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

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  5.  St. Petersburg - Clearwater
  6.  Pinellas Trail

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91 Best Cottage Rentals in Pinellas Trail (Starting from $118)

Largo Pool House and Firepit
Largo Pool House and Firepit
Cottage
11350 116th Avenue North, Largo, FL, 33778, United States
1.0k from Pinellas Trail center

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

New to Booking
$2910
Average price / night
Check Availability
11083 106th Ave
11083 106th Ave
Cottage
11083 106th Avenue North, Largo, FL, 33778, United States
1.8k from Pinellas Trail center

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

New to Booking
$3155
Average price / night
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Close to Beaches, quiet and private new guest house - full kitchen, deck & patio
Close to Beaches, quiet and private new guest house - full kitchen, deck & patio
Cottage
Seminole, FL, 33776, United States
2.5k from Pinellas Trail center

AC, Balcony, Free Parking, Heater, Internet, Kitchen, Living Area, Microwave, No Smoking

1 Bedroom2 Guests
10.0

Exceptional

7 reviews

$118
Average price / night
Check Availability
Private Surf Shack Less Than 5 Minutes to Indian Rocks Beach\nBikes Included!
Private Surf Shack Less Than 5 Minutes to Indian Rocks Beach\nBikes Included!
Cottage
Largo, FL, 33774, United States
2.6k from Pinellas Trail center

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

1 Bedroom2 Guests
10.0

Exceptional

36 reviews

$125
Average price / night
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`Palms` Gulf-View Historic Beachside Cottage 2/1
`Palms` Gulf-View Historic Beachside Cottage 2/1
Cottage
Indian Rocks Beach, FL, 33785, United States
4.0k from Pinellas Trail center

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

2 Bedrooms6 Guests
10.0

Exceptional

2 reviews

$445
Average price / night
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🏡Cottage near Clearwater & Belleair Beaches🏖🌴☀️
🏡Cottage near Clearwater & Belleair Beaches🏖🌴☀️
Cottage
Largo, FL, 33770, United States
4.1k from Pinellas Trail center

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

2 Bedrooms8 Guests
10.0

Exceptional

7 reviews

$189
Average price / night
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Ocean View, Pool & Boat Dock: Indian Rocks Retreat
Ocean View, Pool & Boat Dock: Indian Rocks Retreat
Cottage
521 Harbor Dr N, Indian Rocks Beach, FL, 33785, United States
4.2k from Pinellas Trail center

AC, Barbecue, Crib, Free Parking, Heater, Internet, Kitchen, Living Area, Microwave

New to Booking
$741
Average price / night
Check Availability
SOL Cottage, Best Experience in IRB, new AC, totally remodeled, free parking
SOL Cottage, Best Experience in IRB, new AC, totally remodeled, free parking
Cottage
Indian Rocks Beach, FL, 33785, United States
4.2k from Pinellas Trail center

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

2 Bedrooms4 Guests
10.0

Exceptional

6 reviews

$270
Average price / night
Check Availability
LUNA Cottage, Best Experience in IRB, new AC, totally remodeled, free parking
LUNA Cottage, Best Experience in IRB, new AC, totally remodeled, free parking
Cottage
Indian Rocks Beach, FL, 33785, United States
4.2k from Pinellas Trail center

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

2 Bedrooms4 Guests
10.0

Exceptional

11 reviews

$290
Average price / night
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Coquina Cove #6—Coastal Retreat Steps from Indian Rocks Beach with Breezy Décor & Walkable Dining
Coquina Cove #6—Coastal Retreat Steps from Indian Rocks Beach with Breezy Décor & Walkable Dining
Cottage
Indian Rocks Beach, FL, 33785, United States
4.2k from Pinellas Trail center

AC, Barbecue, Free Parking, Heater, Internet, Kitchen, Microwave, Patio, Pool

2 Bedrooms4 Guests
10.0

Exceptional

12 reviews

$347
Average price / night
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Indian Rocks Beach Home - 2 Blocks to Beach!
Indian Rocks Beach Home - 2 Blocks to Beach!
Cottage
1203 Bay Palm Blvd, Indian Rocks Beach, FL, 33785, United States
4.2k from Pinellas Trail center

AC, Barbecue, Crib, Free Parking, Heater, Internet, Kitchen, Living Area, Microwave

New to Booking
$715
Average price / night
Check Availability
Triplex- Family Fun Oasis! 1 Block to Beach with Heated Pool, Putt-Putt, + bikes
Triplex- Family Fun Oasis! 1 Block to Beach with Heated Pool, Putt-Putt, + bikes
Cottage
Indian Rocks Beach, FL, 33785, United States
4.3k from Pinellas Trail center

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

1 Bedroom4 Guests
10.0

Exceptional

1 reviews

$488
Average price / night
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Triplex- 1 Block to the Beach, Heated Pool ,Putt-Putt, bikes, games
Triplex- 1 Block to the Beach, Heated Pool ,Putt-Putt, bikes, games
Cottage
Indian Rocks Beach, FL, 33785, United States
4.3k from Pinellas Trail center

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

1 Bedroom4 Guests
10.0

Exceptional

4 reviews

$303
Average price / night
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The Arbors Seaside Cottages—Beachfront Compound w/ Pool, Pavilion & Walkable Dining
The Arbors Seaside Cottages—Beachfront Compound w/ Pool, Pavilion & Walkable Dining
Cottage
Indian Rocks Beach, FL, 33785, United States
4.3k from Pinellas Trail center

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

9 Bedrooms30 Guests
9.6

Exceptional

13 reviews

$2260
Average price / night
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Reef at The Arbors—Charming 50s Cottage Steps from Beach w/ Pool & Lush Grounds
Reef at The Arbors—Charming 50s Cottage Steps from Beach w/ Pool & Lush Grounds
Cottage
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 Bedrooms6 Guests
8.6

Fabulous

27 reviews

$347
Average price / night
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Beach Lodge at The Arbors – Retro Gulf Retreat w/ Heated Pool, Beachfront Cabana & Beach Access
Beach Lodge at The Arbors – Retro Gulf Retreat w/ Heated Pool, Beachfront Cabana & Beach Access
Cottage
Indian Rocks Beach, FL, 33785, United States
4.3k from Pinellas Trail center

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

3 Bedrooms12 Guests
9.2

Superb

25 reviews

$455
Average price / night
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Angler at The Arbors – Retro Beach Cottage w/ Heated Pool, Private Beach Area & Walkable Dining
Angler at The Arbors – Retro Beach Cottage w/ Heated Pool, Private Beach Area & Walkable Dining
Cottage
Indian Rocks Beach, FL, 33785, United States
4.3k from Pinellas Trail center

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

2 Bedrooms6 Guests
9.4

Superb

29 reviews

$365
Average price / night
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Beachfront Cottages GARDEN at Beautiful Sandy Shores on Gulf of America
Beachfront Cottages GARDEN at Beautiful Sandy Shores on Gulf of America
Cottage
INDIAN ROCKS BEACH, FL, 33785, United States
4.3k from Pinellas Trail center

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

1 Bedroom4 Guests
10.0

Exceptional

189 reviews

$285
Average price / night
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Sol & Luna Cottages, bright, modern & beautiful
Sol & Luna Cottages, bright, modern & beautiful
Cottage
Indian Rocks Beach, FL, 33785, United States
4.3k from Pinellas Trail center

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

4 Bedrooms8 Guests
10.0

Exceptional

4 reviews

$544
Average price / night
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Heated Pool/2 min walk 2 the Beach/Sleeps 9/Cute
Heated Pool/2 min walk 2 the Beach/Sleeps 9/Cute
Cottage
Indian Rocks Beach, FL, 33785, United States
4.3k from Pinellas Trail center

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

3 Bedrooms10 Guests
9.2

Superb

108 reviews

$608
Average price / night
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\"Dunes\" Historic Beachside Cottage 1/1 – Steps to Sand!
\"Dunes\" Historic Beachside Cottage 1/1 – Steps to Sand!
Cottage
Indian Rocks Beach, FL, 33785, United States
4.4k from Pinellas Trail center

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

10.0

Exceptional

17 reviews

$356
Average price / night
Check Availability
Luxury Coastal Retreat , Steps to Indian Rocks Beach
Luxury Coastal Retreat , Steps to Indian Rocks Beach
Cottage
Indian Rocks Beach, FL, 33785, United States
4.4k from Pinellas Trail center

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

2 Bedrooms4 Guests
New to Booking
$284
Average price / night
Check Availability
`Oasis` Historic Beachside Cottage 3/2
`Oasis` Historic Beachside Cottage 3/2
Cottage
Indian Rocks Beach, FL, 33785, United States
4.4k from Pinellas Trail center

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

New to Booking
$569
Average price / night
Check Availability
Beachfront Cottages PATIO at Beautiful Sandy Shores on the Gulf of America
Beachfront Cottages PATIO at Beautiful Sandy Shores on the Gulf of America
Cottage
INDIAN ROCKS BEACH, FL, 33785, United States
4.4k from Pinellas Trail center

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

1 Bedroom4 Guests
10.0

Exceptional

174 reviews

$293
Average price / night
Check Availability
Your own private Beachfront Home On the Sands of the Gulf. Can't get any closer
Your own private Beachfront Home On the Sands of the Gulf. Can't get any closer
Cottage
Indian Shores, FL, 33785, United States
4.4k from Pinellas Trail center

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

3 Bedrooms6 Guests
7.8

Good

100 reviews

$734
Average price / night
Check Availability
Beachfront, Chic a si Cottage, original vintage Florida charm right on the Gulf
Beachfront, Chic a si Cottage, original vintage Florida charm right on the Gulf
Cottage
Indian Rocks Beach, FL, 33785, United States
4.4k from Pinellas Trail center

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

3 Bedrooms6 Guests
10.0

Exceptional

102 reviews

$648
Average price / night
Check Availability
El Palmar Cottages LLC
El Palmar Cottages LLC
Cottage
Indian Rocks Beach, FL, 33785, United States
4.4k from Pinellas Trail center

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

4 Bedrooms10 Guests
10.0

Exceptional

34 reviews

$738
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 Cottage Rentals in Pinellas Trail.

Where to stay in Pinellas Trail? Best neighborhoods & areas

Pinellas Trail Cottage Rentals on the Map

Frequently Asked Questions

You can explore 91 verified cottage rentals in Pinellas Trail. Our listings are sourced from a range of trusted booking providers, giving you access to charming coastal cottages, peaceful countryside escapes, and cozy stays—all in one place.

Cottage rental prices in Pinellas Trail vary based on the season, location, and amenities offered. Rates typically start from around $118 per night, with higher prices during peak travel periods or in waterfront locations. Comparing different options can help you find a stay that fits both your preferences and budget.

Many cottages in Pinellas Trail feature inviting outdoor areas such as private gardens, patios, or small yards. These spaces are ideal for relaxing, dining outdoors, or enjoying the surrounding scenery. You can use the available filters to quickly find cottages with outdoor features that match your preferences.

Yes, cottages are often a great choice for travelers with pets thanks to their cozy layouts and access to outdoor space. Currently, 18 listings in Pinellas Trail welcome pets, making it easier to plan a comfortable stay with your companion.

For busy seasons such as summer holidays or long weekends, it’s a good idea to book your cottage 60 to 90 days in advance. Since cottages are typically smaller and more unique, the most desirable options tend to get reserved quickly during peak periods.

Cottages in Pinellas Trail are known for their comfort and charm, often including amenities such as Kitchen, Fireplace/Heating, and Laundry. These features help create a relaxing and home-like atmosphere for guests.

Yes, many cottages in Pinellas Trail are well-suited for longer stays. They often include essentials like full kitchens, laundry facilities, and comfortable living spaces, making them a practical option for extended vacations or remote work.