Title: Raccoon Key Adventure Vacations 2026 | Expedia.com ![](https://a.travel-assets.com/travel-assets-manager/fallback-images-brand/bex_packages.jpeg?impolicy=fcrop&w=1200&h=300&q=medium) # Raccoon Key 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 Raccoon Key Price found within the past 48 hours. Click for updated prices. ![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 $1,011 per person Jun 17 - Jun 21 found 1 day ago Roundtrip non-stop flight included Boston (BOS) to Key West (EYW) 9/10 Wonderful! (1,848 reviews) Amazing location, the room and property were spotless. Staff were very friendly. Would stay here again! Reviewed on Apr 2, 2026 ![Winslow's Bungalows - Key West Historic Inns](https://images.trvl-media.com/lodging/1000000/530000/529700/529611/b5f8742c_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Winslow's Bungalows - Key West Historic Inns Old Town Key West $1,120 per person Jun 17 - Jun 21 found 1 day ago Roundtrip non-stop flight included Boston (BOS) to Key West (EYW) 9.2/10 Wonderful! (1,194 reviews) Second time we have stayed here.Staff is excellent, accommodating. The property is very well maintained and a great location. Reviewed on Apr 1, 2026 ![Casa Marina Key West, Curio Collection by Hilton](https://images.trvl-media.com/lodging/1000000/20000/12400/12346/14292c62_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Casa Marina Key West, Curio Collection by Hilton Old Town Key West Save 100% on your flight $1,157 per person May 28 - Jun 1 found 1 day ago Roundtrip non-stop flight included Boston (BOS) to Key West (EYW) 8.4/10 Very Good! (595 reviews) I had an ocean front suite is was wonderful. The room was very clean and well presented. I ate the restaurant a few times during my stay and it was perfect everytime. I also used the fitness center and valet and everything was wonderful. Reviewed on Apr 3, 2026 ![Southernmost Beach Resort and Guesthouses](https://images.trvl-media.com/lodging/1000000/870000/863400/863329/546caf1e_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Southernmost Beach Resort and Guesthouses Old Town Key West $1,238 per person May 15 - May 18 found 1 day ago Roundtrip non-stop flight included Boston (BOS) to Key West (EYW) 8.8/10 Excellent! (3,162 reviews) We stayed in the Adults ONLY Duval Gardens. We enjoyed the privacy and location on Duval Street. It was nice to have the option of the amenities at the resort for the different pools and beach access. Free breakfast too! We would stay here again. The room was clean, staff is friendly no beach view at the Duval Gardens but you are right on Duval Street where all the restaurants and shopping are. No phones either, staff was accessible through text. Reviewed on Apr 2, 2026 ![The Perry Hotel & Marina Key West](https://images.trvl-media.com/lodging/18000000/17320000/17313700/17313680/deb8b21f_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### The Perry Hotel & Marina Key West $1,036 per person May 15 - May 18 found 1 day ago Roundtrip non-stop flight included Boston (BOS) to Key West (EYW) 9.4/10 Exceptional! (1,234 reviews) Did not eat any meals on the property. Overall it's a nice place to stay. Rooms and furniture are dated in some areas. Very nice staff including Jamey and Mitchell. Reviewed on Apr 2, 2026 Don't see what you're looking for? See all available trips from Columbus to Raccoon Key [View all trips](https://expedia.com/go/package/search/FlightHotel/2026-05-03/2026-05-10/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=EYW&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## 3 Night Adventure vacations in Raccoon Key Price found within the past 48 hours. Click for updated prices. ![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 $740 per person Jun 24 - Jun 27 found 1 day ago Roundtrip non-stop flight included Boston (BOS) to Key West (EYW) 9/10 Wonderful! (1,848 reviews) Amazing location, the room and property were spotless. Staff were very friendly. Would stay here again! Reviewed on Apr 2, 2026 ![Winslow's Bungalows - Key West Historic Inns](https://images.trvl-media.com/lodging/1000000/530000/529700/529611/b5f8742c_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Winslow's Bungalows - Key West Historic Inns Old Town Key West $810 per person Jun 24 - Jun 27 found 1 day ago Roundtrip non-stop flight included Boston (BOS) to Key West (EYW) 9.2/10 Wonderful! (1,194 reviews) Second time we have stayed here.Staff is excellent, accommodating. The property is very well maintained and a great location. Reviewed on Apr 1, 2026 ![Southernmost Beach Resort and Guesthouses](https://images.trvl-media.com/lodging/1000000/870000/863400/863329/546caf1e_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Southernmost Beach Resort and Guesthouses Old Town Key West $1,238 per person May 15 - May 18 found 1 day ago Roundtrip non-stop flight included Boston (BOS) to Key West (EYW) 8.8/10 Excellent! (3,162 reviews) We stayed in the Adults ONLY Duval Gardens. We enjoyed the privacy and location on Duval Street. It was nice to have the option of the amenities at the resort for the different pools and beach access. Free breakfast too! We would stay here again. The room was clean, staff is friendly no beach view at the Duval Gardens but you are right on Duval Street where all the restaurants and shopping are. No phones either, staff was accessible through text. Reviewed on Apr 2, 2026 Don't see what you're looking for? See all available trips from Columbus to Raccoon Key [View all trips](https://expedia.com/go/package/search/FlightHotel/2026-05-03/2026-05-10/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=EYW&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## 4 Night Adventure vacations in Raccoon Key Price found within the past 48 hours. Click for updated prices. ![Winslow's Bungalows - Key West Historic Inns](https://images.trvl-media.com/lodging/1000000/530000/529700/529611/b5f8742c_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Winslow's Bungalows - Key West Historic Inns Old Town Key West Save 100% on your flight $987 per person May 28 - Jun 1 found 1 day ago Roundtrip non-stop flight included Boston (BOS) to Key West (EYW) 9.2/10 Wonderful! (1,194 reviews) Second time we have stayed here.Staff is excellent, accommodating. The property is very well maintained and a great location. Reviewed on Apr 1, 2026 ![Hyatt Vacation Club at Windward Pointe, Key West](https://images.trvl-media.com/lodging/1000000/870000/868700/868697/af5a58cd_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Hyatt Vacation Club at Windward Pointe, Key West Save 100% on your flight $1,161 per person May 28 - Jun 1 found 1 day ago Roundtrip non-stop flight included Boston (BOS) to Key West (EYW) 9.4/10 Exceptional! (1,020 reviews) Beautiful property! Reviewed on Apr 3, 2026 ![Hyatt Vacation Club at Beach House, Key West](https://images.trvl-media.com/lodging/1000000/860000/858000/857962/864ce9f9_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Hyatt Vacation Club at Beach House, Key West Save 100% on your flight $1,107 per person May 28 - Jun 1 found 1 day ago Roundtrip non-stop flight included Boston (BOS) to Key West (EYW) 9.4/10 Exceptional! (1,004 reviews) These are recently renovated “condos” with 2 beds/2 baths, full kitchen, dining, and living area. Master bath is very nicely done with a giant shower for two. Very large deck/porch off each unit. The A/C went out but the friendly front desk and maintenance crew repaired it quickly. Resort has a large pool and large sand beach area with plenty of chairs and cabanas. New gas grills are near the pool area. There is a tiki bar on site with food. No complaints about this property whatsoever. There is a kayak tour guide right next door and I highly recommend their night kayak tour. The property is at the opposite end of the island to Old town/Duvall street. It’s about a 20 min bike ride to Duvall, and a 9 minute bike ride to Publix. Reviewed on Apr 1, 2026 Don't see what you're looking for? See all available trips from Columbus to Raccoon Key [View all trips](https://expedia.com/go/package/search/FlightHotel/2026-05-03/2026-05-10/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=EYW&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## Find awesome Raccoon Key adventure vacations #### How can I book the best Raccoon Key adventure trips? Choose your own adventure in Raccoon Key, 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 Raccoon Key family adventure vacation? Adventure awaits when you select the family-friendly filter. There’s plenty of excitement for all ages in Raccoon Key. 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 Raccoon Key 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 Raccoon Key adventure vacation for couples? Book a Raccoon Key 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 Raccoon Key? 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 Raccoon Key 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 Raccoon Key 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. ## More vacations you might like ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/06/08/all-inclusive_holidays_US.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh) All Inclusive Vacations [](https://expedia.com/lp/theme-vacations/all-inclusive-vacations?rfrr=editorial.All_Inclusive%20Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/10/17/XPC_Beach_Overview_HR_v3.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Beach Vacations [](https://expedia.com/lp/theme-vacations/beach-vacations?rfrr=editorial.Beach_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/06/08/Family_holidays_US_3_.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Kid Friendly Vacations [](https://expedia.com/lp/theme-vacations/kid-friendly-vacations?rfrr=editorial.Kid_Friendly%20Vacations.click) 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](https://expedia.com/Cheap-Flights-To-Raccoon-Key.d180164.Travel-Guide-Flights)[ Raccoon Key Hotels ](https://expedia.com/Raccoon-Key-Hotels.d180164.Travel-Guide-Hotels)[ Vacation Rentals in Raccoon Key ](https://expedia.com/Raccoon-Key-Vacation-Rentals.d180164.Travel-Guide-VacationRentals)[ Car Rentals in Raccoon Key ](https://expedia.com/Car-Rentals-In-Raccoon-Key.d180164.Car-Rental-Guide)[ Raccoon Key Vacations ](https://expedia.com/Raccoon-Key.d180164.Destination-Travel-Guides)[ Things to do in Raccoon Key ](https://expedia.com/Things-To-Do-In-Raccoon-Key.d180164.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