Best Vacation Homes in Pinellas County
Condo
10.0(90 Reviews)
3 Bedrooms
2 Baths
10 Guests
1800 ft²
Oceanfront
Parking
Pool
Ocean View
US $417/Night
7 Nights - US $2,919
House
10.0(27 Reviews)
2 Bedrooms
1 Bath
4 Guests
1001.04 ft²
- Parking
Balcony/Terrace
View
Air Conditioner
US $163/Night
7 Nights - US $1,138
Bed & Breakfast
10.0(47 Reviews)
1 Bedroom
1 Bath
Breakfast- Parking
- Pool
- Balcony/Terrace
US $173/Night
7 Nights - US $1,209
House
10.0(67 Reviews)
4 Bedrooms
3 Baths
10 Guests
Private Pool
Hot Tub- Parking
- Pool
US $1,451/Night
7 Nights - US $10,157
Apartment
10.0(25 Reviews)
1 Bedroom
1 Bath
3 Guests
387.5 ft²
- Oceanfront
- Parking
- Ocean View
- Balcony/Terrace
US $250/Night
7 Nights - US $1,748
Condo
10.0(67 Reviews)
3 Bedrooms
2 Baths
7 Guests
1400 ft²
- Hot Tub
- Parking
- Pool
- Ocean View
US $362/Night
7 Nights - US $2,535
New
House
10.0(58 Reviews)
4 Bedrooms
3 Baths
6 Guests
3500 ft²
- Oceanfront
- Hot Tub
- Parking
- Ocean View
US $1,390/Night
7 Nights - US $9,731
Cottage
10.0(55 Reviews)
2 Bedrooms
2 Baths
6 Guests
1100 ft²
- Oceanfront
- Parking
- Ocean View
- Balcony/Terrace
US $287/Night
7 Nights - US $2,011
Pinellas County Luxury Rentals
House
1 Bedroom
1 Bath
- Parking
- Ocean View
- Balcony/Terrace
- View
US $7,767/Night
7 Nights - US $54,370
House
8.0(2 Reviews)
2 Bedrooms
1 Bath
6 Guests
800 ft²
- Parking
- Balcony/Terrace
Kitchen- Air Conditioner
US $7,097/Night
7 Nights - US $49,680
New
Condo
1 Bedroom
1 Bath
4 Guests
- Parking
- Ocean View
- Balcony/Terrace
- View
US $6,304/Night
7 Nights - US $44,130
House
1 Bedroom
2 Baths
13 Guests
2034.38 ft²
- Oceanfront
- Hot Tub
- Parking
- Pool
US $5,000/Night
7 Nights - US $35,000
House
1 Bedroom
1 Bath
- Parking
- Ocean View
- Balcony/Terrace
- View
US $4,859/Night
7 Nights - US $34,015
US $4,768/Night
7 Nights - US $33,374
House
12 Bedrooms
13 Baths
28 Guests
6522.93 ft²
- Parking
- Pool
- View
- Air Conditioner
US $4,596/Night
7 Nights - US $32,172
Villa
10.0(7 Reviews)
12 Bedrooms
13 Baths
54 Guests
10000 ft²
- Private Pool
- Hot Tub
- Parking
- Pool
US $4,208/Night
7 Nights - US $29,454
Pinellas County Pet Friendly Vacation Rentals
House
10.0(40 Reviews)
3 Bedrooms
2 Baths
8 Guests
1400 ft²
- Private Pool
- Oceanfront
- Parking
- Pool
US $678/Night
7 Nights - US $4,744
House
10.0(14 Reviews)
3 Bedrooms
2 Baths
8 Guests
1991.32 ft²
- Oceanfront
- Parking
- 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
- Parking
US $1,605/Night
7 Nights - US $11,232
House
10.0(31 Reviews)
3 Bedrooms
3 Baths
9 Guests
- Oceanfront
- Hot Tub
- Parking
- Ocean View
US $709/Night
7 Nights - US $4,966
House
10.0(10 Reviews)
3 Bedrooms
3 Baths
11 Guests
1496.18 ft²
- Parking
- Pool
- View
- Air Conditioner
US $481/Night
7 Nights - US $3,370
Cottage
10.0(22 Reviews)
2 Bedrooms
1 Bath
4 Guests
550 ft²
- Oceanfront
- Parking
- Pool
- Ocean View
US $239/Night
7 Nights - US $1,674
New
Cottage
10.0(13 Reviews)
1 Bedroom
1 Bath
2 Guests
890 ft²
- Parking
- Kitchen
- Air Conditioner
Internet
US $344/Night
7 Nights - US $2,405
New
House
10.0(10 Reviews)
7 Bedrooms
5 Baths
28 Guests
- Hot Tub
- Pool
- Balcony/Terrace
- Kitchen
US $2,139/Night
7 Nights - US $14,973
Pinellas County Large Vacation Homes
New
House
10.0(38 Reviews)
4 Bedrooms
3 Baths
10 Guests
- Parking
- Ocean View
- Balcony/Terrace
- View
US $435/Night
7 Nights - US $3,045
House
10.0(13 Reviews)
4 Bedrooms
3 Baths
12 Guests
4800.7 ft²
- Private Pool
- Oceanfront
- Parking
- Pool
US $1,270/Night
7 Nights - US $8,891
Villa
8.4(5 Reviews)
1 Bedroom
1 Bath
- Oceanfront
- Parking
- Ocean View
- Balcony/Terrace
US $79/Night
7 Nights - US $551
New
House
10.0(17 Reviews)
4 Bedrooms
3 Baths
10 Guests
2424 ft²
- Oceanfront
- Hot Tub
- Parking
- Ocean View
US $655/Night
7 Nights - US $4,584
House
10.0(10 Reviews)
6 Bedrooms
4 Baths
12 Guests
10763.91 ft²
- Oceanfront
- Parking
- Pool
- Ocean View
US $1,058/Night
7 Nights - US $7,406
House
10.0(12 Reviews)
7 Bedrooms
5 Baths
22 Guests
- Private Pool
- Parking
- Pool
- Balcony/Terrace
US $2,518/Night
7 Nights - US $17,626
New
House
10.0(8 Reviews)
5 Bedrooms
4 Baths
18 Guests
2700 ft²
- Oceanfront
- Pool
- Ocean View
- Balcony/Terrace
US $569/Night
7 Nights - US $3,982
New
House
10.0(7 Reviews)
1 Bedroom
2 Baths
10 Guests
1600 ft²
- Private Pool
- Oceanfront
- Parking
- Pool
US $496/Night
7 Nights - US $3,474
Why Choose Rent By Owner for your Pinellas County Vacation Rental Homes?
What makes our Vacation Rentals 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.
Best Times to Visit Pinellas County
When should you plan your Vacation Rentals stay?
Choosing the right time to visit here can enhance your experience, as seasonal changes in this destination influence everything from weather to local events, helping you select the ideal period for your perfect getaway.
Peak Season Highlights
Spring (March to May)
During spring, the area experiences warm temperatures and abundant sunshine, making it an ideal time for outdoor activities and beach visits in your vacation rentals.
Average Temperature Daytime: 75°F to 85°F - Nighttime: 60°F to 70°F
Winter (December to February)
Winter months bring mild weather with comfortable daytime temperatures, attracting visitors seeking a sunny getaway in this popular Florida destination.
Average Temperature Daytime: 65°F to 75°F - Nighttime: 50°F to 60°F
Off-Season Highlights
Summer (June to August)
In summer, the region tends to be hotter and more humid, which can be perfect for water sports enthusiasts looking to enjoy the beaches and nearby waters.
Average Temperature Daytime: 85°F to 90°F - Nighttime: 75°F to 80°F
Fall (September to November)
Fall offers slightly cooler temperatures and fewer visitors, providing a peaceful environment to relax at your favorite vacation rentals in this coastal region.
Average Temperature Daytime: 75°F to 85°F - Nighttime: 60°F to 70°F
Weekly Weather Forecast for Pinellas County
How to Book Your Pinellas County Vacation Rental Home
What's our booking process?
Our platform allows you to browse a curated selection of vacation rentals. 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 Vacation Rentals Amenities
What amenities can you expect?
Our Vacation Rentals 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
Outdoor Amenities
- Enjoy outdoor dining areas perfect for relaxing meals with beach or water views.
- Take advantage of private pools or hot tubs to unwind after a day exploring the area.
- Make the most of spacious patios or decks for morning coffee or sunset watching.
- Benefit from access to lush garden spaces or landscaped yards ideal for outdoor activities.
- Utilize outdoor showers, especially popular in coastal settings for rinsing off after the beach.
- Observe the local wildlife or simply enjoy the fresh air from screened-in porches or verandas.
- Get active with outdoor sports amenities like tennis courts, volleyball, or walking trails often available here.
Top Attractions Around Pinellas County
What attractions are nearby?
While staying in the area, you can enjoy a variety of outdoor activities such as relaxing on beautiful beaches, exploring scenic parks, and engaging in water sports that highlight the natural beauty of this destination.
Family Activities
- Clearwater Marine Aquarium: Discover the wonders of marine life and enjoy interactive exhibits that captivate both kids and adults alike.
- Fort De Soto Park: Spend a day exploring pristine beaches, scenic trails, and fun-filled playgrounds perfect for family picnics and outdoor activities.
- The Pier 60 in Clearwater Beach: Experience daily sunset celebrations, street performers, and family-friendly entertainment right on the waterfront.
- John's Pass Village and Boardwalk: Explore charming shops, dine at casual restaurants, and take boat tours that showcase the area's natural beauty and marine life.
Adult Activities
- Sunset Beach Walks: Experience stunning sunsets and pristine shoreline as you stroll along the beaches of this coastal region, a perfect way to unwind during your stay.
- Visit the Clearwater Marine Aquarium: Discover marine life conservation efforts and enjoy interactive exhibits that showcase local aquatic animals in the area.
- Explore Downtown St. Petersburg: Enjoy vibrant arts, diverse dining options, and lively entertainment in the heart of this cultural hub here.
- Take a Boat Tour of the Gulf Coast: Embark on an outdoor adventure exploring the scenic waterways and spotting local wildlife right from your watercraft here.
Other Places to Stay in Pinellas County, FL
St. Petersburg - Clearwater
Clearwater-St. Pete Beaches
St. Petersburg
Clearwater Beach
Treasure Island
Madeira Beach
Indian Rocks Beach
Indian Shores
St. Petersburg - Clearwater Beaches
St. Pete Beach
Downtown St. Petersburg
Pinellas County Travel Tips
How Can You Make the Most of Your Stay?
- Plan Your Visits to Popular Beaches: Make the most of your stay by exploring the area’s renowned beaches early in the day to enjoy less crowded, peaceful shoreline experiences.
- Explore Local Dining Options: Sample authentic flavors at local eateries and waterfront restaurants to immerse yourself in the region’s culinary scene during your visit.
- Utilize Water Transportation: Take advantage of boat rentals or water taxis to discover hidden coves and scenic spots exclusive to this coastal destination.
- Check for Seasonal Events and Festivals: Stay updated on local happenings to experience vibrant festivals and cultural events that showcase the area's unique community spirit.
Transportation Options
- Pinellas Suncoast Transit Authority (PSTA): This regional bus service offers convenient transportation throughout the area, making it easy for you to explore Pinellas County without hassle.
- St. Pete-Clearwater International Airport: Located nearby, this airport provides out-of-state and international flights, giving you quick access to your vacation rental here.
- Rental Cars: Numerous local providers offer flexible options for exploring the region at your own pace, ideal for reaching those hidden beaches or coastal attractions.
- Rideshare Services: Popular services like Uber and Lyft operate throughout the area, providing a reliable way to travel comfortably between your accommodations and popular destinations.
Local Customs Options
- Sunset Celebrations: Locals here cherish watching daily sunsets over the Gulf, making sunset gatherings a cherished tradition.
- Beach Etiquette: Respect for the shoreline and marine life is deeply rooted, with visitors encouraged to follow local guidelines to preserve the area's natural beauty.
- Seafood Traditions: Fresh seafood, especially from the Gulf, plays a vital role in the region’s culinary customs, often enjoyed during community festivals.
- Art in Public Spaces: Outdoor art displays and murals reflect the area's vibrant artistic culture, inviting you to explore and appreciate local creativity.
Pinellas County Vacation Rental Frequently Asked Questions
1. 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:
- 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!
- Rare Direct Beachfront Cottage Ground-Floor Walk-Out to the Sand No Stairs!
- Beachfront Condo w/breathtaking full ocean & pool views, Top Flr, Small complex
- Spacious top floor 3 bedroom condo overlooking the beautiful Gulf of America!
2. How many vacation rentals have private pools in Pinellas County?
There are 3230 vacation rentals with private pools near Pinellas County. Top-rated RBO homes that have access to a swimming pool include:
3. 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:
4. How many Rentbyowner vacation rentals are available in Pinellas County?
Currently, the total number of properties listed by Rent By Owner in 2026 is over 21931 in the Pinellas County area, and still counting. By aggregating listings from multiple websites, Rent By Owner offers an immense amount of choice of the best RBO properties in Pinellas County.
5. What is the cancellation policy for vacation rentals in this area?
Cancellation policies vary by property. You should review the specific listing details or contact the owner directly to understand the terms, including any potential fees or restrictions.
6. Are there any additional fees I should be aware of when booking a vacation rental here?
Additional fees such as cleaning fees, security deposits, or service charges are typically listed on the property page. Be sure to read the full listing and reach out to the owner if you have questions about extra costs.
7. How do I confirm my reservation and what is the check-in process?
Once you complete your booking online, you'll receive confirmation details. The check-in process varies by property; some may offer self-check-in options, while others require direct communication with the host.
8. Is it possible to modify or extend my stay at a vacation rental here?
Modifications to your reservation depend on the property's policies and availability. Contact the owner directly through the platform to inquire about extending your stay or making changes.
9. What amenities are typically included in vacation rentals in this region?
Amenities can vary but often include essentials like Wi-Fi, kitchen facilities, air conditioning, and parking. Always review the property listing for detailed information about included amenities before booking.
Pinellas County Top Rated Vacation Rentals
US $180/Night
7 Nights - US $1,258
Condo
10.0(334 Reviews)
3 Bedrooms
3 Baths
8 Guests
2048 ft²
- Pool
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $572/Night
7 Nights - US $4,006
Condo
10.0(316 Reviews)
2 Bedrooms
2 Baths
6 Guests
950 ft²
- Oceanfront
- Parking
- Pool
- Ocean View
US $516/Night
7 Nights - US $3,613
Hotel
10.0(307 Reviews)
1 Bath
912 ft²
- Hot Tub
- Parking
- Pool
- Ocean View
US $593/Night
7 Nights - US $4,154
House
10.0(292 Reviews)
3 Bedrooms
2 Baths
6 Guests
1320 ft²
- Private Pool
- Hot Tub
- Parking
- Pool
US $374/Night
7 Nights - US $2,615
New
Condo
10.0(240 Reviews)
3 Bedrooms
2 Baths
8 Guests
1275 ft²
- Oceanfront
- Hot Tub
- Parking
- Pool
US $464/Night
7 Nights - US $3,251
Condo
10.0(225 Reviews)
3 Bedrooms
2 Baths
8 Guests
1585 ft²
- Parking
- Pool
- Ocean View
- Balcony/Terrace
US $522/Night
7 Nights - US $3,653
Condo
10.0(215 Reviews)
2 Bedrooms
2 Baths
8 Guests
- Oceanfront
- Hot Tub
- Parking
- Pool
US $312/Night
7 Nights - US $2,182
