Name: Chesapeake Beach Resort
Price range: $186 total
Rating: 9.2

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The Latest Lower Matecumbe Key vacation packages

Price found within the past 48 hours. Click for updated prices.

President Hotel

South Beach

$864

per person

Dec 3 - Dec 10

found 1 day ago

Roundtrip flight included

Boston (BOS) to Miami (MIA)

8.4/10 Very Good! (1,905 reviews)

The staff is very helpful with information specially Henry and the lady who works at the same desk when he is off duty. Even the guy who is parking cars offered a usufull information about the area.

Reviewed on Oct 29, 2025

The Shelborne By Proper, a Member of Design Hotels

South Beach

$933

per person

Jan 22 - Jan 26

found 1 day ago

Roundtrip flight included

Boston (BOS) to Miami (MIA)

9.8/10 Exceptional! (39 reviews)

Fantastic experience. One of the best hotels we have stayed at. Shout out to Jenny, Marta , Shane and Louis, William and Josh and all of the other wonderful staff. Definitely recommend it and will certainly go back !

Reviewed on Nov 1, 2025

The Retreat Collection at 1 Hotel & Homes South Beach

South Beach

$8,153

per person

Jan 27 - Jan 31

found 1 day ago

Roundtrip flight included

Boston (BOS) to Miami (MIA)

8/10 Very Good! (1 review)

Park Central South Beach

South Beach

$1,122

per person

Dec 3 - Dec 10

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Miami (MIA)

8.6/10 Excellent! (217 reviews)

Stayed for one night before a cruise. Excellent views, Excellent service, Excellent atmosphere!

Reviewed on Nov 1, 2025

President Villa

South Beach

$933

per person

Dec 3 - Dec 10

found 1 day ago

Roundtrip flight included

Boston (BOS) to Miami (MIA)

8.2/10 Very Good! (1,000 reviews)

Very nice staff. Very accommodating.

Reviewed on Oct 28, 2025

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Discover the most popular places to visit in Lower Matecumbe Key

Anne's Beach

3.5/5(139 reviews)

If a restful vacation is part of your travel plans, Anne's Beach might be the perfect place to seek out during your trip to Islamorada.

Sunset Drive Beach

Why not spend a lazy afternoon at Sunset Drive Beach during your trip to Islamorada?

Lower Matecumbe Key Hotel Deals

Matecumbe Resort

76261 Overseas Hwy, Islamorada, FL

8.8/10 Excellent! (81 reviews)

Quiet, simple and clean. Office staff is not available before 9:30am or after 4pm. Parking is supposed to be 1 per unit. However, lack of office staff meant that when people had multiple cars or friends over, there was no parking. Could not complain to anyone.

Reviewed on Oct 20, 2025

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Cheeca Lodge & Spa

81801 Overseas Highway, Mile Marker 82, Marker 82, Islamorada, FL

Fully refundableReserve now, pay when you stay

$259 nightly

$291 total

Nov 3 - Nov 4

Total with taxes and fees

9/10 Wonderful! (1,265 reviews)

Always a great stay at Cheeca. Lovely property, great restaurants, clean rooms and wonderful service by the staff.

Reviewed on Oct 30, 2025

Chesapeake Beach Resort

83409 Overseas Hwy, Islamorada, FL

Fully refundableReserve now, pay when you stay

$165 nightly

$186 total

Nov 5 - Nov 6

Total with taxes and fees

9.2/10 Wonderful! (1,548 reviews)

I was very pleased with the resort. It’s a quiet hidden gem with a friendly and helpful staff. I would love to stay here again.

Reviewed on Oct 27, 2025

See all 2,135 properties in Lower Matecumbe Key

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.