Casa Marina Key West, Curio Collection by Hilton is one of The 15 Best Places with a Swimming Pool in Key West.

1. Casa Marina Key West, Curio Collection by Hilton

7.9
1500 Reynolds St, Key West, FL
Hotel · 87 tips and reviews

Kristen B.Kristen Bailey: Go see Jan at the SunSun poolside bar! She'll fix you right up! They have the best Conch Fritters in all of Key West!

Tasha C.Tasha Cosenza-Mechels: Beautiful clean rooms. Awesome beachside resort-they take care of you here! Very nice staff. 2 big pools! Get the piña colada!!!

Dan M.Dan Murphy: Alternative to the NorthWest side Westin properties, is the southward facing Casa Marina. Oceanfront and Poolside for Sunrise.

Truman Hotel is one of The 15 Best Places with a Swimming Pool in Key West.

2. Truman Hotel

7.9
611 Truman Ave, Key West, FL
Motel · 19 tips and reviews

eduedu: Uno de los mejores y mas bonitos hoteles de Key West. Piscina pequeña pero acogedora, parking y wifi gratuitos, muy cerca de Duval Str... Totalmente aconsejable

Richard M.Richard Mooring: Get a room with a balcony on the poolside.

PatzPatz: La piscina por la noche es riquísima . Todo el hotel es schön ;)

Angelina Guest House is one of The 15 Best Places with a Swimming Pool in Key West.

3. Angelina Guest House

7.9
302 Angela St, Key West, FL
Bed and Breakfast · 8 tips and reviews

David K.David Klink: Great place! Friendly staff, perfect location, comfortable room. Pool area is a highlight

Joerg W.Joerg Wagner: Totally recommendable. Warm welcome, great rooms, amazing pool area, high performance WiFi, and and and

Marcel P.Marcel P.: Close to duval street but quiet. Friendly staff, clean rooms, bike rental is available (really reasonable prices). Beautiful pool area.

Dante's is one of The 15 Best Places with a Swimming Pool in Key West.

4. Dante's

7.7
955 Caroline St, Key West, FL
Cuban Restaurant · 50 tips and reviews

Matt L.Matt Leese: Plenty of specialty rum drinks, poolside bar with waterfall, hidden from the street and bayside. All good so far!

Ashley AnnAshley Ann: Swimming pool! Decent service... Fun place!

Savannah B.Savannah Brown: Loud music, poolside bar, & restaurant right next to the marina. Not my usual scene but it was still a fun time.

Best Western Key Ambassador Resort Inn is one of The 15 Best Places with a Swimming Pool in Key West.

5. Best Western Key Ambassador Resort Inn

7.4
3755 S Roosevelt Blvd, Key West, FL
Hotel · 10 tips and reviews

Scott R.Scott Rudd: Come hang poolside with an amaretto coloda or mango margarita. Local friendly- come on down! Scott or Judy or Lenay will hook you up!

Björn T.Björn Tamara: WiFi , swimming pool

mya w.mya w: Great pool area, love seeing the iguanas

The Gates Hotel is one of The 15 Best Places with a Swimming Pool in Key West.

6. The Gates Hotel

8.2
3824 N Roosevelt Blvd, Key West, FL
Hotel · 7 tips and reviews

Luceli M.Luceli Miola: Hotel novo com quartos modernos e confortáveis. A área da piscina é bem bacana também. Há um truckfood que serve comidas deliciosas e o bar com música ao vivo é outro benefício.

Souza S.Souza Souza: Excelentes quartos e uma ótima piscina

TamaraTamara: Amazing place! We really enjoyed our stay here...they loved our dogs and they got a gift for staying at The Gates:) clean, neat beautiful bungalow style large rooms! Starbucks Coffee ...GREAT STAFF!

Pool Bar at Bourbon Complex is one of The 15 Best Places with a Swimming Pool in Key West.

7. Pool Bar at Bourbon Complex

7.6
724 Duval St (Petronia St.), Key West, FL
Gay Bar · 8 tips and reviews

Silver T.Silver Tears: TJ works days in the pool bar - great bartender - u will have a blast

Brice C.Brice Cook: Great pool bar.

DeVaun D.DeVaun Davis: The pool and hot tub is awesome. Always best enjoyed with friends

The Marker Key West is one of The 15 Best Places with a Swimming Pool in Key West.

8. The Marker Key West

9.2
200 William St (Caroline), Key West, FL
Hotel · 5 tips and reviews

Cathy B.Cathy Belcher: Great poolside bar. Stop for a drink... Or a pizza!

Maddie L.Maddie Lippincott: Beautiful hotel with scenic views, luxurious ambiance, and within walking distance of all kinds of things to see and do. Little pricey but totally worth it if you ask me.

Jerrell T.Jerrell Thompson: 212 has a awesome view

The Southernmost Inn is one of The 15 Best Places with a Swimming Pool in Key West.

9. The Southernmost Inn

8.3
525 United St (Simonton Street), Key West, FL
Resort · 3 tips and reviews

Catalina F.Catalina Fravega: Buenísima ubicación. Buen patio con piscina y bar. Ojo, no se permiten niños/menores de edad.

Sergio D.Sergio Delfanti: Very clean and good service. Small swimmingpool an location ok at southern end of Duval

Duke K.Duke Knutson: Great place for a adult vacation. Great location. Super staff. Treated us like family.

The Gardens Hotel Key West is one of The 15 Best Places with a Swimming Pool in Key West.

10. The Gardens Hotel Key West

8.5
526 Angela St, Key West, FL
Hotel · 12 tips and reviews

Jon E.Jon Etkins: Free jazz by the pool bar on Sunday afternoons.

Norm T.Norm Thomas: Worth going to the Sunday Jazz at the pool bar. Bring your friends and have a great time!

Paula B.Paula Bendfeldt-Diaz: For breakfast you must try the yogurt martinis. YUM!

Ocean Key Resort & Spa is one of The 15 Best Places with a Swimming Pool in Key West.

11. Ocean Key Resort & Spa

8.8
0 Duval Street (Wall St), Key West, FL
Resort · 20 tips and reviews

California GirlCalifornia Girl: Definitely great service by the pool, Diane & Jessica (pictured here) are top! Attentive, kind and quick service. Loved my day poolside. #californiagirl

Lindsey E.Lindsey E: Staff is really helpful and friendly. Sunsets are gorgeous. Rooms are spacious and clean! Loved it.

AT&TAT&T: Another great reason to stay here: AT&T Wi-Fi is one of the many amenities here for guests. It’s fast and easy to connect.

Eden House is one of The 15 Best Places with a Swimming Pool in Key West.

12. Eden House

8.6
1015 Fleming St (Grinnell & Frances), Key West, FL
Hotel · 17 tips and reviews

Jason K.Jason Korenblit: No phone in the room? Kinda weird. But helpful staff, beautiful pool area, and free liquor from 4 to 5.

Rebecca W.Rebecca Wright: Happy hour is great. The staff here is very friendly and make you feel welcome

Shn J.Shn Juay: Quaint place with heated pool & Jacuzzi, hammocks,sundeck, free parking, this got to be the best hotel in this area! Free beers as welcome drink & free-flow at the bar (by the pool) 4-5pm. AWESOME!

Hilton Garden Inn is one of The 15 Best Places with a Swimming Pool in Key West.

13. Hilton Garden Inn

8.6
3850 N Roosevelt Blvd, Key West, FL
Hotel · 7 tips and reviews

In The K.In The Keys: Ana (poolside bar) is one of Key West's best bartenders.

Jay L.Jay L: Great relaxing hotel, with the perfect location few miles away for the beach. Very clean and modern, showers are amazing. Good parking highly recommend.

Olga W.Olga Wieczorek: Nice and clean quite far from all atractions.

Silver Palms Inn is one of The 15 Best Places with a Swimming Pool in Key West.

14. Silver Palms Inn

8.3
830 Truman Ave, Key West, FL
Hotel · 22 tips and reviews

Viviane F.Viviane Fleury: Ótimo hotel, acomodação muito confortável, área da piscina muito charmosa. Um pouco caro.Poucas vagas para estacionamento. Se sair com o carro corre o risco de não ter onde estacionar depois.

Sibila S.Sibila Silva: Great rooms, very modern style, clean, free parking and free WiFi!. Also nice breakfast ... price good for the service.

Austin H.Austin Haight: For Key West, this place is very nice. Quiet, clean, great service, and free parking. The location is a bit far from the scene, but still comfortably walkable & no issue with bikes or a cab.

NYAH is one of The 15 Best Places with a Swimming Pool in Key West.

15. NYAH

7.5
420 Margaret St (Fleming St), Key West, FL
Hotel · 10 tips and reviews

PhilPhil: Management (Mandy) is nice & flexible. Neat swimming pools & hot tubs. 5 blocks away from Duval st, which is nice. Bad: woke up to lots of tiny worms in the bathroom ://

Daniela C.Daniela Correia: Ótimo hotel! Bons quartos, com ar-condicionado, bons chuveiros, piscinas e tem até uma de água quente (muito bom depois de um dia caminhando para cima e para baixo na cidade)!

Emily S.Emily Schetman: Friendly staff and nice clean rooms with plentiful outlets and storage space. Happy hour at 4:20PM with free wine and cheese- don't miss it!