Title: Summerland Key Cheap 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 Cheap Vacations ## Book a Cheap 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 Cheap 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 $456 per person Apr 26 - Apr 29 found 1 day ago Roundtrip flight included Boston (BOS) to Miami (MIA) 8.2/10 Very Good! (81 reviews) Everything was beautiful. I have been here before and it is so much better than the first time I came here. The only issue we had was the walls seem so thin. We heard our neighbors all night and it was frustrating trying to sleep. It was as if they were in our room with us. That’s how clear we could hear them. Other than that what an amazing place to stay for a getaway. I will def stay there again. The hospitality and cleanliness was amazing. 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 Save 100% on your flight $8,037 per person Apr 17 - Apr 20 found 1 day ago Roundtrip 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 $1,355 per person Apr 24 - Apr 28 found 1 day ago Roundtrip flight included Boston (BOS) 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 ![Hotel Riu Plaza Miami Beach](https://images.trvl-media.com/lodging/1000000/80000/74600/74574/3532c352_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Hotel Riu Plaza Miami Beach Mid Beach Save 100% on your flight $1,302 per person May 23 - May 30 found 18 hours ago Roundtrip flight included Boston (BOS) to Miami (MIA) 8/10 Very Good! (1,165 reviews) Perfectly located, friendly staff Reviewed on Mar 15, 2026 ![Nomada Residences - Downtown](https://images.trvl-media.com/lodging/113000000/112940000/112935000/112934920/48b5c91a_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Nomada Residences - Downtown Downtown Miami Save 100% on your flight $1,580 per person May 27 - Jun 1 found 1 day ago Roundtrip flight included New York (JFK) to Miami (MIA) No reviews 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\* Cheap vacations in Summerland Key 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 $1,550 per person Apr 29 - May 6 found 1 day ago Roundtrip flight included Boston (BOS) to Miami (MIA) 9.2/10 Wonderful! (1,308 reviews) We did not use the spa services, we may have been able to barely see a small portion of the ocean out a window Reviewed on Mar 12, 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 Save 100% on your flight $8,037 per person Apr 17 - Apr 20 found 1 day ago Roundtrip flight included Boston (BOS) to Miami (MIA) 8/10 Very Good! (1 review) ![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 Save 100% on your flight $2,507 per person Apr 19 - Apr 24 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 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 Cheap 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 $987 per person May 28 - May 31 found 12 hours ago Roundtrip flight included Newark Liberty Intl. Airport (EWR) 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 Save 100% on your flight $8,037 per person Apr 17 - Apr 20 found 1 day ago Roundtrip flight included Boston (BOS) to Miami (MIA) 8/10 Very Good! (1 review) ![Kimpton Surfcomber Hotel by IHG](https://images.trvl-media.com/lodging/1000000/20000/16000/15996/93c84cb9_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Kimpton Surfcomber Hotel by IHG South Beach Save 100% on your flight $1,004 per person May 29 - Jun 1 found 5 hours ago Roundtrip flight included Boston (BOS) to Miami (MIA) 8.2/10 Very Good! (1,007 reviews) Smallish rooms but very clean and fabulous outdoor amenities including pool and restaurant bar. Reviewed on Mar 10, 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 Cheap 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 23 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 $635 per person Jun 1 - Jun 5 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 $7,038 per person May 4 - May 8 found 1 day ago Roundtrip 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 amazing cheap vacations in Summerland Key #### How can I find budget-friendly Summerland Key vacation packages on Expedia? Playing around with the easy-to-use search wizard is one of the best ways to find affordable Summerland Key vacation packages on Expedia. Tap your dates in and it'll offer some of the cheapest Summerland Key getaways within seconds. You can also use the maximum price filter to view deals within your budget. If you're traveling during peak season dates, it's a good idea to book early to snag some of the best offers. You may score irresistible [last-minute specials](https://www.expedia.com/lp/b/vacations/last-minute-deals) for travel in low season. #### How to find cheap last-minute Summerland Key travel deals? On Expedia's [last-minute](https://www.expedia.com/lp/b/vacations/last-minute-deals) travel deals page, you'll encounter a plethora of special offers for late vacations to Summerland Key. Remember, you're more likely to bag savings on last-minute travel during off-peak periods. Consider checking different departure dates, too. Expedia's nifty search tool lets you compare some of the best last-minute Summerland Key vacation packages. The handy filters let you tailor your trip according to your preferences, including hotel star rating, amenities, and property location. #### When is the best time to visit Summerland Key on a budget? For some of the cheapest vacation packages to Summerland Key from $456, it's best to travel during low season dates. With fewer people traveling during these periods, flights and hotels usually have lower prices. It's also a good idea to avoid popular travel times. These include spring break, Thanksgiving, and other federal holidays. On Expedia, you'll encounter some of the best travel deals to Summerland Key. Best of all, vacation [payment plans](https://www.expedia.com/lp/b/vacations/planning) mean you can spread the cost of your trip over 3, 6, or 12 months. #### Can I cancel my Summerland Key vacation package booking? Yes, many of Expedia's cheap Summerland Key getaway packages allow for free cancellation in case your plans change. Follow the easy steps to cancel by logging into your Expedia account and clicking on “Trips” page'. Keep in mind, though, that each vacation package has different cancellation policies, so be sure to look over them before booking. The good news is you'll clearly see this information on Expedia when you book. There's even a free cancellation search filter that lets you view flexible vacations to Summerland Key. #### Why should I book my Summerland Key vacation with Expedia? A multitude of exclusive travel deals you won't find anywhere else is one of the top reasons to book your cheap Summerland Key vacation package with Expedia. And with one of the widest choices of flights and hotels available, you'll easily find the right trip for you. The handy search wizard and filters let you compare hundreds of great deals in seconds, too. It's not only the cheap prices either: Expedia's booking protection and 24/7 support give you peace of mind before and during your 2026 trip. #### How to find cheap Summerland Key vacation packages on Expedia? When searching for budget vacations to Summerland Key, look out for the green savings label. This indicates you've snagged a deal only available on Expedia. Another popular way of getting money off your 2026Summerland Key vacation is by joining [One Key](https://www.expedia.com/welcome-one-key). Expedia's amazing reward program gives you access to hundreds of member-only discounts on select hotels. Keep a look out for the blue savings label in the search results. Best of all, One Key is free to join. #### Why should I book a package to Summerland Key? You'll often snag package savings on your Summerland Key vacation when bundling together your flights and accommodation. Expedia even shows you how much you're saving by booking a package. It's not just cheaper prices, either. Packages often have more flexible booking conditions, meaning you're more likely to get a refund in case your 2026 plans change. While booking flights and hotels separately usually requires full payment, Summerland Key vacation packages often let you pay a small upfront deposit to confirm. #### How to plan a cheap vacation to Summerland Key? Settling on your dates is usually the first step to planning an affordable Summerland Key getaway. If you're traveling during peak season dates, it's a good idea to book your trip in advance. This way, you're more likely to bag early-bird deals. Don't rule out a [last-minute travel deal](https://www.expedia.com/lp/b/vacations/last-minute-deals) for low season dates, though. Once you've picked your dates, tap them into the search wizard to see some of the best Summerland Key vacation package deals. Hop over to Expedia's [vacation planning page](https://www.expedia.com/lp/b/vacations/planning) for more tips for your dream vacation. ## 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/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