Upper Matecumbe Key Beach Vacations
Book a Beach Hotel + Flight or Car together to unlock savings
Photo by Cameron Abbott
- Plan, book, travel with confidence
- Better togetherSave up to ￥45,448 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
Top Beach vacation packages in Upper Matecumbe Key
Price found within the past 48 hours. Click for updated prices.
Fort Lauderdale Beach Resort by Vacatia
East Fort Lauderdale
Price was ￥140,536, price is now ￥101,229 per person
￥101,229
per person
Feb 13 - Feb 15
found 1 day ago
Roundtrip flight included
Chicago (CHI) to Miami (MIA)
8.4/10 Very Good! (436 reviews)
Location was great… easy walk to beach. Condo a bit outdated but overall would stay again!
Reviewed on Jan 6, 2026
Pelican Grand Beach Resort - A Noble House Resort
East Fort Lauderdale
Save 100% on your flight
Price was ￥332,936, price is now ￥215,504 per person
￥215,504
per person
Feb 13 - Feb 16
found 1 day ago
Roundtrip non-stop flight included
Chicago (ORD) to Miami (MIA)
8.6/10 Excellent! (1,330 reviews)
Incredible beach view and access with food/beverage service on the beach. It’s a family friendly spot both inside the resort, the pool and beach side. Restaurant on site has tasty food as well.
The biggest negative was the inconsistency in service by staff throughout the resort whether it was food/beverage service, housekeeping or front desk. More times we found things were done very slowly, forgotten about and sometimes unhelpful. Some staff were top-notch and helped make the stay enjoyable!
Reviewed on Jan 10, 2026
The Shelborne By Proper, a Member of Design Hotels
South Beach
Save 100% on your flight
Price was ￥289,686, price is now ￥191,229 per person
￥191,229
per person
Feb 13 - Feb 15
found 1 day ago
Roundtrip non-stop flight included
Chicago (CHI) to Miami (MIA)
9.4/10 Exceptional! (56 reviews)
The holding fee is ridiculously high
Reviewed on Jan 8, 2026
Fontainebleau Miami Beach
Mid Beach
Price was ￥239,680, price is now ￥190,416 per person
￥190,416
per person
Feb 13 - Feb 15
found 1 day ago
Roundtrip flight included
Chicago (CHI) to Miami (MIA)
8.2/10 Very Good! (7,303 reviews)
Everything was great except for the building location. The walk to my room was very far. I’ve noticed that when I book through third-party websites, I’m often assigned to the farthest building, while booking directly with the hotel usually places guests in buildings closer to the front. This has happened several times, and I was wondering if there’s any way to improve the website so guests can select or request their preferred building.
The hotel was very quiet and peaceful, with no disturbances, which I really appreciated. However, I was quite surprised that there was no coffee provided in the room. For an exclusive-level hotel, not offering complimentary coffee is unusual and disappointing. Even more affordable hotels usually provide free coffee for guests. This is definitely an area the hotel should improve.
The room was very clean and spacious enough to comfortably accommodate all my needs.
The room I stayed in did not have a bathtub, which I was not aware of at the time of booking. This was not clearly mentioned, and as someone who prefers a bathtub, I was disappointed once again.
The elevator was fast and efficient, with minimal waiting time.
I noticed a few popcorn crumbs near by the table, which may have been missed during cleaning.
Reviewed on Jan 10, 2026
Don't see what you're looking for?
See all available trips from Chicago to Upper Matecumbe Key
View all trips5* Beach vacations in Upper Matecumbe Key
Price found within the past 48 hours. Click for updated prices.
Pier Sixty-Six (Pier 66)
East Fort Lauderdale
Price was ￥218,323, price is now ￥190,037 per person
￥190,037
per person
Feb 13 - Feb 15
found 1 day ago
Roundtrip non-stop flight included
Chicago (CHI) to Miami (MIA)
9.8/10 Exceptional! (273 reviews)
Great stay. Great hotel staff. Enjoyed the spa.
Room keepers could be more timely, but still got the job done.
Reviewed on Jan 9, 2026
Don't see what you're looking for?
See all available trips from Chicago to Upper Matecumbe Key
View all trips3 Night Beach vacations in Upper Matecumbe Key
Price found within the past 48 hours. Click for updated prices.
Fort Lauderdale Beach Resort by Vacatia
East Fort Lauderdale
Save 100% on your flight
Price was ￥188,004, price is now ￥117,102 per person
￥117,102
per person
Feb 13 - Feb 16
found 1 day ago
Roundtrip non-stop flight included
Chicago (ORD) to Miami (MIA)
8.4/10 Very Good! (436 reviews)
Location was great… easy walk to beach. Condo a bit outdated but overall would stay again!
Reviewed on Jan 6, 2026
The Shelborne By Proper, a Member of Design Hotels
South Beach
Save 100% on your flight
Price was ￥410,639, price is now ￥241,337 per person
￥241,337
per person
Feb 13 - Feb 16
found 1 day ago
Roundtrip non-stop flight included
Chicago (ORD) to Miami (MIA)
9.4/10 Exceptional! (56 reviews)
The holding fee is ridiculously high
Reviewed on Jan 8, 2026
Don't see what you're looking for?
See all available trips from Chicago to Upper Matecumbe Key
View all trips* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
