Islamorada Adventure Vacations
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Flight and Adventure hotel deals in Islamorada
Price found within the past 48 hours. Click for updated prices.
Cheeca Lodge & Spa
Matecumbe
Price was CA $3,732, price is now CA $2,676 per person
CA $2,676
per person
May 21 - May 25
found 1 day ago
Roundtrip non-stop flight included
Ottawa (YOW) to Miami (MIA)
9.2/10 Wonderful! (1,308 reviews)
We did not use the spa services, we may have been able to barely see a small portion of the ocean out a window
Reviewed on Mar 12, 2026
Amara Cay Resort
Matecumbe
Price was CA $2,002, price is now CA $1,740 per person
CA $1,740
per person
May 21 - May 25
found 1 day ago
Roundtrip non-stop flight included
Ottawa (YOW) to Miami (MIA)
8.8/10 Excellent! (1,268 reviews)
This was a wonderful place to stay in Islamorada! The staff was super helpful and friendly. They allow dogs so we were able to bring our Maltipo. Pool, restaurant, roosters, all were perfect. You also get to go to their other properties which were amazing. Rooms were clean and very comfortable. Location is perfect! We are already planning our next trip.
Reviewed on Mar 20, 2026
Islander Resort
Matecumbe
Price was CA $2,136, price is now CA $1,980 per person
CA $1,980
per person
May 21 - May 25
found 1 day ago
Roundtrip non-stop flight included
Ottawa (YOW) to Miami (MIA)
9.2/10 Wonderful! (1,014 reviews)
This resort had everything! So much to do and staff that was friendly and always helpful. Only complaint is that the restaurants had no options for gluten free diet, so we had to go elsewhere.
Reviewed on Mar 19, 2026
5* Adventure holidays in Islamorada
Price found within the past 48 hours. Click for updated prices.
Cheeca Lodge & Spa
Matecumbe
Price was CA $3,732, price is now CA $2,676 per person
CA $2,676
per person
May 21 - May 25
found 1 day ago
Roundtrip non-stop flight included
Ottawa (YOW) to Miami (MIA)
9.2/10 Wonderful! (1,308 reviews)
We did not use the spa services, we may have been able to barely see a small portion of the ocean out a window
Reviewed on Mar 12, 2026
3 Night Adventure holidays in Islamorada
Price found within the past 48 hours. Click for updated prices.
4 Night Adventure holidays in Islamorada
Price found within the past 48 hours. Click for updated prices.
Cheeca Lodge & Spa
Matecumbe
Price was CA $3,732, price is now CA $2,676 per person
CA $2,676
per person
May 21 - May 25
found 1 day ago
Roundtrip non-stop flight included
Ottawa (YOW) to Miami (MIA)
9.2/10 Wonderful! (1,308 reviews)
We did not use the spa services, we may have been able to barely see a small portion of the ocean out a window
Reviewed on Mar 12, 2026
Adventure Hotels in Islamorada
Cheeca Lodge & Spa
81801 Overseas Highway, Mile Marker 82 Islamorada FL
Book a stay at this luxury resort in Islamorada. Enjoy free parking, 3 outdoor pools, and a full-service spa. Our guests praise the pool and the helpful staff ...
Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort
84001 Overseas Hwy Islamorada FL
Book a stay at this beach resort in Islamorada. Enjoy free WiFi, 3 outdoor pools, and 4 restaurants. Our guests praise the helpful staff and the clean rooms ...
9/10 Wonderful! (173 reviews)
The ocean was visible from our room and it was a beautiful resort. The staff was friendly and there was a lot to do for families.
Reviewed on Mar 20, 2026
Amara Cay Resort
80001 Overseas Hwy Islamorada FL
Book a stay at this beach resort in Islamorada. Enjoy 2 restaurants, a private beach, and 3 bars/lounges. Our guests praise the pool and the helpful staff in ...
8.8/10 Excellent! (1,255 reviews)
Room was small
Reviewed on Mar 20, 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.
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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
