
Holiday rentals near Pinellas Trail
We found 12,461 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 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
7% off
Price is NZ$5,918
NZ$5,918
NZ$845 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 NZ$3,197
NZ$3,197
NZ$457 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 NZ$5,477
NZ$5,477
NZ$782 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 NZ$3,115
NZ$3,115
NZ$445 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 NZ$12,161
NZ$12,161
NZ$1,737 per night
includes taxes & fees
Image gallery for Jade House at The Gemma

1010 out of 10 rating
Exceptional
(7 reviews)
Jade House at The Gemma
Clearwater Beach, Florida
5% off
Price is NZ$20,801
NZ$20,801
NZ$2,972 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 NZ$3,378
NZ$3,378
NZ$483 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 NZ$3,520
NZ$3,520
NZ$503 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 NZ$5,486
NZ$5,486
NZ$784 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 NZ$4,215
NZ$4,215
NZ$602 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 NZ$3,864
NZ$3,864
NZ$552 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 NZ$8,066
NZ$8,066
NZ$1,152 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 NZ$3,133
NZ$3,133
NZ$448 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 NZ$3,594
NZ$3,594
NZ$513 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 NZ$5,124
NZ$5,124
NZ$732 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 NZ$6,601
NZ$6,601
NZ$943 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 NZ$8,151
NZ$8,151
NZ$1,164 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 NZ$6,864
NZ$6,864
NZ$981 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 NZ$5,083
NZ$5,083
NZ$726 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 NZ$2,330
NZ$2,330
NZ$333 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 NZ$4,644
NZ$4,644
NZ$663 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 NZ$3,471
NZ$3,471
NZ$496 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 NZ$3,328
NZ$3,328
NZ$475 per night
includes taxes & fees
Image gallery for Stunning, spacious, comfortable beach front condo on Gulf of Mexico

9.89.8 out of 10 rating
Exceptional
(157 reviews)
Stunning, spacious, comfortable beach front condo on Gulf of Mexico
Redington Shores, FL
8% off
Price is NZ$7,311
NZ$7,311
NZ$1,044 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