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 Shelborne By Proper, a Member of Design Hotels](https://images.trvl-media.com/lodging/1000000/30000/25500/25451/e49031f1_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 $711 per person Apr 26 - Apr 29 found 1 day ago Roundtrip flight included Boston (BOS) to Miami (MIA) 9.4/10 Exceptional! (56 reviews) Clean room, excellent staff at the front desk, dining room, pool staff, and beach staff. Sergiy was especially helpful telling us all about the hotel. Reviewed on Feb 13, 2026 ![The Retreat Collection at 1 Hotel & Homes South Beach](https://images.trvl-media.com/lodging/13000000/12320000/12316600/12316590/dffb9d2c_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### The Retreat Collection at 1 Hotel & Homes South Beach South Beach $9,646 per person Apr 8 - Apr 12 found 1 day ago Roundtrip flight included Boston (BOS) to Miami (MIA) 8/10 Very Good! (1 review) ![Cheeca Lodge & Spa](https://images.trvl-media.com/lodging/1000000/10000/5800/5780/617c0723_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Cheeca Lodge & Spa Matecumbe Save 100% on your flight $1,113 per person May 7 - May 12 found 1 day ago Roundtrip flight included Boston (BOS) to Miami (MIA) 9.2/10 Wonderful! (1,262 reviews) Room was very nice and plenty of room. First time visitor. Tub on the balcony was unexpected bonus Reviewed on Feb 17, 2026 ![Hotel Riu Plaza Miami Beach](https://images.trvl-media.com/lodging/1000000/80000/74600/74574/7ff98ba1_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Hotel Riu Plaza Miami Beach Mid Beach Save 100% on your flight $932 per person Apr 8 - Apr 12 found 1 day ago Roundtrip flight included Boston (BOS) to Miami (MIA) 8/10 Very Good! (1,120 reviews) Staff are great but the bed and pillows were uncomfortable. Especially the pillows they are horrible. I had to use a towel as my pillow. Other hotels have feather pillows that are far more comfortable. It would be nice to have a choice. For this reason we won’t return. It’s too bad because everything else was nice. Reviewed on Feb 19, 2026 ![Park Central South Beach](https://images.trvl-media.com/lodging/1000000/10000/1200/1168/280efeed_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Park Central South Beach South Beach Save 100% on your flight $784 per person Apr 25 - Apr 30 found 1 day ago Roundtrip flight included Boston (BOS) to Miami (MIA) 8.6/10 Excellent! (385 reviews) Excellent stay. Great pools, great location, great lobby. Probably best value on the road across from the beach. Only hang up is the single elevator if that is an issue for you. We took the stairs other than check in and check out Reviewed on Feb 21, 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/2026-03-21/2026-03-28/?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/1000000/10000/5800/5780/617c0723_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Cheeca Lodge & Spa Matecumbe Save 100% on your flight $1,113 per person May 7 - May 12 found 1 day ago Roundtrip flight included Boston (BOS) to Miami (MIA) 9.2/10 Wonderful! (1,262 reviews) Room was very nice and plenty of room. First time visitor. Tub on the balcony was unexpected bonus Reviewed on Feb 17, 2026 ![The Retreat Collection at 1 Hotel & Homes South Beach](https://images.trvl-media.com/lodging/13000000/12320000/12316600/12316590/dffb9d2c_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### The Retreat Collection at 1 Hotel & Homes South Beach South Beach $9,646 per person Apr 8 - Apr 12 found 1 day ago Roundtrip flight included Boston (BOS) to Miami (MIA) 8/10 Very Good! (1 review) ![Waterfront House with Boat Dock](https://images.trvl-media.com/lodging/110000000/109730000/109724500/109724487/5d9195bd_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Waterfront House with Boat Dock Hammer Point Save 100% on your flight $1,363 per person May 1 - May 8 found 1 day ago Roundtrip flight included New York (NYC) to Miami (MIA) 6/10 (1 review) Everything was fine except half way through the stay the water department came and shut off the water at the street. It came back on a few hours later, so it all worked out. The house was fine Reviewed on Jan 9, 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/2026-03-21/2026-03-28/?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. ![The Shelborne By Proper, a Member of Design Hotels](https://images.trvl-media.com/lodging/1000000/30000/25500/25451/e49031f1_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 $711 per person Apr 26 - Apr 29 found 1 day ago Roundtrip flight included Boston (BOS) to Miami (MIA) 9.4/10 Exceptional! (56 reviews) Clean room, excellent staff at the front desk, dining room, pool staff, and beach staff. Sergiy was especially helpful telling us all about the hotel. Reviewed on Feb 13, 2026 ![The Retreat Collection at 1 Hotel & Homes South Beach](https://images.trvl-media.com/lodging/13000000/12320000/12316600/12316590/dffb9d2c_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### The Retreat Collection at 1 Hotel & Homes South Beach South Beach $7,858 per person Apr 1 - Apr 4 found 1 day ago Roundtrip flight included Boston (BOS) to Miami (MIA) 8/10 Very Good! (1 review) ![Solé Miami, A Noble House Resort](https://images.trvl-media.com/lodging/3000000/2810000/2803900/2803820/387d2cd6_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Solé Miami, A Noble House Resort Ocean Four Save 100% on your flight $752 per person Apr 1 - Apr 4 found 1 day ago Roundtrip flight included Boston (BOS) to Miami (MIA) 8.4/10 Very Good! (1,935 reviews) Cleanliness, Friendly front desk staff ( Shelly) Beach boys are excellent & attentive to your likes. Only dislike was the pool was a bit small & the elevator takes forever! I would definitely recommend & The Sole will see me again. Reviewed on Feb 20, 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/2026-03-21/2026-03-28/?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. ![The Penguin Hotel](https://images.trvl-media.com/lodging/1000000/70000/62900/62824/d4ab7ebb_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### The Penguin Hotel South Beach Save 100% on your flight $426 per person May 7 - May 11 found 1 day ago Roundtrip flight included Boston (BOS) to Miami (MIA) 8.2/10 Very Good! (1,491 reviews) The staff was amazing and the hotel was cute and clean. Terrific stay! Reviewed on Feb 20, 2026 ![Creekside Inn](https://images.trvl-media.com/lodging/2000000/1580000/1576800/1576773/5e43c05b_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Creekside Inn $594 per person Apr 27 - May 1 found 1 day ago Roundtrip flight included Boston (BOS) to Miami (MIA) 8/10 Very Good! (1,004 reviews) This was our second time staying here and it’s wonderful. Everyone was super nice. We will definitely be back. Reviewed on Feb 20, 2026 ![President Hotel](https://images.trvl-media.com/lodging/1000000/580000/575900/575859/5a013cab_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### President Hotel South Beach Save 100% on your flight $457 per person May 7 - May 11 found 1 day ago Roundtrip flight included Boston (BOS) to Miami (MIA) 8.4/10 Very Good! (1,775 reviews) We had a lovely time. Reviewed on Feb 21, 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/2026-03-21/2026-03-28/?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 $426, 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