Title: Book the Best Hotels with POOL in Truman Annex in 2025 | Expedia.ca [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)[Truman Annex Car Rentals](https://expedia.ca/Car-Rentals-In-Truman-Annex.d553248635976473207.Car-Rental-Guide)[Truman Annex Vacations](https://expedia.ca/Truman-Annex.d553248635976473207.Destination-Travel-Guides) ![Harry S. Truman Little White House which includes a garden, a house and heritage elements](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/63000/63930-Harry-S-Truman-Little-White-House.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # Find Hotels with a Pool in Truman Annex, FL from CA $157 - ![](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 Truman Annex Hotels with a Pool Tonight [Nov 5 - Nov 6](https://www.expedia.ca/Hotel-Search?regionId=553248635976473207&startDate=2025-11-05&endDate=2025-11-06&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Nov 6 - Nov 7](https://www.expedia.ca/Hotel-Search?regionId=553248635976473207&startDate=2025-11-06&endDate=2025-11-07&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Nov 7 - Nov 9](https://www.expedia.ca/Hotel-Search?regionId=553248635976473207&startDate=2025-11-07&endDate=2025-11-09&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Nov 14 - Nov 16](https://www.expedia.ca/Hotel-Search?regionId=553248635976473207&startDate=2025-11-14&endDate=2025-11-16&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Top Truman Annex Hotels with a Pool ![Outdoor pool](https://images.trvl-media.com/lodging/1000000/860000/858000/857964/376faaf1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![20-inch TV with satellite channels, DVD player](https://images.trvl-media.com/lodging/1000000/860000/858000/857964/45293052.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/860000/858000/857964/489ad80a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Two Bedroom Villa | Private kitchen](https://images.trvl-media.com/lodging/1000000/860000/858000/857964/639869f6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hyatt Vacation Club at Sunset Harbor, Key West Old Town Key West 8.4/10 Very good (314) "Good location " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Paula CA $313 CA $400 total includes taxes & fees Nov 30 - Dec 1 [](https://www.expedia.ca/Key-West-Hotels-Hyatt-Vacation-Club-At-Sunset-Harbor.h857964.Hotel-Information) ![Premium bedding, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/2000000/1750000/1749500/1749434/83214581.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Premium bedding, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/2000000/1750000/1749500/1749434/c579b899.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property](https://images.trvl-media.com/lodging/2000000/1750000/1749500/1749434/3347744a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Courtyard](https://images.trvl-media.com/lodging/2000000/1750000/1749500/1749434/f17f7f22.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Weatherstation Inn Old Town Key West 9.4/10 Exceptional (983) "Nice place to stay" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Victoria CA $308 CA $346 total includes taxes & fees Dec 3 - Dec 4 [](https://www.expedia.ca/Key-West-Hotels-Weatherstation-Inn.h1749434.Hotel-Information) ![A heated pool](https://images.trvl-media.com/lodging/84000000/83970000/83967800/83967706/2c7ae7f0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/84000000/83970000/83967800/83967706/dc854c50.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/84000000/83970000/83967800/83967706/76ff56fd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV](https://images.trvl-media.com/lodging/84000000/83970000/83967800/83967706/8a0b6948.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Beach Paradise in the Keys! Location! Location! 2 Blocks to Duval St Old Town Key West 9.4/10 Exceptional (47) "We had a great time in Key West, and you can't beat this location. It was a little bit hard to figure out how to get in, but we figured it out. You won't regret staying here." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Theresa H. CA $657 CA $1,547 total includes taxes & fees Nov 19 - Nov 20 [](https://www.expedia.ca/Key-West-Hotels-Beach-Paradise-In-The-Keys-Location-Location-2-Blocks-To-Duval-St.h83967706.Hotel-Information) ![Building design](https://images.trvl-media.com/lodging/5000000/4290000/4280800/4280752/a8250942.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/5000000/4290000/4280800/4280752/34b65216.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free daily continental breakfast](https://images.trvl-media.com/lodging/5000000/4290000/4280800/4280752/db77bb38.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Suite, 1 King Bed with Sofa bed (ADULT ONLY)](https://images.trvl-media.com/lodging/5000000/4290000/4280800/4280752/ee1be58b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Southernmost Inn - Adults Only Old Town Key West 8.2/10 Very good (1176) "What a cute little place, very clean, breakfast had great variety. 2 pools and a hot tub out back. About a 10 minute walk to duval st. We were able to check in and leave our luggage in a secure spot until the room was ready which epwas very convenient. Will stay there again. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) amy CA $238 CA $330 total includes taxes & fees Nov 30 - Dec 1 [](https://www.expedia.ca/Key-West-Hotels-The-Southernmost-Inn-Adults-Only.h4280752.Hotel-Information) ![2 outdoor pools, open 8:00 AM to 10:00 PM, sun loungers](https://images.trvl-media.com/lodging/18000000/17320000/17313700/17313680/e4eb7fd5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 restaurants, breakfast, lunch, dinner served; seafood](https://images.trvl-media.com/lodging/18000000/17320000/17313700/17313680/89147e75.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/18000000/17320000/17313700/17313680/54c5f4f8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Aerial view](https://images.trvl-media.com/lodging/18000000/17320000/17313700/17313680/d6618f5e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Perry Hotel & Marina Key West Stock Island 9.4/10 Exceptional (1140) "The rooms were very clean the staff was extremely nice and helpful. Would definitely stay here again" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Richard CA $177 CA $278 total includes taxes & fees Nov 12 - Nov 13 [](https://www.expedia.ca/Key-West-Hotels-The-Perry-Hotel-Marina-Key-West.h17313680.Hotel-Information) ![Outdoor spa tub](https://images.trvl-media.com/lodging/8000000/7510000/7500600/7500588/77f11bb4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Basic Quadruple Room](https://images.trvl-media.com/lodging/8000000/7510000/7500600/7500588/070a211a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![NYAH Private Balcony Room 6 Single Beds | Balcony view](https://images.trvl-media.com/lodging/8000000/7510000/7500600/7500588/a350e3cb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property](https://images.trvl-media.com/lodging/8000000/7510000/7500600/7500588/eb10500d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### NYAH Key West - Adults Only Key West Historic District 7.8/10 Good (1017) "Clean great staff and perfect pool!! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Kristy CA $145 CA $227 total includes taxes & fees Nov 11 - Nov 12 [](https://www.expedia.ca/Key-West-Hotels-NYAH-Key-West-Adults-Only.h7500588.Hotel-Information) ![Outdoor pool](https://images.trvl-media.com/lodging/4000000/3920000/3918200/3918121/83592c1d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lake](https://images.trvl-media.com/lodging/4000000/3920000/3918200/3918121/a0504154.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/4000000/3920000/3918200/3918121/125c52d9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Balcony](https://images.trvl-media.com/lodging/4000000/3920000/3918200/3918121/a36bdda4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Sugar Loaf Lodge Summerland Key 8.2/10 Very good (1003) "Tiki hit closed, wish I had known Staff very nice, rooms fine" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) James CA $139 CA $157 total includes taxes & fees Dec 3 - Dec 4 [](https://www.expedia.ca/Sugarloaf-Key-Hotels-Sugar-Loaf-Lodge.h3918121.Hotel-Information) ![Outdoor pool, open 6:00 AM to 10:00 PM, cabanas (surcharge)](https://images.trvl-media.com/lodging/1000000/10000/1400/1376/5c83029c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/10000/1400/1376/d5aad7de.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Courtyard](https://images.trvl-media.com/lodging/1000000/10000/1400/1376/ee750f93.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Daily continental breakfast (USD 18 per person)](https://images.trvl-media.com/lodging/1000000/10000/1400/1376/3484f3ab.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hilton Garden Inn Key West / The Keys Collection New Town 8.0/10 Very good (1109) "Everything was wonderful, clean room, great staff, lovely facility" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Elizabeth A CA $130 CA $186 total includes taxes & fees Dec 3 - Dec 4 [](https://www.expedia.ca/Key-West-Hotels-Hilton-Garden-Inn-Key-West.h1376.Hotel-Information) ![2 outdoor pools, open 7:00 AM to 11:00 PM, cabanas (surcharge)](https://images.trvl-media.com/lodging/13000000/12600000/12599300/12599231/cb0a4c1e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Poolside bar](https://images.trvl-media.com/lodging/13000000/12600000/12599300/12599231/5792173a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Bicycling](https://images.trvl-media.com/lodging/13000000/12600000/12599300/12599231/4a54e511.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/13000000/12600000/12599300/12599231/44728c35.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Blue Flamingo Resort Key West New Town 8.0/10 Very good (1656) "Beautiful room, great view, love the pools, bars and lawn games" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Douglas CA $142 CA $239 total includes taxes & fees Nov 11 - Nov 12 [](https://www.expedia.ca/Key-West-Hotels-24-North-Hotel-Key-West-Newly-Renovated.h12599231.Hotel-Information) ![4 outdoor pools, pool umbrellas, sun loungers](https://images.trvl-media.com/lodging/1000000/30000/24700/24615/67735d0c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Aerial view](https://images.trvl-media.com/lodging/1000000/30000/24700/24615/f896e9da.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Premium bedding, minibar, in-room safe, individually decorated](https://images.trvl-media.com/lodging/1000000/30000/24700/24615/b166f8e3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor wedding area](https://images.trvl-media.com/lodging/1000000/30000/24700/24615/b17e59c3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Parrot Key Hotel & Villas Northside Resort 9.0/10 Wonderful (1146) "The property was great. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Richard CA $201 CA $307 total includes taxes & fees Nov 16 - Nov 17 [](https://www.expedia.ca/Key-West-Hotels-Parrot-Key-Hotel-Villas.h24615.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=2025-11-19&endDate=2025-11-20®ionId=553248635976473207&adults=2&amenities=POOL&sort=RECOMMENDED&openPlayBack=true) ## Top Truman Annex Hotel Reviews ![The Perry Hotel & Marina Key West](//images.trvl-media.com/lodging/18000000/17320000/17313700/17313680/e4eb7fd5_y.jpg) ### The Perry Hotel & Marina Key West 10/10 Excellent "Clean, out of the busy Key West Center. Very nice property." [](https://expedia.ca/Key-West-Hotels-The-Perry-Hotel-Marina-Key-West.h17313680.Hotel-Information) ![Fairfield Inn and Suites by Marriott Key West](//images.trvl-media.com/lodging/1000000/10000/9000/8946/7b2c8a2c_y.jpg) ### Fairfield Inn and Suites by Marriott Key West 10/10 Excellent "Good room. Great breakfast!" [](https://expedia.ca/Key-West-Hotels-Fairfield-Inn-And-Suites-By-Marriott-Key-West.h8946.Hotel-Information) ![DoubleTree Resort by Hilton Grand Key - Key West](//images.trvl-media.com/lodging/1000000/480000/470900/470834/be4147fb_y.jpg) ### DoubleTree Resort by Hilton Grand Key - Key West 10/10 Excellent "Nice and clean, very curtious staff. Free Shuttle service was great. Food in restaurant was great. " [](https://expedia.ca/Key-West-Hotels-DoubleTree-Resort-By-Hilton-Grand-Key-Key-West.h470834.Hotel-Information) ![Hilton Garden Inn Key West / The Keys Collection](//images.trvl-media.com/lodging/1000000/10000/1400/1376/5c83029c_y.jpg) ### Hilton Garden Inn Key West / The Keys Collection 10/10 Excellent "Clean, comfortable room. Great breakfast, nice pool. " [](https://expedia.ca/Key-West-Hotels-Hilton-Garden-Inn-Key-West.h1376.Hotel-Information) ![Oceans Edge Key West Resort, Hotel & Marina](//images.trvl-media.com/lodging/17000000/16210000/16203000/16202992/3a4457a0_y.jpg) ### Oceans Edge Key West Resort, Hotel & Marina 10/10 Excellent "We’ve stayed here twice now. Staff is great, the shuttle into town is super convenient (hi Jeffrey!). We love that you can use the kayaks or paddleboards every day. The tiki hut crew is the best! The place is clean and I feel safe walking around there. It’s well lit and easy to navigate. " [](https://expedia.ca/Key-West-Hotels-Oceans-Edge-Key-West-Resort.h16202992.Hotel-Information) ![Southernmost Beach Resort and Guesthouses](//images.trvl-media.com/lodging/1000000/870000/863400/863329/026f10af_y.jpg) ### Southernmost Beach Resort and Guesthouses 10/10 Excellent "Excellent time " [](https://expedia.ca/Key-West-Hotels-Southernmost-Beach-Resort.h863329.Hotel-Information) ![Beachside Resort & Residences](//images.trvl-media.com/lodging/1000000/30000/25900/25865/290b242a_y.jpg) ### Beachside Resort & Residences 10/10 Excellent "Loved the atmosphere. Beautiful & clean room. Heated pool well maintained and open 24 hours. Plan on staying again. future " [](https://expedia.ca/Key-West-Hotels-Key-West-Marriott-Beachside-Hotel.h25865.Hotel-Information) ![Blue Flamingo Resort Key West](//images.trvl-media.com/lodging/13000000/12600000/12599300/12599231/cb0a4c1e_y.jpg) ### Blue Flamingo Resort Key West 10/10 Excellent "The front desk clerk was very polite & attentive. She looked very presentable as well. The blueberry lemonade 🍋 was a perfect touch. The room was cute as a button!" [](https://expedia.ca/Key-West-Hotels-24-North-Hotel-Key-West-Newly-Renovated.h12599231.Hotel-Information) ![Hyatt Centric Key West Resort and Spa](//images.trvl-media.com/lodging/1000000/10000/1000/901/0b72a249_y.jpg) ### Hyatt Centric Key West Resort and Spa 10/10 Excellent "Room was large and beautiful views. Location was super convenient and could walk almost everywhere we needed to. Loved being able to walk right in the water. Housekeeping was excellent." [](https://expedia.ca/Key-West-Hotels-Hyatt-Centric-Key-West-Resort-And-Spa.h901.Hotel-Information) ## Frequently asked questions ### What's it like visiting Truman Annex? > If spending time by the pool is your idea of a great getaway, you might want to think about Truman Annex, which offers 16 places to stay with pools. While you're here, you can explore attractions like Duval Street, and then unwind poolside at one of the accommodations in Truman Annex that travelers like for their pools. ### What are some accommodations with pools in Truman Annex? > [Weatherstation Inn](https://www.expedia.ca/Key-West-Hotels-Weatherstation-Inn.h1749434.Hotel-Information): B&B, 5-minute walk from Duval Street. Features continental, an outdoor pool, and free self parking. [Hyatt Vacation Club at Sunset Harbor, Key West](https://www.expedia.ca/Key-West-Hotels-Hyatt-Vacation-Club-At-Sunset-Harbor.h857964.Hotel-Information): Apartment, 4-minute walk from Duval Street. Offers complimentary wireless internet access, an outdoor pool, and televisions. [Oceans Edge Key West Resort, Hotel & Marina](https://www.expedia.ca/Key-West-Hotels-Oceans-Edge-Key-West-Resort.h16202992.Hotel-Information): Hotel located near Smathers Beach. Provides complimentary bicycles, 6 outdoor pools, and complimentary wireless internet access. [Blue Flamingo Resort Key West](https://www.expedia.ca/Key-West-Hotels-24-North-Hotel-Key-West-Newly-Renovated.h12599231.Hotel-Information): Hotel located near Smathers Beach. Features 2 restaurants, 2 outdoor pools, and 2 pool bars. [Hyatt Centric Key West Resort and Spa](https://www.expedia.ca/Key-West-Hotels-Hyatt-Centric-Key-West-Resort-And-Spa.h901.Hotel-Information): Resort, 3-minute walk from Duval Street. Offers a full-service spa, a pool, and a snack bar/deli. ### How many hotels with pools can I expect to find in Truman Annex? > Expedia's 16 hotels in Truman Annex give you a great choice for your poolside getaway. ### What is there to see and do in Truman Annex? > Explore places like Duval Street while you're in the area. 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[Hotels with a Pool in Key West](https://www.expedia.ca/Key-West-Hotels-Hotel-With-Pool.0-0-d1187-tHotelwithPool.Travel-Guide-Filter-Hotels) - [Hotels with a Lazy River in Key West](https://www.expedia.ca/Key-West-Hotels-Hotels-With-A-Lazy-River.0-0-d1187-tHotelswithaLazyRiver.Travel-Guide-Filter-Hotels) - [Hotels with Balconies in Key West](https://www.expedia.ca/Key-West-Hotels-Hotels-With-Balconies.0-0-d1187-tHotelswithBalconies.Travel-Guide-Filter-Hotels) - [Hotels with Bar in Key West](https://www.expedia.ca/Key-West-Hotels-Hotels-With-Bar.0-0-d1187-tHotelswithBar.Travel-Guide-Filter-Hotels) - [Hotels with Childcare in Key West](https://www.expedia.ca/Key-West-Hotels-Hotels-With-Childcare.0-0-d1187-tHotelswithChildcare.Travel-Guide-Filter-Hotels) - [Hotels with Free Airport Shuttle in Key West](https://www.expedia.ca/Key-West-Hotels-Hotels-With-Free-Airport-Shuttle.0-0-d1187-tHotelswithFreeAirportShuttle.Travel-Guide-Filter-Hotels) - [Hotels with Free Breakfast in Key West](https://www.expedia.ca/Key-West-Hotels-Hotels-With-Free-Breakfast.0-0-d1187-tHotelswithFreeBreakfast.Travel-Guide-Filter-Hotels) - 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