A calm waterway flanked by dense mangrove trees under a clear sky.

Find Hotels with a Pool in Flamingo, FL

Q: 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. Lime Tree Bay Resort : Offers a private beach, 3 outdoor pools, and free self parking.

Dates

November 2026

December 2026

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Our top choices for Flamingo hotels with a pool

A tropical resort with a swimming pool, palm trees, and a waterfall.

1. Cheeca Lodge & Spa

Matecumbe

Tropical paradise swim experience awaits with three refreshing pools and poolside service.

￥43,640 total

includes taxes & fees

Nov 19 - Nov 20

A resort pool with palm trees, beach chairs, and umbrellas.

2. Amara Cay Resort

Matecumbe

Splash into serenity at this resort's private beach and outdoor pool with lounge chairs and umbrellas.

￥39,509 total

includes taxes & fees

Nov 17 - Nov 18

A swimming pool with lounge chairs and umbrellas, surrounded by palm trees and a building with a red facade.

3. Holiday Inn Express & Suites Florida City by IHG

Florida City

Escape to the outdoor pool and fitness center at this Florida City hotel where sunny splashes await.

￥15,839 total

includes taxes & fees

Dec 7 - Dec 8

A beach with palm trees, lounge chairs, and a clear view of the ocean.

4. Hampton Inn Key Largo Manatee Bay

Key Largo

Pool paradise awaits with breathtaking bay views and a pristine private beach just steps away.

￥23,101 total

includes taxes & fees

Nov 16 - Nov 17

A dining area with tables set for two, overlooking a beach with palm trees and a sunset view.

5. Reefhouse Resort & Marina

Key Largo

Dive into coastal bliss with a splashy pool scene and beachfront perks for aquatic adventures.

￥45,102 total

includes taxes & fees

Nov 30 - Dec 1

An aerial view of a resort with a central swimming pool surrounded by palm trees and a sandy beach.

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

Key Largo

Escape to a beachside oasis with two outdoor pools, a hot tub, and poolside dining and cocktails.

￥55,314 total

includes taxes & fees

Nov 29 - Nov 30

A beach with palm trees and lounge chairs.

7. Chesapeake Beach Resort

Matecumbe

Splash into paradise with two stunning outdoor pools overlooking a private white sand beach.

￥34,256 total

includes taxes & fees

Nov 10 - Nov 11

A rectangular swimming pool with a tiled edge, surrounded by a white fence and palm trees.

8. Fairfield by Marriott Inn & Suites Homestead Florida City

Florida City

Sunshine escape in Florida City with a perfect poolside sanctuary for your summer getaway.

￥16,737 total

includes taxes & fees

Nov 16 - Nov 17

A resort with a swimming pool, lounge chairs, and palm trees.

9. 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.

￥29,032 total

includes taxes & fees

Nov 17 - Nov 18

A swimming pool with a poolside area, palm trees, and a building with a balcony.

10. Best Western Gateway to the Keys

Florida City

Tranquil Florida pool oasis makes a splash with loungers and umbrellas for all-day sun.

￥12,749 total

includes taxes & fees

Nov 11 - Nov 12

View all properties

Choose what matters most at hotels with a pool in Flamingo

Breakfast included

4 stars

Top Flamingo Hotel Reviews

Cheeca Lodge & Spa

Matecumbe

10/10 Excellent

David

A clear blue pool surrounded by palm trees and a thatched-roof structure, with a sign indicating no diving.

Kona Kai Resort and Gallery - Adults Only

Rock Harbor

10/10 Excellent

Audrey

Reefhouse Resort & Marina

Key Largo

10/10 Excellent

Deb

Holiday Inn Express & Suites Florida City by IHG

Florida City

10/10 Excellent

Ann-Marie

Chesapeake Beach Resort

Matecumbe

10/10 Excellent

Paco

Lime Tree Bay Resort

Long Key

10/10 Excellent

Jack

A swimming pool with a 5 ft depth marker, surrounded by palm trees and lounge chairs.

Atlantic Bay Resort

Tavernier

10/10 Excellent

Emily

Hampton Inn Key Largo Manatee Bay

Key Largo

10/10 Excellent

Samuel

An aerial view of a resort with two swimming pools surrounded by palm trees and sun loungers.

Islander Resort

Matecumbe

10/10 Excellent

Patrick

A resort with a pool, palm trees, and beach chairs.

Coconut Palm Inn

Tavernier

10/10 Excellent

A beautiful, hidden gem right on the water. They have kayaks and paddleboards to use with no cost. Complimentary breakfast, smores and wine. Everything was cleaned well. All the staff was friendly and helpful, especially Ashley. We were beyond impressed with the communication and helpfulness. We spoke to the gentleman who was renovating the rooms (even when he worked it was a quiet and peaceful place), and learned there will soon be a houseboat as a room to rent.

A pool area with lounge chairs and a covered seating area.

Dolphin Point Villas

Key Largo

10/10 Excellent

We stayed here on our way back from key west to lighten trip to FLL airport. We were in love with this place! Every thing about it, location, the high ceilings, the incredibly comfortable beds-the brand new smell of all dwellings. I also was in love with the toiletries that were provided!!! Never have I love a hotel toiletry before. All staff was very professional and friendly. The sunset on the pier was incredible, and our suite was overlooking the pool and it was amazing for a late night swim,...

Sherrie L.

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

Key Largo

10/10 Excellent

The property is beautiful. Well maintained and the beach is gorgeous. Our room was clean but could use a coat of paint. The activities at the beach are wonderful. Kayaking and paddle boarding was fun. The hut at the beach for drinks is cute but it’s $20 for one drink with all the fees they add on. The food was meh. There are much better places to eat for the money. Also, there is a $49 a day resort charge that we were unaware of. With all the being said, we plan on going back. Just a little more...

Kathleen

A pool area with a white fence, palm trees, and a building with a white exterior and multiple windows.

La Jolla Resort

Matecumbe

10/10 Excellent

Kathleen

A beach hut with a thatched roof, surrounded by lounge chairs and a picnic table, overlooking a calm sea.

Rock Reef Resort

Rock Harbor

10/10 Excellent

Jackson

Fairfield by Marriott Inn & Suites Homestead Florida City

Florida City

10/10 Excellent

Gissell

A pool area with lounge chairs and umbrellas, a clear sky, and palm trees.

Playa Largo Resort & Spa, Autograph Collection

Rock Harbor

10/10 Excellent

jose

Amara Cay Resort

Matecumbe

10/10 Excellent

Kasha

A beach with rows of sun loungers and palm trees.

Ragged Edge Resort & Marina

Islamorada

10/10 Excellent

Alejandro

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. 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 West Lake, 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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Find Hotels with a Pool in Flamingo, FL

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Flamingo hotels with a pool

1. Cheeca Lodge & Spa

2. Amara Cay Resort

3. Holiday Inn Express & Suites Florida City by IHG

4. Hampton Inn Key Largo Manatee Bay

5. Reefhouse Resort & Marina

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

7. Chesapeake Beach Resort

8. Fairfield by Marriott Inn & Suites Homestead Florida City

9. Lime Tree Bay Resort

10. Best Western Gateway to the Keys

Choose what matters most at hotels with a pool in Flamingo

Top Flamingo Hotel Reviews

Cheeca Lodge & Spa

10/10 Excellent

Frequently Asked Questions

What are some accommodations with pools in Flamingo?

What is there to see and do in Flamingo?

When is the best time to book a hotel with a pool in Flamingo?

Explore a world of travel with Expedia