---
title: "5 Stars Hotels in Flamingo, Florida from CA $258 - Find Cheap Flamingo Hotels With 5 Stars | Expedia.ca"
description: "Book the best 5 Star Hotels in Flamingo, FL in 2026. Compare room rates, hotel reviews and availability. Most hotels are fully refundable."
canonical: "https://www.expedia.ca/5Star-Flamingo-Hotels.s50-0-d553248635074842070.Travel-Guide-Filter-Hotels"
language: en-CA
market: CA
currency: CAD
prices_as_of: 2026-11-14T15:51:47Z
---

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![A calm waterway flanked by dense mangrove trees under a clear sky.](https://images.trvl-media.com/place/54987/20484210-6274-494d-b164-9768873b2317.jpg?impolicy=fcrop&w=1200&h=500&q=medium)

Photo by Jim Fiorelli

# 5 Stars Hotels in Flamingo, Florida from CA $258

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## Check prices for these dates

[Check prices for these dates, December 14–15, 2026](https://www.expedia.ca/Hotel-Search?regionId=553248635074842070&startDate=2026-12-14&endDate=2026-12-15&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&star=50)

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## Our top choices for Flamingo 5-star hotels

### [1\. Cheeca Lodge & Spa](https://www.expedia.ca/Islamorada-Hotels-Cheeca-Lodge-Spa.h5780.Hotel-Information)

![A bathroom with a large bathtub, a window with curtains, and a view of palm trees and the sea.](https://images.trvl-media.com/lodging/1000000/10000/5800/5780/4608d7e2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

- Location: Matecumbe
- Guest rating: 9.2/10 (Wonderful, 1516 reviews)
- Price: CA $259, CA $395 total, includes taxes & fees, Nov 18 - Nov 19, for Our top choices for Flamingo 5-star hotels
- Review: Clean room, friendly staff and food was good., by Nicholas

### [2\. The Islands of Islamorada](https://www.expedia.ca/Islamorada-Hotels-The-Islands-Of-Islamorada.h54774228.Hotel-Information)

![A balcony with a wooden table, two chairs, and a view of the ocean and palm trees.](https://images.trvl-media.com/lodging/55000000/54780000/54774300/54774228/c9a3968b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)
- Location: Matecumbe
- Guest rating: 9.6/10 (Exceptional, 83 reviews)
- Price: CA $1,002, CA $1,231 total, includes taxes & fees, Nov 30 - Dec 1, for Our top choices for Flamingo 5-star hotels
- Review: We had an AMAZING stay! The staff was wonderful, providing excellent customer service and providing local recommendations for activities and dining. The property is pristine and gorgeous. My only critique would be a lack of on property food options. We will definitely be back., by Catherine

## Find out more about Flamingo

Luxury is the name of the game at the best 5 Stars hotels in Flamingo. If you want to vacation like a true VIP, these are the places to go; from spacious resorts to boutique-inspired hot spots, the top Flamingo 5 Stars hotels are dedicated to immersing you in the ultimate experience. Want to relax with a serene treatment at a designer spa? These properties offer them.

Interested in tasting delicious dishes from top chefs? The gourmet restaurants at the 5 Stars Flamingo hotels have you covered. You’ll even find first-class hotels near the city’s must-see attractions and most upscale entertainment districts. Plus, when you book your trip with Expedia.ca, you’ll get access to fantastic rates and seasonal discounts, so you can take advantage of a cheap deal on 5 Stars hotels Flamingo without giving up even an inch of quality. Everything your heart desires (and a few perks designed to make it skip a beat): That’s what’s on offer when you plan a trip to the hotels with 5 Stars in Flamingo.

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