Title: Islamorada Cheap Vacations 2026 | Expedia.com ![](https://images.trvl-media.com/place/10768/fc4588ee-e7f3-44af-8fce-e7aa6a494cda.jpg?impolicy=fcrop&w=1200&h=300&q=medium) # Islamorada Cheap Vacations ## Book a Cheap Hotel + Flight or Car together to unlock savings ## Top Cheap vacation packages in Islamorada Price found within the past 48 hours. Click for updated prices. ![Amara Cay Resort](https://images.trvl-media.com/lodging/1000000/70000/62000/61976/4186365f_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Amara Cay Resort Matecumbe $487 per person Apr 20 - Apr 22 found 13 hours ago Roundtrip flight included Boston (BOS) to Miami (MIA) 8.8/10 Excellent! (1,268 reviews) This was a wonderful place to stay in Islamorada! The staff was super helpful and friendly. They allow dogs so we were able to bring our Maltipo. Pool, restaurant, roosters, all were perfect. You also get to go to their other properties which were amazing. Rooms were clean and very comfortable. Location is perfect! We are already planning our next trip. Reviewed on Mar 20, 2026 ![La Siesta Resort & Villas](https://images.trvl-media.com/lodging/3000000/2480000/2477600/2477508/18023e21_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### La Siesta Resort & Villas Matecumbe Save 100% on your flight $1,008 per person Apr 20 - Apr 24 found 13 hours ago Roundtrip flight included Boston (BOS) to Miami (MIA) 8.8/10 Excellent! (1,004 reviews) We Love this place! Reviewed on Mar 17, 2026 ![Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort](https://images.trvl-media.com/lodging/1000000/20000/11900/11864/4671ebc2_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort Save 100% on your flight $946 per person Apr 20 - Apr 24 found 9 hours ago Roundtrip non-stop flight included Pittsburgh (PIT) to Miami (MIA) 9/10 Wonderful! (165 reviews) The room was great. Very clean and up to date. We had a great view of the marina and the ocean. Might need to mention that this particular building only has stairs. There was an issue with a faulty structure that could had been handled much better but overall good. Reviewed on Mar 19, 2026 ![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 $1,476 per person May 21 - May 24 found 14 hours ago Roundtrip flight included Cleveland (CLE) 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 ![Islander Resort](https://images.trvl-media.com/lodging/1000000/480000/475500/475438/f8d2863e_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Islander Resort Matecumbe $548 per person Apr 20 - Apr 22 found 13 hours ago Roundtrip flight included Boston (BOS) to Miami (MIA) 9.2/10 Wonderful! (1,014 reviews) This resort had everything! So much to do and staff that was friendly and always helpful. Only complaint is that the restaurants had no options for gluten free diet, so we had to go elsewhere. Reviewed on Mar 19, 2026 Don't see what you're looking for? See all available trips from Columbus to Islamorada [View all trips](https://expedia.com/go/package/search/FlightHotel/2026-04-21/2026-04-28/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=MIA&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## 5\* Cheap vacations in Islamorada 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 $1,476 per person May 21 - May 24 found 14 hours ago Roundtrip flight included Cleveland (CLE) 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 Don't see what you're looking for? See all available trips from Columbus to Islamorada [View all trips](https://expedia.com/go/package/search/FlightHotel/2026-04-21/2026-04-28/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=MIA&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## 3 Night Cheap vacations in Islamorada Price found within the past 48 hours. Click for updated prices. ![La Siesta Resort & Villas](https://images.trvl-media.com/lodging/3000000/2480000/2477600/2477508/18023e21_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### La Siesta Resort & Villas Matecumbe Save 100% on your flight $578 per person Apr 21 - Apr 24 found 16 hours ago Roundtrip flight included Atlanta (ATL) to Miami (MIA) 8.8/10 Excellent! (1,004 reviews) We Love this place! Reviewed on Mar 17, 2026 ![Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort](https://images.trvl-media.com/lodging/1000000/20000/11900/11864/4671ebc2_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort Save 100% on your flight $636 per person Apr 21 - Apr 24 found 16 hours ago Roundtrip flight included Atlanta (ATL) to Miami (MIA) 9/10 Wonderful! (165 reviews) The room was great. Very clean and up to date. We had a great view of the marina and the ocean. Might need to mention that this particular building only has stairs. There was an issue with a faulty structure that could had been handled much better but overall good. Reviewed on Mar 19, 2026 ![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 $1,476 per person May 21 - May 24 found 14 hours ago Roundtrip flight included Cleveland (CLE) 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 Don't see what you're looking for? See all available trips from Columbus to Islamorada [View all trips](https://expedia.com/go/package/search/FlightHotel/2026-04-21/2026-04-28/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=MIA&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## 4 Night Cheap vacations in Islamorada Price found within the past 48 hours. Click for updated prices. ![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 $472 per person Apr 20 - Apr 24 found 1 day ago Roundtrip flight included Atlanta (ATL) to Miami (MIA) 7.8/10 Good! (1,027 reviews) Kind of run down. Need updates bad Reviewed on Mar 20, 2026 ![La Siesta Resort & Villas](https://images.trvl-media.com/lodging/3000000/2480000/2477600/2477508/18023e21_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### La Siesta Resort & Villas Matecumbe Save 100% on your flight $1,008 per person Apr 20 - Apr 24 found 13 hours ago Roundtrip flight included Boston (BOS) to Miami (MIA) 8.8/10 Excellent! (1,004 reviews) We Love this place! Reviewed on Mar 17, 2026 ![Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort](https://images.trvl-media.com/lodging/1000000/20000/11900/11864/4671ebc2_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort Save 100% on your flight $946 per person Apr 20 - Apr 24 found 9 hours ago Roundtrip non-stop flight included Pittsburgh (PIT) to Miami (MIA) 9/10 Wonderful! (165 reviews) The room was great. Very clean and up to date. We had a great view of the marina and the ocean. Might need to mention that this particular building only has stairs. There was an issue with a faulty structure that could had been handled much better but overall good. Reviewed on Mar 19, 2026 Don't see what you're looking for? See all available trips from Columbus to Islamorada [View all trips](https://expedia.com/go/package/search/FlightHotel/2026-04-21/2026-04-28/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=MIA&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## Find amazing cheap vacations in Islamorada #### How can I find budget-friendly Islamorada vacation packages on Expedia? Playing around with the easy-to-use search wizard is one of the best ways to find affordable Islamorada vacation packages on Expedia. Tap your dates in and it'll offer some of the cheapest Islamorada 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 Islamorada 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 Islamorada. 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 Islamorada 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 Islamorada on a budget? For some of the cheapest vacation packages to Islamorada from $472, 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 Islamorada. 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 Islamorada vacation package booking? Yes, many of Expedia's cheap Islamorada 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 Islamorada. #### Why should I book my Islamorada 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 Islamorada 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 Islamorada vacation packages on Expedia? When searching for budget vacations to Islamorada, 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 2026Islamorada 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 Islamorada? You'll often snag package savings on your Islamorada 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, Islamorada vacation packages often let you pay a small upfront deposit to confirm. #### How to plan a cheap vacation to Islamorada? Settling on your dates is usually the first step to planning an affordable Islamorada 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 Islamorada 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. ## Top Cheap Islamorada Hotels ![Chesapeake Beach Resort](https://images.trvl-media.com/lodging/1000000/10000/4200/4170/689f4306_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Chesapeake Beach Resort 83409 Overseas Hwy Islamorada FL - 22 min walk from Theater of the Sea Book a stay at this beach hotel in Islamorada. Enjoy free breakfast, free WiFi, and 2 outdoor pools. Our guests praise the breakfast and the pool in our reviews. ... 9.2/10 Wonderful! (1,670 reviews) So I did like our stay. However, we didn’t sleep great because the air conditioner is right at the foot of the master bedroom and it blows wind in your face constantly. We reached out to the property manager and he didn’t help us because it was broken and wouldn’t work the way intended. So overall ... Reviewed on Mar 20, 2026 [](https://expedia.com/Islamorada-Hotels-Chesapeake-Beach-Resort.h4170.Hotel-Information) [See all 2,205 properties in Islamorada](https://expedia.com/Hotel-Search?rfrrid=TG.LP.Hotels.Package®ionId=10768) Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. 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Savings not available on all packages.