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

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  5.  St. Petersburg - Clearwater

  6.  Pinellas Trail

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108 Best Villa Rentals in Pinellas Trail (Starting from $120)

Great located home with pool near beach
Great located home with pool near beach
Villa
Walsingham, FL, USA
1.5k from Pinellas Trail center

Parking, Security/Safety, Pet Friendly, Child Friendly

2 Bedrooms9 Guests
New to Booking
$221
Average price / night
Check Availability
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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Heated Pool, 10min from Beach, Lux 3Br 2Ba, Coco Cabana
Heated Pool, 10min from Beach, Lux 3Br 2Ba, Coco Cabana
Villa
Largo, FL, USA
1.8k from Pinellas Trail center

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

3 Bedrooms8 Guests
New to Booking
$307
Average price / night
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Spacious Pool Villa Just Minutes from the Beach
Spacious Pool Villa Just Minutes from the Beach
Villa
Largo, FL, 33774, United States
1.0k from Pinellas Trail center

AC, Dryer, Free Parking, Heater, Internet, Kitchen, Microwave, No Smoking, TV

4 Bedrooms10 Guests
New to Booking
$323
Average price / night
Check Availability
Mini-Golf 2-1 with Heated pool
Mini-Golf 2-1 with Heated pool
Villa
Largo, FL, USA
2.6k from Pinellas Trail center

Pool, Ocean View, Air Conditioner, Barbecue/Outdoor Cooking, Balcony/Terrace, View, Internet

2 Bedrooms4 Guests
New to Booking
$179
Average price / night
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Luxury Villa with Heated Saltwater Pool & Spa, Mini Golf, BBQ, 5 Mins to Beach
Luxury Villa with Heated Saltwater Pool & Spa, Mini Golf, BBQ, 5 Mins to Beach
Villa
Largo, FL, 33774, United States
1.5k from Pinellas Trail center

AC, Arcade, Balcony, Barbecue, Crib, Dryer, Fitness Equipment, Free Parking, Heater

8 Bedrooms20 Guests
10.0

Exceptional

44 reviews

$1773
Average price / night
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Heated Pool House: Beach 3Miles · Bar · BBQ & GYM!
Heated Pool House: Beach 3Miles · Bar · BBQ & GYM!
Villa
Largo, FL, USA
2.7k from Pinellas Trail center

Barbecue/Outdoor Cooking, Balcony/Terrace, View, Security/Safety, Bar, Parking, Internet

4 Bedrooms14 Guests
10.0

Exceptional

1 reviews

$495
Average price / night
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Private Resort Villa | Heated Pool + Game Room + Near Gulf Beaches
Private Resort Villa | Heated Pool + Game Room + Near Gulf Beaches
Villa
Largo, FL, 33778, United States
1.9k from Pinellas Trail center

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

3 Bedrooms8 Guests
10.0

Exceptional

14 reviews

$320
Average price / night
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Private 3 bedroom Home in beautiful beach community
Private 3 bedroom Home in beautiful beach community
Villa
Largo, FL, USA
2.8k from Pinellas Trail center

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

3 Bedrooms8 Guests
New to Booking
$120
Average price / night
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Waterfront Cove Paradise with Pool and Canoes - Dolphin and Manatee Viewpoint
Waterfront Cove Paradise with Pool and Canoes - Dolphin and Manatee Viewpoint
Villa
Largo, FL, USA
2.9k from Pinellas Trail center

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

3 Bedrooms10 Guests
New to Booking
$996
Average price / night
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Relaxing home Mini-Golf/ heated pool 2/2
Relaxing home Mini-Golf/ heated pool 2/2
Villa
Largo, FL, 33770, United States
2.6k from Pinellas Trail center

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

2 Bedrooms4 Guests
10.0

Exceptional

2 reviews

$315
Average price / night
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Lakeside Retreat-4plex Sleeps 20
Lakeside Retreat-4plex Sleeps 20
Villa
Largo, FL, USA
3.0k from Pinellas Trail center

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

9 Bedrooms20 Guests
New to Booking
$1068
Average price / night
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The Sofia-Cozy 2-bedroom villa with a king-sized bed, complimentary bikes.
The Sofia-Cozy 2-bedroom villa with a king-sized bed, complimentary bikes.
Villa
Largo, FL, 33774, United States
2.7k from Pinellas Trail center

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

2 Bedrooms4 Guests
10.0

Exceptional

1 reviews

$151
Average price / night
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Waterfront Heated Pool, Sleeps 20 - 4plex
Waterfront Heated Pool, Sleeps 20 - 4plex
Villa
Largo, FL, 33773, United States
3.0k from Pinellas Trail center

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

11 Bedrooms16 Guests
New to Booking
$1021
Average price / night
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Ultimate Beach Getaway · Mins from Beach · Hot Tub · Heated Pool · Game Room
Ultimate Beach Getaway · Mins from Beach · Hot Tub · Heated Pool · Game Room
Villa
Seminole, FL, USA
3.1k from Pinellas Trail center

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

5 Bedrooms10 Guests
New to Booking
$512
Average price / night
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2,100sqf Villa  · KING Beds  · Heated Pool · Game Room · GYM · Beach 2miles
2,100sqf Villa · KING Beds · Heated Pool · Game Room · GYM · Beach 2miles
Villa
Largo, FL, 33770, United States
3.2k from Pinellas Trail center

AC, Arcade, Barbecue, Dryer, Fitness Equipment, Free Parking, Heater, Internet, Kitchen

4 Bedrooms11 Guests
10.0

Exceptional

27 reviews

$596
Average price / night
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King Beds - Game Room - Pool - Beach 2m - 2,100sqft
King Beds - Game Room - Pool - Beach 2m - 2,100sqft
Villa
FL, USA
3.1k from Pinellas Trail center

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

4 Bedrooms11 Guests
New to Booking
$449
Average price / night
Check Availability
6BR Waterfront • Heated Pool • Hot Tub • Game Room
6BR Waterfront • Heated Pool • Hot Tub • Game Room
Villa
Largo, FL, 33773, United States
3.3k from Pinellas Trail center

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

7 Bedrooms25 Guests
10.0

Exceptional

1 reviews

$917
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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The Beach House B.
The Beach House B.
Villa
Largo, FL, 33770, United States
3.3k from Pinellas Trail center

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

2 Bedrooms4 Guests
New to Booking
$174
Average price / night
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Luxury Cristiano Manor 8BR w Pool - 20 Guests
Luxury Cristiano Manor 8BR w Pool - 20 Guests
Villa
Largo, FL, USA
3.1k from Pinellas Trail center

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

8 Bedrooms20 Guests
10.0

Exceptional

1 reviews

$1794
Average price / night
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Resort Backyard! Heated Pool! Pool Table! PingPong
Resort Backyard! Heated Pool! Pool Table! PingPong
Villa
Largo, FL, 33770, United States
3.4k from Pinellas Trail center

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

4 Bedrooms10 Guests
New to Booking
$686
Average price / night
Check Availability
A Tennis Community Near the Beach!
A Tennis Community Near the Beach!
Villa
Largo, FL, 33774, United States
3.6k from Pinellas Trail center

AC, Dryer, Internet, Kitchen, Laundry, Microwave, No Smoking, Pool, Tennis Court

2 Bedrooms4 Guests
8.4

Very Good

11 reviews

$181
Average price / night
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Vintage Florida Beach Cottage, one block to the sand of Indian Rocks Beach FL
Vintage Florida Beach Cottage, one block to the sand of Indian Rocks Beach FL
Villa
Indian Rocks Beach, FL, 33785, United States
4.2k from Pinellas Trail center

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

2 Bedrooms4 Guests
10.0

Exceptional

9 reviews

$204
Average price / night
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Newly renovated Clean, Bright Beach Villa in Best location.
Newly renovated Clean, Bright Beach Villa in Best location.
Villa
Indian Rocks Beach, FL, 33785, United States
4.3k from Pinellas Trail center

AC, Barbecue, Dryer, Extra Bed, Free Parking, Heater, Internet, Kitchen, Laundry

2 Bedrooms5 Guests
9.2

Superb

108 reviews

$243
Average price / night
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Remodeled Clean , Bright Indian Rocks Beach Villa. Pet Friendly
Remodeled Clean , Bright Indian Rocks Beach Villa. Pet Friendly
Villa
Indian Rocks Beach, FL, 33785, United States
4.3k from Pinellas Trail center

AC, Barbecue, Dryer, Extra Bed, Free Parking, Heater, Internet, Kitchen, Laundry

2 Bedrooms5 Guests
9.2

Superb

67 reviews

$233
Average price / night
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Ocean View | Heated Pool | 3 Bedroom | Golf Cart
Ocean View | Heated Pool | 3 Bedroom | Golf Cart
Villa
indian rocks beach, FL, 33785, United States
4.4k from Pinellas Trail center

AC, Barbecue, Crib, Dryer, Extra Bed, Free Parking, Heater, Internet, Kitchen

3 Bedrooms8 Guests
10.0

Exceptional

8 reviews

$1454
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 Villa Rentals in Pinellas Trail.

Where to stay in Pinellas Trail? Best neighborhoods & areas

Pinellas Trail Villa Rentals on the Map

Frequently Asked Questions

You can currently explore 108 verified villa rentals in Pinellas Trail. Our listings are sourced from multiple leading booking platforms, giving you a broad and up-to-date selection of luxury and private villas in one place.

Villa prices in Pinellas Trail vary depending on the season, location, and amenities. Rates typically start from around $120 per night, with premium properties costing more during peak travel periods. Comparing options across different platforms can help you find the best value for your dates.

Many villas in Pinellas Trail are designed for privacy and comfort, and a large number of them feature private pools. You can easily filter your search to find villas with pools, helping you choose the perfect stay for relaxation or group travel in Pinellas Trail.

Yes, Pinellas Trail offers a wide range of villas ideal for group stays. Many properties include 4 or more bedrooms, making them well-suited for family gatherings, events, or trips with friends. You can filter by bedroom count to quickly find options that match your group size.

For popular travel periods, it’s generally recommended to book your Pinellas Trail villa around 60 to 90 days in advance to secure the best selection. However, since we compare 10+ sites, it’s still possible to find great last-minute options even 2 to 4 weeks before your trip.

Villas in Pinellas Trail often include highly sought-after amenities such as Fireplace/Heating, Laundry, and View. These features enhance comfort and convenience, making them especially popular among travelers visiting Pinellas Trail.

To discover top-rated villas in Pinellas Trail, you can sort listings by guest ratings and reviews. Our platform aggregates feedback from multiple trusted sources, helping you identify highly rated properties based on real guest experiences. Use the "Rating" filter above to start your search.