Title: Summerland Key Adventure Vacations 2026 | Expedia.com ![](https://images.trvl-media.com/place/6177802/bda449a1-0506-4d80-94a6-fb19766bc7f4.jpg?impolicy=fcrop&w=1200&h=300&q=medium) # Summerland 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 Summerland Key Price found within the past 48 hours. Click for updated prices. ![The Sunny](https://images.trvl-media.com/lodging/2000000/1150000/1145300/1145283/edbd844f_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### The Sunny Ocean Four $546 per person Apr 26 - Apr 30 found 1 day ago Roundtrip flight included Boston (BOS) to Miami (MIA) 8.2/10 Very Good! (81 reviews) Property was beautiful. The only thing missing was a sit down breakfast place or the ability to order room service. The pool bar was great, the hotel staff was friendly and welcoming, the hotel was clean and views gorgeous! Reviewed on Mar 15, 2026 ![The Retreat Collection at 1 Hotel & Homes South Beach](https://images.trvl-media.com/lodging/13000000/12320000/12316600/12316590/e518a34f_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### The Retreat Collection at 1 Hotel & Homes South Beach South Beach $7,419 per person May 22 - May 25 found 1 day ago Roundtrip non-stop flight included Boston (BOS) to Miami (MIA) 8/10 Very Good! (1 review) ![Villas At Hawks Cay Resort](https://images.trvl-media.com/lodging/100000000/99930000/99920100/99920083/8638cc9f_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Villas At Hawks Cay Resort Save 100% on your flight $1,881 per person Jun 6 - Jun 13 found 1 day ago Roundtrip non-stop flight included Boston (BOS) to Miami (MIA) 8.4/10 Very Good! (174 reviews) Property was clean and staff were helpful. Would stay again. Reviewed on Mar 11, 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 Save 100% on your flight $1,163 per person May 30 - Jun 6 found 1 day ago Roundtrip non-stop flight included Boston (BOS) to Key West (EYW) 9/10 Wonderful! (1,825 reviews) Room was nice, but the toilet had a terrible smell the last day. It was clean, but stunk of what seemed like sewer gas coming up. It was gross. Reviewed on Mar 14, 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 $1,166 per person Jun 7 - Jun 13 found 1 day ago Roundtrip flight included Boston (BOS) to Miami (MIA) 8/10 Very Good! (1,008 reviews) Pool was enjoyable. Room was clean. Reviewed on Mar 15, 2026 Don't see what you're looking for? See all available trips from Columbus to Summerland Key [View all trips](https://expedia.com/go/package/search/FlightHotel/2026-04-16/2026-04-23/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=MIA&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## 5\* Adventure vacations in Summerland Key Price found within the past 48 hours. Click for updated prices. ![EAST Miami Residences](https://images.trvl-media.com/lodging/79000000/78580000/78570600/78570563/759b33fa_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### EAST Miami Residences Brickell $1,359 per person Apr 24 - Apr 28 found 1 day ago Roundtrip flight included Boston (BOS) to Miami (MIA) 9/10 Wonderful! (109 reviews) We loved staying here and will definitely be back! Yes, it is very expensive, but compared to other Miami hotels this one is the best overall deal for what you get. Reviewed on Mar 1, 2026 ![The Retreat Collection at 1 Hotel & Homes South Beach](https://images.trvl-media.com/lodging/13000000/12320000/12316600/12316590/e518a34f_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### The Retreat Collection at 1 Hotel & Homes South Beach South Beach $7,419 per person May 22 - May 25 found 1 day ago Roundtrip non-stop flight included Boston (BOS) to Miami (MIA) 8/10 Very Good! (1 review) ![1 Hotel South Beach](https://images.trvl-media.com/lodging/2000000/1800000/1790100/1790087/5c0d327a_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### 1 Hotel South Beach South Beach Save 100% on your flight $1,980 per person May 19 - May 23 found 1 day ago Roundtrip non-stop flight included Boston (BOS) to Miami (MIA) 9.4/10 Exceptional! (1,455 reviews) This hotel is so beautiful and the staff is so kind and accommodating. The pool and beach areas are stunning, the food is delicious, the rooms are spacious, the beds are so comfortable, and the location is perfect. It’s the best hotel experience I’ve ever had, and I can’t wait to go back again! Reviewed on Mar 7, 2026 Don't see what you're looking for? See all available trips from Columbus to Summerland Key [View all trips](https://expedia.com/go/package/search/FlightHotel/2026-04-16/2026-04-23/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=MIA&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## 3 Night Adventure vacations in Summerland Key Price found within the past 48 hours. Click for updated prices. ![Villas At Hawks Cay Resort](https://images.trvl-media.com/lodging/100000000/99930000/99920100/99920083/8638cc9f_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Villas At Hawks Cay Resort Save 100% on your flight $954 per person May 5 - May 8 found 21 hours ago Roundtrip flight included Boston (BOS) to Miami (MIA) 8.4/10 Very Good! (174 reviews) Property was clean and staff were helpful. Would stay again. Reviewed on Mar 11, 2026 ![The Retreat Collection at 1 Hotel & Homes South Beach](https://images.trvl-media.com/lodging/13000000/12320000/12316600/12316590/e518a34f_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### The Retreat Collection at 1 Hotel & Homes South Beach South Beach $7,419 per person May 22 - May 25 found 1 day ago Roundtrip non-stop flight included Boston (BOS) to Miami (MIA) 8/10 Very Good! (1 review) ![The Shelborne By Proper, a Member of Design Hotels](https://images.trvl-media.com/lodging/1000000/30000/25500/25451/6d55d96d_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### The Shelborne By Proper, a Member of Design Hotels South Beach Save 100% on your flight $989 per person Jun 11 - Jun 14 found 1 day ago Roundtrip flight included Newark Liberty Intl. Airport (EWR) to Miami (MIA) 9.4/10 Exceptional! (140 reviews) Amazing stay at the Shelborne! The rooms and amenities are beautiful. We’ll be back! Reviewed on Mar 7, 2026 Don't see what you're looking for? See all available trips from Columbus to Summerland Key [View all trips](https://expedia.com/go/package/search/FlightHotel/2026-04-16/2026-04-23/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=MIA&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## 4 Night Adventure vacations in Summerland Key Price found within the past 48 hours. Click for updated prices. ![Casablanca Miami Beach](https://images.trvl-media.com/lodging/32000000/31660000/31652200/31652150/f54c02bb_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Casablanca Miami Beach North Beach Save 100% on your flight $515 per person Apr 17 - Apr 21 found 10 hours ago Roundtrip flight included Philadelphia (PHL) to Miami (MIA) 5.8/10 (320 reviews) Room was clean and great location beside the beach. Room had kitchette and big fridge, microwave etc. so was great. It was dated and internet didn't work in our room but worked well in the lobby. Great value for money :) happy with it. Reviewed on Feb 22, 2026 ![Creekside Inn](https://images.trvl-media.com/lodging/2000000/1580000/1576800/1576773/4743fa46_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Creekside Inn $630 per person May 10 - May 14 found 1 day ago Roundtrip flight included Boston (BOS) to Miami (MIA) 7.8/10 Good! (1,027 reviews) This place was fine, but not worth the money paid. Reviewed on Mar 16, 2026 ![The Retreat Collection at 1 Hotel & Homes South Beach](https://images.trvl-media.com/lodging/13000000/12320000/12316600/12316590/e518a34f_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### The Retreat Collection at 1 Hotel & Homes South Beach South Beach $6,981 per person May 18 - May 22 found 18 hours ago Roundtrip non-stop flight included Boston (BOS) to Miami (MIA) 8/10 Very Good! (1 review) Don't see what you're looking for? See all available trips from Columbus to Summerland Key [View all trips](https://expedia.com/go/package/search/FlightHotel/2026-04-16/2026-04-23/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=MIA&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## Find awesome Summerland Key adventure vacations #### How can I book the best Summerland Key adventure trips? Choose your own adventure in Summerland 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 Summerland Key family adventure vacation? Adventure awaits when you select the family-friendly filter. There’s plenty of excitement for all ages in Summerland 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 Summerland 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 Summerland Key adventure vacation for couples? Book a Summerland 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 Summerland 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 Summerland 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 Summerland 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-Summerland-Key.d6177802.Travel-Guide-Flights)[ Summerland Key Hotels ](https://expedia.com/Summerland-Key-Hotels.d6177802.Travel-Guide-Hotels)[ Vacation Rentals in Summerland Key ](https://expedia.com/Summerland-Key-Vacation-Rentals.d6177802.Travel-Guide-VacationRentals)[ Car Rentals in Summerland Key ](https://expedia.com/Car-Rentals-In-Summerland-Key.d6177802.Car-Rental-Guide)[ Summerland Key Vacations ](https://expedia.com/Summerland-Key.d6177802.Destination-Travel-Guides)[ Things to do in Summerland Key ](https://expedia.com/Things-To-Do-In-Summerland-Key.d6177802.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