Name: Chesapeake Beach Resort
Price range: $220 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.

Cavalier Hotel South Beach

South Beach

$488

per person

Jan 27 - Jan 31

found 1 day ago

Roundtrip flight included

Boston (BOS) to Miami (MIA)

8.4/10 Very Good! (1,001 reviews)

Nice staff, great area

Reviewed on Dec 9, 2025

Hawks Cay Resort

$802

per person

Jan 24 - Jan 31

found 1 day ago

Roundtrip flight included

Boston (BOS) to Miami (MIA)

8/10 Very Good! (1,003 reviews)

Outstanding in every wat

Reviewed on Dec 15, 2025

Flow Miami Hotel

Downtown Miami

$1,036

per person

Mar 1 - Mar 8

found 1 day ago

Roundtrip flight included

Boston (BOS) to Miami (MIA)

9.2/10 Wonderful! (172 reviews)

Excellent value for money. 10/10 location. Staff eas wonderful and accomodating. The amenities are just what you need for a vacation

Reviewed on Dec 5, 2025

Pelican Hotel

South Beach

$956

per person

Mar 1 - Mar 8

found 1 day ago

Roundtrip flight included

Boston (BOS) to Miami (MIA)

9.2/10 Wonderful! (394 reviews)

The staff were friendly and professional. The rooms were great, comfortable beds and pillows. The cocktails and breakfasts were good too.

Reviewed on Dec 16, 2025

The Shelborne By Proper, a Member of Design Hotels

South Beach

$1,028

per person

Jan 21 - Jan 25

found 1 day ago

Roundtrip flight included

Boston (BOS) to Miami (MIA)

9.4/10 Exceptional! (56 reviews)

Really great spot. Love the low key aesthetic and cool design. The tiles in the bar area are great. Nice breakfast spot by pool, and beach club is outstanding. Only small issue is there were a bunch of loud little kids shouting and cannon-balling into the pool. Super disruptive to the peaceful setting and zero was done to ask the kids to chill just a bit. Overall - super spot and renovation has made it a gem again.

Reviewed on Dec 14, 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

$157 nightly

$177 total

Jan 14 - Jan 15, 2026

Total with taxes and fees

8.8/10 Excellent! (85 reviews)

Matecumbe Resort is a nice old school but very up-to-date place to stay. They have everything you need. The pool is awesome. The marina for parking your boat a boat ramp. Everybody there was very nice and the place is well-maintained. And you can see they’re constantly doing upgrades.

Reviewed on Nov 21, 2025

Chesapeake Beach Resort

83409 Overseas Hwy Islamorada FL

Fully refundableReserve now, pay when you stay

$195 nightly

$220 total

Dec 18 - Dec 19

Total with taxes and fees

9.2/10 Wonderful! (1,588 reviews)

Room was great. Staff was awesome views amazing !!!!!

Reviewed on Dec 11, 2025

Lime Tree Bay Resort

68500 Overseas Hwy Long Key FL

$165 nightly

$186 total

Dec 18 - Dec 19

Total with taxes and fees

9.2/10 Wonderful! (1,116 reviews)

The room was spotless and the staff was pleasant. The staff checked in on me daily to make sure i was comfortable.

Reviewed on Dec 14, 2025

See all 2,147 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.