Condo
10.0(320 Reviews)
2 Bedrooms
6 Guests
Oceanfront
Parking
Pool
Ocean View
US $450/Night
7 Nights - US $3,147
Pinellas County Holiday Rentals
We compare holiday rentals from owners across Booking.com, Vrbo and Expedia.
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Compare Holiday Rentals, Villas & Resorts in Pinellas County
10.0
House
10.0(27 Reviews)
2 Bedrooms
4 Guests
- Parking
Balcony/Terrace
View
Air Conditioner
US $163/Night
7 Nights - US $1,138
Cottage
2 Bedrooms
4 Guests
- Air Conditioner
Internet
Child Friendly
Laundry
US $169/Night
7 Nights - US $1,180
Condo
10.0(300 Reviews)
2 Bedrooms
4 Guests
- Oceanfront
- Parking
- Ocean View
- Balcony/Terrace
US $439/Night
7 Nights - US $3,072
Apartment
10.0(25 Reviews)
1 Bedroom
3 Guests
- Oceanfront
- Parking
- Ocean View
- Balcony/Terrace
US $250/Night
7 Nights - US $1,748
Cottage
10.0(246 Reviews)
1 Bedroom
4 Guests
- Oceanfront
- Parking
- Ocean View
- Balcony/Terrace
US $370/Night
7 Nights - US $2,592
House
10.0(232 Reviews)
2 Bedrooms
6 Guests
- Oceanfront
- Parking
- Ocean View
- Balcony/Terrace
US $546/Night
7 Nights - US $3,820
Condo
10.0(218 Reviews)
2 Bedrooms
8 Guests
- Oceanfront
Hot Tub- Parking
- Pool
US $288/Night
7 Nights - US $2,015
Condo
10.0(201 Reviews)
2 Bedrooms
6 Guests
- Parking
- Ocean View
- Balcony/Terrace
- View
US $552/Night
7 Nights - US $3,861
Luxury Holiday Rentals in Pinellas County
Over 10000+ Luxury Holiday Rentals in or Near Pinellas County
House
3 Bedrooms
6 Guests
- Air Conditioner
- Internet
- Child Friendly
- Laundry
Unlock the Best Price
New
House
1 Bedroom
4 Guests
- Oceanfront
- Parking
- Ocean View
- Balcony/Terrace
Unlock the Best Price
Unlock the Best Price
New
House
2 Bedrooms
4 Guests
- Air Conditioner
- Internet
Pet Friendly- Child Friendly
Unlock the Best Price
US $9,442/Night
7 Nights - US $66,091
House
1 Bedroom
- Parking
- Ocean View
- Balcony/Terrace
- View
US $7,767/Night
7 Nights - US $54,370
Condo
1 Bedroom
4 Guests
- Parking
- Ocean View
- Balcony/Terrace
- View
US $6,259/Night
7 Nights - US $43,815
New
House
4 Bedrooms
14 Guests
Private Pool- Hot Tub
- Parking
- Pool
US $6,117/Night
7 Nights - US $42,818
House
12 Bedrooms
28 Guests
- Oceanfront
- Hot Tub
- Parking
- Pool
US $4,596/Night
7 Nights - US $32,172
Top-Rated Holiday Rentals with a Pool in Pinellas County
Over 10000+ The Best Private Villas and Holiday Rentals in Pinellas County with a Pool
US $175/Night
7 Nights - US $1,226
Condo
10.0(337 Reviews)
3 Bedrooms
8 Guests
- Pool
- Balcony/Terrace
Kitchen- Air Conditioner
US $747/Night
7 Nights - US $5,230
Hotel
10.0(316 Reviews)
- Hot Tub
- Parking
- Pool
- Ocean View
US $565/Night
7 Nights - US $3,953
Condo
10.0(243 Reviews)
3 Bedrooms
8 Guests
- Oceanfront
- Hot Tub
- Parking
- Pool
US $428/Night
7 Nights - US $2,995
Condo
10.0(200 Reviews)
3 Bedrooms
8 Guests
- Oceanfront
- Hot Tub
- Parking
- Pool
US $463/Night
7 Nights - US $3,243
Condo
10.0(199 Reviews)
2 Bedrooms
6 Guests
- Oceanfront
- Parking
- Pool
- Ocean View
US $268/Night
7 Nights - US $1,879
Condo
10.0(198 Reviews)
2 Bedrooms
6 Guests
- Private Pool
- Oceanfront
- Parking
- Pool
US $499/Night
7 Nights - US $3,492
New
Condo
10.0(196 Reviews)
2 Bedrooms
6 Guests
- Hot Tub
- Parking
- Pool
- Ocean View
US $491/Night
7 Nights - US $3,435
Condo
10.0(187 Reviews)
2 Bedrooms
6 Guests
- Hot Tub
- Parking
- Pool
- Ocean View
US $557/Night
7 Nights - US $3,896
Pet-Friendly Holiday Rentals in Pinellas County
Over 6158+ Pet-Friendly Holiday Rentals in or Near Pinellas County
Apartment
10.0(162 Reviews)
1 Bedroom
2 Guests
- Oceanfront
- Parking
- Ocean View
- Balcony/Terrace
US $359/Night
7 Nights - US $2,513
Apartment
10.0(10 Reviews)
2 Bedrooms
9 Guests
- Parking
- Pool
- Air Conditioner
- Internet
US $461/Night
7 Nights - US $3,229
Cottage
10.0(2 Reviews)
1 Bedroom
- Oceanfront
- Parking
- Pool
- Ocean View
US $536/Night
7 Nights - US $3,755
House
10.0(154 Reviews)
2 Bedrooms
10 Guests
- Oceanfront
- Parking
- Ocean View
- Balcony/Terrace
US $324/Night
7 Nights - US $2,267
House
10.0(9 Reviews)
1 Bedroom
4 Guests
- Parking
- Balcony/Terrace
- View
- Air Conditioner
US $302/Night
7 Nights - US $2,115
Condo
10.0(143 Reviews)
1 Bedroom
3 Guests
- Oceanfront
- Hot Tub
- Parking
- Pool
US $253/Night
7 Nights - US $1,774
Condo
10.0(141 Reviews)
2 Bedrooms
6 Guests
- Oceanfront
- Parking
- Ocean View
- Balcony/Terrace
US $555/Night
7 Nights - US $3,888
Villa
10.0(132 Reviews)
2 Bedrooms
4 Guests
- Parking
- Ocean View
- Balcony/Terrace
- View
US $236/Night
7 Nights - US $1,649
Apartment
10.0(127 Reviews)
1 Bedroom
3 Guests
- Private Pool
- Parking
- Pool
- Ocean View
US $371/Night
7 Nights - US $2,597
Large Holiday Rentals and Private Villas in Pinellas County
Over 2797+ Large Holiday Rentals and Private Villas in or Near Pinellas County
Villa
10.0(111 Reviews)
2 Bedrooms
4 Guests
- Oceanfront
- Parking
- Pool
- Ocean View
US $436/Night
7 Nights - US $3,050
House
10.0(10 Reviews)
6 Bedrooms
12 Guests
- Oceanfront
- Parking
- Pool
- Ocean View
US $1,058/Night
7 Nights - US $7,406
House
9.8(6 Reviews)
6 Bedrooms
16 Guests
- Private Pool
- Oceanfront
- Hot Tub
- Parking
US $1,391/Night
7 Nights - US $9,740
Villa
10.0(101 Reviews)
2 Bedrooms
4 Guests
- Private Pool
- Parking
- Pool
- Balcony/Terrace
US $317/Night
7 Nights - US $2,216
US $455/Night
7 Nights - US $3,184
Villa
10.0(99 Reviews)
2 Bedrooms
4 Guests
- Private Pool
- Oceanfront
- Parking
- Pool
US $430/Night
7 Nights - US $3,010
Villa
10.0(76 Reviews)
2 Bedrooms
4 Guests
- Parking
- Ocean View
- Balcony/Terrace
- View
US $238/Night
7 Nights - US $1,663
Condo
10.0(75 Reviews)
2 Bedrooms
10 Guests
- Oceanfront
- Parking
- Pool
- Ocean View
US $282/Night
7 Nights - US $1,975
Villa
10.0(17 Reviews)
2 Bedrooms
5 Guests
- Parking
- Pool
- Balcony/Terrace
- Kitchen
US $203/Night
7 Nights - US $1,423
Wheelchair Accessible Holiday Homes in Pinellas County
Over 5325+ Wheelchair Accessible Holiday Homes in or Near Pinellas County
Condo
10.0(185 Reviews)
1 Bedroom
3 Guests
- Hot Tub
- Parking
- Pool
- Ocean View
US $302/Night
7 Nights - US $2,112
Apartment
10.0(7 Reviews)
3 Bedrooms
8 Guests
Private Beach- Oceanfront
- Hot Tub
- Parking
US $403/Night
7 Nights - US $2,823
Apartment
10.0(1 Review)
1 Bedroom
- Parking
- Pool
- Ocean View
- View
US $383/Night
7 Nights - US $2,682
Condo
10.0(167 Reviews)
2 Bedrooms
6 Guests
- Parking
- Pool
- Ocean View
- Balcony/Terrace
US $571/Night
7 Nights - US $3,994
House
10.0(3 Reviews)
4 Bedrooms
10 Guests
- Oceanfront
- Parking
- Pool
- Ocean View
US $588/Night
7 Nights - US $4,115
Condo
10.0(164 Reviews)
1 Bedroom
4 Guests
- Private Pool
- Oceanfront
- Hot Tub
- Parking
US $258/Night
7 Nights - US $1,804
Condo
10.0(161 Reviews)
2 Bedrooms
6 Guests
- Oceanfront
- Hot Tub
- Parking
- Pool
US $489/Night
7 Nights - US $3,420
Condo
10.0(161 Reviews)
2 Bedrooms
6 Guests
- Hot Tub
- Parking
- Pool
- Ocean View
US $328/Night
7 Nights - US $2,298
Condo
10.0(155 Reviews)
2 Bedrooms
6 Guests
- Parking
- Pool
- Ocean View
- Balcony/Terrace
US $375/Night
7 Nights - US $2,623
Pinellas County Private Villas and Holiday Homes Under $200
Over 5808+ Pinellas County Private Villas and Holiday Homes Under $200
House
10.0(134 Reviews)
2 Bedrooms
4 Guests
- Oceanfront
- Parking
- Ocean View
- Balcony/Terrace
US $154/Night
7 Nights - US $1,080
House
10.0(10 Reviews)
1 Bedroom
2 Guests
- Oceanfront
- Hot Tub
Breakfast- Parking
US $194/Night
7 Nights - US $1,356
US $145/Night
7 Nights - US $1,013
Apartment
10.0(102 Reviews)
2 Bedrooms
4 Guests
- Oceanfront
- Parking
- Ocean View
- Balcony/Terrace
US $163/Night
7 Nights - US $1,142
House
10.0(8 Reviews)
1 Bedroom
2 Guests
- Oceanfront
- Parking
- Ocean View
- Balcony/Terrace
US $68/Night
7 Nights - US $473
House
10.0(95 Reviews)
1 Bedroom
4 Guests
- Oceanfront
- Parking
- Ocean View
- Balcony/Terrace
US $176/Night
7 Nights - US $1,233
Apartment
10.0(94 Reviews)
1 Bedroom
2 Guests
- Oceanfront
- Parking
- Ocean View
- Balcony/Terrace
US $185/Night
7 Nights - US $1,298
Apartment
10.0(84 Reviews)
1 Bedroom
4 Guests
- Oceanfront
- Parking
- Ocean View
- Balcony/Terrace
US $181/Night
7 Nights - US $1,269
House
10.0(83 Reviews)
1 Bedroom
2 Guests
- Parking
- Ocean View
- Balcony/Terrace
- View
US $148/Night
7 Nights - US $1,034
Instantly Bookable Holiday Homes in Pinellas County
Over 14310+ Instantly Bookable Holiday Homes in or Near Pinellas County
Condo
10.0(178 Reviews)
2 Bedrooms
6 Guests
- Oceanfront
- Parking
- Pool
- Ocean View
US $283/Night
7 Nights - US $1,983
House
10.0(1 Review)
1 Bedroom
4 Guests
- Parking
- Pool
- Balcony/Terrace
- Kitchen
US $147/Night
7 Nights - US $1,029
Apartment
10.0(9 Reviews)
1 Bedroom
2 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $199/Night
7 Nights - US $1,393
House
10.0(172 Reviews)
2 Bedrooms
4 Guests
- Oceanfront
- Parking
- Pool
- Ocean View
US $380/Night
7 Nights - US $2,658
House
10.0(1 Review)
1 Bedroom
6 Guests
- Parking
- Pool
- Balcony/Terrace
- Kitchen
US $163/Night
7 Nights - US $1,141
Cottage
10.0(171 Reviews)
1 Bedroom
4 Guests
- Oceanfront
- Parking
- Ocean View
- Balcony/Terrace
US $268/Night
7 Nights - US $1,876
House
10.0(151 Reviews)
1 Bedroom
2 Guests
- Oceanfront
- Parking
- Pool
- Ocean View
US $233/Night
7 Nights - US $1,631
Cottage
10.0(148 Reviews)
2 Bedrooms
4 Guests
- Oceanfront
- Parking
- Ocean View
- Balcony/Terrace
US $255/Night
7 Nights - US $1,784
Apartment
10.0(145 Reviews)
2 Bedrooms
4 Guests
- Parking
- Kitchen
- Air Conditioner
- Internet
US $381/Night
7 Nights - US $2,664
Book a Last Minute Place to Stay in Pinellas County
About Casai's Private Villas and Holiday Rentals in Pinellas County
Discover more than 22163 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 846.31 ft², with nightly prices averaging US $382.
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.
Other Places to Stay in Pinellas County, FL
There are 22163 Pinellas County, FL Holiday Rentals
- Prices for a holiday home in Pinellas County start at US $32
- Top rated vacation home in Pinellas County is Ivory Sands Beach Suites
- Most popular short term in Pinellas County is Wyndham Grand Clearwater Beach
- Cheapest place to stay in Pinellas County is Bungalow Bleu
- Most expensive holiday rental in Pinellas County is Renovated luxury with resort like back yard
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:
- 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
- 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
- PRIVATE COTTAGE OCEAN VIEW 44 PACES TO BEACH, CLOSE TO RESTAURANTS AND SHOPS
- Lulu's NEW WATERFRONT RARE 2 BAL 2 BD, 2 BA, SLEEPS 8-4 DAILY WATER PARK PASSES
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.
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:
How many Casai.nz holiday rentals are available in Pinellas County?
As of 2026, Casai boasts over 22163 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.
