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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 5 - Sep 6
Tomorrow
Sep 6 - Sep 7
Next weekend
Sep 11 - Sep 13
In two weeks
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 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.

1. Chesapeake Beach Resort

Chesapeake Beach Resort
Matecumbe
  • Splash into paradise with two stunning outdoor pools overlooking a private white sand beach.
￥17,302
￥28,254 total
includes taxes & fees
Oct 7 - Oct 8
Chesapeake Beach Resort
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.

2. 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.
￥17,513
￥26,734 total
includes taxes & fees
Sep 8 - Sep 9
Lime Tree Bay Resort
A nighttime swimming pool with a blue tint, surrounded by palm trees and a fenced area with 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 beach with palm trees, thatched-roof huts, and lounge chairs.
A modern kitchen with a microwave, stove, and refrigerator. There is a dining area with a table and chairs.

3. 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.
￥11,138
￥15,022 total
includes taxes & fees
Sep 7 - Sep 8
Breezy Palms Resort
A clear blue swimming pool with a metal railing, surrounded by palm trees and a view of the ocean.
A marina with a boat docked at a wooden pier, surrounded by palm trees and buildings.
A beach pathway with palm trees, a lifeguard tower, and the ocean in the background.
Three Adirondack chairs facing a sunset over a body of water.

4. Ragged Edge Resort & Marina

Ragged Edge Resort & Marina
Islamorada
  • Dive into poolside paradise with comfy loungers at Ragged Edge Resort, a cyclist-friendly escape.
￥11,234
￥12,639 total
includes taxes & fees
Sep 8 - Sep 9
Ragged Edge Resort & Marina
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.
￥23,283
￥37,620 total
includes taxes & fees
Sep 7 - Sep 8
Cheeca Lodge & Spa
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.

6. Amara Cay Resort

Amara Cay Resort
Matecumbe
  • Splash into serenity at this resort's private beach and outdoor pool with lounge chairs and umbrellas.
￥22,463
￥36,698 total
includes taxes & fees
Sep 14 - Sep 15
Amara Cay Resort
An aerial view of a resort with two swimming pools surrounded by palm trees and sun loungers.
A paved pathway leading to a beach with palm trees and a view of the ocean.
A wooden pier leading to a beach with palm trees and a row of beach huts.
A bar area with a wooden counter, bar stools, and potted plants.

7. Islander Resort

Islander Resort
Matecumbe
  • Dive into this Florida Keys paradise with two shimmering pools, beachside bars, and water adventures waiting for you.
￥30,588
￥44,960 total
includes taxes & fees
Sep 13 - Sep 14
Islander Resort
Two people relaxing on sun loungers by a poolside with a view of the ocean and palm trees in the background.
A deck with two blue chairs and a white table, overlooking a body of water and palm trees.
A beachfront hotel with a pool, beach chairs, and a view of the ocean at sunset.
A modern hotel room with a balcony, a bed, a TV, and a dining area with chairs and a table.

8. 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.
￥19,791
￥27,363 total
includes taxes & fees
Sep 21 - Sep 22
Fisher Inn Resort & Marina
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 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.

9. 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.
￥14,653
￥16,485 total
includes taxes & fees
Sep 10 - Sep 11
Rock Reef Resort
A swimming pool with a rock waterfall feature and a 3 ft depth marker.
A waterfront patio with outdoor seating, a yellow umbrella, and a view of the water.
A wooden dock extending over calm turquoise water, lined with white railings and palm trees.
A balcony with a view of a river, a wooden cabinet, and a door leading to a shower.

10. Creekside Inn

Creekside Inn
Tavernier
  • Soak in serene pool bliss by the marina, where ocean adventures begin at this freshly updated coastal escape.
￥21,407
￥24,083 total
includes taxes & fees
Sep 20 - Sep 21
Creekside Inn
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

Waterside Suites & Marina

Waterside Suites & Marina

8/10 Good
"Great suite. Very comfortable and inviting"
Laurence 1-night trip
Posted 2 hours ago
Waterside Suites & 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 STAY! Book here for a couple, family or solo trip. Amazing amenities , private beach, pool and restaurants on site. The grounds are gorgeous and clean. Staff super friendly and rooms are great. Nicky at front desk was a great help Look no further for beautiful sunsets and sunrises"
Irene 1-night trip
Posted 4 hours ago
Baker's Cay Resort Key Largo, Curio Collection by Hilton
Chesapeake Beach Resort

Chesapeake Beach Resort

10/10 Excellent
"On arrival, was met by friendly staff, who made us very very welcome! Room was fantastic and very clean! Breakfast was amazing... overall had a great stay, in future will stay longer."
Daniel 1-night trip
Posted 5 hours ago
Chesapeake Beach Resort
Reefhouse Resort & Marina

Reefhouse Resort & Marina

8/10 Good
"We enjoyed our stay here, were upgraded to a partial view room, and noticed to have been among the only people in the pool or dining area when we took did these activities. The staff was attentive, but seemed bothered by the lack of business that they were having, and we felt like a bit of an afterthought at times despite enjoying the resort being “to ourselves”."
Brian 1-night trip
Posted 1 day ago
Reefhouse Resort & Marina

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.

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