value for every stay.
Diverse Options
From cozy cabins to luxurious villas, find a rental that suits your style and needs.
Weekly Weather Forecast for Pinellas County
How to Book Your Pinellas County Winter Rental
What's our booking process?
Our platform allows you to browse a curated selection of winter rental. Once you find the ideal property, you’ll be redirected to a trusted booking partner to complete your reservation securely.
Booking Steps
01
Search Properties
Use our filters to find the right property that fits your needs.
02
Select a Rental
Click on your preferred listing to view details, amenities, and pricing.
03
Book Online
Follow the link to finalize your reservation directly on the partner’s website.
Explore and book the perfect rental in Pinellas County
Common Winter Rental Amenities
What amenities can you expect?
Our Winter Rental are designed to offer all the comforts of home, often with added perks to make your stay unforgettable. Here’s some common amenities to look forward to:
Indoor Features
- Fully-equipped kitchens with modern appliances
- Comfortable living areas with flat-screen TVs
- Free Wi-Fi for staying connected
- Air conditioning and heating for year-round comfort
- In-unit washers and dryers for convenience
- Luxurious bedrooms with premium bedding
- Spa-like bathrooms with soaking tubs or walk-in showers
Other Places to Stay in Pinellas County, FL
St. Petersburg - Clearwater
Clearwater-St. Pete Beaches
St. Petersburg
Clearwater Beach
Madeira Beach
Treasure Island
Indian Rocks Beach
Indian Shores
St. Petersburg - Clearwater Beaches
St. Pete Beach
Downtown St. Petersburg
Pinellas County Winter Rental Frequently Asked Questions
1. What are the top Winter 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 Winter Rentals in Pinellas County:
- Casa Dolphina: 6BR Waterfront Mini-Resort—Pool & Spa, Sunsets, Dock, St. Pete FL
- 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
- Exquisite 2 BR/2 BA Waterfront Beach Condo + Free Water Park!
- Beautiful Clearwater Beach Home just across from the Beach - Drive to your door.
2. How many Winter Rentals are available in Pinellas County?
Currently, the total number of properties listed by RBO in 2026 is over 11470 in the Pinellas County area, and still counting. By aggregating listings from multiple websites, RBO offers an immense amount of choice of the best Winter Rentals in Pinellas County.
More Rentals You May Like Near Pinellas County
House
10.0(5 Reviews)
3 Bedrooms
2 Baths
6 Guests
1905.21 ft²
- Oceanfront
- Hot Tub
- Fireplace/Heating
- Pool
US $405/Night
7 Nights - US $2,835
House
3 Bedrooms
3 Baths
9 Guests
850 ft²
- Oceanfront
- Fireplace/Heating
- Pool
- Ocean View
US $580/Night
7 Nights - US $4,063
New
Condo
3 Bedrooms
2 Baths
7 Guests
1250 ft²
- Oceanfront
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
US $554/Night
7 Nights - US $3,878
House
4 Bedrooms
3 Baths
10 Guests
- Hot Tub
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
US $537/Night
7 Nights - US $3,757
New
House
2 Bedrooms
3 Baths
8 Guests
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
- View
US $514/Night
7 Nights - US $3,599
New
Condo
3 Bedrooms
2 Baths
6 Guests
- Fireplace/Heating
- Pool
- Ocean View
- Balcony/Terrace
US $463/Night
7 Nights - US $3,243
New
Apartment
3 Bedrooms
2 Baths
6 Guests
- Oceanfront
- Hot Tub
- Fireplace/Heating
- Pool
US $453/Night
7 Nights - US $3,172
New
House
4 Bedrooms
3 Baths
9 Guests
1352 ft²
- Oceanfront
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
US $448/Night
7 Nights - US $3,135
New
House
4 Bedrooms
3 Baths
12 Guests
- Private Pool
- Fireplace/Heating
- Pool
- Balcony/Terrace
US $430/Night
7 Nights - US $3,009
New
Condo
3 Bedrooms
2 Baths
8 Guests
1300 ft²
- Oceanfront
- Hot Tub
- Fireplace/Heating
- Pool
US $423/Night
7 Nights - US $2,964
New
House
3 Bedrooms
2 Baths
6 Guests
- Private Pool
- Oceanfront
- Fireplace/Heating
- Pool
US $423/Night
7 Nights - US $2,964
New
Condo
3 Bedrooms
2 Baths
8 Guests
- Hot Tub
- Fireplace/Heating
- Pool
- Ocean View
US $411/Night
7 Nights - US $2,880
