Islamorada Cheap Vacations
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Flight and Cheap hotel deals in Islamorada
Price found within the past 48 hours. Click for updated prices.
Amara Cay Resort
Matecumbe
Price was CA $1,373, price is now CA $1,029 per person
CA $1,029
per person
Jun 13 - Jun 17
found 17 hours ago
Roundtrip flight included
Toronto (YTO) to Miami (MIA)
8.8/10 Excellent! (1,269 reviews)
Pedí una cuna y una bañera y nunca la vi en la habitación
Reviewed on May 11, 2026
Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort
Price was CA $3,029, price is now CA $1,812 per person
CA $1,812
per person
Jul 16 - Jul 23
found 18 hours ago
Roundtrip flight included
Montreal (YUL) to Miami (MIA)
9/10 Wonderful! (192 reviews)
The resort, staff and facilities are excellent. The location in Islamorada is great either for a few days in the keys or as a stopping point to or from Key West. We didn’t get time to use all of the facilities but there are restaurants on site, kayaks, pools, a lively beach and breakfast so you don’t have to leave if you don’t want to.
Reviewed on May 10, 2026
La Siesta Resort & Villas
Matecumbe
Price was CA $3,207, price is now CA $2,258 per person
CA $2,258
per person
Jul 1 - Jul 8
found 1 day ago
Roundtrip non-stop flight included
St. John's (YYT) to Miami (MIA)
8.6/10 Excellent! (1,003 reviews)
We stayed for mother’s day and we had a good time there. Staff were very friendly
Reviewed on May 12, 2026
Islander Resort
Matecumbe
Price was CA $2,684, price is now CA $2,007 per person
CA $2,007
per person
Jul 16 - Jul 23
found 18 hours ago
Roundtrip flight included
Montreal (YUL) to Miami (MIA)
9.2/10 Wonderful! (1,004 reviews)
Everything about this property was excellent, from the wonderful staff to the kid-friendly atmosphere. We loved the breakfast brunch and the overall vibe of the place. However, dinner at The Drift was a letdown. For the price, the quality just wasn't there. I’d highly recommend the stay, but I suggest looking for other dinner options nearby. We will definitely be back!
Reviewed on May 10, 2026
Cheeca Lodge & Spa
Matecumbe
Price was CA $1,906, price is now CA $1,465 per person
CA $1,465
per person
Jun 13 - Jun 17
found 17 hours ago
Roundtrip flight included
Toronto (YTO) to Miami (MIA)
9.2/10 Wonderful! (1,323 reviews)
Exelente service but the room need more clean and attention
Reviewed on May 11, 2026
5* Cheap holidays in Islamorada
Price found within the past 48 hours. Click for updated prices.
Cheeca Lodge & Spa
Matecumbe
Price was CA $1,906, price is now CA $1,465 per person
CA $1,465
per person
Jun 13 - Jun 17
found 17 hours ago
Roundtrip flight included
Toronto (YTO) to Miami (MIA)
9.2/10 Wonderful! (1,323 reviews)
Exelente service but the room need more clean and attention
Reviewed on May 11, 2026
3 Night Cheap holidays in Islamorada
Price found within the past 48 hours. Click for updated prices.
Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort
Price was CA $1,205, price is now CA $911 per person
CA $911
per person
Jun 14 - Jun 17
found 1 hour ago
Roundtrip flight included
Toronto (YTO) to Miami (MIA)
9/10 Wonderful! (192 reviews)
The resort, staff and facilities are excellent. The location in Islamorada is great either for a few days in the keys or as a stopping point to or from Key West. We didn’t get time to use all of the facilities but there are restaurants on site, kayaks, pools, a lively beach and breakfast so you don’t have to leave if you don’t want to.
Reviewed on May 10, 2026
4 Night Cheap holidays in Islamorada
Price found within the past 48 hours. Click for updated prices.
Creekside Inn
Price was CA $887, price is now CA $613 per person
CA $613
per person
Jun 13 - Jun 17
found 17 hours ago
Roundtrip flight included
Toronto (YTO) to Miami (MIA)
7.8/10 Good! (1,003 reviews)
Had a nice time however lobby closes at 6 and when we returned to our room after dinner to watch some tv found there was NO remote for the tv and lobby was closed. I sent a message to them that still (2 days later) has gone unaddressed
Reviewed on May 12, 2026
Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort
Price was CA $1,670, price is now CA $1,156 per person
CA $1,156
per person
Jun 13 - Jun 17
found 17 hours ago
Roundtrip flight included
Toronto (YTO) to Miami (MIA)
9/10 Wonderful! (192 reviews)
The resort, staff and facilities are excellent. The location in Islamorada is great either for a few days in the keys or as a stopping point to or from Key West. We didn’t get time to use all of the facilities but there are restaurants on site, kayaks, pools, a lively beach and breakfast so you don’t have to leave if you don’t want to.
Reviewed on May 10, 2026
Amara Cay Resort
Matecumbe
Price was CA $1,373, price is now CA $1,029 per person
CA $1,029
per person
Jun 13 - Jun 17
found 17 hours ago
Roundtrip flight included
Toronto (YTO) to Miami (MIA)
8.8/10 Excellent! (1,269 reviews)
Pedí una cuna y una bañera y nunca la vi en la habitación
Reviewed on May 11, 2026
Cheap Hotels in Islamorada
Chesapeake Beach Resort
83409 Overseas Hwy Islamorada FL
Book a stay at this beach hotel in Islamorada. Enjoy free breakfast, free WiFi, and 2 outdoor pools. Our guests praise the breakfast and the pool in our reviews. ...
9.2/10 Wonderful! (1,738 reviews)
Just
Reviewed on May 12, 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.
