Vacation Rentals in Pinellas Trail, FL: Compare 10+ Sites & Save

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  5.  St. Petersburg - Clearwater
  6.  Pinellas Trail

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3644 Best Vacation Rentals in Pinellas Trail (Starting from $119)

Coastal Cottage Beach retreat jacuzzi firepit
Coastal Cottage Beach retreat jacuzzi firepit
House
Largo, FL, USA
0.4k from Pinellas Trail center

Cheap, Accommodations, Parking, Villas, Vacation homes, Cottages, Pet-friendly, Lodgings, Hot tubs

2 Bedrooms6 Guests
9.7

Exceptional

12 reviews

$121
Average price / night
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🌊 Villa Maria - Salt & Sun 🌴7 minutes to Indian Shores
🌊 Villa Maria - Salt & Sun 🌴7 minutes to Indian Shores
House
Largo, FL, 33778, United States
0.1k from Pinellas Trail center

AC, Dryer, Extra Bed, Free Parking, Heater, Hot Tub, Internet, Kitchen, Laundry

3 Bedrooms7 Guests
10.0

Exceptional

5 reviews

$582
Average price / night
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Resort-Style Oasis Pool Mini Golf Playground
Resort-Style Oasis Pool Mini Golf Playground
House
Walsingham, FL, USA
0.6k from Pinellas Trail center

Accommodations, Pools, Parking, Villas, Vacation homes, Cottages, Pet-friendly, Lodgings, Places to stay

1 Bedroom10 Guests
New to Booking
$584
Average price / night
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💙Blue flower (🦋Pet friendly)
💙Blue flower (🦋Pet friendly)
House
Largo, FL, 33778, United States
0.2k from Pinellas Trail center

AC, Barbecue, Extra Bed, Free Parking, Internet, Kitchen, Microwave, No Smoking, Outdoor Grill

1 Bedroom4 Guests
9.6

Exceptional

43 reviews

$310
Average price / night
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Heated Pool and Spa, 4 Mi to Beach Seminole Home
Heated Pool and Spa, 4 Mi to Beach Seminole Home
House
Seminole, FL, USA
0.6k from Pinellas Trail center

Accommodations, Pools, Parking, Villas, Vacation homes, Spa, Cottages, Pet-friendly, Lodgings

4 Bedrooms15 Guests
9.0

Fabulous

1 reviews

$416
Average price / night
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Villa Maria Salt Sun 7 minutes to Indian Rocks Beach
Villa Maria Salt Sun 7 minutes to Indian Rocks Beach
House
Largo, FL, USA
0.6k from Pinellas Trail center

Cheap, Accommodations, Pools, Parking, Villas, Vacation homes, Cottages, Lodgings, Vacation rentals

3 Bedrooms9 Guests
9.8

Exceptional

17 reviews

$338
Average price / night
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Sleeps 14 • Heated Pool • Spa • Arcade • Putt Putt
Sleeps 14 • Heated Pool • Spa • Arcade • Putt Putt
House
Largo, FL, 33778, United States
0.6k from Pinellas Trail center

AC, Arcade, Balcony, Barbecue, Crib, Dryer, Free Parking, Heater, Hot Tub

4 Bedrooms10 Guests
New to Booking
$717
Average price / night
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Peaceful Largo Vacation Rental with Sauna and Yard!
Peaceful Largo Vacation Rental with Sauna and Yard!
House
Largo, FL, USA
0.6k from Pinellas Trail center

Accommodations, Parking, Villas, Vacation homes, Spa, Cottages, Pet-friendly, Lodgings, Vacation rentals

1 Bedroom2 Guests
New to Booking
$130
Average price / night
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❤️Red flower (Where you are welcome)
❤️Red flower (Where you are welcome)
Apartment
Largo, FL, 33778, United States
0.6k from Pinellas Trail center

AC, Free Parking, Internet, Kitchen, Microwave, No Smoking, Outdoor Grill, Patio, TV

1 Bedroom3 Guests
9.2

Superb

16 reviews

$221
Average price / night
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Avocado Cottage
Avocado Cottage
House
Seminole, FL, USA
0.8k from Pinellas Trail center

Accommodations, Villas, Vacation homes, Cottages, Lodgings, Places to stay, Accessible hotels

2 Bedrooms5 Guests
New to Booking
$119
Average price / night
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Heated Pool & Spa, 4 Mi to Beach: Seminole Home
Heated Pool & Spa, 4 Mi to Beach: Seminole Home
House
Seminole, FL, 33778, United States
0.6k from Pinellas Trail center

AC, Barbecue, Dryer, Extra Bed, Free Parking, Internet, Kitchen, Laundry, Living Area

4 Bedrooms15 Guests
9.8

Exceptional

23 reviews

$596
Average price / night
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Central Oasis 4BR Pool Home Close To Beach Parks
Central Oasis 4BR Pool Home Close To Beach Parks
House
Largo, FL, USA
0.9k from Pinellas Trail center

Air Conditioner, Parking, Kitchen, Pool, Pet Friendly, Internet

5 Bedrooms12 Guests
New to Booking
$405
Average price / night
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🍉Watermelon Dome  ❌not a tent❌
🍉Watermelon Dome ❌not a tent❌
House
Largo, FL, 33778, United States
0.6k from Pinellas Trail center

AC, Barbecue, Free Parking, Internet, Microwave, No Smoking, TV

1 Bedroom3 Guests
9.4

Superb

12 reviews

$309
Average price / night
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Snook Haven - Hot Tub, Pool, Minigolf, Dog Space
Snook Haven - Hot Tub, Pool, Minigolf, Dog Space
House
Largo, FL, USA
0.9k from Pinellas Trail center

Cheap, Accommodations, Pools, Parking, Villas, Vacation homes, Cottages, Pet-friendly, Lodgings

3 Bedrooms6 Guests
10.0

Exceptional

3 reviews

$296
Average price / night
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Charming 3-bedroom house with heated pool
Charming 3-bedroom house with heated pool
House
Largo, FL, 33778, United States
0.7k from Pinellas Trail center

AC, Barbecue, Crib, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry

3 Bedrooms8 Guests
10.0

Exceptional

3 reviews

$327
Average price / night
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Sunroom - Master King - Games - Close to IRB
Sunroom - Master King - Games - Close to IRB
House
Walsingham, FL, USA
0.9k from Pinellas Trail center

Accommodations, Parking, Villas, Vacation homes, Cottages, Lodgings, Beach, Places to stay, Family

2 Bedrooms4 Guests
New to Booking
$245
Average price / night
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❌not a tent❌ Unique DOME 💜Blue Moon 💜
❌not a tent❌ Unique DOME 💜Blue Moon 💜
House
Largo, FL, 33778, United States
0.7k from Pinellas Trail center

AC, Free Parking, Internet, Microwave, No Smoking, TV

1 Bedroom2 Guests
9.4

Superb

15 reviews

$348
Average price / night
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Sunny Spacious 4BR Comfort Pool
Sunny Spacious 4BR Comfort Pool
House
Largo, FL, USA
1.0k from Pinellas Trail center

Accommodations, Pools, Villas, Vacation homes, Cottages, Lodgings, Places to stay

4 Bedrooms10 Guests
2.0

Review score

1 reviews

$461
Average price / night
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Pinellas Trail Retreat | Near Beaches, Parks & Dining
Pinellas Trail Retreat | Near Beaches, Parks & Dining
House
Largo, FL, 33778, United States
0.8k from Pinellas Trail center

AC, Balcony, Barbecue, Dryer, Free Parking, Heater, Internet, Kitchen, Microwave

2 Bedrooms7 Guests
9.2

Superb

5 reviews

$185
Average price / night
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Flamingo Lounge - Pool, Firepit, Grill, Sleeps 10
Flamingo Lounge - Pool, Firepit, Grill, Sleeps 10
House
Largo, FL, USA
1.0k from Pinellas Trail center

Accommodations, Pools, Parking, Villas, Vacation homes, Cottages, Pet-friendly, Lodgings, Places to stay

4 Bedrooms10 Guests
New to Booking
$496
Average price / night
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Pet Friendly Pool Home close to beach and Walsingham Park
Pet Friendly Pool Home close to beach and Walsingham Park
House
Pinellas County, FL, 33778, United States
0.8k from Pinellas Trail center

AC, Barbecue, Dryer, Internet, Kitchen, Living Area, Microwave, No Smoking, Pool

3 Bedrooms6 Guests
New to Booking
$423
Average price / night
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3Bd 2Ba House with Parking Laundry and Large Patio
3Bd 2Ba House with Parking Laundry and Large Patio
House
Largo, FL, USA
1.2k from Pinellas Trail center

Cheap, Accommodations, Parking, Villas, Vacation homes, Cottages, Lodgings, Beach, Places to stay

3 Bedrooms6 Guests
9.4

Superb

13 reviews

$194
Average price / night
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The Oasis Retreat | Pool + Game Room + Basketball + Massive Yard | Near Beach & Golf
The Oasis Retreat | Pool + Game Room + Basketball + Massive Yard | Near Beach & Golf
Villa
Largo, FL, 33778, United States
0.8k from Pinellas Trail center

AC, Arcade, Barbecue, Crib, Dryer, Heater, Hot Tub, Internet, Kitchen

7 Bedrooms22 Guests
9.0

Fabulous

37 reviews

$1019
Average price / night
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Convenient located in Largo with King size Bed (119th)
Convenient located in Largo with King size Bed (119th)
House
Largo, FL, 33778, United States
0.8k from Pinellas Trail center

AC, Arcade, Barbecue, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry

3 Bedrooms8 Guests
9.2

Superb

11 reviews

$367
Average price / night
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8 min Beach, Hot Tub, Pool & Games @ Snook Haven
8 min Beach, Hot Tub, Pool & Games @ Snook Haven
House
Largo, FL, 33778, United States
0.9k from Pinellas Trail center

AC, Barbecue, Crib, Dryer, Heater, Hot Tub, Internet, Kitchen, Laundry

3 Bedrooms6 Guests
9.6

Exceptional

5 reviews

$662
Average price / night
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Unique Home| Mins to Beaches | Sleeps 8 | Shops & Dining & Golf |  Coffee Bar
Unique Home| Mins to Beaches | Sleeps 8 | Shops & Dining & Golf | Coffee Bar
House
Largo, FL, 33778, United States
0.9k from Pinellas Trail center

AC, Barbecue, Crib, Dryer, Fireplace, Free Parking, Heater, Internet, Kitchen

4 Bedrooms8 Guests
10.0

Exceptional

6 reviews

$502
Average price / night
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Coastal Bliss with hot tub - 4 miles to beaches
Coastal Bliss with hot tub - 4 miles to beaches
Apartment
Largo, FL, 33778, United States
0.9k from Pinellas Trail center

AC, Barbecue, Free Parking, Hot Tub, Internet, Laundry, Microwave, No Smoking, Patio

1 Bedroom2 Guests
9.4

Superb

22 reviews

$140
Average price / night
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Pro Tip:
VacationByOwnerRentals aggregates the best inventory from leading travel sites, including Booking.com, Agoda.com, Expedia.com, Vrbo.com, and Airbnb.com. Use our Advanced Filters to compare verified homes, villas, cabins, condos, cottages, vacation rentals, hotels, and eco-friendly stays. Our goal is to help you find the absolute best Vacation Rentals in Pinellas Trail.

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Frequently Asked Questions

You can explore 3644 verified vacation rentals in Pinellas Trail. Our listings are sourced from a range of trusted providers, giving you access to a wide selection of private homes, apartments, and unique stays—all in one place.

Vacation rental prices in Pinellas Trail vary depending on the season, property size, and location. Rates typically start from around $119 per night, with higher prices for larger homes or peak travel periods. Comparing available options can help you find a stay that matches both your budget and travel plans.

Most vacation rentals in Pinellas Trail include fully equipped kitchens, making it easy to prepare meals and enjoy a more flexible stay. This is especially useful for families, longer stays, or travelers who prefer a home-like experience.

Yes, many vacation rentals in Pinellas Trail welcome pets. Currently, 52 listings allow pets, although specific policies may vary by property. You can filter for pet-friendly options to quickly find suitable accommodations.

For popular travel periods such as holidays or peak seasons, it’s recommended to book your vacation rental 60 to 90 days in advance to secure the best options. During quieter times, you may still find good availability closer to your travel dates.

Vacation rentals in Pinellas Trail often include amenities such as Wellness Facilities, Kitchen, and Balcony/Terrace. These features provide added comfort and convenience, making them a popular choice for travelers seeking more space and privacy.

You can use filters to narrow down your search by criteria such as number of bedrooms, guest ratings, or specific amenities like private pools or beachfront access. This makes it easier to find a property that fits your exact needs and preferences.