Title: Romantic 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 Romantic 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 Romantic hotel deals in Upper Matecumbe 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/1000000/30000/25500/25451/6d55d96d_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### The Shelborne By Proper, a Member of Design Hotels South Beach CA $1,603 per person May 21 - May 25 found 1 day ago Roundtrip flight included Montreal (YMQ) 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 CA $2,128 per person May 3 - May 10 found 5 hours ago Roundtrip non-stop flight included Montreal (YMQ) to Miami (MIA) 8/10 Very Good! (1,165 reviews) Perfectly located, friendly staff Reviewed on Mar 15, 2026 ![Carillon Miami Wellness Resort](https://images.trvl-media.com/lodging/12000000/11350000/11344400/11344361/75c6ca53_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Carillon Miami Wellness Resort North Beach CA $1,982 per person Apr 17 - Apr 21 found 1 day ago Roundtrip flight included Toronto (YTO) to Miami (MIA) 8.8/10 Excellent! (787 reviews) The staff were so so nice! The hotel was so clean and so green and so cool and I loved every minute of it Reviewed on Feb 5, 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 CA $1,915 per person May 1 - May 8 found 8 hours ago Roundtrip non-stop flight included Toronto (YTO) to Miami (MIA) 8.8/10 Excellent! (1,004 reviews) We Love this place! Reviewed on Mar 17, 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/2026-04-18/2026-04-25/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=MIA&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## 5\* Romantic holidays in Upper Matecumbe Key Price found within the past 48 hours. Click for updated prices. ![Carillon Miami Wellness Resort](https://images.trvl-media.com/lodging/12000000/11350000/11344400/11344361/75c6ca53_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Carillon Miami Wellness Resort North Beach CA $1,982 per person Apr 17 - Apr 21 found 1 day ago Roundtrip flight included Toronto (YTO) to Miami (MIA) 8.8/10 Excellent! (787 reviews) The staff were so so nice! The hotel was so clean and so green and so cool and I loved every minute of it Reviewed on Feb 5, 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 CA $2,612 per person May 21 - May 26 found 11 hours ago Roundtrip flight included Toronto (YYZ) 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 Upper Matecumbe Key [View all trips](https://expedia.ca/go/package/search/FlightHotel/2026-04-18/2026-04-25/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=MIA&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## 3 Night Romantic holidays in Upper Matecumbe 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/1000000/30000/25500/25451/6d55d96d_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### The Shelborne By Proper, a Member of Design Hotels South Beach CA $1,341 per person May 29 - Jun 1 found 13 hours ago Roundtrip non-stop flight included Toronto (YTO) 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 ![1 Hotel South Beach](https://images.trvl-media.com/lodging/2000000/1800000/1790100/1790087/5c0d327a_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### 1 Hotel South Beach South Beach CA $3,031 per person Apr 23 - Apr 26 found 1 day ago Roundtrip non-stop flight included Montreal (YMQ) to Miami (MIA) 9.4/10 Exceptional! (1,455 reviews) This hotel is so beautiful and the staff is so kind and accommodating. The pool and beach areas are stunning, the food is delicious, the rooms are spacious, the beds are so comfortable, and the location is perfect. It’s the best hotel experience I’ve ever had, and I can’t wait to go back again! Reviewed on Mar 7, 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/2026-04-18/2026-04-25/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=MIA&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## 4 Night Romantic holidays in Upper Matecumbe Key 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 CA $1,021 per person Jun 9 - Jun 13 found 1 day ago Roundtrip flight included Toronto (YYZ) to Miami (MIA) 7.8/10 Good! (1,027 reviews) Older, but near our kayaking. On the canal & near several restaurants- walkable. Quiet, cool Reviewed on Mar 16, 2026 ![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 CA $3,549 per person Jun 7 - Jun 11 found 17 hours ago Roundtrip flight included Toronto (YTO) to Miami (MIA) 5.8/10 (321 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 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/2026-04-18/2026-04-25/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=MIA&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## Plan unforgettable romantic Upper Matecumbe Key vacations #### What are some of the benefits of booking a romantic Upper Matecumbe Key vacation? When booking a romantic Upper Matecumbe Key vacation, you'll find quite a few options to make the experience with your partner absolutely unforgettable. Luxury amenities like hot tubs and spa facilities are prominent, but a lot of romantic vacation getaways also make it easy to explore some of the best spots in Islamorada. #### How can I find the best vacation packages for couples? If you're looking for a romantic vacation getaway, all you have to do is implement the romantic search filter. That will automatically remove any property that isn't suitable for couples. Just put in your travel dates and the Upper Matecumbe Key destination, and you'll be met with an array of options for you and your partner to enjoy. #### Can I find cheap romantic vacations for 2 in Upper Matecumbe Key? Yes, there are several options for booking cheap romantic vacations that don't break the bank. You'll find prices as low as CA $1,021 and can enjoy savings of up to 35 when you book your hotel and flight together. Budget and luxury options are both available along with everything in between. Sorting your results by price will allow you to view the cheapest options first. #### What do I need to consider when booking a romantic getaway in Upper Matecumbe Key? Romantic vacation getaways succeed based on catering to what you and your partner specifically want to do. Think about what your partner enjoys and what you want to do as a couple, then opt for something that is especially geared toward fulfilling your ideal romantic vacation getaway experience. Search filters for amenities and proximity to certain attractions throughout Upper Matecumbe Key certainly come in handy here. #### What amenities should I look for in a luxury romantic vacation? If you and your partner are interested in luxury, you won't have to look far for a romantic vacation getaway that fits. In luxury accommodations, you can enjoy amenities like room service and a hot tub. Some accommodations may even have their own spa facilities complete with massage services that will add an extra touch of romance to your excursion to Upper Matecumbe Key. #### Can I book a romantic Upper Matecumbe Key vacation with a hot tub? Yes, and it's easy when you take advantage of available search filters. All you have to do is implement the hot tub filter from the amenities section into your search. This will automatically remove any stays from your search results that do not have hot tubs in them. #### How can I find romantic vacation getaways that are all-inclusive? An all-inclusive trip allows you to plan out your romantic vacation getaway in advance, letting you get a solid number on cost and a full itinerary before you set out. To start this kind of planning, simply apply the filter for all-inclusive trips in your Upper Matecumbe Key search. #### Can I book a romantic trip to Upper Matecumbe Key that is fully refundable? Several romantic Upper Matecumbe Key vacations come with fully refundable reservations. You can filter for this specifically, but every accommodation will list its policy for cancellation in their policy section, which is visible after clicking on a search result. Always make sure to check their policy to determine the requirements. #### Why should I book a romantic vacation with Expedia? Booking your trip with Expedia makes the entire planning process that much easier, as we're your convenient, all-in-one stop for all your travel needs. You can book your stay and your flight, with special discounts potentially available for booking together. Additionally, you can enjoy more discounts by becoming an Expedia Rewards member and getting points to put toward your next booking. Becoming a member is free, so don't hesitate to take advantage. ## 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 Romantic Vacation Destinations > - [Romantic vacations in Toronto ](https://www.expedia.ca/lp/theme-vacations/romantic-vacations/178314/Toronto) > - [Romantic vacations in Nova Scotia ](https://www.expedia.ca/lp/theme-vacations/romantic-vacations/11173/Nova-Scotia) > - [Romantic vacations in Montreal ](https://www.expedia.ca/lp/theme-vacations/romantic-vacations/178288/Montreal) > - [Romantic vacations in Vancouver ](https://www.expedia.ca/lp/theme-vacations/romantic-vacations/178315/Vancouver) > - [Romantic vacations in Quebec ](https://www.expedia.ca/lp/theme-vacations/romantic-vacations/180017/Quebec) > - [Romantic vacations in the Niagara Falls ](https://www.expedia.ca/lp/theme-vacations/romantic-vacations/602721/Niagara-Falls) > - [Romantic vacations in Alberta ](https://www.expedia.ca/lp/theme-vacations/romantic-vacations/11111/Alberta) > - [Romantic vacations in Victoria ](https://www.expedia.ca/lp/theme-vacations/romantic-vacations/1418/Victoria) > - [Romantic vacations in Jasper ](https://www.expedia.ca/lp/theme-vacations/romantic-vacations/8028/Jasper) > - [Romantic vacations in Banff ](https://www.expedia.ca/lp/theme-vacations/romantic-vacations/4332/Banff) > - [Romantic vacations in Ottawa ](https://www.expedia.ca/lp/theme-vacations/romantic-vacations/178296/Ottawa) > - [Romantic vacations in Mont Tremblant ](https://www.expedia.ca/lp/theme-vacations/romantic-vacations/55374/Mont-Tremblant) > - [Romantic vacations in Kingston ](https://www.expedia.ca/lp/theme-vacations/romantic-vacations/180034/Kingston) > - [Romantic vacations in Whistler ](https://www.expedia.ca/lp/theme-vacations/romantic-vacations/4115/Whistler) > - [Romantic vacations in Winnipeg ](https://www.expedia.ca/lp/theme-vacations/romantic-vacations/6141041/Winnipeg) > - [Romantic vacations in Muskoka ](https://www.expedia.ca/lp/theme-vacations/romantic-vacations/6343146/Muskoka-District) > - [Romantic vacations in Collingwood ](https://www.expedia.ca/lp/theme-vacations/romantic-vacations/11938/Collingwood) > - [Romantic vacations in Calgary ](https://www.expedia.ca/lp/theme-vacations/romantic-vacations/178245/Calgary) > - [Romantic vacations in Canada ](https://www.expedia.ca/lp/theme-vacations/romantic-vacations/31/Canada) ## 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. 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