Title: Book the Best Hotels with POOL in Florida in 2026 | Expedia.ca [Hotels in Florida](https://expedia.ca/Florida-Hotels.d553248634999031091.Travel-Guide-Hotels)[Vacation Rentals in Florida](https://expedia.ca/Florida-Vacation-Rentals.d553248634999031091.Travel-Guide-VacationRentals)[Florida Car Rentals](https://expedia.ca/Car-Rentals-In-Florida.d553248634999031091.Car-Rental-Guide)[Florida Vacation Packages](https://expedia.ca/Florida.d553248634999031091.Destination-Travel-Guides) ![Two beautiful cascades that combine and form several crystal clear pools along the stream. ](https://images.trvl-media.com/place/553248634999031091/a1407374-cf5a-4fd5-91c7-15f31fa15fae.jpg?impolicy=fcrop&w=1200&h=500&q=medium) Photo by Chris Addams ![](https://images.trvl-media.com/place/553248634999031091/a1407374-cf5a-4fd5-91c7-15f31fa15fae.jpg?impolicy=fcrop&w=1200&h=500&q=medium) - ![](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 Florida Hotels with a Pool Tonight [Jan 15 - Jan 16](https://www.expedia.ca/Hotel-Search?regionId=553248634999031091&startDate=2026-01-15&endDate=2026-01-16&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Jan 16 - Jan 17](https://www.expedia.ca/Hotel-Search?regionId=553248634999031091&startDate=2026-01-16&endDate=2026-01-17&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Jan 16 - Jan 18](https://www.expedia.ca/Hotel-Search?regionId=553248634999031091&startDate=2026-01-16&endDate=2026-01-18&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Jan 23 - Jan 25](https://www.expedia.ca/Hotel-Search?regionId=553248634999031091&startDate=2026-01-23&endDate=2026-01-25&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Our top choices for Florida hotels with a pool ![Seasonal outdoor pool, open 10:00 AM to 8:00 PM, pool umbrellas](https://images.trvl-media.com/lodging/123000000/122980000/122978200/122978111/bbf5ae58.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property amenity](https://images.trvl-media.com/lodging/123000000/122980000/122978200/122978111/c5bdc83b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property amenity](https://images.trvl-media.com/lodging/123000000/122980000/122978200/122978111/67f64adc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property amenity](https://images.trvl-media.com/lodging/123000000/122980000/122978200/122978111/a0514206_edited_9a33.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hideaway Inn Mt. Snow [](https://www.expedia.ca/West-Dover-Hotels-Hideaway-Inn-Mt-Snow.h122978111.Hotel-Information) West Dover 8.8/10 Excellent (24 reviews) "Great cozy hotel very close to Mount Snow. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Yuhui CA $183 CA $202 total includes taxes & fees Jan 20 - Jan 21 [](https://www.expedia.ca/West-Dover-Hotels-Hideaway-Inn-Mt-Snow.h122978111.Hotel-Information) ![Indoor pool](https://images.trvl-media.com/lodging/1000000/10000/2100/2067/91284a89.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Restaurant](https://images.trvl-media.com/lodging/1000000/10000/2100/2067/a50a3d54.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Hypo-allergenic bedding, desk, laptop workspace, blackout drapes](https://images.trvl-media.com/lodging/1000000/10000/2100/2067/a97806ae.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Hypo-allergenic bedding, desk, laptop workspace, blackout drapes](https://images.trvl-media.com/lodging/1000000/10000/2100/2067/207845f4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Holiday Inn & Suites Pittsfield-Berkshires by IHG [](https://www.expedia.ca/Pittsfield-Hotels-Holiday-Inn-Suites-Pittsfield-Berkshires.h2067.Hotel-Information) Pittsfield 8.0/10 Very good (1,000 reviews) "Everyone that works here is so nice! I’ve stayed here twice and had such a nice time. Thank youN" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Melissa CA $136 CA $152 total includes taxes & fees Jan 23 - Jan 24 [](https://www.expedia.ca/Pittsfield-Hotels-Holiday-Inn-Suites-Pittsfield-Berkshires.h2067.Hotel-Information) ![Indoor pool](https://images.trvl-media.com/lodging/2000000/1200000/1192000/1191981/7884a10e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Desk, blackout drapes, iron/ironing board, travel crib](https://images.trvl-media.com/lodging/2000000/1200000/1192000/1191981/c7a3db42.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/2000000/1200000/1192000/1191981/aadd5504.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/2000000/1200000/1192000/1191981/b8d928ab.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hampton Inn Bennington [](https://www.expedia.ca/Bennington-Hotels-Hampton-Inn-Bennington.h1191981.Hotel-Information) Bennington 8.6/10 Excellent (1,000 reviews) "Clean rooms, friendly staff, good breakfast, comfy beds." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) William CA $181 CA $197 total includes taxes & fees Feb 1 - Feb 2 [](https://www.expedia.ca/Bennington-Hotels-Hampton-Inn-Bennington.h1191981.Hotel-Information) ![Outdoor pool](https://images.trvl-media.com/lodging/2000000/1760000/1753400/1753359/7549d558.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/2000000/1760000/1753400/1753359/dccac924.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/2000000/1760000/1753400/1753359/65150c76.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/2000000/1760000/1753400/1753359/3ba2e773.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Willows Motel Williamstown [](https://www.expedia.ca/Williamstown-Hotels-Willows-Motel-Williamstown.h1753359.Hotel-Information) Williamstown 9.0/10 Wonderful (1,001 reviews) "Wonderful. Great hosts. Would 100% stay again" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Ben CA $106 CA $119 total includes taxes & fees Jan 16 - Jan 17 [](https://www.expedia.ca/Williamstown-Hotels-Willows-Motel-Williamstown.h1753359.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/120000000/119110000/119106200/119106200/439bea3f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby sitting area](https://images.trvl-media.com/lodging/120000000/119110000/119106200/119106200/3d1e6eef.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Superior Suite, 1 King Bed with Sofa bed, Kitchen | Private kitchen](https://images.trvl-media.com/lodging/120000000/119110000/119106200/119106200/f2112a41.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Signature Studio | Private kitchen](https://images.trvl-media.com/lodging/120000000/119110000/119106200/119106200/0716f688.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Knotty Pine [](https://www.expedia.ca/Bennington-Hotels-Knotty-Pine.h119106200.Hotel-Information) Bennington 8.8/10 Excellent (55 reviews) "Great property and a great value!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Keith CA $210 CA $229 total includes taxes & fees Jan 16 - Jan 17 [](https://www.expedia.ca/Bennington-Hotels-Knotty-Pine.h119106200.Hotel-Information) ![Gazebo](https://images.trvl-media.com/lodging/5000000/4600000/4595900/4595809/6df66696.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Standard Room, 1 Queen Bed, Non Smoking](https://images.trvl-media.com/lodging/5000000/4600000/4595900/4595809/7aabad6c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/5000000/4600000/4595900/4595809/af22be9d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Point of interest](https://images.trvl-media.com/lodging/5000000/4600000/4595900/4595809/c0f1d776.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cozy Corner Motel [](https://www.expedia.ca/Williamstown-Hotels-Cozy-Corner-Motel.h4595809.Hotel-Information) Williamstown 9.2/10 Wonderful (890 reviews) "Excellent service and a beautifully decorated property." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Ivana CA $96 CA $114 total includes taxes & fees Feb 1 - Feb 2 [](https://www.expedia.ca/Williamstown-Hotels-Cozy-Corner-Motel.h4595809.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/3000000/2580000/2577700/2577695/9fde074c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Deluxe Room, 1 King Bed, Non Smoking](https://images.trvl-media.com/lodging/3000000/2580000/2577700/2577695/3bbe75f0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/3000000/2580000/2577700/2577695/1495f28f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/3000000/2580000/2577700/2577695/6cfdbbaf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hotel Vervana, Trademark Collection by Wyndham [](https://www.expedia.ca/Bennington-Hotels-Paradise-Inn.h2577695.Hotel-Information) Bennington 8.2/10 Very good (1,001 reviews) "Large rooms, great staff. Will stay again!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Kristyn CA $164 CA $179 total includes taxes & fees Jan 22 - Jan 23 [](https://www.expedia.ca/Bennington-Hotels-Paradise-Inn.h2577695.Hotel-Information) ![Lobby sitting area](https://images.trvl-media.com/lodging/2000000/1070000/1066500/1066423/03675fdd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/2000000/1070000/1066500/1066423/db44d375.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property - evening/night](https://images.trvl-media.com/lodging/2000000/1070000/1066500/1066423/9e460e0a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Indoor pool, outdoor pool, pool umbrellas](https://images.trvl-media.com/lodging/2000000/1070000/1066500/1066423/76732b8d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Vacation Village in the Berkshires [](https://www.expedia.ca/Williamstown-Hotels-Vacation-Village-In-The-Berkshires.h1066423.Hotel-Information) Williamstown 8.8/10 Excellent (2,209 reviews) "I great place to stay!!" ![United Kingdom](https://a.travel-assets.com/egds/marks/flags/uk.svg) Maricel CA $144 CA $176 total includes taxes & fees Jan 19 - Jan 20 [](https://www.expedia.ca/Williamstown-Hotels-Vacation-Village-In-The-Berkshires.h1066423.Hotel-Information) ![Seasonal outdoor pool, open 9 AM to 8 PM, pool umbrellas, sun loungers](https://images.trvl-media.com/lodging/14000000/13280000/13279000/13278987/92f285fa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Buffet](https://images.trvl-media.com/lodging/14000000/13280000/13279000/13278987/fb19d853.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/14000000/13280000/13279000/13278987/25f05b7c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property - evening/night](https://images.trvl-media.com/lodging/14000000/13280000/13279000/13278987/f3854c71.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Maple Terrace Motel [](https://www.expedia.ca/Williamstown-Hotels-Maple-Terrace-Motel.h13278987.Hotel-Information) Williamstown 9.6/10 Exceptional (595 reviews) "Cute place" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Lisa CA $137 CA $154 total includes taxes & fees Jan 20 - Jan 21 [](https://www.expedia.ca/Williamstown-Hotels-Maple-Terrace-Motel.h13278987.Hotel-Information) ![Seasonal outdoor pool](https://images.trvl-media.com/lodging/96000000/95130000/95124600/95124564/45b65286.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Cabin, 3 Bedrooms, Mountainside | Living area](https://images.trvl-media.com/lodging/96000000/95130000/95124600/95124564/2f0dc604_edited_9c5b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Honeymoon Suite, 1 King Bed, Patio](https://images.trvl-media.com/lodging/96000000/95130000/95124600/95124564/8c32bd34.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Courtyard](https://images.trvl-media.com/lodging/96000000/95130000/95124600/95124564/9722ad97.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Springs Motel [](https://www.expedia.ca/New-Ashford-Hotels-The-Springs-Motel.h95124564.Hotel-Information) New Ashford 9.2/10 Wonderful (90 reviews) "Great vibe. Comfortable great staff" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Bart CA $190 CA $208 total includes taxes & fees Jan 29 - Jan 30 [](https://www.expedia.ca/New-Ashford-Hotels-The-Springs-Motel.h95124564.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=2026-01-29&endDate=2026-01-30®ionId=553248634999031091&adults=2&amenities=POOL&sort=RECOMMENDED&openPlayBack=true) ## Top Florida Hotel Reviews ![Holiday Inn & Suites Pittsfield-Berkshires by IHG](https://images.trvl-media.com/lodging/1000000/10000/2100/2067/a50a3d54_y.jpg) ### Holiday Inn & Suites Pittsfield-Berkshires by IHG 10/10 Excellent "Staff was very courteous and rooms clean." [](https://expedia.ca/Pittsfield-Hotels-Holiday-Inn-Suites-Pittsfield-Berkshires.h2067.Hotel-Information) ![Hampton Inn Bennington](https://images.trvl-media.com/lodging/2000000/1200000/1192000/1191981/aadd5504_y.jpg) ### Hampton Inn Bennington 10/10 Excellent "Good Beautiful stay" [](https://expedia.ca/Bennington-Hotels-Hampton-Inn-Bennington.h1191981.Hotel-Information) ![The Porches Inn at Mass MoCA](https://images.trvl-media.com/lodging/8000000/7670000/7662400/7662392/dcf42e0d_y.jpg) ### The Porches Inn at Mass MoCA 10/10 Excellent "Wow. This hotel is such a great find. Not only is it clean and unique, the rooms are large and the staff are super helpful and nice. Breakfast was nice. The pool was slightly colder than I expected but it was 5 degrees outside and windy so its understandable. The hot tub was very comfortable. I would love to stay here again. My kids said this is their favorite hotel we have ever stayed at which is high praise since we travel frequently and have stayed in a ton of hotels!" [](https://expedia.ca/North-Adams-Hotels-The-Porches-Inn.h7662392.Hotel-Information) ![Vacation Village in the Berkshires](https://images.trvl-media.com/lodging/2000000/1070000/1066500/1066423/012d1fc0_y.jpg) ### Vacation Village in the Berkshires 10/10 Excellent "The rooms are clean, the pool is nice and the location is perfect for Jiminy Peak! " [](https://expedia.ca/Williamstown-Hotels-Vacation-Village-In-The-Berkshires.h1066423.Hotel-Information) ![Hotel Downstreet, an Ascend Collection Hotel](https://images.trvl-media.com/lodging/1000000/10000/3000/2943/73bb1216_y.jpg) ### Hotel Downstreet, an Ascend Collection Hotel 10/10 Excellent "friendly accommodating staff" [](https://expedia.ca/North-Adams-Hotels-Holiday-Inn-Berkshires.h2943.Hotel-Information) ![Hampton Inn & Suites Greenfield](https://images.trvl-media.com/lodging/2000000/1610000/1601100/1601018/72e137d6_y.jpg) ### Hampton Inn & Suites Greenfield 10/10 Excellent "very quiet" [](https://expedia.ca/Greenfield-Hotels-Hampton-Inn-Suites-Greenfield.h1601018.Hotel-Information) ![Mount Snow Grand Summit Resort](https://images.trvl-media.com/lodging/1000000/670000/663200/663170/57303655_y.jpg) ### Mount Snow Grand Summit Resort 10/10 Excellent "Ski slopes were accessible and pool was really nice. " [](https://expedia.ca/West-Dover-Hotels-Mount-Snow-Grand-Summit-Resort.h663170.Hotel-Information) ## Frequently asked questions ### What are some accommodations with pools in Florida? ### What is there to see and do in Florida? ### When is the best time to book a hotel with a pool in Florida? ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - More ways to book - [4 Star Hotels in North Adams ](https://www.expedia.ca/4Star-North-Adams-Hotels.s40-0-d9137.Travel-Guide-Filter-Hotels) - [Farmstay in Adams ](https://www.expedia.ca/Adams-Agritourism.d6005393-aaAgritourism.Travel-Guide-Accommodation) - [Aparthotels in Adams ](https://www.expedia.ca/Adams-Apart-Hotels.d6005393-aaApartHotels.Travel-Guide-Accommodation) - [B&B in Adams ](https://www.expedia.ca/Adams-Bed-And-Breakfast.d6005393-aaBedAndBreakfast.Travel-Guide-Accommodation) - [Chalets in Adams ](https://www.expedia.ca/Adams-Chalets.d6005393-aaChalets.Travel-Guide-Accommodation) - [Guest Houses in Adams ](https://www.expedia.ca/Adams-Guest-Houses.d6005393-aaGuestHouses.Travel-Guide-Accommodation) - 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