Holiday rentals near Pinellas Trail
We found 12,268 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 NZ$3,450
NZ$3,450
NZ$493 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 NZ$5,103
NZ$5,103
NZ$729 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 NZ$14,171
NZ$14,171
NZ$2,024 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 NZ$18,484
NZ$18,484
NZ$2,641 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 NZ$4,419
NZ$4,419
NZ$631 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 NZ$3,810
NZ$3,810
NZ$544 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 NZ$3,449
NZ$3,449
NZ$493 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 NZ$4,351
NZ$4,351
NZ$622 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 NZ$4,478
NZ$4,478
NZ$640 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 NZ$8,931
NZ$8,931
NZ$1,276 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 NZ$5,102
NZ$5,102
NZ$729 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 NZ$4,407
NZ$4,407
NZ$630 per night
includes taxes & fees
Image gallery for Pool | King Bed | Amenity Packed | Family Friendly
9.89.8 out of 10 rating
Exceptional
(17 reviews)
Pool | King Bed | Amenity Packed | Family Friendly
Largo, FL
9% off
Price is NZ$4,253
NZ$4,253
NZ$608 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 NZ$5,406
NZ$5,406
NZ$772 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
(77 reviews)
Top-Floor Waterfront Condo with Bay view + Pool and Hot Tub
St. Petersburg, FL
8% off
Price is NZ$2,485
NZ$2,485
NZ$355 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 NZ$1,655
NZ$1,655
NZ$236 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 NZ$1,962
NZ$1,962
NZ$280 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 NZ$1,798
NZ$1,798
NZ$257 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 NZ$10,419
NZ$10,419
NZ$1,488 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
7% off
Price is NZ$2,712
NZ$2,712
NZ$387 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 NZ$2,292
NZ$2,292
NZ$327 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 NZ$3,304
NZ$3,304
NZ$472 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 NZ$5,462
NZ$5,462
NZ$780 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 NZ$10,270
NZ$10,270
NZ$1,467 per night
includes taxes & fees
Find spaces that suit your style
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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