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

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  1. VBOR
  2. Vacation Rentals with Pool
  3.  USA

  4.  Florida
  5.  St. Petersburg - Clearwater
  6.  Pinellas Trail

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4265 Best Vacation Rentals with Pool in Pinellas Trail (Starting from $121)

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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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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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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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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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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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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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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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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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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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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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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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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Pet-Friendly Home with Pool and BBQ in Largo
Pet-Friendly Home with Pool and BBQ in Largo
House
Largo, FL, USA
1.2k from Pinellas Trail center

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

4 Bedrooms8 Guests
9.0

Fabulous

2 reviews

$258
Average price / night
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Lovely full house 3/2 w/ pool, few min from beach
Lovely full house 3/2 w/ pool, few min from beach
House
Largo, FL, 33778, United States
0.9k from Pinellas Trail center

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

3 Bedrooms8 Guests
9.6

Exceptional

5 reviews

$322
Average price / night
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Poolside Fun Games Perfect Family Escape
Poolside Fun Games Perfect Family Escape
House
Largo, FL, USA
1.3k from Pinellas Trail center

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

4 Bedrooms14 Guests
8.0

Good

2 reviews

$473
Average price / night
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Salt Water Heated Pool, Mini Golf, 10Min To Beach
Salt Water Heated Pool, Mini Golf, 10Min To Beach
House
Largo, FL, 33778, United States
1.0k from Pinellas Trail center

AC, Balcony, Barbecue, Dryer, Heater, Internet, Kitchen, Laundry, Microwave

3 Bedrooms8 Guests
10.0

Exceptional

1 reviews

$374
Average price / night
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Palm House~Heated Pool~8 min to Beach
Palm House~Heated Pool~8 min to Beach
House
Largo, FL, USA
1.3k from Pinellas Trail center

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

3 Bedrooms6 Guests
10.0

Exceptional

1 reviews

$175
Average price / night
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Light Sand with Heated POOL
Light Sand with Heated POOL
House
Largo, FL, USA
1.4k from Pinellas Trail center

Fireplace/Heating, Barbecue/Outdoor Cooking, Air Conditioner, Parking, Ocean View, Oceanfront, Pet Friendly

2 Bedrooms8 Guests
New to Booking
$264
Average price / night
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Largo Pool House & Firepit
Largo Pool House & Firepit
House
Largo, FL, 33778, United States
1.0k from Pinellas Trail center

AC, Arcade, Barbecue, Elevator, Fireplace, Free Parking, Heater, Internet, Kitchen

5 Bedrooms10 Guests
6.0

Review score

1 reviews

$442
Average price / night
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Dancing Seahorse Beach House with Heated Pool!
Dancing Seahorse Beach House with Heated Pool!
House
Largo, FL, 33778, United States
1.0k from Pinellas Trail center

AC, Barbecue, Free Parking, Heater, Internet, Kitchen, Laundry, Microwave, No Smoking

3 Bedrooms6 Guests
10.0

Exceptional

1 reviews

$286
Average price / night
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Pet-friendly pool house near beach with office
Pet-friendly pool house near beach with office
House
Largo, FL, 33778, United States
1.0k from Pinellas Trail center

AC, Dryer, Fireplace, Free Parking, Heater, Internet, Kitchen, Laundry, Living Area

3 Bedrooms6 Guests
10.0

Exceptional

3 reviews

$292
Average price / night
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Sleeps 16! Heated Pool Villa Just 8Mi from Clearwater Beach
Sleeps 16! Heated Pool Villa Just 8Mi from Clearwater Beach
House
Largo, FL, 33778, United States
1.0k from Pinellas Trail center

AC, Arcade, Balcony, Crib, Dryer, Free Parking, Heater, Internet, Kitchen

5 Bedrooms16 Guests
New to Booking
$744
Average price / night
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Heated Pool! Pickleball! Fire Pit! Outdoor Theatre
Heated Pool! Pickleball! Fire Pit! Outdoor Theatre
House
Largo, FL, 33778, United States
1.0k from Pinellas Trail center

AC, Arcade, Balcony, Crib, Dryer, Free Parking, Heater, Internet, Kitchen

4 Bedrooms12 Guests
New to Booking
$590
Average price / night
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Casa Indigo | The Designer Pool home Experience + Hot Tub
Casa Indigo | The Designer Pool home Experience + Hot Tub
House
Largo, FL, 33778, United States
1.1k from Pinellas Trail center

AC, Barbecue, Dryer, Free Parking, Heater, Hot Tub, Internet, Kitchen, Laundry

4 Bedrooms10 Guests
8.8

Fabulous

13 reviews

$437
Average price / night
Check Availability

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 with Pool in Pinellas Trail.

Where to stay in Pinellas Trail? Best neighborhoods & areas

Pinellas Trail Vacation Rentals with Pool on the Map

Frequently Asked Questions

You can explore 4265 verified vacation rentals with a pool in Pinellas Trail. These include a wide range of private homes, villas, and condos that offer on-site swimming facilities for a more relaxing stay.

Prices for vacation rentals with a pool in Pinellas Trail vary depending on the season, property size, and whether the pool is private or shared. Rates typically start from around $121 per night, with private pool homes and peak travel periods often costing more.

Many rentals in Pinellas Trail offer private pools for exclusive use, while others provide access to shared or community pools. You can use filters to specifically find properties with private pools if that is your preference.

Yes, some vacation rentals with pools in Pinellas Trail welcome pets. Currently, 60 listings allow pets, although policies may vary by property. It’s a good idea to review any rules related to pets around pool areas before booking.

Properties with pools are often in high demand, especially during warmer months and holidays, so booking 90 to 120 days in advance is recommended for the best selection. During off-peak seasons, you may still find availability closer to your travel dates.

Vacation rentals with pools in Pinellas Trail often include additional outdoor features such as Pool, Fireplace/Heating, and Laundry. These amenities enhance comfort and make it easier to enjoy outdoor living during your stay.

Some vacation rentals in Pinellas Trail offer heated pools, which can be especially useful during cooler months. In certain cases, pool heating may be available for an additional fee, so it’s best to check the property details before booking.