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Cottages in Oldsmar

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

9.8 out of 10, Exceptional, (56)
"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

Gulfport Art District! One block from the beach!

10.0 out of 10, Exceptional, (38)
"The location was perfect for my wife and I. It’s right in the heart of the small town of Gulfport and our pup had a great time. The hosts were very responsive and thoughtful. We hope to go back! "
Gulfport Art District! One block from the beach!

Historic Beach Cottage steps from beach. Pet friendly!

9.2 out of 10, Wonderful, (123)
"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!"
$321 nightly
The price is $358
Sep 28 - Sep 29
Total with taxes and fees
Historic Beach Cottage steps from beach. Pet friendly!

Escondido Boutique Bungalow in Crystal Beach- Inquire for Seasonal Savings!

10.0 out of 10, Exceptional, (14)
"Absolutely amazing property and location. The bikes were a wonderful addition! Will be returning!"
Escondido Boutique Bungalow in Crystal Beach- Inquire for Seasonal Savings!

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

9.8 out of 10, Exceptional, (60)
"Loved our stay! "
“A” Beachy Keen Cottage! Just Steps From Indian Rocks Beach!

Your own private Beachfront Home On the Sands of the Gulf. Can't get any closer

7.8 out of 10, Good, (97)
"Perfect location on the beach! Lower level bed was so comfy that we already went and bought one very similar. Everything needed was provided. Could use some updating but the rental makes that known in the description when reserving. Very nice property, beautiful sunsets "
Your own private Beachfront Home On the Sands of the Gulf. Can't get any closer

Grove Keeper Cottage unit has a tree house atmosphere

10.0 out of 10, Exceptional, (40)
"Really enjoyed the privacy that this spot gave us from the area. The landscaping was beautiful. There are a lot of great places to eat right around the corner. "
Grove Keeper Cottage unit has a tree house atmosphere

Kayaks, Canoe, Private Lake Community

9.4 out of 10, Exceptional, (16)
"Great place and hosts! "
$204 nightly
The price is $226
Sep 27 - Sep 28
Total with taxes and fees
Kayaks, Canoe, Private Lake Community

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

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

9.8 out of 10, Exceptional, (145)
"We loved the stay there. It is very close to the beach. One of the best places I’ve stayed at in a long time. "
Cute and Cozy Beach Bungalow. Steps to the Beach. Free off-street Parking!

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

10.0 out of 10, Exceptional, (29)
"We love this place so beautiful and most of all a private beach, great get away "
Two-bedroom bungalow - Old FL Cottage - Gulf Side - Ground Level

Cozy and roomy cottage

10.0 out of 10, Exceptional, (61)
"Absolutely wonderful. Can't wait to return. "
Cozy and roomy cottage

Perfect Cottage In Art District of Gulfport

9.6 out of 10, Exceptional, (95)
"Very Clean and plenty of room for 2."
Perfect Cottage In Art District of Gulfport

Updated Key West Style Cottage.

10.0 out of 10, Exceptional, (8)
"Our stay was lovely. The location is perfect and a short walk to John's pass and its on the beach side of the main road. The owners were super friendly, quick to contact, and cared deeply about the safety of all guests. The amenities were awesome and privacy of the courtyard that separated the cottage from the street was comforting."
Updated Key West Style Cottage.

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

9.8 out of 10, Exceptional, (144)
"Really well kept old style Florida home. Beautifully decorated and comfortable. Location is perfect for beach access. We’ll be back."
White beaches, walk to restaurants and shops! Family vacation /Romantic getaway!

Chic Cottage Walk to Downtown Dunedin & Waterfront Pets Ok- Barefoot Parrot 3

10.0 out of 10, Exceptional, (24)
"Great place and Location to stay and very close to Main Street .Host Jen is fantastic and always available."
$304 nightly
The price is $340
Oct 21 - Oct 22
Total with taxes and fees
Chic Cottage Walk to Downtown Dunedin & Waterfront Pets Ok- Barefoot Parrot 3

Charming Upstairs Unit in a Cottage, steps to the beach. Across from John's Pass

9.4 out of 10, Exceptional, (148)
"Comfortable, no-frills stay for one or a couple. Easy access to beach as well as restaurants and shopping at John’s Pass. Handy parking, nice deck and patio with grill. A few basic items that would be helpful: kitchen linens, basic storage containers and hand soap. "
Charming Upstairs Unit in a Cottage, steps to the beach. Across from John's Pass

Key West Style Cottage - with pool/hot-tub

9.4 out of 10, Exceptional, (6)
"Great stay and located close to downtown."
$190 nightly
The price is $212
Sep 28 - Sep 29
Total with taxes and fees
Key West Style Cottage - with pool/hot-tub

Coral Cottage pool/gas firepit a 2 bedr 2 bath sleeps 6

10.0 out of 10, Exceptional, (42)
"Very clean, relaxing property. Close to everything, especially the Greek restaurants in Tarpon Sorings! "
Coral Cottage pool/gas firepit a 2 bedr 2 bath sleeps 6

Private Surf Shack Less Than 5 Minutes to Indian Rocks Beach Bikes Included!

10.0 out of 10, Exceptional, (25)
"Beautiful option for the beach."
Private Surf Shack Less Than 5 Minutes to Indian Rocks Beach Bikes Included!
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 Oldsmar Hotel Reviews

Find out more about Oldsmar

Find out more about Oldsmar

Oldsmar Cottages information

Number of reviews
1,126
Accommodation
498 Cottages
Lowest Price
$212
Highest Price
$358

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