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 ![](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 [Oct 28 - Oct 29](https://www.expedia.ca/Hotel-Search?regionId=553248635976473207&startDate=2025-10-28&endDate=2025-10-29&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Oct 29 - Oct 30](https://www.expedia.ca/Hotel-Search?regionId=553248635976473207&startDate=2025-10-29&endDate=2025-10-30&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Oct 31 - Nov 2](https://www.expedia.ca/Hotel-Search?regionId=553248635976473207&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=553248635976473207&startDate=2025-11-07&endDate=2025-11-09&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Top Truman Annex Hotels with a Pool ![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) ![Courtyard](https://images.trvl-media.com/lodging/2000000/1750000/1749500/1749434/f17f7f22.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) ![Premium bedding, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/2000000/1750000/1749500/1749434/73aa79d6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Weatherstation Inn Old Town Key West 9.4/10 Exceptional (982) "Nice place to stay" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Victoria CA $234 CA $264 total includes taxes & fees Oct 29 - Oct 30 [](https://www.expedia.ca/Key-West-Hotels-Weatherstation-Inn.h1749434.Hotel-Information) ![Outdoor pool](https://images.trvl-media.com/lodging/1000000/860000/858000/857964/376faaf1.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) ![Exterior](https://images.trvl-media.com/lodging/1000000/860000/858000/857964/eca90904.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) "Great hotel with excellent location " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Rony CA $290 CA $374 total includes taxes & fees Oct 29 - Oct 30 [](https://www.expedia.ca/Key-West-Hotels-Hyatt-Vacation-Club-At-Sunset-Harbor.h857964.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) ![Aerial view](https://images.trvl-media.com/lodging/18000000/17320000/17313700/17313680/d6618f5e.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) ### The Perry Hotel & Marina Key West Stock Island 9.4/10 Exceptional (1134) "Nice stay. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) SHAMBRE CA $167 CA $266 total includes taxes & fees Oct 30 - Oct 31 [](https://www.expedia.ca/Key-West-Hotels-The-Perry-Hotel-Marina-Key-West.h17313680.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) ![Courtyard](https://images.trvl-media.com/lodging/5000000/4290000/4280800/4280752/2b7e8bad.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 (1163) "Great area, amenities are great" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Luis Armando CA $136 CA $216 total includes taxes & fees Oct 29 - Oct 30 [](https://www.expedia.ca/Key-West-Hotels-The-Southernmost-Inn-Adults-Only.h4280752.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) ![Exterior](https://images.trvl-media.com/lodging/13000000/12600000/12599300/12599231/44728c35.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) ![Lobby sitting area](https://images.trvl-media.com/lodging/13000000/12600000/12599300/12599231/dcdeb665.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Blue Flamingo Resort Key West New Town 8.0/10 Very good (1636) "Amazing resort with lovely amenities:)" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Wakglene CA $125 CA $219 total includes taxes & fees Oct 30 - Oct 31 [](https://www.expedia.ca/Key-West-Hotels-24-North-Hotel-Key-West-Newly-Renovated.h12599231.Hotel-Information) ![Outdoor pool, pool umbrellas, sun loungers](https://images.trvl-media.com/lodging/1000000/30000/25900/25865/290b242a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby sitting area](https://images.trvl-media.com/lodging/1000000/30000/25900/25865/c646d9fe.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Ocean Front 3BR Presidential Suite | Living area](https://images.trvl-media.com/lodging/1000000/30000/25900/25865/d01b8b60.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Balcony view](https://images.trvl-media.com/lodging/1000000/30000/25900/25865/ce510800.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Beachside Resort & Residences Key West 8.6/10 Excellent (1636) "Very cool place to vacation " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Gabriel CA $151 CA $241 total includes taxes & fees Oct 29 - Oct 30 [](https://www.expedia.ca/Key-West-Hotels-Key-West-Marriott-Beachside-Hotel.h25865.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) ![Terrace/patio](https://images.trvl-media.com/lodging/1000000/10000/1400/1376/470ffe1c.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) ![Lobby](https://images.trvl-media.com/lodging/1000000/10000/1400/1376/d5aad7de.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hilton Garden Inn Key West / The Keys Collection New Town 7.8/10 Good (1105) "Great location " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Johann CA $141 CA $198 total includes taxes & fees Nov 18 - Nov 19 [](https://www.expedia.ca/Key-West-Hotels-Hilton-Garden-Inn-Key-West.h1376.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) ![Restaurant](https://images.trvl-media.com/lodging/4000000/3920000/3918200/3918121/95d2903e.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) ![Property grounds](https://images.trvl-media.com/lodging/4000000/3920000/3918200/3918121/125c52d9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Sugar Loaf Lodge Summerland Key 8.2/10 Very good (1001) "Nice family owned spot. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Terry CA $166 CA $187 total includes taxes & fees Oct 29 - Oct 30 [](https://www.expedia.ca/Sugarloaf-Key-Hotels-Sugar-Loaf-Lodge.h3918121.Hotel-Information) ![Courtyard](https://images.trvl-media.com/lodging/1000000/910000/900500/900423/9013d891.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Courtyard](https://images.trvl-media.com/lodging/1000000/910000/900500/900423/586198d8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Apartment (Adults Only) | Private kitchen](https://images.trvl-media.com/lodging/1000000/910000/900500/900423/4c7ce9b2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Garden](https://images.trvl-media.com/lodging/1000000/910000/900500/900423/d8ea2dc3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Duval House Old Town Key West 9.4/10 Exceptional (1030) "Great location, excellent breakfast and amazing customer service!! Definitely i would recommend!👍Aliyah very attentive and makes our staying wonderful!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Alejandro CA $166 CA $217 total includes taxes & fees Oct 29 - Oct 30 [](https://www.expedia.ca/Key-West-Hotels-Duval-House.h900423.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) ![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) ![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) ![Aerial view](https://images.trvl-media.com/lodging/1000000/30000/24700/24615/f896e9da.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Parrot Key Hotel & Villas Northside Resort 9.0/10 Wonderful (1141) "Loved the room and the shuttle service. It was super nice to book excursions from the hotel. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Heather CA $189 CA $293 total includes taxes & fees Nov 20 - Nov 21 [](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=2025-11-11&endDate=2025-11-12®ionId=553248635976473207&adults=2&amenities=POOL&sort=RECOMMENDED&openPlayBack=true) ## Top Truman Annex Hotel Reviews ## 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. [Southernmost Beach Resort and Guesthouses](https://www.expedia.ca/Key-West-Hotels-Southernmost-Beach-Resort.h863329.Hotel-Information): Hotel steps from South Beach. Features 2 pool bars, 3 outdoor pools, and a full-service spa. [Margaritaville Beach House Key West](https://www.expedia.ca/Key-West-Hotels-Margaritaville-Beach-House-Key-West.h48713884.Hotel-Information): Hotel, 13-minute walk from Florida Keys Beaches. Offers a 24-hour fitness center, an outdoor pool, and televisions. ### 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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