A large flock of flamingos standing in shallow water.

Find Hotels with a Pool in Flamingo, FL

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check availability on Flamingo Hotels with a Pool

Tonight
Sep 9 - Sep 10
Tomorrow
Sep 10 - Sep 11
This weekend
Sep 11 - Sep 13
Next weekend
Sep 18 - Sep 20

Our top choices for Flamingo hotels with a pool

A swimming pool with clear blue water, surrounded by a white deck and a black metal fence.
A beach with palm trees and lounge chairs.
A waterfront hotel with multiple floors, palm trees, and a calm reflective pool.
A balcony with two blue lounge chairs, a wooden ceiling, and a view of the ocean and palm trees.

1. Chesapeake Beach Resort

Chesapeake Beach Resort
Matecumbe
  • Splash into paradise with two stunning outdoor pools overlooking a private white sand beach.
￥18,331
￥29,269 total
includes taxes & fees
Sep 10 - Sep 11
Chesapeake Beach Resort
A clear blue swimming pool with a metal railing, surrounded by palm trees and a view of the ocean.
Three Adirondack chairs facing a sunset over a body of water.
A beach pathway with palm trees, a lifeguard tower, and the ocean in the background.
A wooden deck with a thatched roof, wooden railings, and yellow chairs.

2. Ragged Edge Resort & Marina

Ragged Edge Resort & Marina
Islamorada
  • Dive into poolside paradise with comfy loungers at Ragged Edge Resort, a cyclist-friendly escape.
￥10,770
￥12,116 total
includes taxes & fees
Sep 13 - Sep 14
Ragged Edge Resort & Marina
A pool area with a view of the ocean, surrounded by palm trees and a clear sky.
A beach with palm trees, lounge chairs, and a view of the ocean.
A covered outdoor area with a view of a beach and palm trees.
A wooden interior with a large window overlooking a beach with a thatched umbrella and lounge chairs.

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.
￥15,228
￥17,131 total
includes taxes & fees
Sep 27 - Sep 28
Rock Reef Resort
A nighttime swimming pool with a blue tint, surrounded by palm trees and a fenced area with 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.
A modern kitchen with a microwave, stove, and refrigerator. There is a dining area with a table and chairs.

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.
￥12,972
￥17,046 total
includes taxes & fees
Sep 17 - Sep 18
Breezy Palms 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 bathroom with a large bathtub, a window with curtains, and a view of palm trees and the sea.
A balcony with a view of palm trees and the sea, a white railing, and a table with chairs.

5. Cheeca Lodge & Spa

Cheeca Lodge & Spa
Matecumbe
  • Tropical paradise swim experience awaits with three refreshing pools and poolside service.
￥22,968
￥37,113 total
includes taxes & fees
Sep 15 - Sep 16
Cheeca Lodge & Spa
A resort with a swimming pool, lounge chairs, 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 balcony with wicker furniture and a view of the ocean and palm trees.
A spacious living area with a large island, wooden furniture, and a ceiling fan.

6. 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.
￥17,277
￥26,373 total
includes taxes & fees
Sep 13 - Sep 14
Lime Tree Bay 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 tropical resort with a paved pathway leading to a building, surrounded by palm trees and lush greenery.
A beachside resort with lounge chairs, a pool, and palm trees.

7. 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.
￥20,614
￥27,515 total
includes taxes & fees
Sep 10 - Sep 11
Kona Kai Resort and Gallery - Adults Only
A swimming pool with lounge chairs and umbrellas, a fenced area, and a building with a door.
A balcony with wicker furniture and a glass table, overlooking a marina with boats and palm trees.
A balcony with a view of the sea, a table, and two chairs.
A marina with boats docked along a waterfront, surrounded by buildings and palm trees.

8. Waterside Suites & Marina

Waterside Suites & Marina
Key Largo
  • Dive into poolside paradise with marina views, where rental bicycles and tropical adventures await each day.
￥13,386
￥19,383 total
includes taxes & fees
Sep 10 - Sep 11
Waterside Suites & Marina
A clear blue pool with lounge chairs, a thatched umbrella, and palm trees.
A beach with a thatched hut, palm trees, and a calm sea.
A resort with a pool, lounge chairs, and a dock.
A beachside seating area with two white Adirondack chairs and a small table under a thatched roof structure.

9. Amoray Dive Resort

Amoray Dive Resort
Key Largo
  • Tranquil poolside paradise meets private beach access for sun-soaked water adventures.
￥14,167
￥20,274 total
includes taxes & fees
Sep 15 - Sep 16
Amoray Dive Resort
A resort with a pool, cabanas, and a waterway.
A wooden dock extending into calm water, with tables and chairs under umbrellas, and a thatched-roof building in the background.
A resort with a pool, multiple buildings, and a waterfront view.
A modern kitchen with a built-in stove, a large island, and a view to a balcony with outdoor seating.

10. Dove Creek Resort & Marina, Trademark Collection by Wyndham

Dove Creek Resort & Marina, Trademark Collection by Wyndham
Key Largo
  • Dive into blissful poolside relaxation at this marina-side retreat with a heated outdoor pool and hot tub.
￥15,080
￥21,839 total
includes taxes & fees
Sep 16 - Sep 17
Dove Creek Resort & Marina, Trademark Collection by Wyndham
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

Lime Tree Bay Resort

Lime Tree Bay Resort

10/10 Excellent
"Amazing !! 💯 recommend. Clean room, excellent location and ocean view. I love this place !!"
Gladys Jeannine 1-night trip
Posted 19 hours ago
Lime Tree Bay Resort
Reefhouse Resort & Marina

Reefhouse Resort & Marina

10/10 Excellent
"Great experience"
Yvon 2-night trip
Posted 19 hours ago
Reefhouse Resort & Marina
Baker's Cay Resort Key Largo, Curio Collection by Hilton

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

10/10 Excellent
"Amazing"
Leilanis 1-night trip
Posted 23 hours ago
Baker's Cay Resort Key Largo, Curio Collection by Hilton
Islander Resort

Islander Resort

10/10 Excellent
"Everything is super great beside Beach If you looking to swim in the ocean not best pick"
Rostyslav 2-night trip
Posted 2 days ago
Islander Resort
Waterside Suites & Marina

Waterside Suites & Marina

10/10 Excellent
"Todo estaba limpio y cómodo..excelente para lugar"
Carlos 1-night trip
Posted 2 days ago
Waterside Suites & Marina
Playa Largo Resort & Spa, Autograph Collection

Playa Largo Resort & Spa, Autograph Collection

8/10 Good
"The room was clean and the staff was kind . Directions of the resort have been given by a map, not really clear without it . I would not suggest you to eat on the premises , the food is not that great , in the Italian restaurant the pizza was Frozen and the lobster pasta with parmesan cheese and not al dente , Italian ?No . Also in the other restaurants the food is décent but doesn’t justify the prices , you pay only for the view and to be in the resort . A family resort more than a solo traveler. Overall a four stars ."
Giulia 1-night trip
Posted 2 days ago
Playa Largo Resort & Spa, Autograph Collection

Frequently asked questions

What are some accommodations with pools in Flamingo?
Cheeca Lodge & Spa: Features a private beach, 3 outdoor pools, and 3 restaurants. Reefhouse Resort & Marina: Hotel, 7-minute walk from John Pennekamp Coral Reef State Park. Offers a private beach, an outdoor pool, and 3 restaurants. Baker's Cay Resort Key Largo, Curio Collection by Hilton: Provides a private beach, 2 outdoor pools, and 2 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. Chesapeake Beach Resort: Offers a private beach, 2 outdoor pools, and daily.
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.

Explore a world of travel with Expedia