Top Beach vacation packages in Upper Matecumbe Key

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

Park Central South Beach

South Beach

$698

per person

Jan 8 - Jan 12

found 1 day ago

Roundtrip flight included

Boston (BOS) to Miami (MIA)

8.6/10 Excellent! (217 reviews)

Stayed for one night before a cruise. Excellent views, Excellent service, Excellent atmosphere!

Reviewed on Nov 1, 2025

The Shelborne By Proper, a Member of Design Hotels

South Beach

$933

per person

Jan 22 - Jan 26

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

The Retreat Collection at 1 Hotel & Homes South Beach

South Beach

$8,153

per person

Jan 27 - Jan 31

found 1 day ago

Roundtrip flight included

Boston (BOS) to Miami (MIA)

8/10 Very Good! (1 review)

Bentley Hotel South Beach

South Beach

$780

per person

Jan 8 - Jan 12

found 1 day ago

Roundtrip flight included

Boston (BOS) to Miami (MIA)

9.4/10 Exceptional! (390 reviews)

The staff was amazing and really helpful. Vanina helped us book a trip and Raenaldo was always most helpful, alingt with all the members of staff on duty for the week we stayed

Reviewed on Nov 2, 2025

1 Hotel South Beach

South Beach

$1,807

per person

Jan 9 - Jan 12

found 1 day ago

Roundtrip flight included

Boston (BOS) to Miami (MIA)

9.4/10 Exceptional! (1,333 reviews)

Overall it was OK…I would not stay there again

Reviewed on Nov 1, 2025

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5* Beach vacations in Upper Matecumbe Key

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

EAST Miami Residences

Downtown Miami

$988

per person

Jan 22 - Jan 25

found 4 hours ago

Roundtrip flight included

Boston (BOS) to Miami (MIA)

9/10 Wonderful! (78 reviews)

Convenient for shopping and food.

Reviewed on Sep 2, 2025

The Retreat Collection at 1 Hotel & Homes South Beach

South Beach

$8,153

per person

Jan 27 - Jan 31

found 1 day ago

Roundtrip flight included

Boston (BOS) to Miami (MIA)

8/10 Very Good! (1 review)

1 Hotel South Beach

South Beach

$1,807

per person

Jan 9 - Jan 12

found 1 day ago

Roundtrip flight included

Boston (BOS) to Miami (MIA)

9.4/10 Exceptional! (1,333 reviews)

Overall it was OK…I would not stay there again

Reviewed on Nov 1, 2025

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3 Night Beach vacations in Upper Matecumbe Key

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

Bentley Hotel South Beach

South Beach

Save 100% on your flight

$919

per person

Jan 2 - Jan 5

found 20 hours ago

Roundtrip non-stop flight included

Boston (BOS) to Miami (MIA)

9.4/10 Exceptional! (390 reviews)

The staff was amazing and really helpful. Vanina helped us book a trip and Raenaldo was always most helpful, alingt with all the members of staff on duty for the week we stayed

Reviewed on Nov 2, 2025

The Retreat Collection at 1 Hotel & Homes South Beach

South Beach

$7,016

per person

Jan 2 - Jan 5

found 1 day ago

Roundtrip flight included

Newark Liberty Intl. Airport (EWR) to Miami (MIA)

8/10 Very Good! (1 review)

1 Hotel South Beach

South Beach

$1,807

per person

Jan 9 - Jan 12

found 1 day ago

Roundtrip flight included

Boston (BOS) to Miami (MIA)

9.4/10 Exceptional! (1,333 reviews)

Overall it was OK…I would not stay there again

Reviewed on Nov 1, 2025

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See all available trips from Columbus to Upper Matecumbe Key

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4 Night Beach vacations in Upper Matecumbe Key

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

Cavalier Hotel South Beach

South Beach

Save 100% on your flight

$500

per person

Jan 8 - Jan 12

found 1 day ago

Roundtrip flight included

Boston (BOS) to Miami (MIA)

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

We had a great stay at the Cavalier Hotel. The interior of the hotel is beautiful. They also have a bar area as well as breakfast, lunch, and dinner options for dine-in or take-out. The beach is only a few steps away! The hotel provided beach towels as well. Our room was clean and beds were comfortable. The bathroom doesn't have a proper door that locks. It's only a sliding door, which we found difficult for privacy. All the staff we met were also very friendly and helpful. The only note for anyone looking to stay at this property is that the hotel itself doesn't have any parking. There is a Municipal Parking Garage right around the corner from the hotel. We found it very convenient to park there (including overnight parking). It's open 24 hours, clean, has stairs and elevators to get to the street.

Reviewed on Oct 28, 2025

The Shelborne By Proper, a Member of Design Hotels

South Beach

$933

per person

Jan 22 - Jan 26

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

The Retreat Collection at 1 Hotel & Homes South Beach

South Beach

$8,153

per person

Jan 27 - Jan 31

found 1 day ago

Roundtrip flight included

Boston (BOS) to Miami (MIA)

8/10 Very Good! (1 review)

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How do I book the best Upper Matecumbe Key beach vacation packages?

Life’s a beach when you dive into our brilliant Upper Matecumbe Key beach vacation deals. Chuck a check in the filter boxes to find ocean views, pools, and resorts just a short saunter from the sizzling sands.

How can I find cheap beach vacations in Upper Matecumbe Key?

A rental steps from the shore creates an amazingly affordable Upper Matecumbe Key beach vacation. Seaside sojourns during low season start from $500. Prices and availability are subject to change. Additional terms may apply.

How can I book the best family beach vacations in Upper Matecumbe Key?

With a flick of a finger, the family-friendly filter brings you the best breaks on offer for the whole brood. Look out for kids’ clubs, waterparks, and other incredible extras for a vacay the little ones will love.

How do I find a Upper Matecumbe Key beachfront vacation?

Check the beachfront filter and, bam, the best available oceanside resorts will appear before your eyes. Along with the incredible view, when you book a beachfront resort, you can get from the lapping waves to your patio lounger in a matter of moments.

Can I book a package including a Upper Matecumbe Key vacation beach house rental?

Hit up the vacation rental filter to book your dream beach house. Once you’ve selected the most alluring abode, add your flights and car rental for the perfect package deal.

Can I find Upper Matecumbe Key beach vacation deals?

Sort your search results by deals to delight in amazing Upper Matecumbe Key beach vacation offers. If you want more pizzazz for your pennies, travel outside the high season or stay a little further from the shoreline.

Can I book a Upper Matecumbe Key beach trip with free cancellation and/or flexible dates?

Just like the Upper Matecumbe Key tides, plans change. Filter by payment option to find trips with free cancellation. Buy now, pay later options are also available for full-on flexibility.

Why should I book my Upper Matecumbe Key beach vacation with Expedia?

Relax long before you see the shore with simple search, fantastic filters, and more great deals than there are grains of sand in Upper Matecumbe Key. (OK, maybe not that last part.)

Top Beach Upper Matecumbe Key Hotels

Cheeca Lodge & Spa

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

5 min drive from Bud n' Mary's Dive Center

Relax at this luxury spa resort and get ready to watch the sunset on the beach in Islamorada, as you'll be near a private beach. 3 outdoor pools, 10 outdoor ...

9/10 Wonderful! (1,265 reviews)

Travelers like: on the beach, sun loungers, beach yoga, massages on beach

Travelers say...

Always a great stay at Cheeca. Lovely property, great restaurants, clean rooms and wonderful service by the staff.

Reviewed on Oct 30, 2025

Amara Cay Resort

80001 Overseas Hwy, Islamorada, FL

5 min walk from Bud n' Mary's Dive Center

You will love your stay at this resort and get ready to walk along the waves in Islamorada, as you'll be a short walk from a private beach. Amenities at Amara ...

8.8/10 Excellent! (1,270 reviews)

Travelers like: on the beach, beach towels, outdoor pool

Travelers say...

We enjoyed our stay a beautiful place, but there was no free breakfast

Reviewed on Oct 24, 2025

Chesapeake Beach Resort

83409 Overseas Hwy, Islamorada, FL

10 min drive from Bud n' Mary's Dive Center

At this hotel, get ready to watch the sunset on the beach in Islamorada, as you'll be close to a private beach. 2 outdoor pools, a bar, and beach towels are ...

9.2/10 Wonderful! (1,548 reviews)

Travelers like: on the beach, sun loungers, beach towels, outdoor pools

Travelers say...

I was very pleased with the resort. It’s a quiet hidden gem with a friendly and helpful staff. I would love to stay here again.

Reviewed on Oct 27, 2025

See all 2,822 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.