Holiday rentals near Pinellas Trail
We found 12,285 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:7 Nov - 14 Nov
Image gallery for Waterfront Home, Dock and Beach
9.89.8 out of 10 rating
Exceptional
(33 reviews)
Waterfront Home, Dock and Beach
Indian Rocks Beach, FL
14% off
Price is AU$3,142
AU$3,142
AU$449 per night
includes taxes & fees
Image gallery for Trailside Fun, .0.5 miles from the Pinellas Bike Heated Pool,Summer Ready!
1010 out of 10 rating
Exceptional
(34 reviews)
Trailside Fun, .0.5 miles from the Pinellas Bike Heated Pool,Summer Ready!
Palm Harbor, FL
8% off
Price is AU$4,650
AU$4,650
AU$664 per night
includes taxes & fees
Image gallery for ★ Ultimate Family Beach Home with Pool ★
1010 out of 10 rating
Exceptional
(52 reviews)
★ Ultimate Family Beach Home with Pool ★
Indian Rocks Beach, FL
8% off
Price is AU$12,700
AU$12,700
AU$1,814 per night
includes taxes & fees
Image gallery for Paradise Living on a Stunning Waterfront Home. Minutes from Belleair Beach.
9.09.0 out of 10 rating
Wonderful
(7 reviews)
Paradise Living on a Stunning Waterfront Home. Minutes from Belleair Beach.
Largo, FL
8% off
Price is AU$16,631
AU$16,631
AU$2,376 per night
includes taxes & fees
Image gallery for Coastal Oasis: 4-Bedroom Home with Heated Pool, Just 3 Minutes to the Beach!
9.89.8 out of 10 rating
Exceptional
(10 reviews)
Coastal Oasis: 4-Bedroom Home with Heated Pool, Just 3 Minutes to the Beach!
Seminole, FL
11% off
Price is AU$4,028
AU$4,028
AU$575 per night
includes taxes & fees
Image gallery for Fun Family Getaway 3bd 2ba•Heated POOL•Clearwater BEACH 5miles
9.49.4 out of 10 rating
Exceptional
(6 reviews)
Fun Family Getaway 3bd 2ba•Heated POOL•Clearwater BEACH 5miles
Clearwater, FL
11% off
Price is AU$3,472
AU$3,472
AU$496 per night
includes taxes & fees
Image gallery for COZY COTTAGE ON PRIVATE BEACH *CLEARWATER/BELLEAIR BEACH
9.49.4 out of 10 rating
Exceptional
(58 reviews)
COZY COTTAGE ON PRIVATE BEACH *CLEARWATER/BELLEAIR BEACH
Belleair Beach, FL
8% off
Price is AU$3,141
AU$3,141
AU$449 per night
includes taxes & fees
Image gallery for The Dunedin Salt Shed: Heated Salt Water Pool with Screen Enclosure
9.89.8 out of 10 rating
Exceptional
(7 reviews)
The Dunedin Salt Shed: Heated Salt Water Pool with Screen Enclosure
Dunedin, FL
7% off
Price is AU$4,081
AU$4,081
AU$583 per night
includes taxes & fees
Image gallery for Paradise Lake
1010 out of 10 rating
Exceptional
(5 reviews)
Paradise Lake
Clearwater, FL
8% off
Price is AU$3,964
AU$3,964
AU$566 per night
includes taxes & fees
Image gallery for Luxury Showstopper!Sleeps16 Pool Spa 2 miles to Beach W/Heated huge pool
9.69.6 out of 10 rating
Exceptional
(87 reviews)
Luxury Showstopper!Sleeps16 Pool Spa 2 miles to Beach W/Heated huge pool
Largo, FL
8% off
Price is AU$8,083
AU$8,083
AU$1,155 per night
includes taxes & fees
Image gallery for Cozy Lake House with Heated Salt Water Pool
9.69.6 out of 10 rating
Exceptional
(32 reviews)
Cozy Lake House with Heated Salt Water Pool
Tampa, FL
7% off
Price is AU$4,651
AU$4,651
AU$664 per night
includes taxes & fees
Image gallery for Beach Retreat with Pool
9.09.0 out of 10 rating
Wonderful
(7 reviews)
Beach Retreat with Pool
Seminole, FL
9% off
Price is AU$4,017
AU$4,017
AU$574 per night
includes taxes & fees
Image gallery for Pool | King Bed | Amenity Packed | Family Friendly
9.89.8 out of 10 rating
Exceptional
(18 reviews)
Pool | King Bed | Amenity Packed | Family Friendly
Largo, FL
9% off
Price is AU$3,875
AU$3,875
AU$554 per night
includes taxes & fees
Image gallery for Can’t Beat This Location walk to restaraunts Large House
1010 out of 10 rating
Exceptional
(62 reviews)
Can’t Beat This Location walk to restaraunts Large House
Palm Harbor, FL
8% off
Price is AU$4,928
AU$4,928
AU$704 per night
includes taxes & fees
Image gallery for Top-Floor Waterfront Condo with Bay view + Pool and Hot Tub
9.89.8 out of 10 rating
Exceptional
(78 reviews)
Top-Floor Waterfront Condo with Bay view + Pool and Hot Tub
St. Petersburg, FL
8% off
Price is AU$2,263
AU$2,263
AU$323 per night
includes taxes & fees
Image gallery for Centrally located cozy, pet-friendly home, quiet, friendly & safe neighborhood
9.29.2 out of 10 rating
Wonderful
(67 reviews)
Centrally located cozy, pet-friendly home, quiet, friendly & safe neighborhood
Pinellas Park, FL
10% off
Price is AU$1,507
AU$1,507
AU$215 per night
includes taxes & fees
Image gallery for TROPlCAL HAVEN-BBQ/WASHER/DRYER-NEAR BEACH/LAKE/PARK/MALL/GYM/RESTAURANT/MARINA!
9.69.6 out of 10 rating
Exceptional
(5 reviews)
TROPlCAL HAVEN-BBQ/WASHER/DRYER-NEAR BEACH/LAKE/PARK/MALL/GYM/RESTAURANT/MARINA!
Seminole, FL
5% off
Price is AU$1,787
AU$1,787
AU$255 per night
includes taxes & fees
Image gallery for Historic Home/Apt...
1010 out of 10 rating
Exceptional
(50 reviews)
Historic Home/Apt...
Tarpon Springs, FL
8% off
Price is AU$1,639
AU$1,639
AU$234 per night
includes taxes & fees
Image gallery for Beautiful waterfront home. 8 min walk to the beach and restaurants private pool.
1010 out of 10 rating
Exceptional
(75 reviews)
Beautiful waterfront home. 8 min walk to the beach and restaurants private pool.
Indian Rocks Beach, FL
8% off
Price is AU$9,531
AU$9,531
AU$1,362 per night
includes taxes & fees
Image gallery for Cozy 2 BR Home, walking distance to Crystal Beach/Park - Quaint Family Getaway!
9.89.8 out of 10 rating
Exceptional
(27 reviews)
Cozy 2 BR Home, walking distance to Crystal Beach/Park - Quaint Family Getaway!
Palm Harbor, FL
8% off
Price is AU$2,458
AU$2,458
AU$351 per night
includes taxes & fees
Image gallery for The Sand Dollar – Charming Bungalow in Gulfport, Minutes from Downtown St. Pete
9.69.6 out of 10 rating
Exceptional
(23 reviews)
The Sand Dollar – Charming Bungalow in Gulfport, Minutes from Downtown St. Pete
Gulfport, FL
7% off
Price is AU$2,102
AU$2,102
AU$300 per night
includes taxes & fees
Image gallery for SUNSETS SUNSETS!! 10% for full week stays May-November!
1010 out of 10 rating
Exceptional
(57 reviews)
SUNSETS SUNSETS!! 10% for full week stays May-November!
St. Petersburg, FL
7% off
Price is AU$3,009
AU$3,009
AU$430 per night
includes taxes & fees
Image gallery for Toucan Luxury Oasis - Heated POOL and SPA option
9.49.4 out of 10 rating
Exceptional
(52 reviews)
Toucan Luxury Oasis - Heated POOL and SPA option
Clearwater, FL
8% off
Price is AU$4,977
AU$4,977
AU$711 per night
includes taxes & fees
Image gallery for Beachfront Classic Florida Family Home
1010 out of 10 rating
Exceptional
(49 reviews)
Beachfront Classic Florida Family Home
Indian Shores, FL
8% off
Price is AU$9,387
AU$9,387
AU$1,341 per night
includes taxes & fees
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Find the best place to stay - Pinellas Trail
💙Blue flower (🦋Pet friendly)
Sleeps 4 · 1 bedroom · 0+ bathrooms
9.69.6 out of 10
Exceptionalexceptional
38 reviews(38 reviews)
Modern Beach Oasis 4Bed 3Bath Fully Furnished 10 minutes to the beach
Sleeps 8 · 4 bedrooms · 3 bathrooms
9.49.4 out of 10
Exceptionalexceptional
Charming bungalow minutes away from the BEACH, local restaurants & shops.
Sleeps 6 · 3 bedrooms · 1 bathroom
1010 out of 10
Exceptionalexceptional
Sweet Little Home 15 Minutes From The Beach
Sleeps 6 · 3 bedrooms · 2 bathrooms
9.89.8 out of 10
Exceptionalexceptional
17 reviews(17 reviews)
COZY RETREAT, short drive to Clearwater Beach
Sleeps 3 · 1 bedroom · 1 bathroom
1010 out of 10
Exceptionalexceptional
101 reviews(101 reviews)
Beach Within Reach Apt 5
Sleeps 4 · 2 bedrooms · 1 bathroom
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