Title: Florida Keys Adventure Vacations 2026 | Expedia.com ![](https://images.trvl-media.com/place/6246822/f00ad239-b8ad-4f0c-b162-acc6426db1e2.jpg?impolicy=fcrop&w=1200&h=300&q=medium) # Florida Keys Adventure Vacations ## Book a Adventure Hotel + Flight or Car together to unlock savings - ## Plan, book, travel with confidence - ### Better together Save up to $1,045 when you book a flight and hotel together\* - ### Find the right fit With over 300,000 hotels worldwide, it's easy to create a perfect package - ### Rest easy Plan, book, and manage your trip all in one place ## Top Adventure vacation packages in Florida Keys Price found within the past 48 hours. Click for updated prices. ![La Siesta Resort & Villas](https://images.trvl-media.com/lodging/3000000/2480000/2477600/2477508/18023e21_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### La Siesta Resort & Villas Matecumbe Save 100% on your flight $315 per person Apr 27 - Apr 29 found 13 hours ago Roundtrip flight included New York (NYC) to Miami (MIA) 8.8/10 Excellent! (1,004 reviews) The best I can say is that it was quiet, calm, and relaxing. Rooms were very good. Some showed sign of work - pencil marks from measuring for mirrors/paintings, and with beds right under a window that opened into the external hallway was a little noisy. Limited food options, no full bar (beer and wine only). The free use of kayaks and paddle boards was a plus. Reviewed on Mar 27, 2026 ![Tranquility Bay Beachfront Hotel and Resort](https://images.trvl-media.com/lodging/1000000/120000/117100/117099/854776a0_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Tranquility Bay Beachfront Hotel and Resort Save 100% on your flight $1,218 per person Apr 27 - May 2 found 19 hours ago Roundtrip non-stop flight included Des Moines (DSM) to Miami (MIA) 8.8/10 Excellent! (1,000 reviews) All 3 pools were beautiful, I loved the surrounding landscape. The two bedroom / 2.5 bath villa was wonderful. I loved sitting on the villas deck each morning to drink my coffee and enjoy the palm tree ocean view. The kitchen had everything we needed to make our meals! I would definitely recommend. Reviewed on Mar 21, 2026 ![Cheeca Lodge & Spa](https://images.trvl-media.com/lodging/1000000/10000/5800/5780/4608d7e2_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Cheeca Lodge & Spa Matecumbe Save 100% on your flight $994 per person May 28 - May 31 found 1 day ago Roundtrip flight included Charlotte (CLT) to Miami (MIA) 9.2/10 Wonderful! (1,308 reviews) The staff was friendly and laid back. The resort was absolutely beautiful! Reviewed on Mar 27, 2026 ![Hawks Cay Resort](https://images.trvl-media.com/lodging/1000000/10000/6100/6068/8671ba74_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Hawks Cay Resort Save 100% on your flight $645 per person Apr 27 - Apr 30 found 4 hours ago Roundtrip flight included Hartford (BDL) to Miami (MIA) 8/10 Very Good! (1,015 reviews) The pool was ok. Super overcrowded since it was the only pool that <21 years old could go to. They are building a waterpark and removed the other pool in prep for that waterpark. They could do a better job cleaning the pool. They had two different people playing music at the pool while we were there. We preferred the DJ over Will the guitar guy. DJ played a better variety of music and took requests from the kids/crowd. Bingo at the pool was a nice touch. All staff encountered were very professional and nice. We stayed in a villa and it was 0.4 mile walk from the front door to the pool. We discovered the bike rental the first day and honestly, just kept them at our villa the whole week. We were probably supposed to return them but it was nice to have to get around the resort grounds. You’ll get lots of steps in otherwise! Not a bad thing. Food at the restaurants within the resort was pretty good. Please do yourself a favor and dine at Salt and Ash and order the potatoes with fresh truffle shavings. Delicious!! Reviewed on Mar 28, 2026 Don't see what you're looking for? See all available trips from Columbus to Florida Keys [View all trips](https://expedia.com/go/package/search/FlightHotel/2026-04-28/2026-05-05/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=MIA&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## 5\* Adventure vacations in Florida Keys Price found within the past 48 hours. Click for updated prices. ![Cheeca Lodge & Spa](https://images.trvl-media.com/lodging/1000000/10000/5800/5780/4608d7e2_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Cheeca Lodge & Spa Matecumbe Save 100% on your flight $994 per person May 28 - May 31 found 1 day ago Roundtrip flight included Charlotte (CLT) to Miami (MIA) 9.2/10 Wonderful! (1,308 reviews) The staff was friendly and laid back. The resort was absolutely beautiful! Reviewed on Mar 27, 2026 Don't see what you're looking for? See all available trips from Columbus to Florida Keys [View all trips](https://expedia.com/go/package/search/FlightHotel/2026-04-28/2026-05-05/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=MIA&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## 3 Night Adventure vacations in Florida Keys Price found within the past 48 hours. Click for updated prices. ![La Siesta Resort & Villas](https://images.trvl-media.com/lodging/3000000/2480000/2477600/2477508/18023e21_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### La Siesta Resort & Villas Matecumbe Save 100% on your flight $500 per person Apr 29 - May 2 found 12 hours ago Roundtrip flight included Newark Liberty Intl. Airport (EWR) to Miami (MIA) 8.8/10 Excellent! (1,004 reviews) The best I can say is that it was quiet, calm, and relaxing. Rooms were very good. Some showed sign of work - pencil marks from measuring for mirrors/paintings, and with beds right under a window that opened into the external hallway was a little noisy. Limited food options, no full bar (beer and wine only). The free use of kayaks and paddle boards was a plus. Reviewed on Mar 27, 2026 ![Oceans Edge Key West Resort, Hotel & Marina](https://images.trvl-media.com/lodging/17000000/16210000/16203000/16202992/f7424907_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Oceans Edge Key West Resort, Hotel & Marina $861 per person Apr 27 - Apr 30 found 1 day ago Roundtrip non-stop flight included Cincinnati (CVG) to Key West (EYW) 9/10 Wonderful! (1,825 reviews) Beautiful and extremely clean; property grounds are well kept. The entire resort is beautiful and everything is constantly cleaned and cared for. Reviewed on Mar 28, 2026 ![Tranquility Bay Beachfront Hotel and Resort](https://images.trvl-media.com/lodging/1000000/120000/117100/117099/854776a0_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Tranquility Bay Beachfront Hotel and Resort Save 100% on your flight $724 per person May 1 - May 4 found 1 day ago Roundtrip non-stop flight included Baltimore (BWI) to Miami (MIA) 8.8/10 Excellent! (1,000 reviews) All 3 pools were beautiful, I loved the surrounding landscape. The two bedroom / 2.5 bath villa was wonderful. I loved sitting on the villas deck each morning to drink my coffee and enjoy the palm tree ocean view. The kitchen had everything we needed to make our meals! I would definitely recommend. Reviewed on Mar 21, 2026 Don't see what you're looking for? See all available trips from Columbus to Florida Keys [View all trips](https://expedia.com/go/package/search/FlightHotel/2026-04-28/2026-05-05/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=MIA&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## 4 Night Adventure vacations in Florida Keys Price found within the past 48 hours. Click for updated prices. ![La Siesta Resort & Villas](https://images.trvl-media.com/lodging/3000000/2480000/2477600/2477508/18023e21_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### La Siesta Resort & Villas Matecumbe Save 100% on your flight $723 per person Apr 28 - May 2 found 17 hours ago Roundtrip flight included Cleveland (CLE) to Miami (MIA) 8.8/10 Excellent! (1,004 reviews) The best I can say is that it was quiet, calm, and relaxing. Rooms were very good. Some showed sign of work - pencil marks from measuring for mirrors/paintings, and with beds right under a window that opened into the external hallway was a little noisy. Limited food options, no full bar (beer and wine only). The free use of kayaks and paddle boards was a plus. Reviewed on Mar 27, 2026 ![Tranquility Bay Beachfront Hotel and Resort](https://images.trvl-media.com/lodging/1000000/120000/117100/117099/854776a0_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Tranquility Bay Beachfront Hotel and Resort Save 100% on your flight $815 per person May 28 - Jun 1 found 4 hours ago Roundtrip flight included Chicago (ORD) to Miami (MIA) 8.8/10 Excellent! (1,000 reviews) All 3 pools were beautiful, I loved the surrounding landscape. The two bedroom / 2.5 bath villa was wonderful. I loved sitting on the villas deck each morning to drink my coffee and enjoy the palm tree ocean view. The kitchen had everything we needed to make our meals! I would definitely recommend. Reviewed on Mar 21, 2026 ![Hawks Cay Resort](https://images.trvl-media.com/lodging/1000000/10000/6100/6068/8671ba74_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Hawks Cay Resort Save 100% on your flight $822 per person May 28 - Jun 1 found 4 hours ago Roundtrip flight included Chicago (ORD) to Miami (MIA) 8/10 Very Good! (1,015 reviews) The pool was ok. Super overcrowded since it was the only pool that <21 years old could go to. They are building a waterpark and removed the other pool in prep for that waterpark. They could do a better job cleaning the pool. They had two different people playing music at the pool while we were there. We preferred the DJ over Will the guitar guy. DJ played a better variety of music and took requests from the kids/crowd. Bingo at the pool was a nice touch. All staff encountered were very professional and nice. We stayed in a villa and it was 0.4 mile walk from the front door to the pool. We discovered the bike rental the first day and honestly, just kept them at our villa the whole week. We were probably supposed to return them but it was nice to have to get around the resort grounds. You’ll get lots of steps in otherwise! Not a bad thing. Food at the restaurants within the resort was pretty good. Please do yourself a favor and dine at Salt and Ash and order the potatoes with fresh truffle shavings. Delicious!! Reviewed on Mar 28, 2026 Don't see what you're looking for? See all available trips from Columbus to Florida Keys [View all trips](https://expedia.com/go/package/search/FlightHotel/2026-04-28/2026-05-05/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=MIA&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## Find awesome Florida Keys adventure vacations #### How can I book the best Florida Keys adventure trips? Choose your own adventure in Florida Keys, 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 Florida Keys family adventure vacation? Adventure awaits when you select the family-friendly filter. There’s plenty of excitement for all ages in Florida Keys. 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 Florida Keys 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 Florida Keys adventure vacation for couples? Book a Florida Keys 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 Florida Keys? 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 Florida Keys 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 Florida Keys 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 Florida Keys Hotels ![Hawks Cay Resort](https://images.trvl-media.com/lodging/1000000/10000/6100/6068/8671ba74_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Hawks Cay Resort 61 Hawks Cay Blvd Marathon FL - 2 hours drive from Duval Street Book a stay at this luxury hotel in Marathon. Enjoy free WiFi, 5 outdoor pools, and a full-service spa. Our guests praise the pool and the helpful staff in our ... 8/10 Very Good! (1,001 reviews) The pool was ok. Super overcrowded since it was the only pool that <21 years old could go to. They are building a waterpark and removed the other pool in prep for that waterpark. They could do a better job cleaning the pool. They had two different people playing music at the pool while we were there. ... Reviewed on Mar 28, 2026 [](https://expedia.com/Marathon-Hotels-Hawks-Cay-Resort.h6068.Hotel-Information) ![Cheeca Lodge & Spa](https://images.trvl-media.com/lodging/1000000/10000/5800/5780/4608d7e2_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Cheeca Lodge & Spa 81801 Overseas Highway, Mile Marker 82 Islamorada FL - 3 hours drive from Duval Street 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 ... 9.2/10 Wonderful! (1,300 reviews) The staff was friendly and laid back. The resort was absolutely beautiful! Reviewed on Mar 27, 2026 [](https://expedia.com/Islamorada-Hotels-Cheeca-Lodge-Spa.h5780.Hotel-Information) ![Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort](https://images.trvl-media.com/lodging/1000000/20000/11900/11864/4671ebc2_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort 84001 Overseas Hwy Islamorada FL - 3 hours drive from Duval Street 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! (179 reviews) No breakfast bar at this resort. Many onsite options for purchase. I did miss having a microwave. Reviewed on Mar 27, 2026 [](https://expedia.com/Islamorada-Hotels-Three-Waters-Resort-And-Marina.h11864.Hotel-Information) [See all 8,317 properties in Florida Keys](https://expedia.com/Hotel-Search?rfrrid=TG.LP.Hotels.Package®ionId=6023765) Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. 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](https://expedia.com/Cheap-Flights-To-Florida-Keys.d6023765.Travel-Guide-Flights)[ Florida Keys Hotels ](https://expedia.com/Florida-Keys-Hotels.d6023765.Travel-Guide-Hotels)[ Vacation Rentals in Florida Keys ](https://expedia.com/Florida-Keys-Vacation-Rentals.d6023765.Travel-Guide-VacationRentals)[ Car Rentals in Florida Keys ](https://expedia.com/Car-Rentals-In-Florida-Keys.d6023765.Car-Rental-Guide)[ Florida Keys Vacations ](https://expedia.com/Florida-Keys.d6023765.Destination-Travel-Guides)[ Things to do in Florida Keys ](https://expedia.com/Things-To-Do-In-Florida-Keys.d6023765.Travel-Guide-Activities) \* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. ![](https://a.travel-assets.com/mad-service/footer/bnaBanners/BEX_Footer.jpg) ## Go further with the Expedia app Save even more - get up to 20% on select hotels when you book on the app. Our app deals help you to save on trips so you can travel more and manage it all on the go. Scan the QR code with your device camera and download our app