Search Pinellas County Cottages

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Aug 15 - Aug 17
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Aug 22 - Aug 24
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Sep 5 - Sep 7
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Oct 3 - Oct 5

Top Cities in Pinellas County

Fort De Soto Park which includes a sandy beach
CottagesCottages

St. Petersburg - Clearwater

St. Petersburg - Clearwater

Cottages in Pinellas County

The Purple Flower - 30 Second walk to the Beach. Free parking.
Enjoy al fresco dining on the patio with a table and chairs surrounded by a fence, grill, and lush greenery.

The Purple Flower - 30 Second walk to the Beach. Free parking.

9.8 out of 10, Exceptional, (189)
"Loved this place! Perfect with all the needed amenities. Will definitely stay here again if in the area."
$269 nightly
The price is $300
Aug 18 - Aug 19
Total includes taxes and fees
The Purple Flower - 30 Second walk to the Beach. Free parking.
Perfect Cottage In Art District of Gulfport
Step into the vibrant Gulfport Casino, where the entrance beckons with a bold sign.

Perfect Cottage In Art District of Gulfport

9.6 out of 10, Exceptional, (94)
"Very Clean and plenty of room for 2."
Perfect Cottage In Art District of Gulfport
Private family waterfront beach cottage. Best location step out to bay and gulf
Exterior

Private family waterfront beach cottage. Best location step out to bay and gulf

9.0 out of 10, Wonderful, (92)
"This was the most lovely rustic little beach house. Just perfect. I’d live here. "
Private family waterfront beach cottage. Best location step out to bay and gulf
Yachtsman*OCEAN FRONT COTTAGE*Right on the sand*sleeps up to 6*Heated Pool
Relax in a beachfront setting with a gabled roof and a circular window, surrounded by palm trees and a white picket fence.

Yachtsman*OCEAN FRONT COTTAGE*Right on the sand*sleeps up to 6*Heated Pool

9.8 out of 10, Exceptional, (55)
"Perfect beach house for a single family! The kids loved the convenience of being on the beach and the heated pool. "
Yachtsman*OCEAN FRONT COTTAGE*Right on the sand*sleeps up to 6*Heated Pool
White beaches, walk to restaurants and shops! Family vacation /Romantic getaway!
Property grounds

White beaches, walk to restaurants and shops! Family vacation /Romantic getaway!

9.6 out of 10, Exceptional, (110)
"Great location and amenities! The place was cozy and the short walk to the beach was amazing. The bed was a little stiff and was a little warm being on the upper floor of the house but still a great stay overall!"
White beaches, walk to restaurants and shops! Family vacation /Romantic getaway!
The Flip Flop Waterfront Beach Retreat - Close to Beaches
Relax in a serene outdoor space with a table and chair, overlooking a tranquil water view.

The Flip Flop Waterfront Beach Retreat - Close to Beaches

10.0 out of 10, Exceptional, (1)
"Loved our stay, super cute house! Very clean, beds were comfortable. We fished in the pond at the back of the property and caught a few fish! The T.V. doesn't work good, but internet was great. Very close to honeymoon island beach and beautiful park at the end of the road you can walk to and watch the sun set. Local restaurants are great and a dunkin right around the corner. Very quiet neighborhood. We'll definitely come back. "
$196 nightly
The price is $219
Sep 2 - Sep 3
Total includes taxes and fees
The Flip Flop Waterfront Beach Retreat - Close to Beaches
Two-bedroom bungalow - Old FL Cottage - Gulf Side - Ground Level
Enjoy a serene beachfront setting with lush greenery and a sandy beach, featuring a swimming pool and easy access to the property.

Two-bedroom bungalow - Old FL Cottage - Gulf Side - Ground Level

10.0 out of 10, Exceptional, (28)
"One of our favorite places to stay"
Two-bedroom bungalow - Old FL Cottage - Gulf Side - Ground Level
The Seaside Cottages are located just across the street from Indian Rocks Beach!
Enjoy dining under a thatched roof with friends and family in this tropical setting.

The Seaside Cottages are located just across the street from Indian Rocks Beach!

9.6 out of 10, Exceptional, (9)
"This cottage was the perfect place for relaxing and enjoying the beach, as well as visiting friends and family in Tampa."
The Seaside Cottages are located just across the street from Indian Rocks Beach!
Downtown Dunedin Keylime Cottages 4, right in Downtown Dunedin
Exterior

Downtown Dunedin Keylime Cottages 4, right in Downtown Dunedin

10.0 out of 10, Exceptional, (30)
"Great experience!! Will definitely stay there again!"
Downtown Dunedin Keylime Cottages 4, right in Downtown Dunedin
Canary Beach Cottage - steps to the sand!
Stroll along the beachfront pathway to a charming collection of houses, each with its own unique style and character.

Canary Beach Cottage - steps to the sand!

9.6 out of 10, Exceptional, (45)
"Cute cottage in a great location for our beach getaway. Great staff and place was perfect. Would stay again. "
Canary Beach Cottage - steps to the sand!
Downtown Dunedin Cottage Near Beaches + Breweries
Situated in a quiet neighborhood, this two-story home offers a covered outdoor seating area with a bench and table.

Downtown Dunedin Cottage Near Beaches + Breweries

10.0 out of 10, Exceptional, (67)
"Great cottage. Very clean and property Manager was great. Location to downtown bars and breweries was awesome. Would definitely stay there in the future. "
Downtown Dunedin Cottage Near Beaches + Breweries
100 Steps to Beach. Pets Ok, Real Beach House, Daily Rentals
Guests can enjoy a patio area with seating and a table.

100 Steps to Beach. Pets Ok, Real Beach House, Daily Rentals

9.0 out of 10, Wonderful, (76)
"Cute quiet place Fair price and close to beach and restaurants. Would stay again"
$551 nightly
The price is $614
Aug 11 - Aug 12
Total includes taxes and fees
100 Steps to Beach. Pets Ok, Real Beach House, Daily Rentals
Beachside Historic Cottage – Steps to Sand!
Staircase leads to a small elevated structure surrounded by lush greenery and interlocking brick paving.

Beachside Historic Cottage – Steps to Sand!

10.0 out of 10, Exceptional, (13)
"Great location. Beautiful beach. I’d like to visit again "
Beachside Historic Cottage – Steps to Sand!
Historic Beach Cottage steps from beach. Pet friendly!
Welcome to the charming Toy Away Zone, featuring a cozy entrance with a white door and a small porch area.

Historic Beach Cottage steps from beach. Pet friendly!

9.2 out of 10, Wonderful, (120)
"We LOVED staying at Capt. Al's corner cottage. It was such a cute place and perfect for what we were looking for. Walking distance to everything, steps away from the beach and so relaxing! We especially loved the hot tub that was just out the back door and the atmosphere was so "beachy"....5 stars is not enough for this little gem of a place!"
$317 nightly
The price is $354
Aug 14 - Aug 15
Total includes taxes and fees
Historic Beach Cottage steps from beach. Pet friendly!
Cute and Cozy Beach Bungalow. Steps to the Beach. Free off-street Parking!
Enjoy cooking in this well-lit kitchen with a stainless steel refrigerator, microwave, and toaster.

Cute and Cozy Beach Bungalow. Steps to the Beach. Free off-street Parking!

9.8 out of 10, Exceptional, (142)
"Location and house were great! Adorable house close to beach! Exactly what we needed!!"
Cute and Cozy Beach Bungalow. Steps to the Beach. Free off-street Parking!
Beach Lodge:2 Story Sleeps up to 12* Beach front pavilion* heated pool
Relax on the front porch with two Adirondack chairs and a small table.

Beach Lodge:2 Story Sleeps up to 12* Beach front pavilion* heated pool

9.2 out of 10, Wonderful, (24)
"Beautiful place and great location! Highly recommend staying at this rental property!"
Beach Lodge:2 Story Sleeps up to 12* Beach front pavilion* heated pool
BEACHFRONT COTTAGE! Step out the door and into the sand! On the Gulf of Mexico!!
Enjoy the serene beach view from your balcony, featuring a set of lounge chairs on the sand and a clear ocean view.

BEACHFRONT COTTAGE! Step out the door and into the sand! On the Gulf of Mexico!!

9.8 out of 10, Exceptional, (214)
"My wife & I totally enjoyed our stay in Linda’s little bungalow on the ocean. Perfect beach location."
$397 nightly
The price is $443
Aug 13 - Aug 14
Total includes taxes and fees
BEACHFRONT COTTAGE! Step out the door and into the sand! On the Gulf of Mexico!!
Island Vibes Cottage | Amazing Location
Enjoy sunbathing and beach activities on the wide sandy beach, surrounded by a mix of residential and commercial properties.

Island Vibes Cottage | Amazing Location

9.0 out of 10, Wonderful, (35)
"We had a beautiful stay in Clearwater. The cottage was perfect for two and great walk to the beach as well as downtown. Great food everywhere we turned! We will be back!"
Island Vibes Cottage | Amazing Location
Beachfront Cottages (Patio) at Beautiful Sandy Shores on Gulf of Mexico
Relax in a serene coastal setting with a picnic table, lounge chairs, and a blue umbrella.

Beachfront Cottages (Patio) at Beautiful Sandy Shores on Gulf of Mexico

10.0 out of 10, Exceptional, (159)
"Sandy Shores was a perfect place to soak up the sun and enjoy a balance of peace and quiet and activities. The Patio Cottage was clean and comfortable with all the amenities we needed. A king size bed, cable tv, internet, kitchen, bath, grill, patio and right next to the beach. Good restaurants within walking distance. Our hostess, Myrtle responded to emails and texts and really made us feel welcome. Our area did not feel overly commercial and had a nice neighborhood feel. It was great and we...
Beachfront Cottages (Patio) at Beautiful Sandy Shores on Gulf of Mexico
“A” Beachy Keen Cottage! Just Steps From Indian Rocks Beach!
Situated on a gravel driveway, this single-story home features a blue door and a white picket fence, surrounded by palm trees.

“A” Beachy Keen Cottage! Just Steps From Indian Rocks Beach!

9.8 out of 10, Exceptional, (56)
"Great location! One block from beach. Host provided all the beach necessities including chairs, towels, umbrellas, coolers, & boogie boards. Walking distance to restaurants, bars, coffee shops & ice cream. And then you can relax at night in the hot tub. We loved our stay!"
“A” Beachy Keen Cottage! Just Steps From Indian Rocks Beach!
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Pinellas County Hotel Reviews

ChartHouse Clearwater Beach Marina Hotel

ChartHouse Clearwater Beach Marina Hotel

10/10 Excellent
"No free breakfast. "
Eugenia 1-night trip
Posted 8 hours ago
ChartHouse Clearwater Beach Marina Hotel