Title: Book the Best Hotels with POOL in Hillcrest Heights in 2026 | Expedia.ca [Hotels in Hillcrest Heights](https://expedia.ca/Hillcrest-Heights-Hotels.d553248634998801888.Travel-Guide-Hotels)[Vacation Rentals in Hillcrest Heights](https://expedia.ca/Hillcrest-Heights-Vacation-Rentals.d553248634998801888.Travel-Guide-VacationRentals)[Hillcrest Heights Car Rentals](https://expedia.ca/Car-Rentals-In-Hillcrest-Heights.d553248634998801888.Car-Rental-Guide)[Hillcrest Heights Vacation Packages](https://expedia.ca/Hillcrest-Heights.d553248634998801888.Destination-Travel-Guides) ![Default HTG hotel image](https://a.travel-assets.com/travel-assets-manager/fallback-images-brand/bex_lodging_v2.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # Find Hotels with a Pool in Hillcrest Heights, FL from CA $130 - ![](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 Hillcrest Heights Hotels with a Pool Tonight [Dec 16 - Dec 17](https://www.expedia.ca/Hotel-Search?regionId=553248634998801888&startDate=2025-12-16&endDate=2025-12-17&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Dec 17 - Dec 18](https://www.expedia.ca/Hotel-Search?regionId=553248634998801888&startDate=2025-12-17&endDate=2025-12-18&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Dec 19 - Dec 21](https://www.expedia.ca/Hotel-Search?regionId=553248634998801888&startDate=2025-12-19&endDate=2025-12-21&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Dec 26 - Dec 28](https://www.expedia.ca/Hotel-Search?regionId=553248634998801888&startDate=2025-12-26&endDate=2025-12-28&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Our top choices for Hillcrest Heights hotels with a pool ![Outdoor pool, open 9:00 AM to 9:00 PM, pool umbrellas, sun loungers](https://images.trvl-media.com/lodging/31000000/30540000/30538000/30537958/228a563a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/31000000/30540000/30538000/30537958/123acaa7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Desk, laptop workspace, WiFi](https://images.trvl-media.com/lodging/31000000/30540000/30538000/30537958/abef6619.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Children's play area - outdoor](https://images.trvl-media.com/lodging/31000000/30540000/30538000/30537958/a3da91f6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### LEGOLAND Beach Retreat [](https://www.expedia.ca/Winter-Haven-Hotels-LEGOLAND-Beach-Retreat.h30537958.Hotel-Information) Winter Haven 9.2/10 Wonderful (141) "Overall great exsprience. Satff,rooms and amenities were great" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Tanisha CA $370 CA $469 total includes taxes & fees Jan 2 - Jan 3, 2026 [](https://www.expedia.ca/Winter-Haven-Hotels-LEGOLAND-Beach-Retreat.h30537958.Hotel-Information) ![Outdoor pool](https://images.trvl-media.com/lodging/1000000/870000/869100/869008/86782e20.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/870000/869100/869008/5d59340b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Iron/ironing board, free WiFi, bed sheets, alarm clocks](https://images.trvl-media.com/lodging/1000000/870000/869100/869008/f9ff5c5b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/870000/869100/869008/151260d6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Rodeway Inn Lake Wales - Winter Haven [](https://www.expedia.ca/Lake-Wales-Hotels-Rodeway-Inn.h869008.Hotel-Information) Lake Wales 8.2/10 Very good (167) "Easy check-in friendly staff quiet atmosphere clean rooms" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Erica CA $116 CA $130 total includes taxes & fees Dec 22 - Dec 23 [](https://www.expedia.ca/Lake-Wales-Hotels-Rodeway-Inn.h869008.Hotel-Information) ![Seasonal outdoor pool](https://images.trvl-media.com/lodging/107000000/106210000/106204500/106204409/b3fa944f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![LED TV, Netflix, streaming services](https://images.trvl-media.com/lodging/107000000/106210000/106204500/106204409/5a55f480.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/107000000/106210000/106204500/106204409/533a79f7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Coffee/tea maker, eco-friendly cleaning products](https://images.trvl-media.com/lodging/107000000/106210000/106204500/106204409/320658cf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Home2 Suites By Hilton Winter Haven [](https://www.expedia.ca/Winter-Haven-Hotels-Home2-Suites-By-Hilton-Winter-Haven.h106204409.Hotel-Information) Winter Haven 9.4/10 Exceptional (262) "Great room and location " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Ashley CA $197 CA $221 total includes taxes & fees Jan 12 - Jan 13, 2026 [](https://www.expedia.ca/Winter-Haven-Hotels-Home2-Suites-By-Hilton-Winter-Haven.h106204409.Hotel-Information) ![Outdoor pool, sun loungers](https://images.trvl-media.com/lodging/3000000/2850000/2840600/2840563/8a9cb8cc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/3000000/2850000/2840600/2840563/3bc566b4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free buffet breakfast](https://images.trvl-media.com/lodging/3000000/2850000/2840600/2840563/21f69873.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Standard Room, 2 Queen Beds (310 Sq Ft)](https://images.trvl-media.com/lodging/3000000/2850000/2840600/2840563/543dab5c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Holiday Inn Express Lake Wales N-Winter Haven by IHG [](https://www.expedia.ca/Lake-Wales-Hotels-Holiday-Inn-Express-Lake-Wales-N-Winter-Haven.h2840563.Hotel-Information) Lake Wales 9.2/10 Wonderful (1008) "Room was comfortable, breakfast was good, and fresh grind and brew individual coffee was excellent." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jaci CA $168 CA $188 total includes taxes & fees Jan 1 - Jan 2, 2026 [](https://www.expedia.ca/Lake-Wales-Hotels-Holiday-Inn-Express-Lake-Wales-N-Winter-Haven.h2840563.Hotel-Information) ![Outdoor pool, sun loungers](https://images.trvl-media.com/lodging/2000000/1890000/1887700/1887650/91512114.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor banquet area](https://images.trvl-media.com/lodging/2000000/1890000/1887700/1887650/20bcb6ae.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/2000000/1890000/1887700/1887650/7dd4826d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/2000000/1890000/1887700/1887650/db1d10af.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Lake Roy Beach Inn [](https://www.expedia.ca/Winter-Haven-Hotels-Lake-Roy-Beach-Inn.h1887650.Hotel-Information) Winter Haven 7.0/10 Good (989) "Great very nice comfortable room" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Rian CA $124 CA $139 total includes taxes & fees Dec 19 - Dec 20 [](https://www.expedia.ca/Winter-Haven-Hotels-Lake-Roy-Beach-Inn.h1887650.Hotel-Information) ![Outdoor pool, pool umbrellas, sun loungers](https://images.trvl-media.com/lodging/1000000/570000/564300/564220/6f77a3fa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/570000/564300/564220/ce28e0a8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/1000000/570000/564300/564220/a0e09929.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Restaurant](https://images.trvl-media.com/lodging/1000000/570000/564300/564220/fee4543f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hampton Inn Winter Haven [](https://www.expedia.ca/Winter-Haven-Hotels-Hampton-Inn-Winter-Haven.h564220.Hotel-Information) Winter Haven 9.0/10 Wonderful (1003) "Clean room, staff was nice, breakfast was good, easy parking." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jessica CA $178 CA $200 total includes taxes & fees Dec 21 - Dec 22 [](https://www.expedia.ca/Winter-Haven-Hotels-Hampton-Inn-Winter-Haven.h564220.Hotel-Information) ![Outdoor pool, open 8:30 AM to 9:00 PM, pool umbrellas, sun loungers](https://images.trvl-media.com/lodging/1000000/10000/8800/8718/24439804.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior entrance](https://images.trvl-media.com/lodging/1000000/10000/8800/8718/e9fdf4e1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free daily continental breakfast](https://images.trvl-media.com/lodging/1000000/10000/8800/8718/fda6d33f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Blackout drapes, iron/ironing board, free cribs/infant beds](https://images.trvl-media.com/lodging/1000000/10000/8800/8718/71d67783.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Howard Johnson by Wyndham Winter Haven FL [](https://www.expedia.ca/Winter-Haven-Hotels-Howard-Johnson-By-Wyndham-Winter-Haven-FL.h8718.Hotel-Information) Winter Haven 7.0/10 Good (1014) "Nice hotel. Clean and great location. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Raylene CA $117 CA $131 total includes taxes & fees Dec 30 - Dec 31 [](https://www.expedia.ca/Winter-Haven-Hotels-Howard-Johnson-By-Wyndham-Winter-Haven-FL.h8718.Hotel-Information) ![Outdoor pool, pool umbrellas, sun loungers](https://images.trvl-media.com/lodging/32000000/31540000/31534300/31534220/a1efacf5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Cabin, 1 Bedroom (Cabin 61) | Living area](https://images.trvl-media.com/lodging/32000000/31540000/31534300/31534220/c42f24ff.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Cabin, 1 Bedroom (Cabin 55)](https://images.trvl-media.com/lodging/32000000/31540000/31534300/31534220/0d30c658.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Marina](https://images.trvl-media.com/lodging/32000000/31540000/31534300/31534220/aa2b95a9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Camp Mack Lodge, Marina & RV Resort [](https://www.expedia.ca/Lake-Wales-Hotels-Guy-Harvey-Camp-Mack-Lodge-RV-Resort.h31534220.Hotel-Information) Lake Wales 9.0/10 Wonderful (190) "We lived our stay and can't wait to come back soon" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Ramona [](https://www.expedia.ca/Lake-Wales-Hotels-Guy-Harvey-Camp-Mack-Lodge-RV-Resort.h31534220.Hotel-Information) ![Outdoor pool](https://images.trvl-media.com/lodging/92000000/91230000/91221300/91221257/41f09c21.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, video games, books](https://images.trvl-media.com/lodging/92000000/91230000/91221300/91221257/ad804664.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior detail](https://images.trvl-media.com/lodging/92000000/91230000/91221300/91221257/435432d0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, video games, books](https://images.trvl-media.com/lodging/92000000/91230000/91221300/91221257/4d2e3d0f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Heated Pool and Hot tub-near Legoland, Disney, Theme parks [](https://www.expedia.ca/Winter-Haven-Hotels-Pool-Home-Near-Legoland.h91221257.Hotel-Information) Winter Haven 9.8/10 Exceptional (39) "We had a great stay!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Harper B. CA $160 CA $431 total includes taxes & fees Dec 18 - Dec 19 [](https://www.expedia.ca/Winter-Haven-Hotels-Pool-Home-Near-Legoland.h91221257.Hotel-Information) ![Outdoor pool, pool umbrellas, sun loungers](https://images.trvl-media.com/lodging/92000000/91030000/91030000/91029909/0b1acfca.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property amenity](https://images.trvl-media.com/lodging/92000000/91030000/91030000/91029909/a610a46d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Standard Room, 2 Queen Beds, Non Smoking, Bathtub (Larger Room)](https://images.trvl-media.com/lodging/92000000/91030000/91030000/91029909/b48185c3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Standard Room, 2 Queen Beds, Non Smoking, Kitchenette | Private kitchen](https://images.trvl-media.com/lodging/92000000/91030000/91030000/91029909/2eced5ea.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Best Western Plus Winter Haven Inn & Suites [](https://www.expedia.ca/Winter-Haven-Hotels-Best-Western-Plus-Winter-Haven-Inn-Suites.h91029909.Hotel-Information) Winter Haven 9.6/10 Exceptional (1082) "Clean rooms, great staff" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Whitney CA $185 CA $207 total includes taxes & fees Dec 21 - Dec 22 [](https://www.expedia.ca/Winter-Haven-Hotels-Best-Western-Plus-Winter-Haven-Inn-Suites.h91029909.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=2025-12-30&endDate=2025-12-31®ionId=553248634998801888&adults=2&amenities=POOL&sort=RECOMMENDED&openPlayBack=true) ## Top Hillcrest Heights Hotel Reviews ![Holiday Inn Express Lake Wales N-Winter Haven by IHG](https://images.trvl-media.com/lodging/3000000/2850000/2840600/2840563/ec483d12_y.jpg) ### Holiday Inn Express Lake Wales N-Winter Haven by IHG 10/10 Excellent "Clean room, friendly staff, good breakfast, close to gas station, restaurants, shopping. " [](https://expedia.ca/Lake-Wales-Hotels-Holiday-Inn-Express-Lake-Wales-N-Winter-Haven.h2840563.Hotel-Information) ![Howard Johnson by Wyndham Winter Haven FL](https://images.trvl-media.com/lodging/1000000/10000/8800/8718/71d67783_y.jpg) ### Howard Johnson by Wyndham Winter Haven FL 10/10 Excellent "A very curious staff! Which was very nice! We had a good time! The hotel was nice!Will definitely use them again!" [](https://expedia.ca/Winter-Haven-Hotels-Howard-Johnson-By-Wyndham-Winter-Haven-FL.h8718.Hotel-Information) ![Hampton Inn & Suites Lake Wales](https://images.trvl-media.com/lodging/2000000/1850000/1844900/1844847/864352b8_y.jpg) ### Hampton Inn & Suites Lake Wales 10/10 Excellent "Everything was first class." [](https://expedia.ca/Lake-Wales-Hotels-Hampton-Inn-Suites-Lake-Wales.h1844847.Hotel-Information) ![Holiday Inn Winter Haven by IHG](https://images.trvl-media.com/lodging/1000000/10000/7900/7835/1b5518c0_y.jpg) ### Holiday Inn Winter Haven by IHG 10/10 Excellent "Staff very nice and efficient. " [](https://expedia.ca/Winter-Haven-Hotels-Holiday-Inn-Winter-Haven.h7835.Hotel-Information) ![Lake Roy Beach Inn](https://images.trvl-media.com/lodging/2000000/1890000/1887700/1887650/66ef3784_y.jpg) ### Lake Roy Beach Inn 10/10 Excellent "Great very nice comfortable room" [](https://expedia.ca/Winter-Haven-Hotels-Lake-Roy-Beach-Inn.h1887650.Hotel-Information) ![Hampton Inn Winter Haven](https://images.trvl-media.com/lodging/1000000/570000/564300/564220/ce28e0a8_y.jpg) ### Hampton Inn Winter Haven 10/10 Excellent "Everything was great! " [](https://expedia.ca/Winter-Haven-Hotels-Hampton-Inn-Winter-Haven.h564220.Hotel-Information) ![Rodeway Inn & Suites Winter Haven Chain Of Lakes](https://images.trvl-media.com/lodging/2000000/1610000/1604200/1604174/06c96288_y.jpg) ### Rodeway Inn & Suites Winter Haven Chain Of Lakes 10/10 Excellent "Great night " [](https://expedia.ca/Winter-Haven-Hotels-Rodeway-Inn-Suites-Winter-Haven-Chain-Of-Lakes.h1604174.Hotel-Information) ![Rodeway Inn & Suites Haines City - Winter Haven](https://images.trvl-media.com/lodging/1000000/10000/9700/9688/2f9ce223_y.jpg) ### Rodeway Inn & Suites Haines City - Winter Haven 10/10 Excellent "Will stay again" [](https://expedia.ca/Haines-City-Hotels-Rodeway-Inn-And-Suites.h9688.Hotel-Information) ![OYO Hotel Dundee By Crystal Lake](https://images.trvl-media.com/lodging/1000000/30000/27200/27155/1e5aab46_y.jpg) ### OYO Hotel Dundee By Crystal Lake 10/10 Excellent "Everything is fine " [](https://expedia.ca/Dundee-Hotels-OYO-Hotel-Dundee-By-Crystal-Lake.h27155.Hotel-Information) ## Frequently asked questions ### What are some hotels with pools in Hillcrest Heights? ### What is there to see and do in Hillcrest Heights? ### When is the best time to book a hotel with a pool in Hillcrest Heights? ## Explore a world of travel with Expedia - 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