Lower Matecumbe Key Vacation Packages 2026 from $415

The Latest Lower Matecumbe Key vacation packages

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

Cavalier Hotel South Beach

South Beach

Save 100% on your flight

$415

per person

Dec 9 - Dec 13

found 1 day ago

Roundtrip flight included

Boston (BOS) to Miami (MIA)

8.6/10 Excellent! (1,008 reviews)

Nice hotel

Reviewed on Oct 2, 2026

The Retreat Collection at 1 Hotel & Homes South Beach

South Beach

$9,499

per person

Nov 12 - Nov 17

found 1 day ago

Roundtrip flight included

Boston (BOS) to Miami (MIA)

8/10 Very Good! (1 review)

Horrible checkin / checkout... Would never stay there again...Double charged me entire stay and still fighting to get someone to refund 2nd one that is so clearly a duplicate for same stay....

Reviewed on Jun 22, 2016

President Hotel Villa

South Beach

Save 100% on your flight

$629

per person

Dec 3 - Dec 6

found 1 day ago

Roundtrip flight included

Boston (BOS) to Miami (MIA)

8.2/10 Very Good! (1,001 reviews)

EAST Miami Residences

Brickell

Save 100% on your flight

$1,051

per person

Dec 10 - Dec 13

found 1 day ago

Roundtrip flight included

Boston (BOS) to Miami (MIA)

9.2/10 Wonderful! (151 reviews)

beatiful place

Reviewed on Sep 30, 2026

Miami Vacation Rentals - Downtown

Downtown Miami

Save 100% on your flight

$1,087

per person

Dec 5 - Dec 11

found 13 hours ago

Roundtrip flight included

Boston (BOS) to Miami (MIA)

9/10 Wonderful! (92 reviews)

Really enjoyed the area and the room and view was awesome!!!!

Reviewed on Oct 1, 2026

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Stay near popular Lower Matecumbe Key attractions

Anne's Beach

7.8/10 (597 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.

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Robbie’s of Islamorada

8.4/10 (15 reviews)

Explore the waterfront in Islamorada with a trip to Robbie’s of Islamorada.

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Sunset Drive Beach

9.0/10 (91 reviews)

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

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Lower Matecumbe Key Hotel Deals

Matecumbe Resort

76261 Overseas Hwy Islamorada FL

Fully refundableReserve now, pay when you stay

$160 nightly

$180 total

Oct 4 - Oct 5

Total with taxes and fees

9/10 Wonderful! (170 reviews)

"A very peaceful place."

Reviewed on Oct 1, 2026

Caloosa Cove Resort by CoolVacay

73801 Overseas Hwy Islamorada FL

8.8/10 Excellent! (14 reviews)

"The fact we were never told the restaurant and bar were closed and the property was undergoing yearly renovations was just a lousy way to conduct business. We had to take Ubers all day just to get breakfast and lunch. If we were told we would have never booked. Spent a ton in rides since there is ..."

Reviewed on Sep 21, 2026

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Cheeca Lodge & Spa

81801 Overseas Highway, Mile Marker 82 Islamorada FL

Fully refundableReserve now, pay when you stay

$196 nightly

$221 total

Oct 4 - Oct 5

Total with taxes and fees

9.2/10 Wonderful! (1,464 reviews)

"From check in to a changed flight that required an earlier checkout than planned for, Cheeca did not disappoint. The lodge room with the balcony tub was great. Very clean and a beautiful space to relax. Pool was great. Drink service was a bit spotty at the pool though and we were totally ignored ..."

Reviewed on Oct 2, 2026

See all 2,039 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.