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 ## 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 $765 per person Jun 13 - Jun 16 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 $1,011 per person May 10 - May 14 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 $1,143 per person May 10 - May 14 found 1 day ago Roundtrip non-stop flight included Boston (BOS) to Key West (EYW) 8.8/10 Excellent! (3,162 reviews) Clean and very friendly staff. Beach view adequate for side of building. Great breakfast variety. Overall, enjoyable experience. 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 $844 per person Jun 13 - Jun 16 found 1 day ago Roundtrip non-stop flight included Boston (BOS) to Key West (EYW) 8.4/10 Very Good! (572 reviews) Beach is beautiful. Reviewed on Apr 1, 2026 ![The Marker Key West Harbor Resort](https://images.trvl-media.com/lodging/10000000/9150000/9148400/9148379/821176b1_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### The Marker Key West Harbor Resort Key West Historic District $1,000 per person Jun 13 - Jun 16 found 1 day ago Roundtrip non-stop flight included Boston (BOS) to Key West (EYW) 9.2/10 Wonderful! (1,011 reviews) We stayed at the Marker for our anniversary in a Harbor View room. Room was very nice and we looked out over a marina and had a nice balcony to sit out and enjoy a glass of wine. Breakfast was good at the bar by the pool but not great. Staff very friendly and helpful. Good enough fitness room to get a decent workout in but no universal machines. Close enough to walk to just about anything you need. If you do stay in the Herbirview room be aware that the Schooner Bar across the path plays music til around 11 am or later each night and you can hear it from your room though it’s muffled. The first night we were there the band playing was way too loud and I could hear the words of the songs inside my room while the door was closed. But if you want a very nice hotel with 3 pools and attentive staff in a great location whilst having the Key West vibe all around you the Marker is very good. 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/2026-05-02/2026-05-09/?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 $765 per person Jun 13 - Jun 16 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 ![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 $844 per person Jun 13 - Jun 16 found 1 day ago Roundtrip non-stop flight included Boston (BOS) to Key West (EYW) 8.4/10 Very Good! (572 reviews) Beach is beautiful. Reviewed on Apr 1, 2026 ![The Marker Key West Harbor Resort](https://images.trvl-media.com/lodging/10000000/9150000/9148400/9148379/821176b1_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### The Marker Key West Harbor Resort Key West Historic District $1,000 per person Jun 13 - Jun 16 found 1 day ago Roundtrip non-stop flight included Boston (BOS) to Key West (EYW) 9.2/10 Wonderful! (1,011 reviews) We stayed at the Marker for our anniversary in a Harbor View room. Room was very nice and we looked out over a marina and had a nice balcony to sit out and enjoy a glass of wine. Breakfast was good at the bar by the pool but not great. Staff very friendly and helpful. Good enough fitness room to get a decent workout in but no universal machines. Close enough to walk to just about anything you need. If you do stay in the Herbirview room be aware that the Schooner Bar across the path plays music til around 11 am or later each night and you can hear it from your room though it’s muffled. The first night we were there the band playing was way too loud and I could hear the words of the songs inside my room while the door was closed. But if you want a very nice hotel with 3 pools and attentive staff in a great location whilst having the Key West vibe all around you the Marker is very good. 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/2026-05-02/2026-05-09/?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. ![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 $1,309 per person Jun 17 - Jun 21 found 1 day ago Roundtrip non-stop flight included Boston (BOS) to Key West (EYW) 9.4/10 Exceptional! (1,020 reviews) They have everything on site you need!! Reviewed on Apr 2, 2026 ![The Key West Hotel](https://images.trvl-media.com/lodging/9000000/8660000/8657100/8657021/dab63efc_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### The Key West Hotel Key West Historic District Save 100% on your flight $1,436 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! (536 reviews) The tag line of the hotel is "Come Hide" which was appropriate as it is hidden from plain view of the hustle and bustle of Duval St. The entrance is mysterious as it is set back and the pathway leading to the reception office is filled with green ferns/palms. Loved it! The center of the property is highlighted the bar and the permanent stage for the daily entertainment. Great place to stay and close to everything! Reviewed on Mar 30, 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 $1,382 per person Jun 17 - Jun 21 found 1 day ago Roundtrip non-stop flight included Boston (BOS) to Key West (EYW) 9.4/10 Exceptional! (1,019 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/2026-05-02/2026-05-09/?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.