
Find Hotels with a Pool in Flamingo, FL
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Sep 18 - Sep 20Next weekend
Sep 25 - Sep 27Our top choices for Flamingo hotels with a pool




1. Lime Tree Bay Resort
Lime Tree Bay ResortLong Key
- A sun-drenched retreat with three tropical pools and private beach access awaits at this waterfront Florida Keys resort.
¥17,823
¥33,162 total
includes taxes & fees
Sep 20 - Sep 21




2. Chesapeake Beach Resort
Chesapeake Beach ResortMatecumbe
- Splash into paradise with two stunning outdoor pools overlooking a private white sand beach.
¥22,834
¥34,365 total
includes taxes & fees
Sep 20 - Sep 21




3. Cheeca Lodge & Spa
Cheeca Lodge & SpaMatecumbe
- Tropical paradise swim experience awaits with three refreshing pools and poolside service.
¥21,144
¥35,067 total
includes taxes & fees
Sep 29 - Sep 30




4. Breezy Palms Resort
Breezy Palms ResortMatecumbe
- Serene outdoor pool with comfy loungers provides a sunny retreat just steps from the private beach and marina access.
¥12,707
¥16,770 total
includes taxes & fees
Sep 22 - Sep 23




5. Ragged Edge Resort & Marina
Ragged Edge Resort & MarinaIslamorada
- Dive into poolside paradise with comfy loungers at Ragged Edge Resort, a cyclist-friendly escape.
¥11,624
¥13,078 total
includes taxes & fees
Sep 20 - Sep 21




6. Matecumbe Resort
Matecumbe ResortMatecumbe
- Dive into a tranquil paradise with private beach access and a refreshing outdoor pool.
¥19,852
¥22,334 total
includes taxes & fees
Sep 21 - Sep 22




7. Drop Anchor
Drop AnchorIslamorada
- Sun-drenched serenity awaits at this Art Deco hotel's outdoor pool with loungers.
¥16,487
¥23,978 total
includes taxes & fees
Sep 17 - Sep 18




8. Amara Cay Resort
Amara Cay ResortMatecumbe
- Splash into serenity at this resort's private beach and outdoor pool with lounge chairs and umbrellas.
¥22,174
¥36,225 total
includes taxes & fees
Sep 20 - Sep 21
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Top Flamingo Hotel Reviews
Garden Inn Homestead/Everglades/Gateway to Keys
8/10 Good
"The breakfast was great, very pleasant surprise with a lot of options. The place has a policy that they only give 1 towel per person (ladies, good luck washing your hair) and one soap per room, which made our stay very challenging hosting 3 people in the room sharing 1 soap - migrating it between the shower and the sink area — there was no body wash or shampoo, every function was supposed to be filled by that one soap.. same with cups, the cleaning staff gave 3 paper cups for 3 people. When we asked for more at the reception, the staff said it’s against the policy. Apart from these, the staff was friendly, and it is probably about poor mentality by the leadership than anything else. Overall, we enjoyed our stay and the hotel has great location."
Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort
10/10 Excellent
"We had an excellent stay at Three Waters Resort in Islamorada. Everything about the property was great from start to finish. Our room was very clean, comfortable, and well maintained, and the entire resort was beautiful and inviting. One of the things we really enjoyed was all of the included amenities. We took advantage of the complimentary kayaks, and they also had bikes available for guests to use at no additional charge. It was a great way to get out, explore, and enjoy the area. The fire pits at night were another highlight. Sitting outside by the fire was the perfect way to end the day and really added to the relaxing Keys atmosphere. Overall, we had a fantastic experience. The property was clean, the amenities were excellent, and there honestly wasn’t anything we could complain about. We would absolutely stay at Three Waters again and highly recommend it to anyone visiting Islamorada!"
Playa Largo Resort & Spa, Autograph Collection
8/10 Good
"Lovely hotel. Very expensive just to buy drinks though but good location."
Cheeca Lodge & Spa
10/10 Excellent
"Clean and comfortable rooms, but I did get a dated feel, but certainly served our purpose. The property supplied EVERYTHING needed to enjoy your stay. I didn’t have dinner there, but their breakfast was elevated and delish. The Adult pool we used had an exercise instructor, a spa and was crystal clear. Staff was friendly and accommodating. The roosters that roamed were the healthiest looking rooster I ever saw 😉. We wandered off the property but my observation was that you didn’t need to leave to stay busy and active, very self-contained."
Waterside Suites & Marina
10/10 Excellent
"1"
Chesapeake Beach Resort
10/10 Excellent
"/"
Fairway Inn Florida City Homestead Everglades
8/10 Good
"It was okay stay"
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