Name: Chesapeake Beach Resort
Price range: NZ$665
Rating: 9.2

Chesapeake Beach Resort

83409 Overseas Hwy Islamorada FL

NZ$665

12 Feb - 13 Feb

includes taxes & fees

Stay at this beach hotel in Islamorada. Enjoy free breakfast, free Wi-Fi and 2 outdoor pools. Our guests praise the breakfast and the pool in their reviews. ...

9.2/10 Wonderful! (1,675 reviews)

Nice stay

Reviewed on 10 Feb 2026

Fairway Inn Florida City Homestead Everglades

100 SE 1st Ave Florida City FL

Stay at this business-friendly motel in Florida City. Enjoy free Wi-Fi, free parking and a 24-hour front desk. Our guests praise the breakfast and the pool in ...

8.2/10 Very Good! (2,058 reviews)

Clean room. Nightstands on both sides. Plenty of hot water. Spacious grounds with picnic tables and bbqs. Many chain restaurants and markets in walking distance. Amazing Jamaican restaurant - Yardie Soice - a short drive away.

Reviewed on 4 Feb 2026

Get rates

Garden Inn Homestead

51 South Homestead Blvd. Homestead FL

Stay at this business-friendly motel in Homestead. Enjoy free breakfast, free Wi-Fi and free parking. Our guests praise the breakfast and the helpful staff in ...

7.8/10 Good! (2,172 reviews)

Great like always

Reviewed on 6 Feb 2026

Get rates

See all 2,940 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.

Treasure Harbor

200 Treasure Harbor Dr Islamorada FL

Stay at this hotel in Islamorada. Enjoy free Wi-Fi, free parking and premium bedding. Our guests praise the helpful staff in their reviews. Popular attractions ...

8.8/10 Excellent! (129 reviews)

The place was very clean and well set up. The amenities were there however the weather didn’t cooperate. I would definitely recommend it to anyone wanting to stay in the Florida Keys.

Reviewed on 30 Jan 2026

Breezy Palms Resort

80015 Overseas Highway Islamorada FL

Stay at this beach aparthotel in Islamorada. Enjoy free Wi-Fi, a beach locale and a marina. Our guests praise the helpful staff and the clean rooms in their ...

8.8/10 Excellent! (617 reviews)

Room was good staff was excellent

Reviewed on 20 Jan 2026

The Islands of Islamorada

82779 Old Hwy Islamorada FL

Stay at this beach villa in Islamorada. Enjoy free Wi-Fi, free parking and 2 outdoor pools. Popular attractions History of Diving Museum and Islamorada Brewery ...

9.6/10 Exceptional! (70 reviews)

Beautiful accommodations and location, very clean, many activities available at resort

Reviewed on 25 Nov 2025

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.

Popular places to visit

Flamingo Visitor Center

Explore the great outdoors at Flamingo Visitor Center, a lovely green space in Flamingo. While you're in the area, wander around the natural setting.

West Lake

Commune with nature and explore the great outdoors at West Lake during your travels in Flamingo. While you're in the area, stroll along the marina.

Snake Bight

Commune with nature and explore the great outdoors at Snake Bight during your travels in Flamingo. While you're in the area, wander around the natural setting.

Eco Pond

Commune with nature and explore the great outdoors at Eco Pond during your travels in Flamingo. While you're in the area, stroll along the marina.

Pa-hay-okee Trail

You can take time to visit Pa-hay-okee Trail during your travels to Flamingo. While you're in the area, wander around the natural setting.

Buttonwood Canal

Commune with nature and explore the great outdoors at Buttonwood Canal during your travels in Flamingo. While you're in the area, wander around the natural setting.