Name: Chesapeake Beach Resort
Price range: $203 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.

Broadmore Miami Beach

North Beach

Save 100% on your flight

$248

per person

Jan 21 - Jan 25

found 15 hours ago

Roundtrip flight included

Boston (BOS) to Miami (MIA)

5.6/10 (369 reviews)

Staff was very nice

Reviewed on Nov 4, 2025

The Shelborne By Proper, a Member of Design Hotels

South Beach

$664

per person

Jan 21 - Jan 24

found 1 day ago

Roundtrip flight included

Boston (BOS) to Miami (MIA)

9.8/10 Exceptional! (39 reviews)

Amenities are really clean, excellent quality ingredients, nice quality decor

Reviewed on Nov 9, 2025

Flow Miami Hotel

Downtown Miami

$750

per person

Jan 10 - Jan 17

found 1 day ago

Roundtrip flight included

Boston (BOS) to Miami (MIA)

9/10 Wonderful! (160 reviews)

The room was awesome. Nice space, everything you could need. Gym was fab as was pool. Location spot on. All round win.

Reviewed on Nov 1, 2025

Cavalier Hotel South Beach

South Beach

$386

per person

Jan 21 - Jan 24

found 1 day ago

Roundtrip flight included

Boston (BOS) to Miami (MIA)

8.4/10 Very Good! (1,004 reviews)

Room was clean. Staff was friendly beach, restaurants and shops nearby. Also a convenient parking garage within walking distance.

Reviewed on Nov 4, 2025

The Retreat Collection at 1 Hotel & Homes South Beach

South Beach

$8,290

per person

Jan 14 - Jan 18

found 8 hours ago

Roundtrip flight included

Boston (BOS) to Miami (MIA)

8/10 Very Good! (1 review)

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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

Fully refundableReserve now, pay when you stay

$125 nightly

$141 total

Nov 12 - Nov 13

Total with taxes and fees

8.8/10 Excellent! (82 reviews)

Safe covered parking and stocked kitchen

Reviewed on Nov 8, 2025

Cheeca Lodge & Spa

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

Fully refundableReserve now, pay when you stay

$247 nightly

$278 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

$180 nightly

$203 total

Nov 16 - Nov 17

Total with taxes and fees

9.2/10 Wonderful! (1,560 reviews)

Beautiful location. The room was very comfortable and clean. The ocean view room with a balcony was perfect. The continental breakfast was great. I would highly recommend staying here.

Reviewed on Nov 9, 2025

See all 2,138 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.