Name: Chesapeake Beach Resort
Price range: $204 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.

Hollywood Gateway Inn

North Central Hollywood

$196

per person

Jan 18 - Jan 23

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Miami (MIA)

6.6/10 (1,005 reviews)

I would say room is okay it was recently renovated wasn't thrilled about the lack of proper patio doors that wouldn't even close because they're so old therefore noisier than it should have been from the parking lot and in the morning the office is locked even though there's people inside and you can't get to the breakfast starting at 7:00 am. Is way too late

Reviewed on Nov 5, 2025

The Shelborne By Proper, a Member of Design Hotels

South Beach

$645

per person

Jan 8 - Jan 11

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

President Villa

South Beach

$643

per person

Jan 14 - Jan 20

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

Broadmore Miami Beach

North Beach

$273

per person

Jan 18 - Jan 23

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Miami (MIA)

5.6/10 (369 reviews)

Staff was very nice

Reviewed on Nov 4, 2025

Bentley Hotel South Beach

South Beach

$1,546

per person

Dec 21 - Dec 28

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Miami (MIA)

9.4/10 Exceptional! (390 reviews)

Beautifully renovated with great additional touches like Continental breakfast and champagne at 5:00

Reviewed on Nov 7, 2025

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Discover the most popular places to visit in Lower Matecumbe Key

Anne's Beach

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

Fully refundableReserve now, pay when you stay

$125 nightly

$141 total

Nov 10 - Nov 11

Total with taxes and fees

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

Cheeca Lodge & Spa

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

Fully refundableReserve now, pay when you stay

$249 nightly

$281 total

Nov 20 - Nov 21

Total with taxes and fees

9/10 Wonderful! (1,250 reviews)

Clean room and well-appointed amenities. Housekeeping did a commendable job. Patrick, the bartender at the tiki bar near outside dining was GREAT !

Reviewed on Nov 6, 2025

Chesapeake Beach Resort

83409 Overseas Hwy, Islamorada, FL

Fully refundableReserve now, pay when you stay

$181 nightly

$204 total

Nov 16 - Nov 17

Total with taxes and fees

9.2/10 Wonderful! (1,552 reviews)

Friendly staff

Reviewed on Nov 2, 2025

See all 2,130 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.