Holiday rentals near Pinellas Trail
We found 12,465 holiday rentals — enter your dates for availability
If you are looking to stay near Pinellas Trail, take a look at holiday rentals to find the perfect home base for your trip. Whether you’re staying in a holiday home with your children or with friends, you'll find the best amenities for hanging out with the people that matter most, which might include parking and a hot tub. No matter what you're looking for, you'll find a property to rent to meet everyone's needs, including accessible or non-smoking choices.
Holiday rentals with weekly discounts - Pinellas Trail
Showing deals for:19 Sept - 26 Sept
Image gallery for Large Family Pool Home - 5 BR w/ 2 Primary Suites!, Sleeps 15+, Very private!
1010 out of 10 rating
Exceptional
(11 reviews)
Large Family Pool Home - 5 BR w/ 2 Primary Suites!, Sleeps 15+, Very private!
Largo, FL
8% off
Price is AU$4,810
AU$4,810
AU$687 per night
includes taxes & fees
Image gallery for Experience waterfront luxury in Tampa Bay! Close to TPA, RayJay and Steinbrenner
1010 out of 10 rating
Exceptional
(110 reviews)
Experience waterfront luxury in Tampa Bay! Close to TPA, RayJay and Steinbrenner
Tampa, FL
8% off
Price is AU$5,475
AU$5,475
AU$782 per night
includes taxes & fees
Image gallery for Beautiful freshly remodeled beachfront condo
9.89.8 out of 10 rating
Exceptional
(84 reviews)
Beautiful freshly remodeled beachfront condo
Belleair Beach, FL
8% off
Price is AU$2,958
AU$2,958
AU$423 per night
includes taxes & fees
Image gallery for Coastal living with water views, sunrises, sunsets and boat slip
1010 out of 10 rating
Exceptional
(12 reviews)
Coastal living with water views, sunrises, sunsets and boat slip
Treasure Island, FL
8% off
Price is AU$5,080
AU$5,080
AU$726 per night
includes taxes & fees
Image gallery for Blue Dolphin Privacy Paradise Screened Pool Home!
1010 out of 10 rating
Exceptional
(11 reviews)
Blue Dolphin Privacy Paradise Screened Pool Home!
Palm Harbor, FL
8% off
Price is AU$2,882
AU$2,882
AU$412 per night
includes taxes & fees
Image gallery for NEW Fully renovated Gulf front home w/private resort style pool, outdoor kitchen
1010 out of 10 rating
Exceptional
(38 reviews)
NEW Fully renovated Gulf front home w/private resort style pool, outdoor kitchen
Crystal Beach, FL
8% off
Price is AU$10,920
AU$10,920
AU$1,560 per night
includes taxes & fees
Image gallery for Barbies pool house & mini golf beach getaway. Centerally located to all beaches.
9.69.6 out of 10 rating
Exceptional
(12 reviews)
Barbies pool house & mini golf beach getaway. Centerally located to all beaches.
Safety Harbor, FL
7% off
Price is AU$3,125
AU$3,125
AU$446 per night
includes taxes & fees
Image gallery for 🌴HEATED POOL AND JACUZZI FOR YEAR ROUND RELAXATION ON OCEAN FRONT BEACH⛱️ !!!!
1010 out of 10 rating
Exceptional
(27 reviews)
🌴HEATED POOL AND JACUZZI FOR YEAR ROUND RELAXATION ON OCEAN FRONT BEACH⛱️ !!!!
Indian Shores, FL
7% off
Price is AU$3,257
AU$3,257
AU$465 per night
includes taxes & fees
Image gallery for 4br 2b Tropical Paradise HEATED POOL & Hot Tub 5min to the BEACH🏝
1010 out of 10 rating
Exceptional
(33 reviews)
4br 2b Tropical Paradise HEATED POOL & Hot Tub 5min to the BEACH🏝
Seminole, FL
7% off
Price is AU$5,087
AU$5,087
AU$727 per night
includes taxes & fees
Image gallery for Enjoy the white sands of the Gulf of Mexico in luxurious and spacious condo.
9.89.8 out of 10 rating
Exceptional
(45 reviews)
Enjoy the white sands of the Gulf of Mexico in luxurious and spacious condo.
North Redington Beach, FL
8% off
Price is AU$3,897
AU$3,897
AU$557 per night
includes taxes & fees
Image gallery for POOLS OPEN! Beach Front Condo, Beautiful Sunsets!
9.89.8 out of 10 rating
Exceptional
(27 reviews)
POOLS OPEN! Beach Front Condo, Beautiful Sunsets!
Treasure Island, FL
8% off
Price is AU$3,570
AU$3,570
AU$510 per night
includes taxes & fees
Image gallery for Tropical Backyard Heated Pool House Close to Beach
1010 out of 10 rating
Exceptional
(37 reviews)
Tropical Backyard Heated Pool House Close to Beach
Largo, FL
7% off
Price is AU$2,897
AU$2,897
AU$414 per night
includes taxes & fees
Image gallery for Beachfront-Directly on the Sand - Sunset Beach, Treasure Island, Florida
9.89.8 out of 10 rating
Exceptional
(118 reviews)
Beachfront-Directly on the Sand - Sunset Beach, Treasure Island, Florida
Treasure Island, FL
8% off
Price is AU$7,336
AU$7,336
AU$1,048 per night
includes taxes & fees
Image gallery for Stay on the beach, not just near the beach
1010 out of 10 rating
Exceptional
(72 reviews)
Stay on the beach, not just near the beach
North Redington Beach, FL
7% off
Price is AU$3,320
AU$3,320
AU$474 per night
includes taxes & fees
Image gallery for ✔Waterfront |3BR |2Kings |Pool |Balcony |Beach
1010 out of 10 rating
Exceptional
(43 reviews)
✔Waterfront |3BR |2Kings |Pool |Balcony |Beach
Clearwater Beach, FL
8% off
Price is AU$4,738
AU$4,738
AU$677 per night
includes taxes & fees
Image gallery for PRIVATE BEACH HOUSE W/PRIVATE POOL, 300ft TO BEACH ON THE SAND! SLEEPS 8!
9.89.8 out of 10 rating
Exceptional
(183 reviews)
PRIVATE BEACH HOUSE W/PRIVATE POOL, 300ft TO BEACH ON THE SAND! SLEEPS 8!
Indian Shores, FL
8% off
Price is AU$6,127
AU$6,127
AU$875 per night
includes taxes & fees
Image gallery for Spectacular Oceanfront condo on the Sands of Treasure Island
1010 out of 10 rating
Exceptional
(153 reviews)
Spectacular Oceanfront condo on the Sands of Treasure Island
Treasure Island, FL
8% off
Price is AU$7,413
AU$7,413
AU$1,059 per night
includes taxes & fees
Image gallery for Spacious 6-bedroom Oceanfront Beach house w/ private pool in Indian Rocks Beach
1010 out of 10 rating
Exceptional
(24 reviews)
Spacious 6-bedroom Oceanfront Beach house w/ private pool in Indian Rocks Beach
Indian Rocks Beach, FL
8% off
Price is AU$21,283
AU$21,283
AU$3,040 per night
includes taxes & fees
Image gallery for Beautiful Condo Close to Beach Private Hot Tub & Elevator
1010 out of 10 rating
Exceptional
(89 reviews)
Beautiful Condo Close to Beach Private Hot Tub & Elevator
Clearwater Beach, FL
8% off
Price is AU$6,375
AU$6,375
AU$911 per night
includes taxes & fees
Image gallery for PRIVATE ESTATE BY BEACH 5BR 3BA 2 king masters, heated pooL, hottub, by beach.
9.89.8 out of 10 rating
Exceptional
(34 reviews)
PRIVATE ESTATE BY BEACH 5BR 3BA 2 king masters, heated pooL, hottub, by beach.
Seminole, FL
28% off
Price is AU$4,708
AU$4,708
AU$673 per night
includes taxes & fees
Image gallery for Family Friendly Centrally Located 3 Bedroom Rental
1010 out of 10 rating
Exceptional
(11 reviews)
Family Friendly Centrally Located 3 Bedroom Rental
Clearwater, FL
8% off
Price is AU$2,182
AU$2,182
AU$312 per night
includes taxes & fees
Image gallery for Sea Gate 206 Beautiful Beach Front Condo/3 BR - 2 BTH
1010 out of 10 rating
Exceptional
(172 reviews)
Sea Gate 206 Beautiful Beach Front Condo/3 BR - 2 BTH
Indian Shores, FL
8% off
Price is AU$4,297
AU$4,297
AU$614 per night
includes taxes & fees
Image gallery for Fantastic Family/Friends Getaway - 6' deep Heated Pool & SPA close to Beaches!
9.69.6 out of 10 rating
Exceptional
(81 reviews)
Fantastic Family/Friends Getaway - 6' deep Heated Pool & SPA close to Beaches!
Seminole, FL
6% off
Price is AU$3,212
AU$3,212
AU$459 per night
includes taxes & fees
Image gallery for Charming Beach Cottage just steps away from Beautiful Clearwater Beach!!
1010 out of 10 rating
Exceptional
(7 reviews)
Charming Beach Cottage just steps away from Beautiful Clearwater Beach!!
Clearwater Beach, FL
8% off
Price is AU$3,079
AU$3,079
AU$440 per night
includes taxes & fees
Find spaces that suit your style
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Find the best place to stay - Pinellas Trail
Florida Haven 4/2.5 Vacation Ready Home! Book Now!
Sleeps 8 · 4 bedrooms · 2+ bathrooms
1010 out of 10
Exceptionalexceptional
5 reviews(5 reviews)
BEACH HOUSE 2 SEMINOLE Bring your Boat or RV
Sleeps 8 · 3 bedrooms · 2 bathrooms
9.09.0 out of 10
Wonderfulwonderful
44 reviews(44 reviews)
2 MI to the Beach- Relaxing and Fun
Sleeps 10 · 4 bedrooms · 2 bathrooms
1010 out of 10
Exceptionalexceptional
4 reviews(4 reviews)
COZY RETREAT, short drive to Clearwater Beach
Sleeps 3 · 1 bedroom · 1 bathroom
1010 out of 10
Exceptionalexceptional
101 reviews(101 reviews)
Home close to Saint Pete pier new & spacious
Sleeps 8 · 4 bedrooms · 2 bathrooms
6.06.0 out of 10
1 review(1 review)
Clearwater Home Away from Home
Sleeps 8 · 4 bedrooms · 2 bathrooms
8.88.8 out of 10
Excellentexcellent
9 reviews(9 reviews)
Peace of mindOur Book with Confidence Guarantee gives you 24/7 support
More quality timeFrom booking to staying, the whole process is simple and enjoyable
All the privacy of homeEnjoy full kitchens, laundry, pools, gardens and more
More for lessMore space, more privacy, more amenities — more value