Title: Book the Best Hotels with INDOOR POOL in Historic Seaport in 2025 | Expedia.ca [Historic Seaport Travel Guide](https://expedia.ca/Key-West-Historic-Seaport.dx553248635976383502)[Flights to Key West](https://expedia.ca/Cheap-Flights-To-Key-West.d1187.Travel-Guide-Flights)[Things to do in Key West](https://expedia.ca/Things-To-Do-In-Key-West.d1187.Travel-Guide-Activities)[Historic Seaport Car Rentals](https://expedia.ca/Car-Rentals-In-Historic-Seaport.d553248635976383502.Car-Rental-Guide)[Historic Seaport Vacations](https://expedia.ca/Historic-Seaport.d553248635976383502.Destination-Travel-Guides) ![](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/497000/497495-mallory-square.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # Find Hotels with an Indoor Pool in Historic Seaport, FL from CA $289 ![](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 Historic Seaport Hotels with an Indoor Pool Tonight [Oct 29 - Oct 30](https://www.expedia.ca/Hotel-Search?regionId=553248635976383502&startDate=2025-10-29&endDate=2025-10-30&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Oct 30 - Oct 31](https://www.expedia.ca/Hotel-Search?regionId=553248635976383502&startDate=2025-10-30&endDate=2025-10-31&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Oct 31 - Nov 2](https://www.expedia.ca/Hotel-Search?regionId=553248635976383502&startDate=2025-10-31&endDate=2025-11-02&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Nov 7 - Nov 9](https://www.expedia.ca/Hotel-Search?regionId=553248635976383502&startDate=2025-11-07&endDate=2025-11-09&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Top Historic Seaport Hotels with an Indoor Pool ![Outdoor pool, a heated pool](https://images.trvl-media.com/lodging/103000000/102250000/102246100/102246019/5e4c70a0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![3 bedrooms, desk, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/103000000/102250000/102246100/102246019/f0faf1c3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/103000000/102250000/102246100/102246019/w2499h1666x1y1-c35caef5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/103000000/102250000/102246100/102246019/7a3d3c9f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### 3 Bedroom Key West Home - Perfect Location & Private Pool Key West Historic District 9.6/10 Exceptional (5) "This was a great place to stay. The house was in a perfect location, close to Duval but far enough off for a quiet night. The backyard and pool were a relaxing place to hang out for a bit as well. If we do this trip again next year I hope we can get this house." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Joseph H. CA $835 CA $1,569 total includes taxes & fees Oct 31 - Nov 1 [](https://www.expedia.ca/Key-West-Hotels-3-Bedroom-Key-West-Home-With-Perfect-Location-Private-Pool.h102246019.Hotel-Information) ![Terrace/patio](https://images.trvl-media.com/lodging/108000000/107050000/107046300/107046273/cefd6ced.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/108000000/107050000/107046300/107046273/aa1993ab.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 bedrooms, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/108000000/107050000/107046300/107046273/0e405e1a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/108000000/107050000/107046300/107046273/a1b328f0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Pet Friendly, & Near Duval - Rose Key Cottage Key West Historic District 6.8/10 (3) "Cute Pink House so very near Duval it will blow your mind. It is not fancy, but has some cute elements and PLENTY of room for 2 up and 2 down. We rented the whole house for our visit. We did not got in the pool as it does not really look like the pictures. It was adorable and you absolutely cannot beat the space or location in Key West. I have stayed in Key West in many hotels and locations. This was a wonderful location and very comfortable. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Kim Keheley F. CA $797 CA $1,634 total includes taxes & fees Nov 3 - Nov 4 [](https://www.expedia.ca/Key-West-Hotels-New-Rose-Retreat-Pool-Parking.h107046273.Hotel-Information) ![Terrace/patio](https://images.trvl-media.com/lodging/74000000/73130000/73124600/73124529/01c62cb4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![7 bedrooms, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/74000000/73130000/73124600/73124529/48bd8c6b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Pool](https://images.trvl-media.com/lodging/74000000/73130000/73124600/73124529/ff31b3f7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, offices](https://images.trvl-media.com/lodging/74000000/73130000/73124600/73124529/55f51245.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### 1 Block to Duval St | Banana's Foster Guesthouse Key West Historic District 10/10 Exceptional (6) "Location is unbeatable. Great place. What set it apart, however, was how incredibly responsive the hosts were both before and during the stay. I had an answer from them within minutes. That went a long way to make this trip so well worth it. Thanks, hosts!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Benjamin C. CA $1,786 CA $4,434 total includes taxes & fees Oct 30 - Oct 31 [](https://www.expedia.ca/Key-West-Hotels-Bananas-Foster-Guesthouse-Stunning-7-BR-Home-Just-1-Block-From-Duval.h73124529.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/108000000/107900000/107899300/107899257/84aad47b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/108000000/107900000/107899300/107899257/4cdf81d2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![6 bedrooms, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/108000000/107900000/107899300/107899257/c715c241.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/108000000/107900000/107899300/107899257/1a4f61a4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Pool & Parking, & Near Duval - The Rigby House Key West Historic District 10/10 Exceptional (10) "The house and location are perfect for a stay in Key West. Excellent outdoor space and the perfect aesthetic in the house. Everything felt luxurious!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Kaitlin W. CA $2,316 CA $3,957 total includes taxes & fees Oct 30 - Oct 31 [](https://www.expedia.ca/Key-West-Hotels-NEW-The-Rigby-House-Pvt-Pool.h107899257.Hotel-Information) ![TV, stereo](https://images.trvl-media.com/lodging/33000000/32460000/32457500/32457415/361c969b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/33000000/32460000/32457500/32457415/627663e7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/33000000/32460000/32457500/32457415/c055bde5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![3 bedrooms, iron/ironing board, internet, bed sheets](https://images.trvl-media.com/lodging/33000000/32460000/32457500/32457415/567c19bd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Spacious home with pool & balcony - 1 block from Duval Street Key West Historic District 9.2/10 Wonderful (81) "Great location! Close to all the activities." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) susan h. CA $865 CA $1,546 total includes taxes & fees Nov 17 - Nov 18 [](https://www.expedia.ca/Key-West-Hotels-Spacious-Home-With-Pool-Balcony-1-Block-From-Duval-Street.h32457415.Hotel-Information) ![Outdoor pool, a heated pool](https://images.trvl-media.com/lodging/97000000/96220000/96219000/96218972/727ef598.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/97000000/96220000/96219000/96218972/d47627bc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/97000000/96220000/96219000/96218972/017afd8b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![6 bedrooms, desk, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/97000000/96220000/96219000/96218972/a11073d4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Historic Mansion in Old Town Key West with Private Pool - Sleeps 16! Key West Historic District 9.8/10 Exceptional (238) "House was great but location was even better" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Evan D. CA $1,114 CA $2,296 total includes taxes & fees Oct 31 - Nov 1 [](https://www.expedia.ca/Key-West-Hotels-Historic-Mansion-In-Old-Town-Key-West-With-Private-Pool-Sleeps-16.h96218972.Hotel-Information) ![Indoor pool, outdoor pool, open 7:00 AM to 10:00 PM, pool umbrellas](https://images.trvl-media.com/lodging/28000000/27160000/27156600/27156592/3158543b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property - evening/night](https://images.trvl-media.com/lodging/28000000/27160000/27156600/27156592/6abe86ae.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![In-room safe, individually decorated, individually furnished, desk](https://images.trvl-media.com/lodging/28000000/27160000/27156600/27156592/c082f6dc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Suite, 1 Bedroom, Ocean View (Spacious | King)](https://images.trvl-media.com/lodging/28000000/27160000/27156600/27156592/cba0d59f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Laureate Key West New Town 9.0/10 Wonderful (1001) "This is our second time staying there. We love the hotel. It close to everything and have a great view " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Nini CA $222 CA $289 total includes taxes & fees Oct 30 - Oct 31 [](https://www.expedia.ca/Key-West-Hotels-The-Laureate-Key-West.h27156592.Hotel-Information) ![Deluxe Suite, 1 King Bed, Private Pool | View from room](https://images.trvl-media.com/lodging/17000000/16400000/16396000/16395930/b744fec6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Point of interest](https://images.trvl-media.com/lodging/17000000/16400000/16396000/16395930/8bca03c3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, premium bedding, pillowtop beds, minibar](https://images.trvl-media.com/lodging/17000000/16400000/16396000/16395930/44a19a01.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Premier Suite, 1 King Bed, Private Pool | View from room](https://images.trvl-media.com/lodging/17000000/16400000/16396000/16395930/320d50ca.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### H2O Suites - Adults Only Old Town Key West 9.8/10 Exceptional (570) "Had a great stay! Property is very nice and conveniently located. Would definitely stay again." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) dwight CA $417 CA $532 total includes taxes & fees Oct 30 - Oct 31 [](https://www.expedia.ca/Key-West-Hotels-H2O-Suites-Adults-Only.h16395930.Hotel-Information) ![Deluxe Apartment, Ensuite, Pool View (Hemingway Retreat) | Exterior](https://images.trvl-media.com/lodging/23000000/22500000/22493000/22492921/953ce744.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Deluxe Apartment, Ensuite, Pool View (Hemingway Retreat) | Exterior](https://images.trvl-media.com/lodging/23000000/22500000/22493000/22492921/b6d7b563.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Family Apartment, Private Bathroom (Sunset Suite) | Exterior](https://images.trvl-media.com/lodging/23000000/22500000/22493000/22492921/7b593bef.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Deluxe Apartment, Ensuite, Pool View (Hemingway Retreat)](https://images.trvl-media.com/lodging/23000000/22500000/22493000/22492921/76b7988f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Suite Dreams Inn by the Beach Old Town Key West 8.4/10 Very good (52) "very nice hospitality " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jeremy CA $297 CA $334 total includes taxes & fees Nov 23 - Nov 24 [](https://www.expedia.ca/Key-West-Hotels-Suite-Dreams-Inn-By-The-Beach.h22492921.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/22000000/21720000/21717500/21717498/5565ea49.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![A heated pool](https://images.trvl-media.com/lodging/22000000/21720000/21717500/21717498/ca11cb5f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/22000000/21720000/21717500/21717498/4b480533.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 bedrooms, internet, bed sheets](https://images.trvl-media.com/lodging/22000000/21720000/21717500/21717498/00b9c303.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Comfortable Cottage with Private Pool & Lovely Garden - Great Location Old Town Key West 8.8/10 Excellent (118) "Great location and a great pool " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) J C. CA $264 CA $630 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/Key-West-Hotels-Comfortable-Cottage-With-Private-Pool-Lovely-Garden-Great-Location.h21717498.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=2025-11-12&endDate=2025-11-13®ionId=553248635976383502&adults=2&property_amenities_group_explore=indoor_pool&sort=RECOMMENDED&openPlayBack=true) ## Price trends for hotels in Historic Seaport | Less expensive | More expensive | Next month | | --- | --- | --- | | October | February | CA $506 | | Month | Price | | --- | --- | | January | CA $618 | | February | CA $789 | | March | CA $675 | | April | CA $571 | | May | CA $539 | | June | CA $461 | | July | CA $503 | | August | CA $414 | | September | CA $329 | | October | CA $313 | | November | CA $506 | | December | CA $522 | Price trend information excludes taxes and fees and is based on base rates for a nightly stay for 2 adults found in the last 7 days on our site and averaged for commonly viewed hotels in Historic Seaport. Select dates and complete search for nightly totals inclusive of taxes and fees. ## Top Historic Seaport Hotel Reviews ## Frequently asked questions ### What is there to do in Historic Seaport? > After a few relaxing laps in the pool, head out and visit some of the top attractions in and around Historic Seaport. Consider a trip to Duval Street, Audubon House and Tropical Gardens, and Key West Shipwreck Museum. A few other contenders are Mallory Square, Florida Keys Beaches, and Key West Historic Seaport. ### Why should I choose a hotel with an indoor pool for my stay in Historic Seaport? > Lounging by the pool is an ideal way to spend drizzly afternoons if it decides to rain during your vacation to Historic Seaport. 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