Title: Book the Best Hotels with POOL in Florida in 2025 | 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 # Find Hotels with a Pool in Florida, MA from CA $124 - ![](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 [Nov 27 - Nov 28](https://www.expedia.ca/Hotel-Search?regionId=553248634999031091&startDate=2025-11-27&endDate=2025-11-28&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Nov 28 - Nov 29](https://www.expedia.ca/Hotel-Search?regionId=553248634999031091&startDate=2025-11-28&endDate=2025-11-29&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Nov 28 - Nov 30](https://www.expedia.ca/Hotel-Search?regionId=553248634999031091&startDate=2025-11-28&endDate=2025-11-30&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Dec 5 - Dec 7](https://www.expedia.ca/Hotel-Search?regionId=553248634999031091&startDate=2025-12-05&endDate=2025-12-07&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Top Florida Hotels with a Pool ![Indoor pool, outdoor pool, pool umbrellas](https://images.trvl-media.com/lodging/2000000/1070000/1066500/1066423/18127ca3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/2000000/1070000/1066500/1066423/012d1fc0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fireplace](https://images.trvl-media.com/lodging/2000000/1070000/1066500/1066423/64adfbe5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining room](https://images.trvl-media.com/lodging/2000000/1070000/1066500/1066423/16150550.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Vacation Village in the Berkshires Williamstown 8.8/10 Excellent (2149) "Great place!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Nicole CA $104 CA $132 total includes taxes & fees Nov 29 - Nov 30 [](https://www.expedia.ca/Williamstown-Hotels-Vacation-Village-In-The-Berkshires.h1066423.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) ![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) ![Front of property](https://images.trvl-media.com/lodging/120000000/119110000/119106200/119106200/5ca030cf.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) ### Knotty Pine Bennington 9.2/10 Wonderful (24) "The rooms were clean and well maintained. The staff was friendly. It is just a motel. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Martha CA $154 CA $168 total includes taxes & fees Dec 1 - Dec 2 [](https://www.expedia.ca/Bennington-Hotels-Knotty-Pine.h119106200.Hotel-Information) ![Seasonal outdoor pool](https://images.trvl-media.com/lodging/89000000/88740000/88730700/88730696/4a7d2d8e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Farmhouse 3, Signature Room, 1 King Bed and 1 Twin Sofa Bed, Non Smoking](https://images.trvl-media.com/lodging/89000000/88740000/88730700/88730696/df1eb844.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/89000000/88740000/88730700/88730696/ef464910.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property](https://images.trvl-media.com/lodging/89000000/88740000/88730700/88730696/dd84fb54.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Farm Road Estate West Dover 10/10 Exceptional (76) "Beautiful, peaceful friendly convenience" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Tammy CA $146 CA $238 total includes taxes & fees Nov 30 - Dec 1 [](https://www.expedia.ca/West-Dover-Hotels-Farm-Road-Estate.h88730696.Hotel-Information) ![Indoor pool, open 6:00 AM to 10 PM, sun loungers](https://images.trvl-media.com/lodging/1000000/10000/3000/2943/41222353.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/1000000/10000/3000/2943/73bb1216.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/1000000/10000/3000/2943/9903b094.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/1000000/10000/3000/2943/a866db4a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hotel Downstreet, an Ascend Collection Hotel North Adams 8.8/10 Excellent (1009) "Staff was very nice!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) David CA $150 CA $168 total includes taxes & fees Dec 20 - Dec 21 [](https://www.expedia.ca/North-Adams-Hotels-Holiday-Inn-Berkshires.h2943.Hotel-Information) ![Meeting facility](https://images.trvl-media.com/lodging/1000000/10000/2100/2067/074b6c4f.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/a25612d3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/10000/2100/2067/5acdf3c7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Meeting facility](https://images.trvl-media.com/lodging/1000000/10000/2100/2067/6b95ddf5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Holiday Inn & Suites Pittsfield-Berkshires by IHG Pittsfield 8.0/10 Very good (972) "Staff was very nice and helpful nice place restaurant was awesome great food and drinks" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Frank CA $130 CA $146 total includes taxes & fees Dec 2 - Dec 3 [](https://www.expedia.ca/Pittsfield-Hotels-Holiday-Inn-Suites-Pittsfield-Berkshires.h2067.Hotel-Information) ![Seasonal outdoor pool](https://images.trvl-media.com/lodging/96000000/95130000/95124600/95124564/52cb5a56.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Honeymoon Suite, 1 King Bed, Patio | Living area](https://images.trvl-media.com/lodging/96000000/95130000/95124600/95124564/d7f7feed.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Premium Chalet | Private kitchen](https://images.trvl-media.com/lodging/96000000/95130000/95124600/95124564/79ede9f7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Premium Chalet | Private kitchen](https://images.trvl-media.com/lodging/96000000/95130000/95124600/95124564/a401c5f5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Springs Motel New Ashford 9.2/10 Wonderful (87) "Love this place! I’ve stayed here several times. It is sweet and uncomplicated and convenient." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jennifer CA $170 CA $186 total includes taxes & fees Nov 29 - Nov 30 [](https://www.expedia.ca/New-Ashford-Hotels-The-Springs-Motel.h95124564.Hotel-Information) ![Outdoor pool, a heated pool](https://images.trvl-media.com/lodging/37000000/36780000/36778100/36778065/04000126.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 bedrooms, free WiFi, bed sheets](https://images.trvl-media.com/lodging/37000000/36780000/36778100/36778065/a8d66378.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/37000000/36780000/36778100/36778065/5200a28c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace, Netflix, streaming services](https://images.trvl-media.com/lodging/37000000/36780000/36778100/36778065/64548e51.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### 2BR 2BA - MT SNOW, SKI BACK TRAIL, FREE SHUTTLE, POOL, BBQ - Green Mountain Den Dover 9.4/10 Exceptional (16) "So cute and in such a great area! It was a perfect stay" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jaden F. CA $55 CA $358 total includes taxes & fees Nov 30 - Dec 1 [](https://www.expedia.ca/West-Dover-Hotels-MT-SNOW-SKI-BACK-TRAIL-FREE-SHUTTLE-Green-Mountain-Den.h36778065.Hotel-Information) ![Outdoor pool](https://images.trvl-media.com/lodging/1000000/670000/663200/663170/2a499f66.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fireplace](https://images.trvl-media.com/lodging/1000000/670000/663200/663170/fea584b8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![BBQ/picnic area](https://images.trvl-media.com/lodging/1000000/670000/663200/663170/047760f4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fireplace](https://images.trvl-media.com/lodging/1000000/670000/663200/663170/910c669e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Mount Snow Grand Summit Resort West Dover 8.8/10 Excellent (242) "Great place to stay!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Sonia CA $161 CA $193 total includes taxes & fees Dec 2 - Dec 3 [](https://www.expedia.ca/West-Dover-Hotels-Mount-Snow-Grand-Summit-Resort.h663170.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/5000000/4600000/4595900/4595809/caece0b8.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) ![Comfort Double Room, 2 Double Beds, Non Smoking](https://images.trvl-media.com/lodging/5000000/4600000/4595900/4595809/53d12ad8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property](https://images.trvl-media.com/lodging/5000000/4600000/4595900/4595809/44727a40.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cozy Corner Motel Williamstown 9.2/10 Wonderful (884) "Clean, Great Staff, Quiet" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) john CA $105 CA $124 total includes taxes & fees Dec 11 - Dec 12 [](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) ![Reception](https://images.trvl-media.com/lodging/3000000/2580000/2577700/2577695/f5baf2df.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Garden](https://images.trvl-media.com/lodging/3000000/2580000/2577700/2577695/b33626c2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/3000000/2580000/2577700/2577695/d2134729.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hotel Vervana, Trademark Collection by Wyndham Bennington 8.2/10 Very good (1002) "Great location near historic downtown area, nice rooms. Overall, a very pleasant stay." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Richard CA $147 CA $160 total includes taxes & fees Dec 9 - Dec 10 [](https://www.expedia.ca/Bennington-Hotels-Paradise-Inn.h2577695.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=2025-12-12&endDate=2025-12-13®ionId=553248634999031091&adults=2&amenities=POOL&sort=RECOMMENDED&openPlayBack=true) ![](https://forever.travel-assets.com/flex/flexmanager/images/2025/11/05/BEX-BF-25_CA_1_Desktop.jpg?impolicy=fcrop&w=1400&h=600&q=mediumHigh) ## Black Friday Sale Limited-time deals: save up to 50% on select hotels [Book now](https://expedia.ca/deals?rfrr=AFFINITY_BF_PROMO_553248634999031091) ## Top Florida Hotel Reviews ![Hampton Inn & Suites Greenfield](https://images.trvl-media.com/lodging/2000000/1610000/1601100/1601018/72e137d6_y.jpg) ### Hampton Inn & Suites Greenfield 10/10 Excellent "Staff was friendly, room was very nice and really appreciate the breakfast." [](https://expedia.ca/Greenfield-Hotels-Hampton-Inn-Suites-Greenfield.h1601018.Hotel-Information) ![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 "Everything was great. " [](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 "Friendly staff, clean comfortable room, great location." [](https://expedia.ca/Bennington-Hotels-Hampton-Inn-Bennington.h1191981.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 "Wonderful Experience " [](https://expedia.ca/North-Adams-Hotels-Holiday-Inn-Berkshires.h2943.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 "Nice place to stay, off season. Price was very reasonable. Room was comfortable, (1st floor, Building 5), entire building was very quiet, hardly anyone on the property. Nice amenities, but we only walked through, did not use (pool, locker rooms, hot tub, fire pit). Room was nicely appointed and comfortable. Gas fireplace worked well, hot water was plentiful, water pressure was good. Kitchen was stocked with just about anything you'd need to cook simple meals. Great option when in the area, would recommend and would stay again." [](https://expedia.ca/Williamstown-Hotels-Vacation-Village-In-The-Berkshires.h1066423.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 "Loved it all. Great place. Highly recommend. Thank you." [](https://expedia.ca/North-Adams-Hotels-The-Porches-Inn.h7662392.Hotel-Information) ![Hotel Vervana, Trademark Collection by Wyndham](https://images.trvl-media.com/lodging/3000000/2580000/2577700/2577695/b33626c2_y.jpg) ### Hotel Vervana, Trademark Collection by Wyndham 10/10 Excellent "Great place for the price! Clean and comfortable. " [](https://expedia.ca/Bennington-Hotels-Paradise-Inn.h2577695.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 "Amazing 2 big hot tubes and warm swim pool on the open air !!! A lot of restaurants around and Beautiful nature! But chairlifts was closed- so check availability " [](https://expedia.ca/West-Dover-Hotels-Mount-Snow-Grand-Summit-Resort.h663170.Hotel-Information) ![Jiminy Peak Mountain Resort](https://images.trvl-media.com/lodging/1000000/920000/911400/911313/cf8c8830_y.jpg) ### Jiminy Peak Mountain Resort 10/10 Excellent "This is our second time staying here. We love the property, the suites work for us as there is a bedroom which is separate from the living space. There are plenty of things to do on the property and in the surrounding area. Mt. Greylock, antiquing, great breakfast spots! The Country Store on the property has great sandwiches and things needed for your stay." [](https://expedia.ca/Hancock-Hotels-Jiminy-Peak-Mountain-Resort.h911313.Hotel-Information) ## Frequently asked questions ### What are some accommodations with pools in Florida? > [Blue Vista Motor Lodge](https://www.expedia.ca/North-Adams-Hotels-Blue-Vista-Motor-Lodge.h84362148.Hotel-Information): Condo, 14-minute walk from Jiminy Peak Mountain Resort. Offers a children's pool, an indoor pool, and free self parking. [Vacation Village in the Berkshires](https://www.expedia.ca/Williamstown-Hotels-Vacation-Village-In-The-Berkshires.h1066423.Hotel-Information): Provides a health club, an indoor pool, and complimentary wired internet access. [Holiday Inn & Suites Pittsfield-Berkshires by IHG](https://www.expedia.ca/Pittsfield-Hotels-Holiday-Inn-Suites-Pittsfield-Berkshires.h2067.Hotel-Information): Offers free self parking, an indoor pool, and complimentary wireless internet access. [The Williams Inn](https://www.expedia.ca/Williamstown-Hotels-The-Williams-Inn.h35658765.Hotel-Information): Resort, 2-minute walk from Mount Snow. Offers a full-service spa, an outdoor pool, and 2 hot tubs. [Hotel Downstreet, an Ascend Collection Hotel](https://www.expedia.ca/North-Adams-Hotels-Holiday-Inn-Berkshires.h2943.Hotel-Information): Condo resort, 1-minute walk from Jiminy Peak Mountain Resort. Features 2 restaurants, an outdoor pool, and 2 bars. ### What is there to see and do in Florida? > The picturesque setting of Deerfield River and Green Mountain National Forest showcase the area's natural beauty. Discover sights such as Florida Town Hall, Hoosac Range, and Reed Brook Preserve during your stay. ### When is the best time to book a hotel with a pool in Florida? > Taking into account the local weather in Florida is an important factor for planning your visit, especially if you plan to spend your trip poolside. The hottest months are usually July and August with an average temp of 66°F, while the coldest months are January and February with an average of 27°F. The snowiest months in Florida are January, March, February, and November, with each month seeing an average of 7 inches of snowfall. ## 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) - [Beach Hotel Hotels in Adams](https://www.expedia.ca/Adams-Hotels-Beach-Hotel.0-0-d6005393-tBeachHotel.Travel-Guide-Filter-Hotels) - 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