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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 23 - Sep 24
Tomorrow
Sep 24 - Sep 25
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 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.
￥16,878
￥26,065 total
includes taxes & fees
Sep 27 - Sep 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 waterfront hotel with multiple floors, palm trees, and a calm reflective pool.
A beach with palm trees and lounge chairs.

2. Chesapeake Beach Resort

Chesapeake Beach Resort
Matecumbe
  • Splash into paradise with two stunning outdoor pools overlooking a private white sand beach.
￥22,573
￥34,244 total
includes taxes & fees
Sep 28 - Sep 29
Chesapeake Beach Resort
A swimming pool with lounge chairs and a building with balconies.
A beach view with palm trees and a thatched-roof structure.
A beach with a thatched umbrella, lounge chairs, and a clear view of the ocean.
A balcony with a view of palm trees and a beach.

3. Matecumbe Resort

Matecumbe Resort
Matecumbe
  • Dive into a tranquil paradise with private beach access and a refreshing outdoor pool.
￥19,538
￥21,980 total
includes taxes & fees
Sep 24 - Sep 25
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 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.
￥12,872
￥16,994 total
includes taxes & fees
Oct 6 - Oct 7
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.
￥21,798
￥36,027 total
includes taxes & fees
Sep 24 - Sep 25
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 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 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.
￥18,586
￥26,042 total
includes taxes & fees
Sep 24 - Sep 25
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 beach with wooden lounge chairs, palm trees, and a clear view of the ocean.
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.
￥15,220
￥21,547 total
includes taxes & fees
Oct 5 - Oct 6
La Jolla 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 wooden interior with a large window overlooking a beach with a thatched umbrella and lounge chairs.
A wooden dock with a boat docked at the pier, a thatched umbrella, and calm water.

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.
￥12,851
￥14,457 total
includes taxes & fees
Sep 28 - Sep 29
Rock Reef Resort
An aerial view of a resort with a swimming pool, palm trees, and a dock extending into the water.
A modern two-story beachfront property with balconies, a pool, and a sandy beach area.
A beachside resort with a pool area, lounge chairs, and palm trees.
A modern kitchen with a central island, a dining area with a view, and a living space with a balcony overlooking the ocean.

9. Pines & Palms Resort

Pines & Palms Resort
Matecumbe
  • Private beach paradise with poolside oasis and marina in the heart of Matecumbe.
￥18,422
￥29,404 total
includes taxes & fees
Sep 24 - Sep 25
Pines & Palms Resort
A resort pool with palm trees, beach chairs, and umbrellas.
A balcony with a view of a beach, palm trees, and a pool.
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.

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.
￥22,614
￥36,945 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

Chesapeake Beach Resort

Chesapeake Beach Resort

10/10 Excellent
"We had a wonderful stay at this hotel. I stayed with my mom, sister, and niece, and we truly loved the property. The location is great, the hotel is beautiful, and we really enjoyed the amenities and our time together. Overall, it was a very nice experience. The only area I feel could use some improvement is the late checkout process. I requested a late checkout until 2:00 PM because we wanted to enjoy the amenities a little longer before leaving. The property did not appear to be fully booked, so I was hoping there might be some flexibility, but unfortunately my request was not accommodated. By the time I returned to the room, packed everything, and was getting ready to leave, it was close to 1:00 PM. A member of the housekeeping staff knocked on the door and spoke to us in a way that felt rushed and unnecessarily rude, saying, “Don’t you know you were supposed to leave by 11:00 AM?” That interaction made us feel very uncomfortable and was disappointing, especially after such an enjoyable stay. I completely understand that hotels have checkout policies and that late checkout cannot always be guaranteed. However, I believe a little more flexibility when occupancy allows, along with a more courteous approach from housekeeping, would make the guest experience even better. Aside from that situation, we really loved the hotel, the location, and our stay. With a little improvement in communication and hospitality around checkout, it would be an even better experience."
J Cristina 1-night trip
Posted 5 hours ago
Chesapeake Beach Resort
Baker's Cay Resort Key Largo, Curio Collection by Hilton

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

10/10 Excellent
"This place feels like paradise! It is so calm and relaxing yet vibrant and fun. We had amazing weather all weekend. The ocean was so nice. The poolside trivia, scavenger hunt, smores and silent disco were so fun. The live music was a hit! We cannot WAIT to come back soon!"
Pilar 2-night trip
Posted 10 hours ago
Baker's Cay Resort Key Largo, Curio Collection by Hilton
Islander Resort

Islander Resort

10/10 Excellent
"Loved the property!!! So quiet and relaxing! Great bar, pools, beaches!!!! Would absolutely stay again!"
Tracy 2-night trip
Posted 10 hours ago
Islander Resort
Amara Cay Resort

Amara Cay Resort

8/10 Good
"We had a great stay and overall I would definitely return as it’s a wonderful property. The hotel rooms are spacious and clean. I appreciated the responsiveness of staff and communication via text and ability to make requests via QR code. I would say breakfast was lackluster and the service was extremely slow. Furthermore, I ordered two scrambled eggs and was served powdered eggs which tasted absolutely disgusting. I send that back, and was asked if I would like “hard shell” eggs instead. I thought this was very odd! You wouldn’t expect this at a resort of this level!"
Olga 2-night trip
Posted 13 hours ago
Amara Cay Resort
Bayside Inn Key Largo

Bayside Inn Key Largo

10/10 Excellent
"Grandma took 2 13 year old boys they loved it used the bikes the paddle boards and did lots of fishing felt very safe here will definitely visit again"
Dianna 2-night trip
Posted 13 hours ago
Bayside Inn Key Largo
Lime Tree Bay Resort

Lime Tree Bay Resort

8/10 Good
"Breakfast at on-site restaurant, average and overpriced. When we checked in our room, garbage left in cans from previous tenants."
Leah 2-night trip
Posted 14 hours ago
Lime Tree Bay Resort
Playa Largo Resort & Spa, Autograph Collection

Playa Largo Resort & Spa, Autograph Collection

10/10 Excellent
"Todo perfecto solo q en los Restaurantes no hay desayuno incluido, y los Plato’s están por en ima de la media de sus precios y en realidad no vale la pens pagarlos en ima de eso se demoran mucho"
Raul 2-night trip
Posted 20 hours ago
Playa Largo Resort & Spa, Autograph Collection
Reefhouse Resort & Marina

Reefhouse Resort & Marina

10/10 Excellent
"Opal takes pride ownership in running a customer service excellence resort The champagne touch is nice Thank you Dr Fajardo Garcia"
Onelia 1-night trip
Posted 2 days 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. 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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