Upper Matecumbe Key Vacation Packages
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Top Upper Matecumbe Key Vacation Deals
Price found within the past 48 hours. Click for updated prices.
Casablanca Miami Beach
North Beach
Price was CA $2,981, price is now CA $1,628 per person
CA $1,628
per person
Aug 4 - Aug 9
found 20 hours ago
Roundtrip non-stop flight included
Montreal (YMQ) to Miami (MIA)
5.8/10 (324 reviews)
This was a very disappointing stay. The apartment was dirty, dusty, and hot. The temperature stayed around 77–78°F all night, yet the only bedding provided was thick comforters, making it impossible to sleep comfortably.
When I simply asked for thin bed sheets, the host became argumentative instead of trying to help. They kept saying they were a private owner, as if that somehow excused poor customer service or making guests uncomfortable. It wasn’t until I contacted Expedia that the host responded by providing what I initially asked for.
I didn’t want to spend my vacation dealing with unnecessary conflict, so we checked out after the first night instead of staying for the remaining five nights of our six-night reservation. I would not stay here again.
Reviewed on Jul 2, 2026
The Retreat Collection at 1 Hotel & Homes South Beach
South Beach
Price was CA $29,526, price is now CA $16,532 per person
CA $16,532
per person
Aug 10 - Aug 16
found 1 day ago
Roundtrip non-stop flight included
Hamilton (YHM) to Miami (MIA)
8/10 Very good! (1 review)
Horrible checkin / checkout... Would never stay there again...Double charged me entire stay and still fighting to get someone to refund 2nd one that is so clearly a duplicate for same stay....
Reviewed on Jun 22, 2016
Upper Matecumbe Key Hotel Deals
Cheeca Lodge & Spa
81801 Overseas Highway, Mile Marker 82 Islamorada FL
Fully refundableReserve now, pay when you stay
The price is CA $257 per night from Jul 16 to Jul 17
CA $257
CA $393 total
Jul 16 - Jul 17
includes taxes & fees
9.2/10 Wonderful! (1,324 reviews)
"Very nicely put together and well maintained. Staff are great and the views are stunning. We will go back again."
Reviewed on Jul 1, 2026
Chesapeake Beach Resort
83409 Overseas Hwy Islamorada FL
Fully refundableReserve now, pay when you stay
The price is CA $237 per night from Aug 3 to Aug 4
CA $237
CA $346 total
Aug 3 - Aug 4
includes taxes & fees
9.2/10 Wonderful! (1,733 reviews)
"The hotel has a fabulous location on the beach the staff were very friendly and we were welcomed with a glass of fizz. Breakfast had a good choice the rooms were spotless you get 2 hours free water sports per day would definitely recommend"
Reviewed on Jul 4, 2026
Amara Cay Resort
80001 Overseas Hwy Islamorada FL
Fully refundableReserve now, pay when you stay
The price is CA $239 per night from Jul 19 to Jul 20
CA $239
CA $372 total
Jul 19 - Jul 20
includes taxes & fees
8.8/10 Excellent! (1,283 reviews)
"We loved everything about it! We will be back!"
Reviewed on Jul 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.
Stay near popular Upper Matecumbe Key attractions
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- Amoray Dive Resort
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- Wyndham Hotels in Islamorada
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- Port Antigua Retreat on Canal with Boat Lift and Private Beach Access
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- Vacation Homes in Layton
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- Layton Hotels
- Apartments in Layton
- Waterfront Home With Swimming Pool
- B&B in Tavernier
- Direct Oceanfront with private staircase to beach prestigious Islamorada CondoComplex
- All Inclusive Resorts and in Key Largo
- Fish
- Best Western Hotels in Key Largo
- La Siesta Resort & Villas
- Manatee Manor ~ 3 Bedroom Island Home on Plantation Key with Pool & Dockage
- Pineapple Beach by Florida Keys Luxury Rentals
- Breathtaking Ocean views! Owners who care. “Sangria Sunrise”! 10% off charters!
- Bayside Villas by Islander Resort
- Boutique Hotels in Islamorada
- Rv Parks in Lignumvitae Key Botanical State Park
- Keys Waterfront Condo
- Oceanfront Hotels in Key Largo
- Hotels near Baker's Cay Resort Beach
- Wynken Blynken and Nod Hotels
- Cottages in Islamorada
- Direct Oceanfront Corner Condo
- Islamorada Hotels
- Marathon Vacations
- Homestead Vacations
- History of Diving Museum
- Visit Key Largo
- Shark Valley Observatory Tower
- Visit Layton
- Visit Seabreeze Trailer Park
- Visit Upper Matecumbe Key
- Baker's Cay Resort Beach
- South Miami Vacations
- Veterans Memorial Park & Beach
- Crane Point Museum and Nature Center
- Visit Islamorada
- Visit Plantation Key
- Islamorada Vacations
- Visit Long Key
- Coral Castle Museum
- Shark Valley Visitor Center
- Sunset Park Beach
- Biscayne National Park
- Zoo Miami
- Sombrero Beach
- Anne's Beach
- Ernest F. Coe Visitor Center
- Florida City Vacations
- Seven Mile Bridge
- Calusa Beach
- Everglades National Park
- Curry Hammock State Park
- Visit Lower Matecumbe Key
- Key Largo Vacations
- Prime Outlets Florida City
- Dagny Johnson Key Largo Hammock Botanical State Park
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
