Title: Oldsmar Cottages from CA $294 | Expedia.ca [Oldsmar Travel Guide](https://expedia.ca/Oldsmar.dx141455)[Hotels in Oldsmar](https://expedia.ca/Oldsmar-Hotels.d141455.Travel-Guide-Hotels)[Vacation Rentals in Oldsmar](https://expedia.ca/Oldsmar-Vacation-Rentals.d141455.Travel-Guide-VacationRentals)[Flights to Oldsmar](https://expedia.ca/Cheap-Flights-To-Oldsmar.d141455.Travel-Guide-Flights)[Oldsmar Car Rentals](https://expedia.ca/Car-Rentals-In-Oldsmar.d141455.Car-Rental-Guide)[Oldsmar Vacation Packages](https://expedia.ca/Oldsmar.d141455.Destination-Travel-Guides) ![](https://mediaim.expedia.com/destination/9/bdfc3ac9f0e70f83dea85c86d485d5b2.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # Search Oldsmar Cottage Rentals from CA $294 ![calendar shield illustration](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__calendar_shield.svg) ### Change your mind Book hotels with free cancellation ![deals illustration](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__deals.svg) ### Treat yourself Sign in to save 10% or more on thousands of hotels [Sign in](https://www.expedia.ca/login) ![bed illustration](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__bed.svg) ### Be picky Search almost a million properties worldwide ## Check prices for these dates Next weekend [Oct 3 - Oct 5](https://www.expedia.ca/Hotel-Search?regionId=141455&startDate=2025-10-03&endDate=2025-10-05&adults=2&lodging=COTTAGE&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two weeks [Oct 10 - Oct 12](https://www.expedia.ca/Hotel-Search?regionId=141455&startDate=2025-10-10&endDate=2025-10-12&adults=2&lodging=COTTAGE&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In one month [Oct 24 - Oct 26](https://www.expedia.ca/Hotel-Search?regionId=141455&startDate=2025-10-24&endDate=2025-10-26&adults=2&lodging=COTTAGE&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [Nov 21 - Nov 23](https://www.expedia.ca/Hotel-Search?regionId=141455&startDate=2025-11-21&endDate=2025-11-23&adults=2&lodging=COTTAGE&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Browse Select Oldsmar Cottages ![Exterior](https://images.trvl-media.com/lodging/22000000/21870000/21867300/21867244/de94a0e9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, DVD player](https://images.trvl-media.com/lodging/22000000/21870000/21867300/21867244/w884h599x16y0-3de7bb6b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, DVD player](https://images.trvl-media.com/lodging/22000000/21870000/21867300/21867244/b05b8220.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![On the beach](https://images.trvl-media.com/lodging/22000000/21870000/21867300/21867244/7f7e1601.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Yachtsman\*OCEAN FRONT COTTAGE\*Right on the sand\*sleeps up to 6\*Heated Pool Indian Rocks Beach 9.8/10 Exceptional (56) "Perfect beach house for a single family! The kids loved the convenience of being on the beach and the heated pool. " [](https://www.expedia.ca/St-Petersburg-Clearwater-Hotels-YachtsmanOCEAN-FRONT-COTTAGERight-On-The-Sandsleeps-Up-To-6Heated-Pool.h21867244.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/28000000/27320000/27312200/27312151/64f5ba61.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV](https://images.trvl-media.com/lodging/28000000/27320000/27312200/27312151/2e0156e4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior detail](https://images.trvl-media.com/lodging/28000000/27320000/27312200/27312151/c46b9a17.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/28000000/27320000/27312200/27312151/4288851c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Gulfport Art District! One block from the beach! Gulfport 10/10 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! " [](https://www.expedia.ca/St-Petersburg-Clearwater-Hotels-Gulfport-Art-District-One-Block-From-The-Beach.h27312151.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/35000000/34150000/34141700/34141655/bd6ba9f0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![On the beach, sun loungers, beach towels](https://images.trvl-media.com/lodging/35000000/34150000/34141700/34141655/653099ec.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor spa tub](https://images.trvl-media.com/lodging/35000000/34150000/34141700/34141655/4b33b6df.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![A heated pool](https://images.trvl-media.com/lodging/35000000/34150000/34141700/34141655/d2a841cd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Historic Beach Cottage steps from beach. Pet friendly! Clearwater 9.2/10 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!" CA $186 CA $498 total includes taxes & fees Sep 28 - Sep 29 [](https://www.expedia.ca/St-Petersburg-Clearwater-Hotels-Sleeps-5.h34141655.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/75000000/74260000/74253500/74253486/a2dff8ff.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/75000000/74260000/74253500/74253486/997b62d3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/75000000/74260000/74253500/74253486/f1e68243.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/75000000/74260000/74253500/74253486/36301b94.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Escondido Boutique Bungalow in Crystal Beach- Inquire for Seasonal Savings! Palm Harbor 10/10 Exceptional (14) "Absolutely amazing property and location. The bikes were a wonderful addition! Will be returning!" [](https://www.expedia.ca/St-Petersburg-Clearwater-Hotels-Escondido-Just-Foot-Steps-To-Crystal-Beacheach.h74253486.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/39000000/38110000/38107200/38107131/3a9737e7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/39000000/38110000/38107200/38107131/d62a959a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/39000000/38110000/38107200/38107131/03382649.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Beach nearby, sun loungers, beach towels](https://images.trvl-media.com/lodging/39000000/38110000/38107200/38107131/f7a6d1b5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### “A” Beachy Keen Cottage! Just Steps From Indian Rocks Beach! Indian Rocks Beach 9.8/10 Exceptional (60) "Loved our stay! " [](https://www.expedia.ca/St-Petersburg-Clearwater-Hotels-A-Beachy-Keen-Cottage-Just-Steps-From-Indian-Rocks-Beach.h38107131.Hotel-Information) ![Outdoor dining](https://images.trvl-media.com/lodging/32000000/31900000/31896800/31896748/9a109424.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Marina](https://images.trvl-media.com/lodging/32000000/31900000/31896800/31896748/6b63ba3f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/32000000/31900000/31896800/31896748/8e1a042a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, fireplace](https://images.trvl-media.com/lodging/32000000/31900000/31896800/31896748/1b753527.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Your own private Beachfront Home On the Sands of the Gulf. Can't get any closer Indian Shores 7.8/10 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 " [](https://www.expedia.ca/St-Petersburg-Clearwater-Hotels-Your-Own-Private-Beachfront-Home-On-The-Sands-Of-The-Gulf-Cant-Get-Any-Closer.h31896748.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/40000000/39210000/39205800/39205790/180-d25287db.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/40000000/39210000/39205800/39205790/c3b9a0eb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/40000000/39210000/39205800/39205790/29810b1c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, coffee/tea maker, electric kettle](https://images.trvl-media.com/lodging/40000000/39210000/39205800/39205790/90-2a2776f8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Grove Keeper Cottage unit has a tree house atmosphere Dunedin 10/10 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. " [](https://www.expedia.ca/St-Petersburg-Clearwater-Hotels-Grove-Keeper-Cottage-Upper-Unit-With-A-Tree-House-Atmosphere.h39205790.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/75000000/74820000/74816900/74816874/w1064h722x0y0-060212bf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Children's area](https://images.trvl-media.com/lodging/75000000/74820000/74816900/74816874/8efeb699.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, video games, DVD player, books](https://images.trvl-media.com/lodging/75000000/74820000/74816900/74816874/2596a8fe.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/75000000/74820000/74816900/74816874/17e88bab.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Kayaks, Canoe, Private Lake Community Odessa 9.4/10 Exceptional (16) "Great place and hosts! " CA $149 CA $314 total includes taxes & fees Sep 27 - Sep 28 [](https://www.expedia.ca/Tampa-Hotels-Kayaks.h74816874.Hotel-Information) ![Beach nearby](https://images.trvl-media.com/lodging/68000000/67590000/67582300/67582240/57c4367f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior detail](https://images.trvl-media.com/lodging/68000000/67590000/67582300/67582240/863fedd4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, stovetop, coffee/tea maker](https://images.trvl-media.com/lodging/68000000/67590000/67582300/67582240/075c3ec6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/68000000/67590000/67582300/67582240/2b0fe09a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Island Vibes Cottage | Amazing Location Clearwater Beach 9.0/10 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!" [](https://www.expedia.ca/St-Petersburg-Clearwater-Hotels-Island-Vibes-Cottage-Amazing-Location.h67582240.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/49000000/48260000/48259500/48259420/ccff7b81.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/49000000/48260000/48259500/48259420/f91116e7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/49000000/48260000/48259500/48259420/90189cdb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/49000000/48260000/48259500/48259420/12cdd415.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cute and Cozy Beach Bungalow. Steps to the Beach. Free off-street Parking! Clearwater 9.8/10 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. " [](https://www.expedia.ca/St-Petersburg-Clearwater-Hotels-Cute-And-Cozy-Beach-Bungalow-Steps-To-The-Beach-Free-Off-Street-Parking.h48259420.Hotel-Information) ![Aerial view](https://images.trvl-media.com/lodging/76000000/75770000/75769900/75769867/w1021h767x3y0-340f1356.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/76000000/75770000/75769900/75769867/702f9a41.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV](https://images.trvl-media.com/lodging/76000000/75770000/75769900/75769867/7faf233c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/76000000/75770000/75769900/75769867/e2e45c31_edited_78f2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Two-bedroom bungalow - Old FL Cottage - Gulf Side - Ground Level Indian Shores 10/10 Exceptional (29) "We love this place so beautiful and most of all a private beach, great get away " [](https://www.expedia.ca/St-Petersburg-Clearwater-Hotels-Two-Bedroom-Bungalow-Old-FL-Beach-Cottage-Gulf-Side-Ground-Level.h75769867.Hotel-Information) ![Outdoor pool](https://images.trvl-media.com/lodging/39000000/38430000/38428800/38428797/50dd0e99.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/39000000/38430000/38428800/38428797/913f34ec.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/39000000/38430000/38428800/38428797/0cf7ee7e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/39000000/38430000/38428800/38428797/bdcbc800.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cozy and roomy cottage Dunedin 10/10 Exceptional (61) "Absolutely wonderful. Can't wait to return. " [](https://www.expedia.ca/St-Petersburg-Clearwater-Hotels-Cozy-And-Roomy-Cottage.h38428797.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/35000000/34510000/34509800/34509749/ebb5fecf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Beach nearby, sun loungers, beach towels](https://images.trvl-media.com/lodging/35000000/34510000/34509800/34509749/3c61b5e6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/35000000/34510000/34509800/34509749/57ae8c5b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/35000000/34510000/34509800/34509749/bb075c28.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Perfect Cottage In Art District of Gulfport Gulfport 9.6/10 Exceptional (95) "Very Clean and plenty of room for 2." [](https://www.expedia.ca/St-Petersburg-Clearwater-Hotels-Perfect-Cottage-In-Art-District-Of-Gulfport.h34509749.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/98000000/97450000/97447100/97447002/61ac61fe.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV](https://images.trvl-media.com/lodging/98000000/97450000/97447100/97447002/6fb5407f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/98000000/97450000/97447100/97447002/b9b503e9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/98000000/97450000/97447100/97447002/e3866135.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Updated Key West Style Cottage. Treasure Island 10/10 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." [](https://www.expedia.ca/St-Petersburg-Clearwater-Hotels-Updated-Key-West-Style-Cottage.h97447002.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/35000000/34010000/34002500/34002443/18161824.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/35000000/34010000/34002500/34002443/881867b1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior detail](https://images.trvl-media.com/lodging/35000000/34010000/34002500/34002443/12aa9f59.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, books](https://images.trvl-media.com/lodging/35000000/34010000/34002500/34002443/1c03884f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### White beaches, walk to restaurants and shops! Family vacation /Romantic getaway! Clearwater 9.8/10 Exceptional (144) "Really well kept old style Florida home. Beautifully decorated and comfortable. Location is perfect for beach access. We’ll be back." [](https://www.expedia.ca/St-Petersburg-Clearwater-Hotels-White-Beaches.h34002443.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/94000000/93430000/93427100/93427024/502ac3be.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, books, offices](https://images.trvl-media.com/lodging/94000000/93430000/93427100/93427024/0e23ba58.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Marina](https://images.trvl-media.com/lodging/94000000/93430000/93427100/93427024/w1440h805x0y1-9f71b1a6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 bedrooms, desk, iron/ironing board, travel crib](https://images.trvl-media.com/lodging/94000000/93430000/93427100/93427024/180561ca.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Chic Cottage Walk to Downtown Dunedin & Waterfront Pets Ok- Barefoot Parrot 3 Downtown Dunedin 10/10 Exceptional (24) "Great place and Location to stay and very close to Main Street .Host Jen is fantastic and always available." CA $205 CA $473 total includes taxes & fees Oct 21 - Oct 22 [](https://www.expedia.ca/St-Petersburg-Clearwater-Hotels-Walk-To-Waterfront-Downtown-Barefoot-Parrot-3.h93427024.Hotel-Information) ![Outdoor dining](https://images.trvl-media.com/lodging/34000000/33650000/33646500/33646470/ac66a6c1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Beach nearby](https://images.trvl-media.com/lodging/34000000/33650000/33646500/33646470/f3ccc7dd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Microwave, stovetop, cookware/dishes/utensils, ice maker](https://images.trvl-media.com/lodging/34000000/33650000/33646500/33646470/d706fbf2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/34000000/33650000/33646500/33646470/8b2d7af7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Charming Upstairs Unit in a Cottage, steps to the beach. Across from John's Pass Madeira Beach 9.4/10 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. " [](https://www.expedia.ca/St-Petersburg-Clearwater-Hotels-Charming-Upstairs-Unit-In-A-Cottage.h33646470.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/93000000/92370000/92367200/92367123/643985fa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Pool](https://images.trvl-media.com/lodging/93000000/92370000/92367200/92367123/1d921d78.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Marina](https://images.trvl-media.com/lodging/93000000/92370000/92367200/92367123/e69f2f95.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/93000000/92370000/92367200/92367123/ed31d2f8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Key West Style Cottage - with pool/hot-tub Dunedin 9.4/10 Exceptional (6) "Great stay and located close to downtown." CA $135 CA $294 total includes taxes & fees Sep 28 - Sep 29 [](https://www.expedia.ca/St-Petersburg-Clearwater-Hotels-Key-West-Style-Cottage-With-Poolhot-Tub.h92367123.Hotel-Information) ![Terrace/patio](https://images.trvl-media.com/lodging/79000000/78100000/78099700/78099619/476314a5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace, table tennis, books](https://images.trvl-media.com/lodging/79000000/78100000/78099700/78099619/9f65dcdc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/79000000/78100000/78099700/78099619/fd44f8b1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 bedrooms, desk, iron/ironing board, travel crib](https://images.trvl-media.com/lodging/79000000/78100000/78099700/78099619/e9970118.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Coral Cottage pool/gas firepit a 2 bedr 2 bath sleeps 6 Baywood Village 10/10 Exceptional (42) "Very clean, relaxing property. Close to everything, especially the Greek restaurants in Tarpon Sorings! " [](https://www.expedia.ca/St-Petersburg-Clearwater-Hotels-Coral-Cottage-Poolgas-Firepit-A-2-Bedr-2-Bath-Sleeps-6.h78099619.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/99000000/98510000/98509500/98509482/w1801h1199x0y0-57f088a3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/99000000/98510000/98509500/98509482/cb8d929d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/99000000/98510000/98509500/98509482/a1839988.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/99000000/98510000/98509500/98509482/26c50359.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Private Surf Shack Less Than 5 Minutes to Indian Rocks Beach Bikes Included! Largo 10/10 Exceptional (25) "Beautiful option for the beach." [](https://www.expedia.ca/St-Petersburg-Clearwater-Hotels-Private-Surf-Shack-Less-Than-5-Minutes-To-Indian-Rocks-BeachBikes-Included.h98509482.Hotel-Information) 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. [View all properties](https://expedia.ca/Hotel-Search?startDate=2025-10-10&endDate=2025-10-11®ionId=141455&adults=2&lodging=COTTAGE&sort=RECOMMENDED&openPlayBack=true) ![](https://a.travel-assets.com/pricing-claim/sparkle_dark.svg) Save an average of 15% on thousands of hotels when you're signed in [Sign in](https://expedia.ca/user/signin?ckoflag=0&uurl=e3id%3Dredr%26rurl%3D%2FOldsmar-Cottages.d141455-aaCottages.Travel-Guide-Accommodation)[Sign up, it's free](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FOldsmar-Cottages.d141455-aaCottages.Travel-Guide-Accommodation) ## Top Oldsmar Hotel Reviews ![Hampton Inn & Suites Tampa Airport Avion Park Westshore](//images.trvl-media.com/lodging/16000000/15820000/15816100/15816033/3e0be467_y.jpg) ### Hampton Inn & Suites Tampa Airport Avion Park Westshore 10/10 Excellent "Enjoyable stay" [](https://expedia.ca/Tampa-Hotels-Hampton-Inn-Suites-Tampa-Airport-Avion-Park-Westshore.h15816033.Hotel-Information) ![Hyatt Regency Clearwater Beach Resort & Spa](//images.trvl-media.com/lodging/3000000/2710000/2703500/2703419/d01b652e_y.jpg) ### Hyatt Regency Clearwater Beach Resort & Spa 10/10 Excellent "Everyone was excellent " [](https://expedia.ca/St-Petersburg-Clearwater-Hotels-Hyatt-Regency-Clearwater-Beach-Resort-Spa.h2703419.Hotel-Information) ![Hotel Tampa Riverwalk](//images.trvl-media.com/lodging/1000000/30000/22400/22354/e58c12ba_y.jpg) ### Hotel Tampa Riverwalk 10/10 Excellent "I loved the Riverwalk. It made getting around the area so nice. I would suggest there be better public access areas to it. " [](https://expedia.ca/Tampa-Hotels-Hotel-Tampa-Riverwalk.h22354.Hotel-Information) ![Hampton Inn Tampa Downtown Channel District](//images.trvl-media.com/lodging/33000000/32920000/32911500/32911463/c5627bb7_y.jpg) ### Hampton Inn Tampa Downtown Channel District 10/10 Excellent "I stayed close to my upcoming cruise very convenient." [](https://expedia.ca/Tampa-Hotels-Hampton-Inn-Tampa-Downtown-Channel-District.h32911463.Hotel-Information) ![Hilton Clearwater Beach Resort & Spa](//images.trvl-media.com/lodging/1000000/30000/28100/28023/da46d3f6_y.jpg) ### Hilton Clearwater Beach Resort & Spa 10/10 Excellent "Very nice. " [](https://expedia.ca/St-Petersburg-Clearwater-Hotels-Hilton-Clearwater-Beach-Resort-Spa.h28023.Hotel-Information) ![Opal Sands Resort](//images.trvl-media.com/lodging/1000000/20000/14200/14189/c4ab1506_y.jpg) ### Opal Sands Resort 10/10 Excellent "The property was very nice and the staff was amazing. The gulf views were great! " [](https://expedia.ca/St-Petersburg-Clearwater-Hotels-Opal-Sands-Resort.h14189.Hotel-Information) ![Wyndham Grand Clearwater Beach](//images.trvl-media.com/lodging/16000000/15920000/15914400/15914352/3e998290_y.jpg) ### Wyndham Grand Clearwater Beach 10/10 Excellent "Everyone was amazing " [](https://expedia.ca/St-Petersburg-Clearwater-Hotels-Wyndham-Grand-Clearwater-Beach.h15914352.Hotel-Information) ![GALAXY HOTEL](//images.trvl-media.com/lodging/94000000/93460000/93451700/93451698/9abe5c82_y.jpg) ### GALAXY HOTEL 10/10 Excellent "Great place to stay and walking distance to the pier! Will come again!" [](https://expedia.ca/St-Petersburg-Clearwater-Hotels-GALAXY-HOTEL.h93451698.Hotel-Information) ![Shephard's Beach Resort](//images.trvl-media.com/lodging/1000000/870000/870000/869973/95dee199_y.jpg) ### Shephard's Beach Resort 10/10 Excellent "The staff was nice kept rooms clean. Only concern music from the club keep me up til after 3am. Other than that beautiful place. " [](https://expedia.ca/St-Petersburg-Clearwater-Hotels-Shephards-Beach-Resort.h869973.Hotel-Information) ## Find out more about Oldsmar ## Oldsmar Cottages information | Number of reviews | 1,125 | | --- | --- | | Accommodation | 500 Cottages | | Lowest Price | CA $294 | | Highest Price | CA $498 | ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - Vacation Rental - More ways to book - [5 Star Hotels in Westchase](https://www.expedia.ca/5Star-Westchase-Tampa-Hotels.s50-n553248635077748315-0.Travel-Guide-Filter-Hotels) - [Bay Towne Hotels](https://www.expedia.ca/Bay-Towne-St-Petersburg-Clearwater-Hotels.0-n553248635976474176-0.Travel-Guide-Filter-Hotels) - [Hotels near Chi Chi Rodriguez Golf Club](https://www.expedia.ca/Chi-Chi-Rodriguez-Golf-Club-Hotels.0-l6277237-0.Travel-Guide-Filter-Hotels) - [Farmstay in Dunedin](https://www.expedia.ca/Dunedin-Agritourism.d7932-aaAgritourism.Travel-Guide-Accommodation) - [Aparthotels in Dunedin](https://www.expedia.ca/Dunedin-Apart-Hotels.d7932-aaApartHotels.Travel-Guide-Accommodation) - 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