A large flock of flamingos standing in shallow water.

Find Hotels with a Pool in Flamingo, FL

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Check availability on Flamingo Hotels with a Pool

Tonight
Sep 16 - Sep 17
Tomorrow
Sep 17 - Sep 18
This weekend
Sep 18 - Sep 20
Next weekend
Sep 25 - Sep 27

Our top choices for Flamingo hotels with a pool

1. Lime Tree Bay Resort

Lime Tree Bay Resort
Long 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
Lime Tree Bay Resort

2. Chesapeake Beach Resort

Chesapeake Beach Resort
Matecumbe
  • 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
Chesapeake Beach Resort

3. Cheeca Lodge & Spa

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

4. Breezy Palms Resort

Breezy Palms Resort
Matecumbe
  • 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
Breezy Palms Resort

5. Ragged Edge Resort & Marina

Ragged Edge Resort & Marina
Islamorada
  • 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
Ragged Edge Resort & Marina

6. Matecumbe Resort

Matecumbe Resort
Matecumbe
  • 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
Matecumbe Resort

7. Drop Anchor

Drop Anchor
Islamorada
  • 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
Drop Anchor

8. Amara Cay Resort

Amara Cay Resort
Matecumbe
  • 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
Amara Cay Resort

9. La Jolla Resort

La Jolla Resort
Matecumbe
  • Splash into Florida Keys bliss with a private beach and poolside paradise perfect for sun seekers.
¥15,625
¥21,943 total
includes taxes & fees
Sep 30 - Oct 1
La Jolla Resort

10. Islander Resort

Islander Resort
Matecumbe
  • Dive into this Florida Keys paradise with two shimmering pools, beachside bars, and water adventures waiting for you.
¥32,509
¥46,986 total
includes taxes & fees
Sep 29 - Sep 30
Islander Resort
View all properties

Choose what matters most at hotels with a pool in Flamingo

Breakfast included
4 stars
5 stars
Hot tub
Spa

Top Flamingo Hotel Reviews

Garden Inn Homestead/Everglades/Gateway to Keys

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."
Lilla 2-night trip
Posted 6 hours ago
Garden Inn Homestead/Everglades/Gateway to Keys
Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort

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!"
Eric 2-night trip
Posted 12 hours ago
Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort
Playa Largo Resort & Spa, Autograph Collection

Playa Largo Resort & Spa, Autograph Collection

8/10 Good
"Lovely hotel. Very expensive just to buy drinks though but good location."
Nichola 3-night trip
Posted 2 days ago
Playa Largo Resort & Spa, Autograph Collection
Cheeca Lodge & Spa

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."
Alice 2-night trip
Posted 2 days ago
Cheeca Lodge & Spa
Waterside Suites & Marina

Waterside Suites & Marina

10/10 Excellent
"1"
e 1-night trip
Posted 2 days ago
Waterside Suites & Marina
Chesapeake Beach Resort

Chesapeake Beach Resort

10/10 Excellent
"/"
billy 1-night trip
Posted 2 days ago
Chesapeake Beach Resort
Fairway Inn Florida City Homestead Everglades

Fairway Inn Florida City Homestead Everglades

8/10 Good
"It was okay stay"
Venisha 2-night trip
Posted 3 days ago
Fairway Inn Florida City Homestead Everglades

Frequently asked questions

What are some accommodations with pools in Flamingo?
Cheeca Lodge & Spa: Features a private beach, 3 outdoor pools, and 3 restaurants. Chesapeake Beach Resort: Offers a private beach, 2 outdoor pools, and daily. Reefhouse Resort & Marina: Hotel, 7-minute walk from John Pennekamp Coral Reef State Park. Provides a private beach, an outdoor pool, and 3 restaurants. Waterside Suites & Marina: Hotel, 7-minute walk from John Pennekamp Coral Reef State Park. Features complimentary wireless internet access, an outdoor pool, and kitchens. Baker's Cay Resort Key Largo, Curio Collection by Hilton: Offers a private beach, 2 outdoor pools, and 2 restaurants.
What is there to see and do in Flamingo?
The picturesque setting of Everglades National Park and Eco Pond showcase the area's natural beauty. During your stay, check out sights such as Flamingo Visitor Center, Pa-hay-okee Trail, and Snake Bight.
When is the best time to book a hotel with a pool in Flamingo?
Taking into account the local weather in Flamingo can help you maximize your time at the pool during your trip. The hottest months are usually August and July with an average temp of 83°F, while the coldest months are January and February with an average of 72°F. Average annual precipitation for Flamingo is 44 inches.

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