Title: Beach Vacations in Upper Matecumbe Key 2026 | Expedia.ca ![](https://images.trvl-media.com/place/10768/414c55a9-82b2-4829-857c-fd7c26e0bd48.jpg?impolicy=fcrop&w=1200&h=300&q=medium) # Upper Matecumbe Key Beach Vacations ## Book a Hotel + Flight or Car together to unlock savings Photo by Cameron Abbott - ## 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 ## Flight and Beach hotel deals in Upper Matecumbe Key Price found within the past 48 hours. Click for updated prices. ![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 $745 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 ![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 $14,612 per person Mar 15 - Mar 20 found 1 day ago Roundtrip flight included Detroit (DTW) to Miami (MIA) 8/10 Very Good! (1 review) ![1 Hotel South Beach](https://images.trvl-media.com/lodging/2000000/1800000/1790100/1790087/w4800h3297x0y3-ab24f575_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### 1 Hotel South Beach South Beach CA $3,478 per person Apr 5 - Apr 10 found 1 day ago Roundtrip flight included Detroit (DTW) to Miami (MIA) 9.4/10 Exceptional! (1,365 reviews) Amazing hotel. Beyond our expectations. Rooms are huge. Modern and stylish Lobby is fabulous as is the bars and restaurants You must stay here !!! Total wow Reviewed on Jan 21, 2026 ![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 CA $2,667 per person Apr 18 - Apr 25 found 1 day ago Roundtrip flight included Toronto (YTO) to Miami (MIA) 8.4/10 Very Good! (145 reviews) Villa had a great few; toilets don’t flush well; handle on showered were backwards. Never came to clean at all during 5 day stay; had to text number to get anything needed; resort was understaffed; did two fishing charters and caught fish, nothing to bring home; rented paddle boards off site bc ones on site can only used in small area. Pools and hot tubs close at sunset which was a bummer we always live night swimming; golf cart was fun to rent a drive around looking at houses; no where to eat on island besides resort. Have to drive at least 20mins in either directions to get anything so if you like a variety of restaurants or happy hours this is not the place. Front desk is very understaffed; the line was always so long. Lots of people complaining about charges that weren’t theirs. We had it also happen to use. We avoided charging anything to the room bc if it. Reviewed on Jan 4, 2026 Don't see what you're looking for? See all available trips from Columbus to Upper Matecumbe Key [View all trips](https://expedia.ca/go/package/search/FlightHotel/2026-02-28/2026-03-07/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=MIA&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## 5\* Beach holidays in Upper Matecumbe Key Price found within the past 48 hours. Click for updated prices. ![Isla Bella Beach Resort & Spa](https://images.trvl-media.com/lodging/25000000/24110000/24101800/24101706/f4f56036_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Isla Bella Beach Resort & Spa CA $3,457 per person Mar 15 - Mar 20 found 12 hours ago Roundtrip flight included Detroit (DTW) to Miami (MIA) 9.2/10 Wonderful! (1,055 reviews) Property was beautiful, room was clean but a little underwhelming compared to the resort we stayed at for a few days before during our trip to Key West. Our only and biggest complaint was that we opted to eat off property during our stay, after spending $48.00 for 2 coffees, muffins a bagel for breakfast our first day. Food was very over priced. Reviewed on Jan 24, 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 $14,612 per person Mar 15 - Mar 20 found 1 day ago Roundtrip flight included Detroit (DTW) to Miami (MIA) 8/10 Very Good! (1 review) ![1 Hotel South Beach](https://images.trvl-media.com/lodging/2000000/1800000/1790100/1790087/w4800h3297x0y3-ab24f575_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### 1 Hotel South Beach South Beach CA $3,478 per person Apr 5 - Apr 10 found 1 day ago Roundtrip flight included Detroit (DTW) to Miami (MIA) 9.4/10 Exceptional! (1,365 reviews) Amazing hotel. Beyond our expectations. Rooms are huge. Modern and stylish Lobby is fabulous as is the bars and restaurants You must stay here !!! Total wow Reviewed on Jan 21, 2026 Don't see what you're looking for? See all available trips from Columbus to Upper Matecumbe Key [View all trips](https://expedia.ca/go/package/search/FlightHotel/2026-02-28/2026-03-07/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=MIA&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## 3 Night Beach holidays in Upper Matecumbe Key Price found within the past 48 hours. Click for updated prices. ![Le Particulier Miami](https://images.trvl-media.com/lodging/115000000/114430000/114425900/114425886/4923d8b3_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Le Particulier Miami Mid Beach CA $425 per person Mar 15 - Mar 18 found 1 day ago Roundtrip flight included Detroit (DTW) to Miami (MIA) 10/10 Exceptional! (1 review) The room was clean and had a great view. Staff friendly and efficient...but the most important thing was the bed: soft and cozy and had a great sleep there. Reviewed on Jan 28, 2026 ![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 $550 per person Mar 15 - Mar 18 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 ![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 $9,191 per person Mar 15 - Mar 18 found 1 day ago Roundtrip flight included Detroit (DTW) to Miami (MIA) 8/10 Very Good! (1 review) Don't see what you're looking for? See all available trips from Columbus to Upper Matecumbe Key [View all trips](https://expedia.ca/go/package/search/FlightHotel/2026-02-28/2026-03-07/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=MIA&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## 4 Night Beach holidays in Upper Matecumbe Key Price found within the past 48 hours. Click for updated prices. ![Hyatt Place Miami Airport-East](https://images.trvl-media.com/lodging/10000000/9520000/9517300/9517242/e322cfbb_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Hyatt Place Miami Airport-East Palmer Lake CA $485 per person Mar 16 - Mar 20 found 1 day ago Roundtrip flight included Detroit (DTW) to Miami (MIA) 8.2/10 Very Good! (2,247 reviews) The staff was caring, helpful, and assisted with all of our needs Reviewed on Jan 26, 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 CA $854 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 ![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 $789 per person Apr 9 - Apr 13 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 Don't see what you're looking for? See all available trips from Columbus to Upper Matecumbe Key [View all trips](https://expedia.ca/go/package/search/FlightHotel/2026-02-28/2026-03-07/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=MIA&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## Find the best beach vacations in Upper Matecumbe Key #### What are some benefits when booking beach vacations in Upper Matecumbe Key? When you travel to the beach in Upper Matecumbe Key, soft sands and inviting waters, warm sun and gentle breezes will help you relax. This applies to the whole family, as kids and adults can find something fun to do, so family beach vacations are the quintessential family trip. #### How can I book the best beach vacations in Upper Matecumbe Key? To find the best beach vacation, you'll need to book the right accommodations for your family. What the best is depends on what you want from your Upper Matecumbe Key trip. Fortunately, you can use various filters combined with the beach filter to sort for what you want. Additionally, you'll need to consider the time of year you visit. #### Can I book cheap beach vacations in Upper Matecumbe Key? There are quite a few things you can do to get cheap beach vacations in Upper Matecumbe Key. Prices range from CA $425, and if you want to keep yours on the lower side, you may want to consider just how close to the beach you are. If you don't mind a bit of a walk, further away is typically cheaper. Additionally booking something with a kitchen can help you save by avoiding dining out. #### Can I book beach packages? Yes, and you'll find quite a few beach packages available in Upper Matecumbe Key. These package deals let you save by booking your accommodation and your flight together with savings of up to 51\. #### Why should I book family beach vacations? When you're travelling with the family to Upper Matecumbe Key, booking your vacation by the beach is one of the best ways to keep everyone happy. There's a reason why some of the most memorable family trips for kids are family beach vacations. You'll be just steps away from the water, and you can often enjoy stunning views of the shore from your room. #### How can I find a beachfront vacation in Upper Matecumbe Key? It's easy to find a beachfront vacation accommodation in Upper Matecumbe Key using the search filter. You can filter for waterfront properties specifically that will only show you results that have beautiful views of the shoreline. #### How can I book last-minute beach vacations? Travelling at the last minute doesn't mean you're out of luck to have a dream beach vacation. Last-minute beach vacations may even offer a nice discount as the owners of hotels or other accommodations try to fill their remaining vacancies. All you have to do is input your travel dates and Upper Matecumbe Key as your destination and see what's available. #### Can I find all-inclusive beach vacations ? Yes, all you have to do to find all-inclusive beach vacations in Upper Matecumbe Key is to use the search filter. It will automatically restrict your results to all-inclusive deals that allow you to plan the entire trip in advance. #### Can I book a beach trip that's fully refundable? Any fully refundable booking can bring peace of mind, and we're happy to offer this feature in several packages and locations throughout Islamorada. All you have to do to find them is check the policies section on each accommodation page. Of course, you can filter for fully-refundable results specifically, too. #### Why should I book beach vacations with Expedia? When you book with Expedia, you'll find a one-stop shop for all your planning needs. You can book your flight and accommodation at the same place and potentially get a discount for booking these together. You can also take advantage of the Expedia Rewards program. Becoming a member is free, and when you do, you'll earn points with every booking will add discounts on subsequent trips. ## Beach Hotels in Upper Matecumbe Key ![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 - 10 min drive from Bud n' Mary's Dive Center 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! (1,655 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/Islamorada-Hotels-Chesapeake-Beach-Resort.h4170.Hotel-Information) ![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 - 5 min drive from Bud n' Mary's Dive Center Book a stay at this luxury resort in Islamorada. Enjoy free parking, 3 outdoor pools, and a full-service spa. Our guests praise the pool and the helpful staff ... 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/Islamorada-Hotels-Cheeca-Lodge-Spa.h5780.Hotel-Information) ![Islander Resort](https://images.trvl-media.com/lodging/1000000/480000/475500/475438/5adae4af_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Islander Resort 82100 Overseas Highway Islamorada FL - 6 min drive from Bud n' Mary's Dive Center Book a stay at this beach hotel in Islamorada. Enjoy free WiFi, free parking, and 2 outdoor pools. Our guests praise the pool and the helpful staff in our reviews. ... 9.2/10 Wonderful! (1,012 reviews) This place is great. A must stay. Everyone is so friendly. Place is spotless clean Reviewed on Jan 22, 2026 [](https://expedia.ca/Islamorada-Hotels-Islander-Resort.h475438.Hotel-Information) [See all 2,819 properties in Upper Matecumbe Key](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Package®ionId=553248635975749648) 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. ## 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.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) ### Top Beach Vacation Destinations > - [Myrtle beach vacations ](https://www.expedia.ca/lp/theme-vacations/beach-vacations/601685/Myrtle-Beach) > - [Miami beach vacations ](https://www.expedia.ca/lp/theme-vacations/beach-vacations/8833/Miami-Beach) > - [Florida beach vacations ](https://www.expedia.ca/lp/theme-vacations/beach-vacations/211/Florida) > - [Barbados beach vacations ](https://www.expedia.ca/lp/theme-vacations/beach-vacations/16/Barbados) > - [South beach vacations ](https://www.expedia.ca/lp/theme-vacations/beach-vacations/6138745/South-Beach) > - [Palm beach vacations ](https://www.expedia.ca/lp/theme-vacations/beach-vacations/9061/Palm-Beach) > - [Daytona beach vacations ](https://www.expedia.ca/lp/theme-vacations/beach-vacations/6023995/Daytona-Beach) > - [Newport beach vacations ](https://www.expedia.ca/lp/theme-vacations/beach-vacations/8111/Newport-Beach) > - [Vero beach vacations ](https://www.expedia.ca/lp/theme-vacations/beach-vacations/6023660/Vero-Beach) > - [India beach vacations ](https://www.expedia.ca/lp/theme-vacations/beach-vacations/80/India) > - [Laguna beach vacations ](https://www.expedia.ca/lp/theme-vacations/beach-vacations/6298668/Laguna-Beach) > - [Ontario beach vacations ](https://www.expedia.ca/lp/theme-vacations/beach-vacations/2680/Ontario) > - [Canada beach vacations ](https://www.expedia.ca/lp/theme-vacations/beach-vacations/31/Canada) > - [Barcelona beach vacations ](https://www.expedia.ca/lp/theme-vacations/beach-vacations/179992/Barcelona) > - [Fort Myers beach vacations ](https://www.expedia.ca/lp/theme-vacations/beach-vacations/7194/Fort-Myers-Beach) > - [Portugal beach vacations ](https://www.expedia.ca/lp/theme-vacations/beach-vacations/147/Portugal) > - [Italy beach vacations ](https://www.expedia.ca/lp/theme-vacations/beach-vacations/86/Italy) > - [Thailand beach vacations ](https://www.expedia.ca/lp/theme-vacations/beach-vacations/178/Thailand) > - [France beach vacations ](https://www.expedia.ca/lp/theme-vacations/beach-vacations/59/France) ## More Vacations Ideas [Flights to Upper Matecumbe Key ](https://expedia.ca/Cheap-Flights-To-Upper-Matecumbe-Key.d553248635975749648.Travel-Guide-Flights)[ Upper Matecumbe Key Hotels ](https://expedia.ca/Upper-Matecumbe-Key-Hotels.d553248635975749648.Travel-Guide-Hotels)[ Upper Matecumbe Key Vacation Rentals ](https://expedia.ca/Upper-Matecumbe-Key-Vacation-Rentals.d553248635975749648.Travel-Guide-VacationRentals)[ Upper Matecumbe Key Car Rentals ](https://expedia.ca/Car-Rentals-In-Upper-Matecumbe-Key.d553248635975749648.Car-Rental-Guide)[ Upper Matecumbe Key Vacations ](https://expedia.ca/Upper-Matecumbe-Key.d553248635975749648.Destination-Travel-Guides) \* 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 on select hotels and earn double points 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