Islamorada Adventure Vacations
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Top Adventure vacation packages in Islamorada
Price found within the past 48 hours. Click for updated prices.
Islander Resort
Matecumbe
Price was $1,368, price is now $1,066 per person
$1,066
per person
Jan 1 - Jan 3
found 1 day ago
Roundtrip non-stop flight included
Detroit (DTT) to Miami (MIA)
9.2/10 Wonderful! (1,005 reviews)
The room was perfect and the outdoor space was great for morning coffees and reading!
Reviewed on Nov 29, 2025
Amara Cay Resort
Matecumbe
Save 100% on your flight
Price was $1,948, price is now $1,091 per person
$1,091
per person
Feb 1 - Feb 6
found 15 hours ago
Roundtrip non-stop flight included
Bismarck (BIS) to Miami (MIA)
8.8/10 Excellent! (1,252 reviews)
This resort was beautiful, clean and fantastic. The staff was friendly and helpful. We had a wonderful day and will be back.
Reviewed on Nov 20, 2025
Cheeca Lodge & Spa
Matecumbe
Save 100% on your flight
Price was $2,473, price is now $1,462 per person
$1,462
per person
Feb 1 - Feb 6
found 15 hours ago
Roundtrip non-stop flight included
Bismarck (BIS) to Miami (MIA)
9.2/10 Wonderful! (1,262 reviews)
We stayed in the newest section of the Cheeca Lodge. It is so incredibly nice! We had other family staying in the lagoon area. We enjoyed all the activities on the property as well. My nephew especially loved the par3 golf course. I really loved the staff at Cheeca Lodge too. Shelia, Amber and David were our poolside attendants, and Jessica at the front desk was very helpful.
Reviewed on Nov 26, 2025
La Siesta Resort & Villas
Matecumbe
Save 100% on your flight
Price was $1,663, price is now $1,088 per person
$1,088
per person
Feb 1 - Feb 6
found 15 hours ago
Roundtrip non-stop flight included
Bismarck (BIS) to Miami (MIA)
8.6/10 Excellent! (1,000 reviews)
Great stay and beautiful space
Reviewed on Dec 1, 2025
5* Adventure vacations in Islamorada
Price found within the past 48 hours. Click for updated prices.
Cheeca Lodge & Spa
Matecumbe
Save 100% on your flight
Price was $2,473, price is now $1,462 per person
$1,462
per person
Feb 1 - Feb 6
found 15 hours ago
Roundtrip non-stop flight included
Bismarck (BIS) to Miami (MIA)
9.2/10 Wonderful! (1,262 reviews)
We stayed in the newest section of the Cheeca Lodge. It is so incredibly nice! We had other family staying in the lagoon area. We enjoyed all the activities on the property as well. My nephew especially loved the par3 golf course. I really loved the staff at Cheeca Lodge too. Shelia, Amber and David were our poolside attendants, and Jessica at the front desk was very helpful.
Reviewed on Nov 26, 2025
3 Night Adventure vacations in Islamorada
Price found within the past 48 hours. Click for updated prices.
Amara Cay Resort
Matecumbe
Price was $1,108, price is now $554 per person
$554
per person
Feb 4 - Feb 7
found 1 day ago
Roundtrip non-stop flight included
Detroit (DTT) to Miami (MIA)
8.8/10 Excellent! (1,252 reviews)
This resort was beautiful, clean and fantastic. The staff was friendly and helpful. We had a wonderful day and will be back.
Reviewed on Nov 20, 2025
Cheeca Lodge & Spa
Matecumbe
Save 100% on your flight
Price was $1,419, price is now $830 per person
$830
per person
Feb 4 - Feb 7
found 1 day ago
Roundtrip non-stop flight included
Detroit (DTT) to Miami (MIA)
9.2/10 Wonderful! (1,262 reviews)
We stayed in the newest section of the Cheeca Lodge. It is so incredibly nice! We had other family staying in the lagoon area. We enjoyed all the activities on the property as well. My nephew especially loved the par3 golf course. I really loved the staff at Cheeca Lodge too. Shelia, Amber and David were our poolside attendants, and Jessica at the front desk was very helpful.
Reviewed on Nov 26, 2025
4 Night Adventure vacations in Islamorada
Price found within the past 48 hours. Click for updated prices.
La Siesta Resort & Villas
Matecumbe
Save 100% on your flight
Price was $1,101, price is now $631 per person
$631
per person
Feb 2 - Feb 6
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Miami (MIA)
8.6/10 Excellent! (1,000 reviews)
Great stay and beautiful space
Reviewed on Dec 1, 2025
Amara Cay Resort
Matecumbe
Save 100% on your flight
Price was $1,413, price is now $713 per person
$713
per person
Feb 2 - Feb 6
just found
Roundtrip non-stop flight included
Cleveland (CLE) to Miami (MIA)
8.8/10 Excellent! (1,252 reviews)
This resort was beautiful, clean and fantastic. The staff was friendly and helpful. We had a wonderful day and will be back.
Reviewed on Nov 20, 2025
Cheeca Lodge & Spa
Matecumbe
Save 100% on your flight
Price was $1,807, price is now $998 per person
$998
per person
Feb 2 - Feb 6
just found
Roundtrip non-stop flight included
Cleveland (CLE) to Miami (MIA)
9.2/10 Wonderful! (1,262 reviews)
We stayed in the newest section of the Cheeca Lodge. It is so incredibly nice! We had other family staying in the lagoon area. We enjoyed all the activities on the property as well. My nephew especially loved the par3 golf course. I really loved the staff at Cheeca Lodge too. Shelia, Amber and David were our poolside attendants, and Jessica at the front desk was very helpful.
Reviewed on Nov 26, 2025
Find awesome Islamorada adventure vacations
How can I book the best Islamorada adventure trips?
Choose your own adventure in Islamorada, whether that’s a white-knuckle experience or a weekend walk. Read the reviews of the adventures that have gone before to be sure your chosen stay is your idea of fun.
How can I plan the perfect Islamorada family adventure vacation?
Adventure awaits when you select the family-friendly filter. There’s plenty of excitement for all ages in Islamorada. Just make sure to check your chosen escapade is within the realms of can-do for the whole clan and will have the whole team grinning.
Can I book all-inclusive Islamorada adventure vacation packages?
By refining your filters, you can explore all-amazing, all-adventurous, all-inclusive vacation packages. Amp up the extravagance with a few more filters too. Pick pristine pools, sensational spas, or wondrous waterparks for a sensational adventure getaway.
Why should I book a Islamorada adventure vacation for couples?
Book a Islamorada couples adventure vacation for the ultimate in romance and memory-making. Stunning scenery, heart-racing happenings, and the grandeur of the great outdoors—it’s the best way to bond.
How can I find the best deals on adventure packages in Islamorada?
It’s easy to unleash fabulously affordable adventures. Enter the dates for your caper, then sort your search results by price or deals.
Can I book an adventure vacation package in Islamorada with free cancellation and/or flexible dates?
Yes! When you’re searching for a great getaway, filter by payment option for free cancellation, so a change of plans won’t mess up your adventures. You’ll find buy now, pay later options, too, for full-on flexibility.
Why should I book a Islamorada adventure trip with Expedia?
Adventure, airfare, accommodation, ATOL protection, and activities—all on one site. And that’s just the benefits that begin with A.
Top Adventure Islamorada Hotels
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 ...
9/10 Wonderful! (1,277 reviews)
We stayed in the newest section of the Cheeca Lodge. It is so incredibly nice! We had other family staying in the lagoon area. We enjoyed all the activities on the property as well. My nephew especially loved the par3 golf course. I really loved the staff at Cheeca Lodge too. Shelia, Amber and David ...
Reviewed on Nov 26, 2025
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 ...
8.8/10 Excellent! (112 reviews)
Beautiful room, stunning views
Reviewed on Nov 19, 2025
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! (1,269 reviews)
Loved the resort
Reviewed on Nov 21, 2025
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.
More vacations you might like
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
