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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
Sep 25 - Sep 26
Tomorrow
Sep 26 - Sep 27
This weekend
Sep 25 - Sep 27
Next weekend
Oct 2 - Oct 4

Our top choices for Flamingo hotels with a pool

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

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.
￥18,173
￥27,523 total
includes taxes & fees
Oct 4 - Oct 5
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 waterfront hotel with multiple floors, palm trees, and a calm reflective pool.
A hotel room with a bed, a bedside table with a lamp, a small table with a basket, a blue and white striped ottoman, and a balcony with a view of palm trees and the ocean.

2. Chesapeake Beach Resort

Chesapeake Beach Resort
Matecumbe
  • Splash into paradise with two stunning outdoor pools overlooking a private white sand beach.
￥22,266
￥33,979 total
includes taxes & fees
Sep 29 - Sep 30
Chesapeake Beach Resort
A swimming pool with lounge chairs and a building with balconies.
A balcony with a view of palm trees and a beach.
A beach with a thatched umbrella, lounge chairs, and a clear view of the ocean.
A compact kitchen with wooden cabinets, a refrigerator, and a window with curtains.

3. Matecumbe Resort

Matecumbe Resort
Matecumbe
  • Dive into a tranquil paradise with private beach access and a refreshing outdoor pool.
￥20,431
￥22,985 total
includes taxes & fees
Sep 27 - Sep 28
Matecumbe Resort
A nighttime swimming pool with a blue tint, surrounded by palm trees and a fenced area with lounge chairs.
A beach with palm trees, thatched-roof huts, and lounge chairs.
A beach with thatched umbrellas, palm trees, and lounge chairs.
A living room with a sofa, armchair, coffee table, and lamp. There is a dining area with a table and chairs. The room has a kitchen area with a stove and cabinets.

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.
￥12,858
￥16,976 total
includes taxes & fees
Sep 29 - Sep 30
Breezy Palms Resort
A tropical resort with a swimming pool, palm trees, and a waterfall.
A balcony with a view of palm trees and the sea, a white railing, and a table with chairs.
A bathroom with a large bathtub, a window with curtains, and a view of palm trees and the sea.
A bar area with a thatched roof, wooden chairs, and a view of the ocean.

5. Cheeca Lodge & Spa

Cheeca Lodge & Spa
Matecumbe
  • Tropical paradise swim experience awaits with three refreshing pools and poolside service.
￥21,998
￥36,357 total
includes taxes & fees
Sep 29 - Sep 30
Cheeca Lodge & Spa
Two people relaxing on sun loungers by a poolside with a view of the ocean and palm trees in the background.
A modern hotel room with a balcony, a bed, a TV, and a dining area with chairs and a table.
A beachfront hotel with a pool, beach chairs, and a view of the ocean at sunset.
A covered outdoor seating area with wicker chairs and a table, overlooking a beach with palm trees and a wooden deck.

6. Fisher Inn Resort & Marina

Fisher Inn Resort & Marina
Islamorada
  • Soak up scenic poolside serenity at this beachfront oasis with complimentary water sports and dreamy sunset views.
￥20,106
￥27,798 total
includes taxes & fees
Sep 28 - Sep 29
Fisher Inn Resort & Marina
A pool area with a white fence, palm trees, and a building with a white exterior and multiple windows.
A wooden deck with rustic furniture, a grill, and a view of the beach and palm trees.
A bedroom with a bed, two chairs, a sofa, a TV, and a large window with a view of the ocean.

7. La Jolla Resort

La Jolla Resort
Matecumbe
  • Splash into Florida Keys bliss with a private beach and poolside paradise perfect for sun seekers.
￥14,130
￥20,363 total
includes taxes & fees
Sep 28 - Sep 29
La Jolla Resort
A pool area with a view of the ocean, surrounded by palm trees and a clear sky.
A wooden dock with a boat docked at the pier, a thatched umbrella, and calm water.
A wooden interior with a large window overlooking a beach with a thatched umbrella and lounge chairs.
A beach with palm trees, lounge chairs, and a view of the ocean.

8. 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.
￥12,928
￥14,544 total
includes taxes & fees
Sep 27 - Sep 28
Rock Reef Resort
An aerial view of a resort with a swimming pool, palm trees, and a dock extending into the water.
A modern kitchen with a central island, a dining area with a view, and a living space with a balcony overlooking the ocean.
A beachside resort with a pool area, lounge chairs, and palm trees.

9. Pines & Palms Resort

Pines & Palms Resort
Matecumbe
  • Private beach paradise with poolside oasis and marina in the heart of Matecumbe.
￥31,289
￥43,952 total
includes taxes & fees
Oct 1 - Oct 2
Pines & Palms Resort
A resort pool with palm trees, beach chairs, and umbrellas.
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.
A beach with palm trees, a dock, and lounge chairs.
A balcony with a view of a beach, palm trees, and a pool.

10. Amara Cay Resort

Amara Cay Resort
Matecumbe
  • Splash into serenity at this resort's private beach and outdoor pool with lounge chairs and umbrellas.
￥22,820
￥37,282 total
includes taxes & fees
Sep 28 - Sep 29
Amara Cay 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

Islander Resort

Islander Resort

8/10 Good
"I liked the fact that our rear outside seating area was quite private because of the trees and bushes growing around the property. Very peaceful and also just a couple of minutes walk from the sea."
norman 4-night trip
Posted 4 hours ago
Islander Resort
Waterside Suites & Marina

Waterside Suites & Marina

8/10 Good
"Comfortable bed, clean . It’s off the busy road and close to restaurants"
Maureen 3-night trip
Posted 5 hours ago
Waterside Suites & Marina
Chesapeake Beach Resort

Chesapeake Beach Resort

8/10 Good
"I liked the breakfast. One pool was being worked on and the pool workers helped themselves to the free breakfast. Some of them stood in the coffee and drink area and ate their free breakfast. The tree trimmers took up some of relaxing areas and they were noisy. The cleaning staff and the front desk staff were very good. The breakfast cook was friendly. The spa was hot but no jet action. We probably won’t be coming back. Thanks"
William 3-night trip
Posted 6 hours ago
Chesapeake Beach Resort
Reefhouse Resort & Marina

Reefhouse Resort & Marina

10/10 Excellent
"There are some nice food and beverage options. Water sports 8n the property."
John 3-night trip
Posted 8 hours ago
Reefhouse Resort & Marina
Lime Tree Bay Resort

Lime Tree Bay Resort

10/10 Excellent
"Very lovely stay, everyone who worked there was super friendly!"
Angela 2-night trip
Posted 11 hours ago
Lime Tree Bay Resort
Bayside Inn Key Largo

Bayside Inn Key Largo

10/10 Excellent
"Great location !!"
Jenny 2-night trip
Posted 2 days ago
Bayside Inn Key Largo

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. Waterside Suites & Marina: Hotel, 7-minute walk from John Pennekamp Coral Reef State Park. Provides complimentary wireless internet access, an outdoor pool, and kitchens. Reefhouse Resort & Marina: Hotel, 7-minute walk from John Pennekamp Coral Reef State Park. Features a private beach, an outdoor pool, and 3 restaurants. Baker's Cay Resort Key Largo, Curio Collection by Hilton: Resort located near Jimmy Johnson's Big Chill. 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 West Lake showcase the area's natural beauty. During your stay, check out sights such as Flamingo Visitor Center, Eco Pond, and Pa-hay-okee Trail.
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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