Flamingo, FL

Name: Chesapeake Beach Resort
Price range: $275 total
Rating: 9.2

Travel Guide

A large flock of flamingos standing in shallow water.

A large flock of flamingos in shallow water with a forested shoreline in the background.

A group of pink flamingos standing in a body of water with reflections.

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

A wooden boardwalk through a mangrove forest.

Visit Flamingo

Cheeca Lodge & Spa

81801 Overseas Highway, Mile Marker 82 Islamorada FL

$254 nightly

$286 total

Jul 8 - Jul 9

Total with taxes and fees

Book a stay at this luxury resort in Islamorada. Enjoy free parking, 3 outdoor pools, and a full-service spa. Our guests praise the pool and the helpful staff ...

9.2/10 Wonderful! (1,330 reviews)

"Todo bueno no lomi"

Reviewed on Jun 29, 2026

Reefhouse Resort & Marina

103800 Overseas Hwy Key Largo FL

$259 nightly

$286 total

Jul 26 - Jul 27

Total with taxes and fees

Book a stay at this luxury hotel in Key Largo. Enjoy free parking, a full-service spa, and 3 restaurants. Our guests praise the pool and the helpful staff in ...

9.4/10 Exceptional! (1,481 reviews)

"Clean room staff nice"

Reviewed on Jun 29, 2026

Chesapeake Beach Resort

83409 Overseas Hwy Islamorada FL

$245 nightly

$275 total

Jul 5 - Jul 6

Total with taxes and fees

Book a stay at this beach hotel in Islamorada. Enjoy free breakfast, free WiFi, and 2 outdoor pools. Our guests praise the breakfast and the pool in our reviews. ...

9.2/10 Wonderful! (1,745 reviews)

"Amazing"

Reviewed on Jun 30, 2026

See all 2,889 properties in Flamingo

Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Breezy Palms Resort

80015 Overseas Highway Islamorada FL

Book a stay at this beach aparthotel in Islamorada. Enjoy free WiFi, a beach locale, and a marina. Our guests praise the helpful staff and the clean rooms in ...

8.8/10 Excellent! (704 reviews)

"We stayed in a cottage. The room was clean and spacious. It had a full kitchen and the cabnets had plates, silverwear, pans, dish detergent. It had a full size refrigerator. There is a separate living room and kichenette from bedroom. The staff was very friendly. There was enough parking for everyone ..."

Reviewed on Jun 26, 2026

Treasure Harbor

200 Treasure Harbor Dr Islamorada FL

Stay at this houseboat in Islamorada. Enjoy free WiFi, free parking, and premium bedding. Our guests praise the helpful staff in our reviews. Popular attractions ...

9/10 Wonderful! (161 reviews)

"Great place for the price. Very quiet and peaceful."

Reviewed on Jun 27, 2026

Island Bay Resort

92530 OVERSEAS HIGHWAY Tavernier FL

Book a stay at this beach aparthotel in Tavernier. Enjoy free WiFi, free parking, and a private beach. Our guests praise the helpful staff in our reviews. Popular ...

10/10 Exceptional! (172 reviews)

"Island Bay was a great experience. The accommodations were just as we expected and the staff could not have been more friendly and help full."

Reviewed on Jun 19, 2026

See all properties in Flamingo

Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.