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Find Hotels with a Pool in Flamingo, FL

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Check availability on Flamingo Hotels with a Pool

Tonight
Aug 25 - Aug 26
Tomorrow
Aug 26 - Aug 27
This weekend
Aug 28 - Aug 30
Next weekend
Sep 4 - Sep 6

Our top choices for Flamingo hotels with a pool

A resort with a swimming pool, lounge chairs, and palm trees.
A balcony with wicker furniture and a view of the ocean and palm trees.
A bedroom with a large bed, a ceiling fan, a TV on the wall, and a view of the beach through a window.
A spacious living area with a large island, wooden furniture, and a ceiling fan.

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.
￥16,532
￥25,750 total
includes taxes & fees
Aug 27 - Aug 28
Lime Tree Bay Resort
A swimming pool with clear blue water, surrounded by a white deck and a black metal fence.
A balcony with two blue lounge chairs, a wooden ceiling, and a view of the ocean and palm trees.
A beach with palm trees and lounge chairs.
A waterfront hotel with multiple floors, palm trees, and a calm reflective pool.

2. Chesapeake Beach Resort

Chesapeake Beach Resort
Matecumbe
  • Splash into paradise with two stunning outdoor pools overlooking a private white sand beach.
￥24,009
￥35,951 total
includes taxes & fees
Aug 26 - Aug 27
Chesapeake Beach Resort
A pool area with a view of the ocean, surrounded by palm trees and a clear sky.
A covered outdoor area with a view of a beach and palm trees.
A beach with palm trees, lounge chairs, and a view of the ocean.
A wooden dock with a boat docked at the pier, a thatched umbrella, and calm water.

3. Rock Reef Resort

Rock Reef Resort
Rock Harbor
  • Dive into a sun-soaked Florida Keys getaway with a heated pool, private beach, and lounger paradise with stunning sunset views.
￥14,186
￥15,959 total
includes taxes & fees
Aug 26 - Aug 27
Rock Reef Resort
A tropical resort with a swimming pool, palm trees, and a waterfall.
A bar area with a thatched roof, wooden chairs, and a view of the ocean.
A hotel room with a large bed, a television, a dining area with chairs, a table, and a view of the ocean.
A bathroom with a large bathtub, a window with curtains, and a view of palm trees and the sea.

4. Cheeca Lodge & Spa

Cheeca Lodge & Spa
Matecumbe
  • Tropical paradise swim experience awaits with three refreshing pools and poolside service.
￥23,684
￥38,269 total
includes taxes & fees
Aug 26 - Aug 27
Cheeca Lodge & Spa
A resort pool with palm trees, beach chairs, and umbrellas.
A beach with palm trees, a dock, and lounge chairs.
A hotel room with a sofa, a small round table, a desk with a chair, and a view of the sea through large windows.
A wooden deck with two lounge chairs, a table with two glasses of champagne and red roses, and a view of the beach and ocean.

5. Amara Cay Resort

Amara Cay Resort
Matecumbe
  • Splash into serenity at this resort's private beach and outdoor pool with lounge chairs and umbrellas.
￥24,600
￥39,309 total
includes taxes & fees
Aug 30 - Aug 31
Amara Cay Resort
A clear blue pool surrounded by palm trees and a thatched-roof structure, with a sign indicating no diving.
A view through a window with metal bars, featuring a beach with palm trees, a thatched umbrella, and a wooden dock.
A beach with kayaks lined up near the water's edge, palm trees, and lounge chairs.
A tropical resort with a paved pathway leading to a building, surrounded by palm trees and lush greenery.

6. Kona Kai Resort and Gallery - Adults Only

Kona Kai Resort and Gallery - Adults Only
Rock Harbor
  • Oceanfront pool sanctuary with sunset views makes this adults-only haven a serene Florida Keys retreat.
￥18,947
￥25,786 total
includes taxes & fees
Aug 26 - Aug 27
Kona Kai Resort and Gallery - Adults Only
A swimming pool with lounge chairs and a building with balconies.
A balcony with a view of palm trees and a beach.
A beach view with palm trees and a thatched-roof structure.
A compact kitchen with wooden cabinets, a refrigerator, and a window with curtains.

7. Matecumbe Resort

Matecumbe Resort
Matecumbe
  • Dive into a tranquil paradise with private beach access and a refreshing outdoor pool.
￥21,334
￥24,001 total
includes taxes & fees
Aug 30 - Aug 31
Matecumbe Resort
A pool area with a white fence, a lifebuoy, and palm trees in the background.
A row of floating cottages with balconies and outdoor seating, docked along a waterway.
A modern kitchen with white cabinets, a microwave, and a dining area with a table and chairs.
A bedroom with a bed, a window with blinds, and a view of the outdoors.

8. Treasure Harbor

Treasure Harbor
Islamorada
￥19,885
￥44,722 total
includes taxes & fees
Aug 26 - Aug 27
Treasure Harbor
A pool area with lounge chairs and a sign indicating a drop-off zone.
A beach with palm trees, a thatched umbrella, and lounge chairs.
A view from a window overlooking a beach with palm trees, a wooden deck, and lounge chairs.
A beach with palm trees, a thatched-roof hut, and beach chairs.

9. Drop Anchor

Drop Anchor
Islamorada
  • Sun-drenched serenity awaits at this Art Deco hotel's outdoor pool with loungers.
￥16,499
￥24,124 total
includes taxes & fees
Aug 27 - Aug 28
Drop Anchor
A pool area with a white fence, palm trees, and a building with a white exterior and multiple windows.
A bedroom with a bed, two chairs, a sofa, a TV, and a large window with a view of the ocean.
A wooden deck with rustic furniture, a grill, and a view of the beach and palm trees.

10. La Jolla Resort

La Jolla Resort
Matecumbe
  • Splash into Florida Keys bliss with a private beach and poolside paradise perfect for sun seekers.
￥18,947
￥25,786 total
includes taxes & fees
Aug 27 - Aug 28
La Jolla 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

Cheeca Lodge & Spa

Cheeca Lodge & Spa

10/10 Excellent
"Service and location"
Joe 2-night trip
Posted 1 hour ago
Cheeca Lodge & Spa
Chesapeake Beach Resort

Chesapeake Beach Resort

8/10 Good
"Vanessa saved the day. I will always appreciate her thoughtfulness. Cookies are good too"
James 2-night trip
Posted 2 hours ago
Chesapeake Beach Resort
Islander Resort

Islander Resort

10/10 Excellent
"Property is beautiful, staff is great and overall an amazing place to stay."
Sonia 1-night trip
Posted 3 hours ago
Islander Resort
Baker's Cay Resort Key Largo, Curio Collection by Hilton

Baker's Cay Resort Key Largo, Curio Collection by Hilton

10/10 Excellent
"Fui y volví a ir antes de un mes ... me encantó"
Mariesly 2-night trip
Posted 4 hours ago
Baker's Cay Resort Key Largo, Curio Collection by Hilton
Travelodge by Wyndham Florida City/Homestead/Everglades

Travelodge by Wyndham Florida City/Homestead/Everglades

8/10 Good
"I like that it was clean with consistent breakfast. The rates were very manageable. I traveled with a student and having a place to eat each day was very convenient. I like the closeness to other places to eat and convenience stores. I will go back for sure. The staff were very helpful and I have already recommended this hotel to other colleagues that are teaching diving courses arriving from out of town. What I did not like was the inconsistency at which the lobby “closed.” I was there for a week. I was asked to leave the lobby three different times, twice by the same person. I stayed to 11:30 pm one night, another around 10:15pm and then one night 9:30pm. (To be fair The times are approximate not exact but there was considerable difference) Either the person at the front desk decided it was closed or a security person very respectfully ask me leave. My headphones broke just before I taught 1 hour online course one afternoon. I began teaching in the lobby from my laptop. I was asked to leave which was fair. I would have liked some grace and consideration because 1. There was no one else in the lobby except me. 2. When I was asked to leave I did explain my headphones were broken. 3. Outside was very hot and the mosquitoes were highly active. I was letting the student study in my room away from the heat. I am just stating the facts of my experience. I am careful not to read anything into it. I was there for 5 days. I was asked to leave the lobby 4 times. Still going back."
Courtlandt 6-night trip
Posted 14 hours ago
Travelodge by Wyndham Florida City/Homestead/Everglades
Reefhouse Resort & Marina

Reefhouse Resort & Marina

10/10 Excellent
"Property is well kept and in great location. Fishing in the back is permitted. Bar is great and staff is friendly. Do t think twice about it."
Juan 3-night trip
Posted 18 hours ago
Reefhouse Resort & Marina
Amara Cay Resort

Amara Cay Resort

10/10 Excellent
"Room was clean. Pool and bar was great. The only complaint I have is the service at breakfast was extremely slow. Seemed they were understaffed."
Arlene 2-night trip
Posted 1 day ago
Amara Cay Resort
Waterside Suites & Marina

Waterside Suites & Marina

10/10 Excellent
"is really amazing very good and really closed to many restaurants ,you'll love it"
Clara 2-night trip
Posted 1 day ago
Waterside Suites & Marina
Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort

Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort

10/10 Excellent
"I’d recommend getting breakfast locally instead of the resort’s breakfast. Very friendly and helpful staff."
Dareen 3-night trip
Posted 2 days ago
Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort

Frequently asked questions

What are some accommodations with pools in Flamingo?
Cheeca Lodge & Spa: Features a private beach, 3 outdoor pools, and 3 restaurants. Baker's Cay Resort Key Largo, Curio Collection by Hilton: Offers a private beach, 2 outdoor pools, and 2 restaurants. Waterside Suites & Marina: Hotel, 7-minute walk from John Pennekamp Coral Reef State Park. Provides complimentary wireless internet access, an outdoor pool, and kitchens. Chesapeake Beach Resort: Features a private beach, 2 outdoor pools, and daily. Lime Tree Bay Resort: Offers a private beach, 3 outdoor pools, and free self parking.
What is there to see and do in Flamingo?
The picturesque setting of Everglades National Park and Flamingo Visitor Center showcase the area's natural beauty. During your stay, check out sights such as Eco Pond, 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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