Title: 5 Stars Hotels in Highland Oaks, St. Petersburg - Clearwater from CA $173 - Find Cheap Highland Oaks Hotels With 5 Stars | Expedia.ca [Highland Oaks Travel Guide](https://expedia.ca/St-Petersburg-Clearwater-Highland-Oaks.dx553248635976473692)[Vacation Rentals in St. Petersburg - Clearwater](https://expedia.ca/St-Petersburg-Clearwater-Vacation-Rentals.d178310.Travel-Guide-VacationRentals)[Flights to St. Petersburg - Clearwater](https://expedia.ca/Cheap-Flights-To-St-Petersburg-Clearwater.d178310.Travel-Guide-Flights)[Things to do in St. Petersburg - Clearwater](https://expedia.ca/Things-To-Do-In-St-Petersburg-Clearwater.d178310.Travel-Guide-Activities)[Highland Oaks Car Rentals](https://expedia.ca/Car-Rentals-In-Highland-Oaks.d553248635976473692.Car-Rental-Guide)[Highland Oaks Vacations](https://expedia.ca/Highland-Oaks.d553248635976473692.Destination-Travel-Guides) ![Default HTG hotel image](https://media.expedia.com/media/content/shared/images/travelguides/sem-hotels-tablet.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # 5 Stars Hotels in Highland Oaks, St. Petersburg - Clearwater from CA $173 ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__calendar_shield.svg) ### Change your mind Book hotels with free cancellation ![](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) ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__bed.svg) ### Be picky Search almost a million properties worldwide ## Check availability on Highland Oaks 5 Star Hotels Tonight [Oct 14 - Oct 15](https://www.expedia.ca/Hotel-Search?regionId=553248635976473692&startDate=2025-10-14&endDate=2025-10-15&adults=2&star=50&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Oct 15 - Oct 16](https://www.expedia.ca/Hotel-Search?regionId=553248635976473692&startDate=2025-10-15&endDate=2025-10-16&adults=2&star=50&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Oct 17 - Oct 19](https://www.expedia.ca/Hotel-Search?regionId=553248635976473692&startDate=2025-10-17&endDate=2025-10-19&adults=2&star=50&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Oct 24 - Oct 26](https://www.expedia.ca/Hotel-Search?regionId=553248635976473692&startDate=2025-10-24&endDate=2025-10-26&adults=2&star=50&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Top Highland Oaks 5 Star Hotels ![Outdoor pool, cabanas (surcharge), pool umbrellas](https://images.trvl-media.com/lodging/84000000/83990000/83980300/83980287/cbddc2cf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Garden](https://images.trvl-media.com/lodging/84000000/83990000/83980300/83980287/8d2fa88d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![3 restaurants, Mediterranean cuisine](https://images.trvl-media.com/lodging/84000000/83990000/83980300/83980287/da223d4f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/84000000/83990000/83980300/83980287/7b52caf6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Tampa EDITION Downtown Tampa 9.2/10 Wonderful (294) "Loved this hotel!" CA $504 CA $628 total includes taxes & fees Oct 30 - Oct 31 [](https://www.expedia.ca/Tampa-Hotels-The-Tampa-Downtown-EDITION.h83980287.Hotel-Information) ![Luxury Townhome | Living area](https://images.trvl-media.com/lodging/102000000/101340000/101338600/101338517/30bd9418.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Luxury Townhome | Private kitchen](https://images.trvl-media.com/lodging/102000000/101340000/101338600/101338517/33df7ff3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Marina](https://images.trvl-media.com/lodging/102000000/101340000/101338600/101338517/w800h531x0y3-531c6d5e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Luxury Townhome | Balcony](https://images.trvl-media.com/lodging/102000000/101340000/101338600/101338517/ac6e0605.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Little Harbor Resort at Bahia Beach Ruskin 9.4/10 Exceptional (21) "Nice place to stay" CA $196 CA $581 total includes taxes & fees Oct 17 - Oct 18 [](https://www.expedia.ca/Tampa-Hotels-Little-Harbor-Resort-At-Bahia-Beach.h101338517.Hotel-Information) ![Deluxe Villa, 5 Bedrooms, Garden View | Private kitchen](https://images.trvl-media.com/lodging/118000000/117150000/117146500/117146493/9b1574d5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Deluxe Villa, 5 Bedrooms, Garden View | Private kitchen](https://images.trvl-media.com/lodging/118000000/117150000/117146500/117146493/b75f0037.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor pool](https://images.trvl-media.com/lodging/118000000/117150000/117146500/117146493/61177646.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Deluxe Villa, 5 Bedrooms, Garden View](https://images.trvl-media.com/lodging/118000000/117150000/117146500/117146493/524ae604.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Indian Rocks Escape Largo [](https://www.expedia.ca/St-Petersburg-Clearwater-Hotels-Indian-Rocks-Escape.h117146493.Hotel-Information) ![Outdoor pool](https://images.trvl-media.com/lodging/51000000/50740000/50730500/50730470/310b4fee.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/51000000/50740000/50730500/50730470/c2071355.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House, Multiple Beds, Private Pool, Beach View | Private kitchen](https://images.trvl-media.com/lodging/51000000/50740000/50730500/50730470/3915a65a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House, Multiple Beds, Private Pool, Beach View | Living room](https://images.trvl-media.com/lodging/51000000/50740000/50730500/50730470/dc4ee32b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Sand Castle Anna Maria [](https://www.expedia.ca/Sarasota-Hotels-Sand-Castle.h50730470.Hotel-Information) ![Outdoor pool](https://images.trvl-media.com/lodging/41000000/40040000/40030300/40030276/d612bc3e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Deluxe Studio Suite, Hot Tub, Bay View | Private kitchen](https://images.trvl-media.com/lodging/41000000/40040000/40030300/40030276/47202bb7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fountain](https://images.trvl-media.com/lodging/41000000/40040000/40030300/40030276/892ad905.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Deluxe Studio Suite, Hot Tub, Bay View | Private kitchen](https://images.trvl-media.com/lodging/41000000/40040000/40030300/40030276/1ecd98b6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Amazing views on Treasure Island Isle of Palms [](https://www.expedia.ca/St-Petersburg-Clearwater-Hotels-Amazing-Views-On-Treasure-Island.h40030276.Hotel-Information) ![](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%2F5Star-Highland-Oaks-St-Petersburg-Clearwater-Hotels.s50-n553248635976473692-0.Travel-Guide-Filter-Hotels)[Sign up, it's free](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2F5Star-Highland-Oaks-St-Petersburg-Clearwater-Hotels.s50-n553248635976473692-0.Travel-Guide-Filter-Hotels) ## Explore similar 4-star hotels Many 4-star hotels have the same amenities as 5-star hotels. See all 4-star hotels in Highland Oaks. ![Hilton Tampa Airport Westshore](https://images.trvl-media.com/lodging/1000000/10000/5900/5870/13bee16f_y.jpg?impolicy=resizecrop&rw=402&ra=fit) ### Hilton Tampa Airport Westshore 2225 N Lois Ave, Tampa, FL CA $178 CA $202 total Nov 2 - Nov 3 includes taxes & fees 8.4/10 Very Good! (1,026 reviews) [](https://expedia.ca/Tampa-Hotels-Hilton-Tampa-Airport-Westshore.h5870.Hotel-Information) ![Hilton St. Petersburg Bayfront](https://images.trvl-media.com/lodging/1000000/30000/24300/24258/4658ed84_y.jpg?impolicy=resizecrop&rw=402&ra=fit) ### Hilton St. Petersburg Bayfront 333 1st St S, St. Petersburg, FL CA $153 CA $173 total Oct 26 - Oct 27 includes taxes & fees 7.6/10 Good! (1,020 reviews) [](https://expedia.ca/St-Petersburg-Clearwater-Hotels-Hilton-St-Petersburg-Bayfront.h24258.Hotel-Information) ![RumFish Beach at TradeWinds](https://images.trvl-media.com/lodging/1000000/10000/8600/8544/37eb40ec_y.jpg?impolicy=resizecrop&rw=402&ra=fit) ### RumFish Beach at TradeWinds 6000 Gulf Blvd, St. Pete Beach, FL CA $214 CA $329 total Oct 19 - Oct 20 includes taxes & fees 8.2/10 Very Good! (1,465 reviews) [](https://expedia.ca/St-Petersburg-Clearwater-Hotels-RumFish-Beach-Resort-By-TradeWinds.h8544.Hotel-Information) Still don't see what you're looking for? [See all properties in Highland Oaks.](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=15%2F10%2F2025&endDate=16%2F10%2F2025®ionId=553248635976473692&star=50) You can also use these popular filters to refine your search. [Pool](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=15%2F10%2F2025&endDate=16%2F10%2F2025®ionId=553248635976473692&star=50&star=50&amenities=POOL)[Spa](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=15%2F10%2F2025&endDate=16%2F10%2F2025®ionId=553248635976473692&star=50&star=50&amenities=SPA_ON_SITE)[Hot tub](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=15%2F10%2F2025&endDate=16%2F10%2F2025®ionId=553248635976473692&star=50&star=50&amenities=HOT_TUB)[Breakfast included](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=15%2F10%2F2025&endDate=16%2F10%2F2025®ionId=553248635976473692&star=50&star=50&amenities=FREE_BREAKFAST)[Waterpark](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=15%2F10%2F2025&endDate=16%2F10%2F2025®ionId=553248635976473692&star=50&star=50&amenities=WATER_PARK) Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. 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