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.
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.
Showing deals for:Aug 22 - Aug 24
Image gallery for Islander Bayside Villas and Boatslips
You can spend an afternoon exploring the galleries in History of Diving Museum during your travels in Islamorada. Amble around this family-friendly area's seaside and enjoy its lively bars.
Learn about the local history of Islamorada with a stop at Hurricane Monument. Discover the beautiful sunsets and lively bars in this family-friendly area.
You can stroll along Bud n' Mary's Dive Center for relaxing water views when you're in Matecumbe. Hotels.com travelers also say the area is family-friendly and has lots of nice beaches.
Find out about the history of Islamorada with a stop at Matecumbe United Methodist Church. Discover the beautiful sunsets in this family-friendly area, or enjoy its fishing spots.
"This was our first time here. The property is beautiful! The kids LOVED playing at the main pool, lagoon & other pool w/ pirate ship splash pad. Our only complaint is the water in all these areas is very warm except the pool by the pirate ship. Maybe when they build the new water slide area they will include a system that keeps the water cool & refreshing. Food & drinks were delicious but also expensive. We mostly ordered from the main pool tiki bar/grill. Jacob & Tomas from Turkey were so friendly & provided excellent service! We tried Salt & Ash for a nice fancy dinner & were not disappointed. Breakfast in the cafe always had a long line so be prepared. They accidentally had us listed as taking our food to go even though we did not request that. They gave us a number to place on our table but the food never came out & sat at the counter forever until we finally inquired as to the wait. We assumed it was taking long bc they were so busy. So that was a bit disappointing. We had the family oasis room w/ bunk beds which was perfect for us. There isn’t a view (looks out to the back of a building), but that didn’t bother us since we were barely in our room. Beds were comfortable, the AC was cold & the shower hot. We spent 3 nights there & didn’t leave the property except for one time to have dinner at Lazy Days in Islamorada which was so good. Though there are some areas that can be improved, overall we had a wonderful trip & look forward to coming back."
"We can't say enough about this property! The front desk staff was beyond accommodating! Olivia and all the girls were absolutely fabulous Staff throughout the hotel were all very friendly! We would highly recommend this hotel. Nicole the Tiki bartender was very pleasant and gave us great suggestions for restaurants which we really enjoyed!"
"Great resort with lots to do on-site, pool/kayak/paddle boards/chess/checkers. Morning omelette was delicious & breakfast with the iguanas was fun! Great spot if you’re traveling through or on a fishing trip."
"We had a great room with a balcony and a marina view and we loved it. It was updated and clean. They have two pools that are open till 11pm and and a tiki bar in between.
Very lovely property."
What accommodations do travelers like in Upper Matecumbe Key?
The Caribbean Resort, Pines & Palms Resort and Cheeca Lodge & Spa are all accommodations that are popular with guests.
Can I book a refundable accommodation in Upper Matecumbe Key?
If you need the flexibility to change your travel plans to Upper Matecumbe Key, most hotels offer refundable* bookable rates. You can see these accommodations by searching our site and using the "fully refundable" filter to narrow the results down.
Which Upper Matecumbe Key hotels do our guests like for their great location?
Travelers like these properties for their convenient location: Chesapeake Beach Resort, Islander Resort and Hadley House Islamorada.
Where can I stay in Upper Matecumbe Key if I want a budget-friendly accommodation?
Two inexpensive options worth considering are Chesapeake Beach Resort and La Jolla Resort.
Where can I stay in Upper Matecumbe Key if I want a vacation rental instead of a traditional hotel?
If you're looking for a good alternative to a hotel, browse our selection of 115 vacation homes. In addition, there are 9 apartments and 13 condos.
Why should I book my Upper Matecumbe Key accommodation with Hotels.com?
There are lots of reasons to book your Upper Matecumbe Key trip with us: our free cancellations on selected hotels gives you flexibility, and with One Key™, our rewards program, you will be able to earn and use OneKeyCash™* on all eligible bookings such as hotels, car rentals, flights, vacation rentals and more on Hotels.com, Expedia and Vrbo.
