Title: Upper Matecumbe Key Vacation Packages 2026 from $587 | 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 $587

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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.

![Solé Miami, A Noble House Resort](https://images.trvl-media.com/lodging/3000000/2810000/2803900/2803820/387d2cd6_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Solé Miami, A Noble House Resort

Ocean Four

$587

per person

Apr 10 - Apr 15

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Miami (MIA)

8.4/10 Very Good! (1,935 reviews)

Location, the view from the room and how clean it was. Staff very friendly

Reviewed on Feb 4, 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

$590

per person

Apr 12 - Apr 18

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

![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

$926

per person

Apr 18 - Apr 24

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

![Cavalier Hotel South Beach](https://images.trvl-media.com/lodging/1000000/20000/13600/13579/c0c3faa8_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Cavalier Hotel South Beach

South Beach

Save 100% on your flight

$633

per person

Apr 16 - Apr 21

found 1 day ago

Roundtrip flight included

Boston (BOS) to Miami (MIA)

8.4/10 Very Good! (1,001 reviews)

Prime location within walking distance to all the hot spots. Included are 2 beach chairs with towels per day. Philip at the concierge received us warmly…checking us in early and giving us great recommendations. Room was a great size, A/C, with bathroom amenities. Overall, totally recommend.

Reviewed on Jan 31, 2026

![Pelican Hotel](https://images.trvl-media.com/lodging/1000000/60000/55100/55046/22b81b04_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Pelican Hotel

South Beach

Save 100% on your flight

$1,007

per person

Apr 17 - Apr 24

found 1 day ago

Roundtrip flight included

Boston (BOS) to Miami (MIA)

9.2/10 Wonderful! (394 reviews)

A reasonably priced art deco hotel in a popular tourist area. Hotel and rooms are stylishly designed. Restaurant food was ok. Maria was a fabulous server. On the downside, there is no pool or fitness center.

Reviewed on Jan 12, 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/2026-03-05/2026-03-12/?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

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 relaxing 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

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

$283 nightly

$319 total

Feb 11 - Feb 12

Total with taxes and fees

9.2/10 Wonderful! (1,665 reviews)

We loved this place. It’s small and easy to get around. Beautiful setting, watched the sunrise from bed, and the best hotel breakfast we’ve ever had.

Reviewed on Feb 3, 2026

[](https://expedia.com/Hotel-Search?startDate=2%2F11%2F2026&endDate=2%2F12%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

$448 nightly

$505 total

Feb 10 - Feb 11

Total with taxes and fees

9.2/10 Wonderful! (1,294 reviews)

We stayed in Premiere ocean front king. The weather was unusually cold and windy so we didn't get to experience the resort as we had hoped. The staff at restaurants were very courteous and service prompt. Beach is lovely -- although not a natural sand beach. Gym could have been larger. We found spa ...

Reviewed on Feb 4, 2026

[](https://expedia.com/Hotel-Search?startDate=2%2F10%2F2026&endDate=2%2F11%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

$320 nightly

$361 total

Feb 11 - Feb 12

Total with taxes and fees

8.8/10 Excellent! (1,263 reviews)

All good, nice bartender inside downstairs, and easy walk to fish and eat

Reviewed on Feb 5, 2026

[](https://expedia.com/Hotel-Search?startDate=2%2F11%2F2026&endDate=2%2F12%2F2026&selected=61976&PinnedHotelID=61976&HadPinnedHotel=true&regionId=553248635975749648)

[See all 2,816 properties in Upper Matecumbe Key](https://expedia.com/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=2%2F6%2F2026&endDate=2%2F7%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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