
Upper Matecumbe Key Vacations from $319
Book a Hotel + Flight or Car together to unlock savings
Photo by Cameron Abbott
- Plan, book, travel with confidence
- Better togetherSave up to $2,000 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, 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.

Casa Colaretta By At Mine Hospitality
South Beach
Price was $693, price is now $319 per person
$319
per person
Jul 5 - Jul 8
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Miami (MIA)
10/10 Exceptional! (11 reviews)
We had a wonderful stay at this hotel and would absolutely return. The room was spacious, clean, and the kitchen was extremely convenient for our family during the trip. The location was excellent and felt safe and comfortable.
Oscar was incredibly attentive over the phone. The maintenance staff was consistently on site and always available.
We also appreciated the support from the front desk staff at the Augustine Hotel, who were very kind and helpful. The beach towels and beach chairs they provided were a great added touch and made our beach days much easier.
Overall, this hotel offered a perfect balance of comfort, convenience, and hospitality. We truly enjoyed our stay.
Reviewed on May 21, 2026

Casablanca Miami Beach
North Beach
Price was $5,785, price is now $2,360 per person
$2,360
per person
Aug 21 - Aug 25
found 1 day ago
Roundtrip non-stop 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



Cavalier Hotel South Beach
South Beach
Price was $1,076, price is now $504 per person
$504
per person
Aug 6 - 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 tripsDiscover the most popular places to visit in Upper Matecumbe Key

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 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
$304 nightly
The price is $342 total per night from Jun 9 to Jun 10
$342 total
Jun 9 - Jun 10
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
$238 nightly
The price is $268 total per night from Jul 1 to Jul 2
$268 total
Jul 1 - Jul 2
Total with taxes and fees
9.2/10 Wonderful! (1,738 reviews)
"Pros....Room was awesome and clean. Amazing views. Close to anything you may need. Cons....Property was a little rough. Cans and trash were kind of everywhere."
Reviewed on Jun 3, 2026

Islander Resort
82100 Overseas Highway Islamorada FL
Fully refundableReserve now, pay when you stay
$292 nightly
The price is $329 total per night from Jun 14 to Jun 15
$329 total
Jun 14 - Jun 15
Total with taxes and fees
9.4/10 Exceptional! (1,031 reviews)
"Safety issue. All paddleboards were worn with cracks and fiberglass splinters in multiple areas. Can easily cut someone. Was not comfortable to use one. EVERYTHING ELSE FANTASTIC."
Reviewed on Jun 3, 2026
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) |
More vacations you might like
Explore a world of travel with Expedia
- Islamorada Hotels
- Hotels near Matecumbe United Methodist Church
- Resorts in Islamorada
- Hotels near Florida Keys Brewing Co.
- Cheap Hotels in Islamorada
- Oceanfront Hotels in Islamorada
- All-Inclusive Resorts in Islamorada
- Pet-Friendly Hotels in Islamorada
- Beach Hotels in Islamorada
- Luxury Hotels in Islamorada
- Adults Only Resorts & in Islamorada
- Hilton Hotels in Islamorada
- Marriott Hotels & Resorts in Islamorada
- Houseboats in Islamorada
- Cottages in Islamorada
- Family Hotels in Islamorada
- Motels in Islamorada
- Hotels near Hurricane Monument
- Hotels with a Swim-up Bar in Islamorada
- Hotels with Bars in Islamorada
- Fishing Resorts & in Islamorada
- Condo Rentals in Islamorada
- Boutique Hotels in Islamorada
- Wyndham Hotels in Islamorada
- Honeymoon Resorts & in Islamorada
- 5 Star Hotels in Islamorada
- Villas in Islamorada
- Hotels with Free Breakfast in Islamorada
- Resorts & Hotels with Spas in Islamorada
- Rv Parks in Islamorada
- Hotels with Restaurants in Islamorada
- Hotel Wedding Venues Hotels in Islamorada
- Romantic Hotels in Islamorada
- Vacation Homes in Islamorada
- 4 Star Hotels in Islamorada
- Gay friendly Hotels in Islamorada
- Apartments in Islamorada
- Hotels with Kitchenettes in Islamorada
- Hotels with Suites in Islamorada
- Hotels with Hot Tubs in Islamorada
- Hotels with Laundry Facilities in Islamorada
- Hotels with Connecting Rooms in Islamorada
- Historic Hotels in Islamorada
- Treehouses in Islamorada
- Golf Hotels in Islamorada
- Guest Houses in Islamorada
- Hotels with a Gym in Islamorada
- Hotels & Resorts for Couples in Islamorada
- 3 Star Hotels in Islamorada
- B&B in Islamorada
- Hersha Hospitality Hotels in Islamorada
- Hotels with smoking rooms in Islamorada
- Hotels with Room Service in Islamorada
- Aimbridge Hospitality Hotels in Islamorada
- Hotels with Tennis Courts in Islamorada
- Hotels with a Pool in Islamorada
- Best Western Hotels in Islamorada
- Hotels with Childcare in Islamorada
- Lodges in Islamorada
- Rainforest & Jungle Hotels in Islamorada
- Quiet Resorts & in Islamorada
- Hotels with a View in Islamorada
- Hotels with Balconies in Islamorada
- Hotels with an Outdoor Pool in Islamorada
- Hotels with Free Parking in Islamorada
- Aparthotels in Islamorada
- Independent Hotels in Islamorada
- Casino Hotels in Islamorada
- Hotels on the River in Islamorada
- Non-Smoking Hotels in Islamorada
- Car rentals near Islamorada
- Car rentals near Hurricane Monument
- Hertz Rental Cars in Islamorada
- Enterprise Rental Cars in Islamorada
- Thrifty Car Rental Rental Cars in Islamorada
- Budget Rental Cars in Islamorada
- Van Car Rentals in Islamorada
- Avis Rental Cars in Islamorada
- Alamo Rent A Car Rental Cars in Islamorada
- Luxury Car Rentals in Islamorada
- National Car Rental Rental Cars in Islamorada
- Convertible Car Rentals in Islamorada
- Sixt Rental Cars in Islamorada
- Dollar Rent A Car Rental Cars in Islamorada
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.



















