Name: Islander Resort
Price range: $329 total
Rating: 9.4

Plan, book, travel with confidence
Better together
Save up to $2,000 when you book a flight and hotel together*
Find the right fit
With over 300,000 hotels worldwide, it's easy to create a perfect package
Rest easy
Plan, book, and manage your trip all in one place

The Latest Upper Matecumbe Key vacation packages

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

MirabileCondoDwntown MIA Brickell w PRKG

Downtown Miami

$378

per person

Jul 24 - Jul 26

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Miami (MIA)

2/10 (2 reviews)

The W - Bayshore Unit 1003

East Fort Lauderdale

$467

per person

Jul 14 - Jul 17

found 19 hours ago

Roundtrip flight included

Atlanta (ATL) to Miami (MIA)

7.4/10 Good! (3 reviews)

I thoroughly enjoyed my stay at this hotel. The host was incredibly friendly and attentive, and the communication was prompt and efficient. The hotel itself was beautiful, and the staff was incredibly kind and helpful.

Reviewed on May 20, 2026

Casablanca Miami Beach

North Beach

$2,462

per person

Aug 21 - Aug 25

found 1 day ago

Roundtrip flight included

Philadelphia (PHL) to Miami (MIA)

5.8/10 (324 reviews)

Room was clean and great location beside the beach. Room had kitchette and big fridge, microwave etc. so was great. It was dated and internet didn't work in our room but worked well in the lobby. Great value for money :) happy with it.

Reviewed on Feb 22, 2026

Brickell Bay 3318

Brickell

$474

per person

Jul 9 - Jul 12

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Miami (MIA)

No reviews

Cavalier Hotel South Beach

South Beach

$427

per person

Aug 7 - Aug 11

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Miami (MIA)

8.6/10 Excellent! (1,006 reviews)

Super cute and great location. Waiting staff was great and front was nice but a little lack of communication. Our room air wasn’t working really well so they switched our room and comp our breakfast the rest of the stay.

Reviewed on Jun 3, 2026

Don't see what you're looking for?

See all available trips from Columbus to Upper Matecumbe Key

View all trips

Discover the most popular places to visit in Upper Matecumbe Key

Bud n' Mary's Dive Center

4.5/5(142 reviews)

Explore the waterfront of Bud n' Mary's Dive Center and enjoy other activities such as fishing in Islamorada. Discover the beautiful sunsets and seafood restaurants in this family-friendly area.

Florida Keys Brewing Co.

You can take time to visit Florida Keys Brewing Co. during your travels to Islamorada.

Matecumbe United Methodist Church

After visiting Matecumbe United Methodist Church, make a plan to see the other sights and activities in Islamorada. Discover the beautiful sunsets in this family-friendly area, or enjoy its fishing spots.

Upper Matecumbe Key Hotel Deals

Cheeca Lodge & Spa

81801 Overseas Highway, Mile Marker 82 Islamorada FL

Fully refundableReserve now, pay when you stay

$258 nightly

$290 total

Jun 7 - Jun 8

Total with taxes and fees

9.2/10 Wonderful! (1,318 reviews)

"Cheeca Lodge is my absolute favorite place in The Keys The property is gorgeous, I love the amenities, the complimentary kayaking, bikes & champagne for Mother’s Day was such a nice touch The rooms are so cozy, just love it there. Ask for Rob at the pool bar, he makes a great drink!"

Reviewed on Jun 4, 2026

Chesapeake Beach Resort

83409 Overseas Hwy Islamorada FL

Fully refundableReserve now, pay when you stay

$233 nightly

$262 total

Jun 9 - Jun 10

Total with taxes and fees

9.2/10 Wonderful! (1,740 reviews)

"The resort is in a great location, clean and well maintained. Our king suite was very comfortable, had a large, lovely bathroom, balcony with a great view of the ocean. Breakfast with made to order omelets and pancakes, as well as breads, muffins, cold cereals, juices, and a nice area to eat on the ..."

Reviewed on Jun 5, 2026

Islander Resort

82100 Overseas Highway Islamorada FL

Fully refundableReserve now, pay when you stay

$292 nightly

$329 total

Jun 14 - Jun 15

Total with taxes and fees

9.4/10 Exceptional! (1,035 reviews)

"Un poco costosa para lo que era pero todo bien"

Reviewed on Jun 5, 2026

See all 2,824 properties in Upper 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.