Title: Upper Matecumbe Key Vacation Packages 2026 from $405 | Expedia.com

[Upper Matecumbe Key Travel Guide](https://expedia.com/Upper-Matecumbe-Key.dx553248635975749648)[Hotels in Upper Matecumbe Key](https://expedia.com/Upper-Matecumbe-Key-Hotels.d553248635975749648.Travel-Guide-Hotels)[Vacation Rentals in Upper Matecumbe Key](https://expedia.com/Upper-Matecumbe-Key-Vacation-Rentals.d553248635975749648.Travel-Guide-VacationRentals)[Flights to Upper Matecumbe Key](https://expedia.com/Cheap-Flights-To-Upper-Matecumbe-Key.d553248635975749648.Travel-Guide-Flights)[Car Rentals in Upper Matecumbe Key](https://expedia.com/Car-Rentals-In-Upper-Matecumbe-Key.d553248635975749648.Car-Rental-Guide)

![](https://images.trvl-media.com/place/10768/414c55a9-82b2-4829-857c-fd7c26e0bd48.jpg?impolicy=fcrop&w=1200&h=300&q=medium)

# Upper Matecumbe Key Vacations from $405

## Book a Hotel + Flight or Car together to unlock savings

Photo by Cameron Abbott

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## The Latest Upper Matecumbe Key vacation packages

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

![Beach Place Hotel](https://images.trvl-media.com/lodging/2000000/1550000/1543200/1543136/b9ae08d4_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Beach Place Hotel

North Beach

$405

per person

Apr 25 - Apr 30

found 1 day ago

Roundtrip flight included

Boston (BOS) to Miami (MIA)

8/10 Very Good! (1,004 reviews)

Was an excellent budget hotel very near the beach. They had an outdoor pool which was unexpected for the price.

Reviewed on Feb 10, 2026

![Creekside Inn](https://images.trvl-media.com/lodging/2000000/1580000/1576800/1576773/5e43c05b_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Creekside Inn

$646

per person

Apr 25 - Apr 30

found 1 day ago

Roundtrip flight included

Boston (BOS) to Miami (MIA)

8/10 Very Good! (1,004 reviews)

Room was clean, spacious with a wonderful canal view.

Reviewed on Jan 27, 2026

![President Hotel Villa](https://images.trvl-media.com/lodging/11000000/10620000/10612900/10612810/06988314_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### President Hotel Villa

South Beach

$452

per person

Apr 25 - Apr 30

found 1 day ago

Roundtrip flight included

Boston (BOS) to Miami (MIA)

8.2/10 Very Good! (997 reviews)

Stayed 5 nights. Room was done only once

Reviewed on Feb 11, 2026

![Casablanca Miami Beach](https://images.trvl-media.com/lodging/32000000/31660000/31652200/31652150/628e521a_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Casablanca Miami Beach

North Beach

$446

per person

Apr 25 - Apr 30

found 1 day ago

Roundtrip flight included

Boston (BOS) to Miami (MIA)

5.8/10 (311 reviews)

I stood in the multiple bed 1 bedroom everything was good beach right there pool and security where very friendly

Reviewed on Nov 12, 2025

![Bay Breeze Premium Apartments By Eskape Collection](https://images.trvl-media.com/lodging/28000000/27610000/27603500/27603405/c37fc122_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Bay Breeze Premium Apartments By Eskape Collection

Save 100% on your flight

$437

per person

Apr 25 - Apr 30

found 1 day ago

Roundtrip flight included

Boston (BOS) to Miami (MIA)

8.6/10 Excellent! (189 reviews)

The staff was courteous and helpful. The apartment was equipped with basic essentials. The area was quiet. I would suggest adding oven mittens in the kitchen as there was nothing to use to take the pan out of the oven with.

Reviewed on Jan 21, 2026

Don't see what you're looking for?

See all available trips from Columbus to Upper Matecumbe Key

[View all trips](https://expedia.com/go/package/search/FlightHotel/2026-03-11/2026-03-18/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=MIA&NumRoom=1&NumAdult=2&NumChild=0&paandie=true)

### Discover the most popular places to visit in Upper Matecumbe Key

![Islamorada_BudnMarysDiveCenter_6069243-0004](https://images.trvl-media.com/place/6069243/da13ffdf-ddd2-4c35-bedc-c5b570b047e9.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

#### Bud n' Mary's Dive Center

4.5/5(141 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. 

[](https://expedia.com/Bud-N-Marys-Dive-Center-Matecumbe.d6069243.Vacation-Attraction)

![Florida Keys Brewing Co. showing signage](https://images.trvl-media.com/place/553248635997958830/30b22f53-286f-436b-ae7a-d035c9062e6c.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

#### Florida Keys Brewing Co.

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

[](https://expedia.com/Florida-Keys-Brewing-Co-Matecumbe.d553248635997958830.Vacation-Attraction)

![History of Diving Museum showing heritage elements](https://images.trvl-media.com/place/6069257/3860ae1a-3cef-4809-8059-43794e9fe7f9.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

#### History of Diving Museum

4.5/5(51 reviews)

Trace one of the world’s most astonishing watersports back through the centuries to see some of the first diving suits as you explore this interactive museum, featuring the world's largest international collection of diving artifacts.

[](https://expedia.com/History-Of-Diving-Museum-Matecumbe.d6069257.Vacation-Attraction)

## Upper Matecumbe Key Hotel Deals

![Chesapeake Beach Resort](https://images.trvl-media.com/lodging/1000000/10000/4200/4170/689f4306_y.jpg?impolicy=resizecrop&rw=340&ch=150)

### 

Chesapeake Beach Resort

83409 Overseas Hwy Islamorada FL

Fully refundableReserve now, pay when you stay

$377 nightly

$425 total

Feb 12 - Feb 13

Total with taxes and fees

9.2/10 Wonderful! (1,675 reviews)

Nice stay

Reviewed on Feb 10, 2026

[](https://expedia.com/Hotel-Search?startDate=2%2F12%2F2026&endDate=2%2F13%2F2026&selected=4170&PinnedHotelID=4170&HadPinnedHotel=true&regionId=553248635975749648)

![Cheeca Lodge & Spa](https://images.trvl-media.com/lodging/1000000/10000/5800/5780/617c0723_y.jpg?impolicy=resizecrop&rw=340&ch=150)

### 

Cheeca Lodge & Spa

81801 Overseas Highway, Mile Marker 82 Islamorada FL

Fully refundableReserve now, pay when you stay

$421 nightly

$474 total

Feb 12 - Feb 13

Total with taxes and fees

9.2/10 Wonderful! (1,301 reviews)

Check in was great. The elevator was out in our building and they failed to let us know at check- in. We were on the 3rd floor and had to use the stairs.

Reviewed on Feb 9, 2026

[](https://expedia.com/Hotel-Search?startDate=2%2F12%2F2026&endDate=2%2F13%2F2026&selected=5780&PinnedHotelID=5780&HadPinnedHotel=true&regionId=553248635975749648)

![Amara Cay Resort](https://images.trvl-media.com/lodging/1000000/70000/62000/61976/84b50729_y.jpg?impolicy=resizecrop&rw=340&ch=150)

### 

Amara Cay Resort

80001 Overseas Hwy Islamorada FL

Fully refundableReserve now, pay when you stay

$423 nightly

$476 total

Feb 25 - Feb 26

Total with taxes and fees

8.8/10 Excellent! (1,270 reviews)

Great staff, good view from room and breakfast was superb. Thanks.

Reviewed on Feb 10, 2026

[](https://expedia.com/Hotel-Search?startDate=2%2F25%2F2026&endDate=2%2F26%2F2026&selected=61976&PinnedHotelID=61976&HadPinnedHotel=true&regionId=553248635975749648)

[See all 2,811 properties in Upper Matecumbe Key](https://expedia.com/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=2%2F12%2F2026&endDate=2%2F13%2F2026&regionId=553248635975749648)

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.

## Find the Best Upper Matecumbe Key Vacation Packages

## Upper Matecumbe Key Essential Information

| Language        | English                      |
| --------------- | ---------------------------- |
| Currency        | U.S dollars                  |
| Closest Airport | Key West Intl. Airport (EYW) |

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- [Non-Smoking Hotels in Islamorada ](https://www.expedia.com/Islamorada-Hotels-Smoke-Free-Hotels.0-0-d10768-tSmokeFreeHotels.Travel-Guide-Filter-Hotels)

- [Flights to Islamorada ](https://www.expedia.com/Cheap-Flights-To-Islamorada.d10768.Travel-Guide-Flights)
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- [Flights from Phoenix to Islamorada ](https://www.expedia.com/lp/flights/178298/10768/phoenix-to-islamorada)

- [Islamorada Vacations ](https://www.expedia.com/Islamorada.d10768.Destination-Travel-Guides)
- [Visit Islamorada ](https://www.expedia.com/Islamorada.dx10768)

- [Car rentals near Islamorada ](https://www.expedia.com/Car-Rentals-In-Islamorada.d10768.Car-Rental-Guide)
- [Car rentals near Hurricane Monument ](https://www.expedia.com/Car-Rentals-In-Hurricane-Monument.d6063543.Car-Rental-Guide)
- [Hertz Rental Cars in Islamorada ](https://www.expedia.com/Hertz-Car-Rentals-In-Islamorada.d10768-c40.Car-Rental-Guide-Suppliers)
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- [Islamorada Vacation Rentals ](https://www.expedia.com/Islamorada-Vacation-Rentals.d10768.Travel-Guide-VacationRentals)

- [Things to do in Islamorada ](https://www.expedia.com/Things-To-Do-In-Islamorada.d10768.Travel-Guide-Activities)

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