Vacation Rentals in Pinellas County
Start comparing over 7,338 rentals in Pinellas County and book at the best price!
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Child-friendly vacation rentals
Clearwater, Caladesi Island
Vacation rental for 2 people, with terrace
Free cancellation
from $89 per night
Clearwater, Caladesi Island
Vacation rental for 2 people, with terrace
Free cancellation
from $225 per night
Clearwater, Caladesi Island
Vacation rental for 2 people, with yard
Free cancellation
from $73 per night
Clearwater, Caladesi Island
Vacation rental for 2 people
Free cancellation
from $74 per night
Vacation rentals with pets allowed
Clearwater, Pinellas County
9.7
Vacation rental for 2 people, with yard and terrace, with pets
Free cancellation
from $132 per night
Treasure Island, Pinellas County
9.3
Vacation rental for 4 people, with terrace
Free cancellation
from $173 per night
Clearwater, Caladesi Island
9.2
Vacation rental for 2 people, with yard and terrace as well as pool, with pets
Free cancellation
from $150 per night
Pinellas County
8.8
Vacation rental for 2 people, with terrace, with pets
Free cancellation
from $122 per night
Vacation rentals in Pinellas County
Pinellas County
9.9
Vacation rental for 2 people, with yard and terrace
Free cancellation
from $125 per night
Clearwater, Caladesi Island
9.9
Vacation rental for 4 people
Free cancellation
from $234 per night
Pinellas County
10.0
Vacation rental for 2 people, with yard and terrace
Free cancellation
from $192 per night
Pinellas County
9.9
Vacation rental for 2 people, with balcony and yard
Free cancellation
from $125 per night
Vacation rentals with sea view
Indian Rocks Beach, Pinellas County
Vacation rental for 5 people, with balcony and yard, kid friendly
Free cancellation
from $263 per night
Indian Rocks Beach, Pinellas County
Vacation rental for 7 people, with terrace and yard, with pets
Free cancellation
from $265 per night
Safety Harbor, Pinellas County
Vacation rental for 4 people, with balcony, kid friendly
Free cancellation
from $129 per night
Indian Rocks Beach, Pinellas County
Vacation rental for 4 people, with terrace
Free cancellation
from $90 per night
Vacation rentals with free cancellation
St. Petersburg (FL), Pinellas County
7.9
Vacation rental for 2 people, with sauna and yard as well as pool
Free cancellation
from $152 per night
Gulfport (FL), Pinellas County
9.7
Vacation rental for 4 people, with yard and terrace, with pets
Free cancellation
from $151 per night
St. Pete Beach, Pinellas County
8.7
Vacation rental for 4 people, with pool and balcony
Free cancellation
from $174 per night
Indian Rocks Beach, Pinellas County
10.0
Vacation rental for 4 people, with yard
Free cancellation
from $226 per night
Current vacation rental deals in Pinellas County
Pinellas County
9.5
Vacation rental for 16 people, with terrace and hot tub as well as yard, with pets
Free cancellation
Sat, 02/14 - Sat, 02/21
$11,053 $10,214 ·
Long stay deal
This accommodation offers a 8% discount on long-term stays.
Pinellas County
6.5
Vacation rental for 20 people, with hot tub and balcony
Free cancellation
Sat, 02/14 - Sat, 02/21
$13,323 $12,310 ·
Long stay deal
This accommodation offers a 8% discount on long-term stays.
Pinellas County
9.6
Vacation rental for 16 people, with terrace
Free cancellation
Sat, 02/14 - Sat, 02/21
$7,880 $7,320 ·
Long stay deal
This accommodation offers a 7% discount on long-term stays.
Pinellas County
8.7
Vacation rental for 22 people
Free cancellation
Sat, 02/14 - Sat, 02/21
$11,847 $10,956 ·
Long stay deal
This accommodation offers a 8% discount on long-term stays.
Find Vacation Rentals in Pinellas County
Popular Destinations in Pinellas County
Best Vacation Rentals in Pinellas County
Guests agree: these stays are highly rated for location, cleanliness, and more.
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Indian Rocks Beach, Pinellas County
Vacation Rental • 4 Guests • 2 Bedrooms
Indian Rocks Beach, Pinellas County
CONSTRUCTION UPDATE 3/1/2025: Please note there is additional maintenance taking place around the building that includes exterior painting and balcony work, this should last through 2025 into early 2026. The balcony will not be available through March 2025 due to construction and the ocean view will be obstructed. The open-concept living area features comfy recliner chairs and sofa, perfect for relaxing and enjoying the company of friends and family. The large flat-screen smart TV provides cable, surround sound, and access to your favorite streaming apps. The private balcony, complete with ...
from $188 / night
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Safety Harbor, Pinellas County
Vacation Rental • 4 Guests • 2 Bedrooms
Safety Harbor, Pinellas County
This first floor apartment's interior boasts modern decor with subtle touches of old-Florida style. Recently updated and newly furnished, "Canopy Cabana" offers everything you need to make this the perfect "home away from home" during your stay in Safety Harbor. Accommodations include 1 King bedroom and 1 Queen bedroom, both with comfy beds, ceiling fans, walk-in closets, and bedside charging ports for your electronic devices. The King bedroom offers a spacious ensuite bath with a double vanity and beautiful walk-in shower with a glass door. The Queen bedroom sits just down the hall from th...
from $129 / night
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Pinellas County
Vacation Rental • 5 Guests • 2 Bedrooms
Pinellas County
10.0
Welcome to our family home, a modern and stunning vacation rental near the beautiful beaches of St. Petersburg and Indian Rocks Beach. This home features 2 full bedrooms and 1 full bath, making it perfect for families or business travelers. Enjoy the spacious layout with a connected carport, paved driveway, and a huge landscaped backyard. The private fenced-in patio is equipped with plenty of furniture and a grill, providing a relaxing outdoor space. This home offers a modern, relaxing getaway that can be used for vacation or business travel! A signed rental agreement and legal ID must be p...
from $51 / night
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Popular Destinations in Pinellas County
Prices and availability
Current Vacation rental prices Pinellas County
$371for 23 Aug - 30 Aug
$399 annual averageSep
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Dec
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Average price per week
FAQs: Vacation Rentals in Pinellas County
How much does it cost to book a vacation rental in Pinellas County?
Based on last year, Pinellas County had an average price of $339 per night, a relatively high one for a destination in the USA.
During which months can you find the best price for vacation rentals in Pinellas County?
According to the previous year, the months with the cheapest prices in Pinellas County are September, October and August, with average prices of $290, $301, and $311, respectively.
When are vacation rentals more expensive in Pinellas County?
When it comes to looking for a vacation rental in Pinellas County, the months that cost the most are, in order of highest to lowest, March, February and April, with average prices per night of $419, $415, and $345, respectively.
Are there usually many vacation rentals available in Pinellas County?
We recommend you to book in advance in Pinellas County as only 14% of the properties are available throughout the year, following the data observed in the previous year.
Which months offer the highest availability?
The months when it's easiest to find free accommodation in Pinellas County are August (the average amount of properties that are available reached 26% of the total last year), September (20%), and October (20%).
When will it be harder to find an available vacation rental in Pinellas County?
The months with the lowest properties available in Pinellas County are, in order, March, February, and April with respective average availability figures of 1%, 2%, and 3%, based on the previous year. During these three months, the availability is very low (2%). It is therefore recommended to book far in advance.
Are there many rentals in Pinellas County?
We have 2,400 properties for you in Pinellas County, provided by our 10 local and international partners.
Vacation destinations in Pinellas County
- St. Petersburg (FL)Vacation Rentals
- St. Pete BeachVacation Rentals
- ClearwaterVacation Rentals
- Indian Rocks BeachVacation Rentals
- Madeira BeachVacation Rentals
- Treasure IslandVacation Rentals
- Indian ShoresVacation Rentals
- DunedinVacation Rentals
- Tarpon SpringsVacation Rentals
- Redington BeachVacation Rentals
- LargoVacation Rentals
- Palm HarborVacation Rentals
- Gulfport (FL)Vacation Rentals
- SeminoleVacation Rentals
- Safety HarborVacation Rentals
- South Pasadena (FL)Vacation Rentals
- Pinellas ParkVacation Rentals