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

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  2. Vacation Rentals with Private Pool
  3.  USA

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

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1348 Best Vacation Rentals with Private Pool in Pinellas Trail (Starting from $85)

4 Mi to Beaches Alluring Largo Hideaway!
4 Mi to Beaches Alluring Largo Hideaway!
House
Largo, FL, USA
1.5k from Pinellas Trail center

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

5 Bedrooms14 Guests
10.0

Exceptional

1 reviews

$706
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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Luxury Retreat: Pool Games Basketball More
Luxury Retreat: Pool Games Basketball More
House
Largo, FL, USA
1.6k from Pinellas Trail center

Luxury, Accommodations, Pools, Parking, Villas, Vacation homes, Cottages, Lodgings, Hot tubs

1 Bedroom12 Guests
New to Booking
$1246
Average price / night
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Resort-Style Oasis • Pool • Mini Golf • Playground
Resort-Style Oasis • Pool • Mini Golf • Playground
House
Largo, FL, 33778, United States
0.6k from Pinellas Trail center

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

4 Bedrooms10 Guests
10.0

Exceptional

1 reviews

$685
Average price / night
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Fun & family-friendly modern beach home with pool
Fun & family-friendly modern beach home with pool
House
Largo, FL, USA
2.4k from Pinellas Trail center

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

3 Bedrooms8 Guests
New to Booking
$1250
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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Luxury 8-BR Villa w Pool Soccer - 20 Guests
Luxury 8-BR Villa w Pool Soccer - 20 Guests
Villa
Largo, FL, USA
3.1k from Pinellas Trail center

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

1 Bedroom20 Guests
New to Booking
$1883
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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8BR w Heated Pool Waterview - Close to Beach
8BR w Heated Pool Waterview - Close to Beach
House
FL, USA
3.6k from Pinellas Trail center

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

1 Bedroom20 Guests
10.0

Exceptional

1 reviews

$924
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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Golden Retreat: Expansive 6BR Home w Heated POOL ~
Golden Retreat: Expansive 6BR Home w Heated POOL ~
House
Seminole, FL, USA
3.9k from Pinellas Trail center

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

6 Bedrooms18 Guests
New to Booking
$1937
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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Waterfront Luxury w/Heated Salt Pool & Golf Cart
Waterfront Luxury w/Heated Salt Pool & Golf Cart
House
Clearwater Beach, FL, USA
4.1k from Pinellas Trail center

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

4 Bedrooms12 Guests
9.8

Exceptional

10 reviews

$1270
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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NICE PLACE Studio
NICE PLACE Studio
Apartment
Largo, FL, USA
4.3k from Pinellas Trail center

Apartments, Cheap, Accommodations, Pools, Parking, Lodgings, Places to stay

1 Bedroom2 Guests
9.6

Exceptional

15 reviews

$85
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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Court Haven Paradise: Your All-In-One Getaway
Court Haven Paradise: Your All-In-One Getaway
House
Seminole, FL, USA
4.8k from Pinellas Trail center

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

1 Bedroom10 Guests
9.0

Fabulous

2 reviews

$898
Average price / night
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Flamingo Lounge | Pool, Firepit, Grill, Sleeps 10
Flamingo Lounge | Pool, Firepit, Grill, Sleeps 10
House
Largo, FL, 33778, United States
1.0k from Pinellas Trail center

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

4 Bedrooms10 Guests
New to Booking
$449
Average price / night
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Kandys Kondo II
Kandys Kondo II
Apartment
Clearwater Beach, FL, USA
5.6k from Pinellas Trail center

Private Pool, Pool, Internet, Sports/Activities, Ocean View, Accessibility, Fireplace/Heating

3 Bedrooms8 Guests
9.0

Fabulous

4 reviews

$544
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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Luna Vacation
Luna Vacation
House
Largo, FL, USA
6.6k from Pinellas Trail center

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

4 Bedrooms12 Guests
8.1

Very Good

11 reviews

$217
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
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Surfs Up! Heated Pool+Golf+Games, Sleeps 10, 15 min to beaches!
Surfs Up! Heated Pool+Golf+Games, Sleeps 10, 15 min to beaches!
House
Largo, FL, 33778, United States
1.1k from Pinellas Trail center

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

3 Bedrooms10 Guests
10.0

Exceptional

1 reviews

$513
Average price / night
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Family Retreat with Heated Pool, Cabana and Mini Golf, 10min to beach
Family Retreat with Heated Pool, Cabana and Mini Golf, 10min to beach
House
Largo, FL, 33778, United States
1.1k from Pinellas Trail center

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

4 Bedrooms8 Guests
6.0

Review score

2 reviews

$566
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 Private Pool in Pinellas Trail.

Where to stay in Pinellas Trail? Best neighborhoods & areas

Pinellas Trail Vacation Rentals with Private Pool on the Map

Frequently Asked Questions

You can explore 1348 verified vacation rentals with a private pool in Pinellas Trail. These include standalone villas and private homes where the pool is reserved exclusively for your group.

Prices for rentals with a private pool in Pinellas Trail vary depending on the property size, location, and travel season. Rates typically start from around $85 per night, with higher prices for larger homes, prime locations, or peak travel periods.

Yes, properties listed with private pools are intended for the exclusive use of guests staying at that home. You can review listing photos and descriptions to better understand the layout and level of privacy offered.

Yes, some vacation rentals with private pools in Pinellas Trail also welcome pets. Currently, 29 listings allow pets, although policies may vary. It’s a good idea to review any rules related to pets and outdoor areas before booking.

Private pool properties are often in high demand, especially during holidays and warmer months, so booking 90 to 120 days in advance is recommended. During quieter periods, you may still find availability closer to your travel dates.

Vacation rentals with private pools in Pinellas Trail often include additional features such as Pool, Private Pool, and Fireplace/Heating. These amenities enhance comfort and create a more relaxing, self-contained stay.

Some family-friendly vacation rentals in Pinellas Trail include safety features such as pool fences, covers, or screened enclosures. It’s recommended to check the property details to confirm whether a specific rental meets your safety preferences.