Title: Poolside Paradise - Monthly Rental Reviews, Deals & Photos 2026 - Expedia [See all properties](http://www.expedia.com/Hotel-Search?regionId=1187&destination=Key+West%2C+Florida%2C+United+States+of+America&selected=121132471&adults=2&children=&sort=RECOMMENDED&useRewards=false&semdtl=&userIntent=&vip=false) Entire apartment # Poolside Paradise - Monthly Rental - Overview - Rooms - Location - Policies Close to Smathers Beach and South Beach, Poolside Paradise - Monthly Rental has plenty to offer. Stay connected with free WiFi in public areas. ## Popular amenities - Parking included - Free WiFi ## Room options ### Check availability for these dates Tonight [Mar 30 - Mar 31](https://www.expedia.com/Hotel-Search?startDate=2026-03-30&endDate=2026-03-31&selected=121132471&PinnedHotelID=121132471&HadPinnedHotel=true®ionId=-1&adults=2) [](https://www.expedia.com/Hotel-Search?startDate=2026-03-30&endDate=2026-03-31&selected=121132471&PinnedHotelID=121132471&HadPinnedHotel=true®ionId=-1&adults=2) Tomorrow [Mar 31 - Apr 1](https://www.expedia.com/Hotel-Search?startDate=2026-03-31&endDate=2026-04-01&selected=121132471&PinnedHotelID=121132471&HadPinnedHotel=true®ionId=-1&adults=2) [](https://www.expedia.com/Hotel-Search?startDate=2026-03-31&endDate=2026-04-01&selected=121132471&PinnedHotelID=121132471&HadPinnedHotel=true®ionId=-1&adults=2) This weekend [Apr 3 - Apr 5](https://www.expedia.com/Hotel-Search?startDate=2026-04-03&endDate=2026-04-05&selected=121132471&PinnedHotelID=121132471&HadPinnedHotel=true®ionId=-1&adults=2) [](https://www.expedia.com/Hotel-Search?startDate=2026-04-03&endDate=2026-04-05&selected=121132471&PinnedHotelID=121132471&HadPinnedHotel=true®ionId=-1&adults=2) Next weekend [Apr 10 - Apr 12](https://www.expedia.com/Hotel-Search?startDate=2026-04-10&endDate=2026-04-12&selected=121132471&PinnedHotelID=121132471&HadPinnedHotel=true®ionId=-1&adults=2) [](https://www.expedia.com/Hotel-Search?startDate=2026-04-10&endDate=2026-04-12&selected=121132471&PinnedHotelID=121132471&HadPinnedHotel=true®ionId=-1&adults=2) ## You may also like Ad ![2 outdoor pools, open 7:00 AM to 11:00 PM, cabanas (surcharge)](https://a.travel-assets.com/media/meso_cm/PAPI/Images/lodging/13000000/12600000/12599300/12599231/854a69ba_b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) #### Blue Flamingo Resort Key West New Town - Pool - Hot tub - Pet friendly - Free WiFi 8.2 Very Good 2,024 reviews $310 nightly $349 total Apr 19 - Apr 20 Total with taxes and fees [](https://www.expedia.com/Key-West-Hotels-24-North-Hotel-Key-West-Newly-Renovated.h12599231.Hotel-Information?chkin=2026-4-19&chkout=2026-4-20&rm1=a2®ionId=1187&destination=Key West&destType=MARKET&latLong=24.554807,-81.802079&searchId=cf5e62e3-717f-4b2f-81fd-559f61fd8ead&top_cur=USD) Ad ![Outdoor pool, pool umbrellas, sun loungers](https://images.trvl-media.com/lodging/1000000/460000/457900/457821/370c9c8f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) #### The Reach Key West, Curio Collection by Hilton Old Town Key West - On private beach - Pool - Spa - Pet friendly 8.6 Excellent 1,002 reviews $399 nightly $448 total Apr 22 - Apr 23 Total with taxes and fees [](https://www.expedia.com/Key-West-Hotels-The-Reach-Key-West.h457821.Hotel-Information?chkin=2026-4-22&chkout=2026-4-23&rm1=a2®ionId=1187&destination=Key West&destType=MARKET&latLong=24.554807,-81.802079&searchId=cf5e62e3-717f-4b2f-81fd-559f61fd8ead&top_cur=USD) Ad ![Outdoor pool](https://a.travel-assets.com/media/meso_cm/PAPI/Images/lodging/9000000/8660000/8657100/8657021/bf80060e_b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) #### The Key West Hotel Key West Historic District - Pool - Pet friendly - Free WiFi - Air conditioning 9.2 Wonderful 541 reviews $440 nightly $489 total Apr 2 - Apr 3 Total with taxes and fees [](https://www.expedia.com/Key-West-Hotels-Casa-325.h8657021.Hotel-Information?chkin=2026-4-2&chkout=2026-4-3&rm1=a2®ionId=1187&destination=Key West&destType=MARKET&latLong=24.554807,-81.802079&searchId=cf5e62e3-717f-4b2f-81fd-559f61fd8ead&top_cur=USD) Ad ![Exterior](https://a.travel-assets.com/media/meso_cm/PAPI/Images/lodging/5000000/4960000/4959000/4958964/f8aaa0e0_b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) #### Ridley House - Key West Historic Inns Key West Historic District - Pool - Breakfast included - Pet friendly - Free WiFi 9.2 Wonderful 896 reviews $424 nightly $477 total Apr 19 - Apr 20 Total with taxes and fees [](https://www.expedia.com/Key-West-Hotels-Kimpton-Ridley-House.h4958964.Hotel-Information?chkin=2026-4-19&chkout=2026-4-20&rm1=a2®ionId=1187&destination=Key West&destType=MARKET&latLong=24.554807,-81.802079&searchId=cf5e62e3-717f-4b2f-81fd-559f61fd8ead&top_cur=USD) Ad ![Private beach, white sand, sun loungers, beach umbrellas](https://a.travel-assets.com/media/meso_cm/PAPI/Images/lodging/1000000/20000/19400/19307/e5d5dd25_b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) #### Pier House Resort & Spa Key West Historic District - On private beach - Pool - Hot tub - Spa 9.0 Wonderful 1,072 reviews $581 nightly $654 total Mar 31 - Apr 1 Total with taxes and fees [](https://www.expedia.com/Key-West-Hotels-Pier-House-Resort-Spa.h19307.Hotel-Information?chkin=2026-3-31&chkout=2026-4-1&rm1=a2®ionId=1187&destination=Key West&destType=MARKET&latLong=24.554807,-81.802079&searchId=cf5e62e3-717f-4b2f-81fd-559f61fd8ead&top_cur=USD) Ad ![Exterior](https://a.travel-assets.com/media/meso_cm/PAPI/Images/lodging/1000000/890000/889900/889862/226bceda_b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) #### The Marquesa Hotel Old Town Key West - Pool - Restaurant - Air conditioning - Parking available 9.8 Exceptional 1,000 reviews $449 nightly $505 total Apr 27 - Apr 28 Total with taxes and fees [](https://www.expedia.com/Key-West-Hotels-The-Marquesa-Hotel.h889862.Hotel-Information?chkin=2026-4-27&chkout=2026-4-28&rm1=a2®ionId=1187&destination=Key West&destType=MARKET&latLong=24.554807,-81.802079&searchId=cf5e62e3-717f-4b2f-81fd-559f61fd8ead&top_cur=USD) Ad ![6 outdoor pools, free cabanas, pool umbrellas](https://a.travel-assets.com/media/meso_cm/PAPI/Images/lodging/17000000/16210000/16203000/16202992/846829dd_b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) #### Oceans Edge Key West Resort, Hotel & Marina Stock Island - Pool - Pet friendly - Free WiFi - Restaurant 9.0 Wonderful 1,846 reviews $278 nightly $313 total Apr 29 - Apr 30 Total with taxes and fees [](https://www.expedia.com/Key-West-Hotels-Oceans-Edge-Key-West-Resort.h16202992.Hotel-Information?chkin=2026-4-29&chkout=2026-4-30&rm1=a2®ionId=1187&destination=Key West&destType=MARKET&latLong=24.554807,-81.802079&searchId=cf5e62e3-717f-4b2f-81fd-559f61fd8ead&top_cur=USD) Ad ![Exterior](https://a.travel-assets.com/media/meso_cm/PAPI/Images/lodging/1000000/10000/3900/3853/92e8bef1_b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) #### La Concha Key West, Autograph Collection Key West Historic District - Pool - Pet friendly - Free WiFi - Restaurant 8.8 Excellent 366 reviews $454 nightly $511 total Apr 13 - Apr 14 Total with taxes and fees [](https://www.expedia.com/Key-West-Hotels-Crowne-Plaza-Key-West-La-Concha.h3853.Hotel-Information?chkin=2026-4-13&chkout=2026-4-14&rm1=a2®ionId=1187&destination=Key West&destType=MARKET&latLong=24.554807,-81.802079&searchId=cf5e62e3-717f-4b2f-81fd-559f61fd8ead&top_cur=USD) Ad ![Food and drink](https://images.trvl-media.com/lodging/49000000/48720000/48713900/48713884/5fd7b8bf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) #### Margaritaville Beach House Key West Key West - Pool - Pet friendly - Restaurant - Air conditioning 8.8 Excellent 1,801 reviews $377 nightly $424 total Apr 28 - Apr 29 Total with taxes and fees [](https://www.expedia.com/Key-West-Hotels-Margaritaville-Beach-House-Key-West.h48713884.Hotel-Information?chkin=2026-4-28&chkout=2026-4-29&rm1=a2®ionId=1187&destination=Key West&destType=MARKET&latLong=24.554807,-81.802079&searchId=cf5e62e3-717f-4b2f-81fd-559f61fd8ead&top_cur=USD) Ad ![Marina](https://images.trvl-media.com/lodging/18000000/17320000/17313700/17313680/deb8b21f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) #### The Perry Hotel & Marina Key West Stock Island - Pool - Pet friendly - Free WiFi - Restaurant 9.4 Exceptional 1,234 reviews $410 nightly $461 total Apr 26 - Apr 27 Total with taxes and fees [](https://www.expedia.com/Key-West-Hotels-The-Perry-Hotel-Marina-Key-West.h17313680.Hotel-Information?chkin=2026-4-26&chkout=2026-4-27&rm1=a2®ionId=1187&destination=Key West&destType=MARKET&latLong=24.554807,-81.802079&searchId=cf5e62e3-717f-4b2f-81fd-559f61fd8ead&top_cur=USD) ![Mod logo](https://a.travel-assets.com/egds/marks/onekey__standard__always_light.svg) Earn OneKeyCash on thousands of hotels when you sign in and book. More rewards for more adventures! [Sign in](https://www.expedia.com/login?ckoflag=0&uurl=e3id%3Dredr%26rurl%3D%2FKey-West-Hotels-Poolside-Paradise-Monthly-Rental.h121132471.Hotel-Information)[Sign up, it's free](https://www.expedia.com/signup?enable_registration=true&uurl=e3id%3Dredr%26rurl%3D%2FKey-West-Hotels-Poolside-Paradise-Monthly-Rental.h121132471.Hotel-Information) ## About the neighborhood Midtown, a neighborhood in Key West, is home to Poolside Paradise - Monthly Rental. Southernmost Point and Ernest Hemingway Home and Museum are notable landmarks, and the area's natural beauty can be seen at Florida Keys Beaches and Fort Zachary Taylor Historic State Park. Key West Butterfly and Nature Conservatory and MLK Community Pool & Community Center are also worth visiting. [Visit our Key West travel guide](https://www.expedia.com/Key-West.dx1187) [View more Apartments in Key West](https://www.expedia.com/Key-West-Apartments.d1187-aaApartments.Travel-Guide-Accommodation) ![Map](https://maps.googleapis.com/maps/api/staticmap?&size=660x330&map_id=3b266eb50d2997c6&zoom=13&markers=icon:https%3A%2F%2Fa.travel-assets.com%2Ftravel-assets-manager%2Feg-maps%2Fproperty.png%7C24.55298%2C-81.78368&channel=expedia-HotelInformation&maptype=roadmap&scale=1&key=AIzaSyCYjQus5kCufOpSj932jFoR_AJiL9yiwOw&signature=T5O0wGBQI3k69gGsA4YtXwBqw88=) Key West, FL ### What's nearby - ![Key West Naval Station](https://images.trvl-media.com/place/553248635976481245/e66923bb-4dc7-449a-bbc6-f6b5c57b69c9.jpg?impolicy=resizecrop&rw=115.61&rh=65.03&ra=fit&q=high) Key West Naval Station 6 min walk \- 0.4 miles - ![Beach and Pier at Sunset, Florida, USA](https://images.trvl-media.com/place/553248635976496782/1bfe637a-381c-425d-ba50-7340e2c8b6bb.jpg?impolicy=resizecrop&rw=115.61&rh=65.03&ra=fit&q=high) Florida Keys Beaches 8 min walk \- 0.4 miles - ![Clarence S. Higgs Memorial Beach Park](https://images.trvl-media.com/place/6246822/85c3e283-463e-4462-91b6-cddba21dfa39.jpg?impolicy=resizecrop&rw=115.61&rh=65.03&ra=fit&q=high) Clarence S. Higgs Memorial Beach Park 8 min walk \- 0.5 miles - ![Smathers Beach](https://images.trvl-media.com/place/6069255/906a25d3-aea9-4560-a01c-5f793021725b.jpg?impolicy=resizecrop&rw=115.61&rh=65.03&ra=fit&q=high) Smathers Beach 13 min walk \- 0.7 miles - ![Duval Street](https://images.trvl-media.com/place/6068616/5997ee0c-eca4-415b-b051-99f4d38fbc11.jpg?impolicy=resizecrop&rw=115.61&rh=65.03&ra=fit&q=high) Duval Street 19 min walk \- 1.0 mile ### Getting around - Key West Intl. Airport (EYW) 6 min drive ### Restaurants - Circle K 12 min walk - Dions Truman & White 14 min walk - Morrison's Market 12 min walk - Sandy's Café 14 min walk - Popeyes Louisiana Kitchen 15 min walk ## About this property ### Poolside Paradise - Monthly Rental Apartment near Florida Keys Beaches Close to Smathers Beach and South Beach, Poolside Paradise - Monthly Rental has plenty to offer. Guests can connect to free WiFi in public areas. Other perks at this apartment include: - Free self parking Room features All guestrooms at Poolside Paradise - Monthly Rental have amenities such as high-speed internet. ## Similar properties ![House | 3 bedrooms, desk, Internet](https://images.trvl-media.com/lodging/110000000/109010000/109003200/109003140/w3000h1993x0y0-17c2fec1.jpg?impolicy=fcrop&w=469&h=201&p=1&q=medium) ### Hidden Oasis Gorgeous Home w Pvt Pool New Town - Parking included - Free WiFi - Outdoor Space - Barbecue grill [](https://www.expedia.com/Hotel-Search?startDate=2026-04-13&endDate=2026-04-14&selected=109003140&PinnedHotelID=109003140&HadPinnedHotel=true®ionId=-1&adults=2) ![A heated pool](https://images.trvl-media.com/lodging/125000000/124560000/124559000/124558979/fde9bd64.jpg?impolicy=fcrop&w=469&h=201&p=1&q=medium) ### \*\*CASA DEL MONO @ MIDTOWN\*\* Stunning Private Home & Pool + LAST KEY SERVICES… Midtown - Pool - Kitchen - Washer - Dryer [](https://www.expedia.com/Hotel-Search?startDate=2026-04-13&endDate=2026-04-14&selected=124558979&PinnedHotelID=124558979&HadPinnedHotel=true®ionId=-1&adults=2) ![A heated pool](https://images.trvl-media.com/lodging/122000000/121490000/121481400/121481338/abf6b88d.jpg?impolicy=fcrop&w=469&h=201&p=1&q=medium) ### POOLSIDE PARADISE \~ Charming 3 BR/2Ba Home w/ Pool! Midtown - Pool - Kitchen - Washer - Dryer [](https://www.expedia.com/Hotel-Search?startDate=2026-04-13&endDate=2026-04-14&selected=121481338&PinnedHotelID=121481338&HadPinnedHotel=true®ionId=-1&adults=2) ![Smart TV, stereo](https://images.trvl-media.com/lodging/45000000/44040000/44039700/44039656/e2de1ff6.jpg?impolicy=fcrop&w=469&h=201&p=1&q=medium) ### \*\*MIDTOWN MOSAIC @ MIDTOWN\*\* Modern Private Home & Pool + LAST KEY SERVICES… Midtown - Pool - Kitchen - Washer - Dryer 10 Exceptional 4 reviews [](https://www.expedia.com/Hotel-Search?startDate=2026-04-13&endDate=2026-04-14&selected=44039656&PinnedHotelID=44039656&HadPinnedHotel=true®ionId=-1&adults=2) [Compare similar properties](/Hotel-Search?startDate=2026-04-13&endDate=2026-04-14&selected=121132471&PinnedHotelID=121132471&HadPinnedHotel=true®ionId=-1&adults=2&comparePropertyIds=121132471,109003140,124558979,121481338,44039656) ## Policies ### Check-in Check-in start time: 3:00 PM; Check-in end time: 5:00 PM Minimum check-in age: 25 ### Check-out Check-out before 11:00 AM ### Special check-in instructions Guests must contact the property for check-in information To make arrangements for check-in please contact the property at least 24 hours before arrival using the information on the booking confirmation Information provided by the property may be translated using automated translation tools ### Pets Pets not allowed ### Children and extra beds Children are welcome ### Property payment types ## Important information ### You need to know Extra-person charges may apply and vary depending on property policy Government-issued photo identification and a credit card, debit card, or cash deposit may be required at check-in for incidental charges Special requests are subject to availability upon check-in and may incur additional charges; special requests cannot be guaranteed This property accepts credit cards Host has not indicated whether there is a carbon monoxide detector on the property; consider bringing a portable detector with you on the trip Host has not indicated whether there is a smoke detector on the property ### We should mention This property does not have elevators A mandatory cleaning fee is included in this property's rental rate ## Frequently asked questions ### Is Poolside Paradise - Monthly Rental pet-friendly? ### How much is parking? ### What time is check-in at Poolside Paradise - Monthly Rental? ### What time is check-out at Poolside Paradise - Monthly Rental? ### Where is Poolside Paradise - Monthly Rental located? ## Have a question? 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