Title: Islamorada Vacation Packages & Trips 2026 from CA $744 | Expedia.ca [Islamorada Travel Guide](https://expedia.ca/Islamorada.dx10768)[Hotels in Islamorada](https://expedia.ca/Islamorada-Hotels.d10768.Travel-Guide-Hotels)[Vacation Rentals in Islamorada](https://expedia.ca/Islamorada-Vacation-Rentals.d10768.Travel-Guide-VacationRentals)[Flights to Islamorada](https://expedia.ca/Cheap-Flights-To-Islamorada.d10768.Travel-Guide-Flights)[Things to do in Islamorada](https://expedia.ca/Things-To-Do-In-Islamorada.d10768.Travel-Guide-Activities)[Islamorada Car Rentals](https://expedia.ca/Car-Rentals-In-Islamorada.d10768.Car-Rental-Guide) ![](https://images.trvl-media.com/place/10768/fc4588ee-e7f3-44af-8fce-e7aa6a494cda.jpg?impolicy=fcrop&w=1200&h=300&q=medium) # Islamorada Vacation Packages ## Book a Hotel + Flight or Car together to unlock savings - ## Plan, book, travel with confidence - ### Better together Save up to CA $1,096 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 #### Your Islamorada Vacation The laid-back lifestyle and spectacular views are just the beginning of the things Islamorada has to offer. Enjoy the sights and sounds of this captivating city the way you want with a customized Islamorada vacation package. You'll want to do some exploring during your trip to Islamorada. Make time for popular attractions like [Theater of the Sea](https://www.expedia.ca/Theater-Of-The-Sea-Islamorada.d6069249.Vacation-Attraction), [Bud n Marys Dive Center](https://www.expedia.ca/Bud-N-Marys-Dive-Center-Islamorada.d6069243.Vacation-Attraction) and [Founders Park](https://www.expedia.ca/Founders-Park-Islamorada.d6277602.Vacation-Attraction). Check out Expedia's wide range of travel options and start organizing your dream vacation to Islamorada today. ## Top Islamorada Vacation Deals Price found within the past 48 hours. Click for updated prices. ![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 CA $744 per person Apr 9 - Apr 13 found 1 day ago Roundtrip flight included Detroit (DTW) to Miami (MIA) 8/10 Very Good! (1,004 reviews) Room was clean, spacious with a wonderful canal view. Reviewed on Jan 27, 2026 ![Cavalier Hotel South Beach](https://images.trvl-media.com/lodging/1000000/20000/13600/13579/c0c3faa8_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Cavalier Hotel South Beach South Beach CA $811 per person Mar 15 - Mar 20 found 1 day ago Roundtrip flight included Detroit (DTW) to Miami (MIA) 8.4/10 Very Good! (1,001 reviews) I had a wondeful time at this hotel (1/20-1/24/2026). The staff was polite, friendly and always ready to help. Room was clean and stylish exacly like the photo. The location is perfect: quiet and peaceful. And the same time not far from popular places. I really enjoyed my stay and would definitely recommend this hotel to others. Reviewed on Jan 26, 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 CA $21,274 per person Mar 3 - Mar 10 found 1 day ago Roundtrip flight included Detroit (DTW) 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 CA $824 per person Mar 15 - Mar 20 found 1 day ago Roundtrip flight included Detroit (DTW) to Miami (MIA) 8.4/10 Very Good! (1,935 reviews) My room was spotless, and the view was absolutely gorgeous. Every staff member I encountered was wonderful, but the bartenders and servers truly stood out—they were phenomenal. Beachside food and drink service was a first for me, and it was such an amazing experience. The food at the on-site Baleen restaurant was also excellent, and valet parking made everything incredibly convenient. Reviewed on Jan 28, 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 CA $859 per person Mar 15 - Mar 20 found 1 day ago Roundtrip flight included Detroit (DTW) to Miami (MIA) 8.4/10 Very Good! (1,775 reviews) Staff was great, love the location! Reviewed on Jan 28, 2026 ## Where to stay in Islamorada Find the best Islamorada areas and neighborhoods for the activities you enjoy most. [Learn more about Islamorada](https://expedia.ca/Islamorada.dx10768) ![Cheeca Pier 🎣 🛶 ](https://images.trvl-media.com/place/10768/d63e1d3a-2c8e-4dba-bca7-1c1af5c02531.jpg?impolicy=fcrop&w=350&h=192&q=medium) ### Matecumbe 5 out of top 10 points of interest in this area If you're spending some time in Matecumbe, Bud n' Mary's Dive Center and Florida Keys Brewing Co. are top sights worth seeing. [Find hotel + flight trips in Matecumbe](https://expedia.ca/go/package/search/FlightHotel/?FromAirport=Downtown%20Columbus,%20Columbus,%20Ohio,%20United%20States%20of%20America&Destination=Matecumbe&DestID=855587555438403584&DaysInFuture=30&StayLength=7&rfrr=TG.LP.Dest.PKG.Neighborhoods) ![Colorful Island Palm Tree Sunset](https://images.trvl-media.com/place/553248635976470270/e99cad96-7ebc-485b-9c82-f30673c7991c.jpg?impolicy=fcrop&w=350&h=192&q=medium) ### Venetian Shores Venetian Shores might not have many top sights, but Islamorada County Park and Windley Key Fossil Reef Geological State Park are two attractions nearby that you can check out. [Find hotel + flight trips in Venetian Shores](https://expedia.ca/go/package/search/FlightHotel/?FromAirport=Downtown%20Columbus,%20Columbus,%20Ohio,%20United%20States%20of%20America&Destination=Venetian%20Shores&DestID=553248635976470270&DaysInFuture=30&StayLength=7&rfrr=TG.LP.Dest.PKG.Neighborhoods) ![Anne’s beach is on Lower Matecumbe Key](https://images.trvl-media.com/place/553248635976195207/ab908e06-f8d5-4131-85de-4fe1a3f5bec9.jpg?impolicy=fcrop&w=350&h=192&q=medium) ### Lower Matecumbe Beach Though Lower Matecumbe Beach might not have many top sights, you can venture to the surrounding area to see attractions like Anne's Beach and Sunset Drive Beach. [Find hotel + flight trips in Lower Matecumbe Beach](https://expedia.ca/go/package/search/FlightHotel/?FromAirport=Downtown%20Columbus,%20Columbus,%20Ohio,%20United%20States%20of%20America&Destination=Lower%20Matecumbe%20Beach&DestID=553248635976195207&DaysInFuture=30&StayLength=7&rfrr=TG.LP.Dest.PKG.Neighborhoods) ![Coastline of Islamorada, panoramic view at dusk](https://images.trvl-media.com/place/553248635976480972/cbbf8137-5222-4c34-bb34-851fa872c5bd.jpg?impolicy=fcrop&w=350&h=192&q=medium) ### Seabreeze Trailer Park If you're looking for some top things to see and do in Seabreeze Trailer Park and surrounding area, you can visit Islamorada County Park and Founders Park. [Find hotel + flight trips in Seabreeze Trailer Park](https://expedia.ca/go/package/search/FlightHotel/?FromAirport=Downtown%20Columbus,%20Columbus,%20Ohio,%20United%20States%20of%20America&Destination=Seabreeze%20Trailer%20Park&DestID=553248635976480972&DaysInFuture=30&StayLength=7&rfrr=TG.LP.Dest.PKG.Neighborhoods) ### Things to do in and around Islamorada Islamorada, Florida, is perfect for family beach vacations and outdoor adventures. Enjoy a variety of activities, including boat tours, oceanfront weekends, and thrilling adventure tours. With ample beach access and renowned fishing resorts, there's something for everyone. Don't forget to explore the local shopping mall and vibrant shopping areas for a complete experience. **Shopping** In Islamorada, visit Rain Barrel Village for unique gifts and souvenirs, featuring local art and crafts in a vibrant atmosphere. If you're up for a drive, head to the nearby Founders Park Marketplace, offering a variety of shops and dining options to enhance your shopping experience. **Recreation** Jacob's Aquatic Center is a family-friendly venue located 27.4km from Islamorada, offering a refreshing aquatic experience. Enjoy swimming, water aerobics, and relaxation by the pool, making it an ideal spot for rejuvenation while soaking up the Florida sun. **Adventure** Experience the thrill of scuba diving at Florida Keys Dive Center, located 12.9km from Islamorada, where you can explore vibrant underwater ecosystems. For an adrenaline rush, visit Keys Cable Park, 35.4km away, offering wakeboarding and water sports. Hike the scenic Pa-hay-okee Trail, 38.6km from Islamorada, for stunning views. **Nightlife** Experience the vibrant nightlife in Islamorada at Jimmy Johnson's Big Chill, a lively pub 27.4km away, offering entertainment and romantic vibes. Alternatively, enjoy the Caribbean Club Bar, located 33.8km away, where you can soak in the lively atmosphere and enjoy a drink with a view. \*Distances are measured in a straight line; actual driving distances may vary depending on the route. ### Find the best attractions in Islamorada Islamorada is perfect for family-friendly beach vacations, offering a range of outdoor activities and cultural experiences. Explore local attractions such as marinas, beaches, and state parks, while the Islamorada County Park provides additional fun for all ages. Don’t miss the chance to discover the unique charm of the Florida Keys, ensuring your visit is filled with unforgettable moments and beautiful scenery. - **[Anne's Beach: ](https://www.expedia.ca/Annes-Beach-Matecumbe.d6282204.Vacation-Attraction)** Experience the serene beauty of Anne's Beach, where you can relax on soft sands and enjoy the tranquil beach vibes. Ideal for sunbathing and swimming, this spot offers a perfect escape to unwind and soak up the Florida sun. - **[Windley Key Fossil Reef Geological State Park: ](https://www.expedia.ca/Windley-Key-Fossil-Reef-Geological-State-Park-Islamorada.d6282211.Vacation-Attraction)** Discover the adventure and stunning scenery at Windley Key Fossil Reef Geological State Park. Explore nature trails and learn about the fascinating geological history of the area, all while enjoying the great outdoors. - **[History of Diving Museum: ](https://www.expedia.ca/History-Of-Diving-Museum-Matecumbe.d6069257.Vacation-Attraction)** Immerse yourself in the rich culture of diving at the History of Diving Museum. This unique museum showcases the evolution of diving equipment and provides insights into underwater exploration, making it a must-visit for history buffs. ### Best time to go to Islamorada The best time to visit Islamorada is dependent on what kind of holiday you are seeking. August is its hottest month on average. At this time, visitor numbers are average and weather is mostly sunny with light rain. January is its coolest month on average. At this time, visitor numbers are average and weather is mostly sunny with no rain. | **![calendar](https://forever.travel-assets.com/flex/flexmanager/images/2024/03/04/calendar.png)Calendar Month** | **![temperature](https://forever.travel-assets.com/flex/flexmanager/images/2024/03/04/weather__hot.png)Temperature** | **![rain](https://forever.travel-assets.com/flex/flexmanager/images/2024/03/04/weather__rain.png)Precipitation** | **![mostly](https://forever.travel-assets.com/flex/flexmanager/images/2024/05/21/weather__day_mostly_cloudy.png)Cloudiness** | **![occupation](https://forever.travel-assets.com/flex/flexmanager/images/2024/10/29/peoplebex.png)Occupancy** | **![price](https://forever.travel-assets.com/flex/flexmanager/images/2024/10/29/currency_dollar.png)Pricing** | | ---------------------------------------------------------------------------------------------------------------- | -------------------------------------------------------------------------------------------------------------------- | ---------------------------------------------------------------------------------------------------------------- | ---------------------------------------------------------------------------------------------------------------------------- | -------------------------------------------------------------------------------------------------------------- | ------------------------------------------------------------------------------------------------------------- | | January | 70.0°F (21.1°C) | No Rain | Mostly Sunny | Average | Average | | February | 71.8°F (22.1°C) | No Rain | Mostly Sunny | Average | Slightly High | | March | 72.9°F (22.7°C) | No Rain | Mostly Sunny | Moderately High | Slightly High | | April | 76.6°F (24.8°C) | No Rain | Mostly Sunny | Moderately High | Slightly High | | May | 79.3°F (26.3°C) | Light Rain | Mostly Sunny | Average | Average | | June | 82.4°F (28.0°C) | Light Rain | Mostly Sunny | Average | Average | | July | 83.8°F (28.8°C) | Light Rain | Mostly Sunny | Moderately High | Average | | August | 84.4°F (29.1°C) | Light Rain | Mostly Sunny | Average | Average | | September | 83.3°F (28.5°C) | Light Rain | Mostly Sunny | Average | Slightly Low | | October | 80.2°F (26.8°C) | Light Rain | Mostly Sunny | Moderately Low | Slightly Low | | November | 75.9°F (24.4°C) | Light Rain | Mostly Sunny | Moderately Low | Slightly Low | | December | 72.9°F (22.7°C) | No Rain | Mostly Sunny | Moderately Low | Average | ### Tips to save on your trip to Islamorada - Take advantage of package deals on Expedia and combine flights, hotels, or car rentals for a convenient and cost-effective trip to Islamorada. - Consider traveling during the off-peak season (typically September to November) for more affordable package holidays to Islamorada. - Use the *Price per traveler* filter on Expedia to find a package deal that suits your budget. - Check the *VIP Access properties* filter to discover outstanding hotels with added member perks at select properties. ## Islamorada Beach Vacation Relax along the shoreline and feel the wind through your hair during your Islamorada vacation. If it's your first time, why not collect some unique seashells as a souvenir of your trip to Islamorada? Spend your nights near Anne's Beach, a popular stretch of coast just 14 kilometres from the town centre. We also offer fantastic Islamorada packages closer to Sunset Drive Beach, another great nearby option. ## Things You Should Know About Islamorada - Escape the daily grind at one of our [Islamorada beach hotels](https://www.expedia.ca/d10768-tBeachHotel.Travel-Guide-Filter-Hotels?lang=en&rfrr=ATG.LP.BodyContent). The sound of the waves and seagulls cawing high in the sky are just a few clicks away. - If you're searching for lots of room to spread out and relax, Islamorada private vacation homes are a great choice. After a much-needed family getaway or a few nights escape with your best friends? [Treasure Harbour](https://www.expedia.ca/Islamorada-Hotels-Treasure-Harbor.h91743042.Hotel-Information) and [Bud N' Mary's Fishing Marina](https://www.expedia.ca/Islamorada-Hotels-Bud-N-MaryS-Fishing-Marina.h92541432.Hotel-Information) will fit the bill. - Roughly 7,100 people reside in Islamorada. If you're after a few helpful tips on what to see and do during your stay, have a chat to some of the friendly locals or have a look at our [Islamorada things to do page](null). ## Ready to book your vacation to Islamorada? Choose your dates ## Islamorada Hotel Deals ![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 Fully refundableReserve now, pay when you stay CA $330 CA $448 total Feb 3 - Feb 4 includes taxes & fees 9.2/10 Wonderful! (1,655 reviews) Staff was very nice. Nice to use the complimentary clear bottom kayaks. Breakfast was good, Didi made a great omelette! Reviewed on Jan 24, 2026 [](https://expedia.ca/Hotel-Search?startDate=03%2F02%2F2026&endDate=04%2F02%2F2026&selected=4170&PinnedHotelID=4170&HadPinnedHotel=true®ionId=10768) ![Cheeca Lodge & Spa](https://images.trvl-media.com/lodging/1000000/10000/5800/5780/617c0723_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Cheeca Lodge & Spa 81801 Overseas Highway, Mile Marker 82 Islamorada FL Fully refundableReserve now, pay when you stay CA $382 CA $530 total Jan 31 - Feb 1 includes taxes & fees 9.2/10 Wonderful! (1,301 reviews) This palce is awesome. Clean rooms. 2 large pools with a view. Covered garage spot. Reviewed on Jan 22, 2026 [](https://expedia.ca/Hotel-Search?startDate=31%2F01%2F2026&endDate=01%2F02%2F2026&selected=5780&PinnedHotelID=5780&HadPinnedHotel=true®ionId=10768) ![Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort](https://images.trvl-media.com/lodging/1000000/20000/11900/11864/d10a018b_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort 84001 Overseas Hwy Islamorada FL Fully refundableReserve now, pay when you stay CA $403 CA $544 total Feb 4 - Feb 5 includes taxes & fees 9/10 Wonderful! (134 reviews) Great place Reviewed on Jan 22, 2026 [](https://expedia.ca/Hotel-Search?startDate=04%2F02%2F2026&endDate=05%2F02%2F2026&selected=11864&PinnedHotelID=11864&HadPinnedHotel=true®ionId=10768) [See all 2,227 properties in Islamorada](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=30%2F01%2F2026&endDate=31%2F01%2F2026®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. Additional terms may apply. ![](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.ca/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.ca/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) Family Vacations [](https://expedia.ca/lp/theme-vacations/kid-friendly-vacations?rfrr=editorial.Family_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/04/29/frCA_Sejours_golf-Portugal.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Golf Vacations [](https://expedia.ca/lp/theme-vacations/golf-vacations?rfrr=editorial.Golf_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/07/15/US_Luxury_VR_Miami.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Luxury Vacations [](https://expedia.ca/lp/theme-vacations/luxury-vacations?rfrr=editorial.Luxury_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/08/29/romantic.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Romantic Vacations [](https://expedia.ca/lp/theme-vacations/romantic-vacations?rfrr=editorial.Romantic_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/10/17/31952_v1_atfraraski22_insta_4.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Ski Vacations [](https://expedia.ca/lp/theme-vacations/ski-vacations?rfrr=editorial.Ski_Vacations.click) ### Discover the most popular places to visit in Islamorada ![Anne\'s Beach featuring a bridge](https://images.trvl-media.com/place/6282204/e9aa2f6d-f9c8-4112-a338-63fd8ae82009.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### Anne's Beach 4/5(14 reviews) If a restful vacation is part of your travel plans, Anne's Beach might be the perfect place to seek out during your trip to Islamorada. [](https://expedia.ca/Annes-Beach-Matecumbe.d6282204.Vacation-Attraction) ![Windley Key Fossil Reef Geological State Park](https://images.trvl-media.com/place/6282211/9f8e583b-bc9a-4a16-b731-daa0b5c7f87b.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### Windley Key Fossil Reef Geological State Park Explore the fossilized reef of a former quarry in this island park, as you learn about the history and ecology from the interpretive trails. [](https://expedia.ca/Windley-Key-Fossil-Reef-Geological-State-Park-Islamorada.d6282211.Vacation-Attraction) ![History of Diving Museum showing heritage elements](https://images.trvl-media.com/place/6069257/3860ae1a-3cef-4809-8059-43794e9fe7f9.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### History of Diving Museum 4/5(1 review) Trace one of the world’s most astonishing watersports back through the centuries to see some of the first diving suits as you explore this interactive museum, featuring the world's largest international collection of diving artifacts. [](https://expedia.ca/History-Of-Diving-Museum-Matecumbe.d6069257.Vacation-Attraction) ### What to do in Islamorada ![Explore the Mangrove Creeks with an All Day Kayak Rental ](https://mediaim.expedia.com/localexpert/677736/f5836570-8b49-49af-a667-33b8a8596ab7.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### Explore Mangrove Creeks with an All Day SUP/single kayak Rental CA $68 per adult [](https://expedia.ca/things-to-do/explore-mangrove-creeks-with-an-all-day-supsingle-kayak-rental.a677736.activity-details) ![Ft. Lauderdale to Key West Bus Tour w/ 6 hours of free time in KW](https://mediaim.expedia.com/localexpert/46991024/43dad7c4-b2cc-4a13-8eb8-76d57d8a8a1e.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### Ft. Lauderdale to Key West Day Trip Quality Day Tours CA $312 per adult [](https://expedia.ca/things-to-do/ft-lauderdale-to-key-west-day-trip-quality-day-tours.a46991024.activity-details) ![Key West Small Group from Miami](https://mediaim.expedia.com/localexpert/49822996/08be7871-f20d-4235-a12e-c7ff80329e3a.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### Key West Small Group from Miami CA $558 per adult [](https://expedia.ca/things-to-do/key-west-small-group-from-miami.a49822996.activity-details) [See all activities in Islamorada](https://expedia.ca/things-to-do/search?rid=10768) ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - Vacation Rental - Other - [2 Star Hotels in Plantation Key ](https://www.expedia.ca/2Star-Plantation-Key-Hotels.s20-0-d553248635083898347.Travel-Guide-Filter-Hotels) - [Hotels near Bud n' Mary's Dive Center ](https://www.expedia.ca/Bud-N-Marys-Dive-Center-Hotels.0-l6069243-0.Travel-Guide-Filter-Hotels) - [Hotels near Florida Keys Brewing Co. ](https://www.expedia.ca/Florida-Keys-Brewing-Co-Hotels.0-l553248635997958830-0.Travel-Guide-Filter-Hotels) - 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