Title: Romantic Vacations in Islamorada 2026 | Expedia.ca ![](https://images.trvl-media.com/place/10768/fc4588ee-e7f3-44af-8fce-e7aa6a494cda.jpg?impolicy=fcrop&w=1200&h=300&q=medium) # Islamorada Romantic Vacations ## 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 ## Flight and Romantic hotel deals 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/eda54a36_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### La Siesta Resort & Villas Matecumbe CA $933 per person May 2 - May 5 found 18 hours ago Roundtrip flight included Detroit (DTT) to Miami (MIA) 8.6/10 Excellent! (1,000 reviews) excellent location very nice simple breakfast close to liz’s of activities great poool Reviewed on Feb 2, 2026 ![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 CA $3,072 per person Apr 17 - Apr 24 found 1 day ago Roundtrip flight included Toronto (YYZ) to Miami (MIA) 9.2/10 Wonderful! (1,262 reviews) Check in was great. The elevator was out in our building and they failed to let us know at check- in. We were on the 3rd floor and had to use the stairs. Reviewed on Feb 9, 2026 ![Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort](https://images.trvl-media.com/lodging/1000000/20000/11900/11864/d10a018b_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort CA $2,221 per person Apr 17 - Apr 24 found 1 day ago Roundtrip flight included Toronto (YYZ) to Miami (MIA) 9/10 Wonderful! (108 reviews) Spotless room, friendly staff, excellent food Reviewed on Feb 6, 2026 ![Islander Resort](https://images.trvl-media.com/lodging/1000000/480000/475500/475438/5adae4af_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Islander Resort Matecumbe CA $3,066 per person Apr 17 - Apr 24 found 1 day ago Roundtrip flight included Toronto (YYZ) to Miami (MIA) 9.2/10 Wonderful! (1,005 reviews) My husband and I stayed 3 nights and we absolutely loved the resort. Beautiful, quiet and serene and with so many amenities. Our room was amazing with a wonderful huge patio that had a path right out to the beach. Breakfast and dinner at the two restaurants was fabulous with excellent food and great service. Would definitely stay here again! Reviewed on Jan 30, 2026 ![Amara Cay Resort](https://images.trvl-media.com/lodging/1000000/70000/62000/61976/84b50729_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Amara Cay Resort Matecumbe CA $2,523 per person Mar 11 - Mar 17 found 1 day ago Roundtrip flight included Montreal (YMQ) to Miami (MIA) 8.8/10 Excellent! (1,252 reviews) Room was ok, beds were comfortable, floors were dirty and slimy. We were there when it was cold and there was no way to turn the heat on, stuck on 68\. It was nice they have a complimentary shuttle that will take you within an 8 mile range. Reviewed on Feb 2, 2026 Don't see what you're looking for? See all available trips from Columbus to Islamorada [View all trips](https://expedia.ca/go/package/search/FlightHotel/2026-03-09/2026-03-16/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=MIA&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## 5\* Romantic holidays in Islamorada Price found within the past 48 hours. Click for updated prices. ![Cheeca Lodge & Spa](https://images.trvl-media.com/lodging/1000000/10000/5800/5780/617c0723_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Cheeca Lodge & Spa Matecumbe CA $3,072 per person Apr 17 - Apr 24 found 1 day ago Roundtrip flight included Toronto (YYZ) to Miami (MIA) 9.2/10 Wonderful! (1,262 reviews) Check in was great. The elevator was out in our building and they failed to let us know at check- in. We were on the 3rd floor and had to use the stairs. Reviewed on Feb 9, 2026 Don't see what you're looking for? See all available trips from Columbus to Islamorada [View all trips](https://expedia.ca/go/package/search/FlightHotel/2026-03-09/2026-03-16/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=MIA&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## 3 Night Romantic holidays 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/eda54a36_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### La Siesta Resort & Villas Matecumbe CA $933 per person May 2 - May 5 found 18 hours ago Roundtrip flight included Detroit (DTT) to Miami (MIA) 8.6/10 Excellent! (1,000 reviews) excellent location very nice simple breakfast close to liz’s of activities great poool Reviewed on Feb 2, 2026 ![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 CA $2,647 per person Mar 19 - Mar 22 found 10 hours ago Roundtrip non-stop flight included Ottawa (YOW) to Miami (MIA) 9.2/10 Wonderful! (1,262 reviews) Check in was great. The elevator was out in our building and they failed to let us know at check- in. We were on the 3rd floor and had to use the stairs. Reviewed on Feb 9, 2026 ![Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort](https://images.trvl-media.com/lodging/1000000/20000/11900/11864/d10a018b_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort CA $1,106 per person May 2 - May 5 found 18 hours ago Roundtrip flight included Detroit (DTT) to Miami (MIA) 9/10 Wonderful! (108 reviews) Spotless room, friendly staff, excellent food Reviewed on Feb 6, 2026 Don't see what you're looking for? See all available trips from Columbus to Islamorada [View all trips](https://expedia.ca/go/package/search/FlightHotel/2026-03-09/2026-03-16/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=MIA&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## 4 Night Romantic holidays in Islamorada Price found within the past 48 hours. Click for updated prices. ![Creekside Inn](https://images.trvl-media.com/lodging/2000000/1580000/1576800/1576773/5e43c05b_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Creekside Inn CA $847 per person Mar 14 - Mar 18 found 1 day ago Roundtrip non-stop 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 ![La Siesta Resort & Villas](https://images.trvl-media.com/lodging/3000000/2480000/2477600/2477508/eda54a36_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### La Siesta Resort & Villas Matecumbe CA $1,597 per person Mar 15 - Mar 19 found 12 hours ago Roundtrip flight included Detroit (DTW) to Miami (MIA) 8.6/10 Excellent! (1,000 reviews) excellent location very nice simple breakfast close to liz’s of activities great poool Reviewed on Feb 2, 2026 ![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 CA $2,833 per person Mar 14 - Mar 18 found 1 day ago Roundtrip non-stop flight included Detroit (DTW) to Miami (MIA) 9.2/10 Wonderful! (1,262 reviews) Check in was great. The elevator was out in our building and they failed to let us know at check- in. We were on the 3rd floor and had to use the stairs. Reviewed on Feb 9, 2026 Don't see what you're looking for? See all available trips from Columbus to Islamorada [View all trips](https://expedia.ca/go/package/search/FlightHotel/2026-03-09/2026-03-16/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=MIA&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## Plan unforgettable romantic Islamorada vacations #### What are some of the benefits of booking a romantic Islamorada vacation? When booking a romantic Islamorada 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 Florida. #### 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 Islamorada 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 Islamorada? Yes, there are several options for booking cheap romantic vacations that don't break the bank. You'll find prices as low as CA $847 and can enjoy savings of up to 29 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 Islamorada? 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 Islamorada 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 Islamorada. #### Can I book a romantic Islamorada 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 Islamorada search. #### Can I book a romantic trip to Islamorada that is fully refundable? Several romantic Islamorada 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. ## Romantic Hotels in Islamorada ![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 - 8 min drive from Theater of the Sea 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! (1,296 reviews) Paradise away from Home!! Thank you! Reviewed on Feb 7, 2026 [](https://expedia.ca/Islamorada-Hotels-Cheeca-Lodge-Spa.h5780.Hotel-Information) ![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! (1,665 reviews) We loved this place. It’s small and easy to get around. Beautiful setting, watched the sunrise from bed, and the best hotel breakfast we’ve ever had. Reviewed on Feb 3, 2026 [](https://expedia.ca/Islamorada-Hotels-Chesapeake-Beach-Resort.h4170.Hotel-Information) ![Amara Cay Resort](https://images.trvl-media.com/lodging/1000000/70000/62000/61976/84b50729_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Amara Cay Resort 80001 Overseas Hwy Islamorada FL - 12 min drive from Theater of the Sea Book a stay at this beach resort in Islamorada. Enjoy 2 restaurants, a private beach, and 3 bars/lounges. Our guests praise the pool and the helpful staff in ... 8.8/10 Excellent! (1,264 reviews) All good, nice bartender inside downstairs, and easy walk to fish and eat Reviewed on Feb 5, 2026 [](https://expedia.ca/Islamorada-Hotels-Amara-Cay-Resort.h61976.Hotel-Information) [See all 2,227 properties in Islamorada](https://expedia.ca/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. 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 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 Islamorada ](https://expedia.ca/Cheap-Flights-To-Islamorada.d10768.Travel-Guide-Flights)[ Islamorada Hotels ](https://expedia.ca/Islamorada-Hotels.d10768.Travel-Guide-Hotels)[ Islamorada Vacation Rentals ](https://expedia.ca/Islamorada-Vacation-Rentals.d10768.Travel-Guide-VacationRentals)[ Islamorada Car Rentals ](https://expedia.ca/Car-Rentals-In-Islamorada.d10768.Car-Rental-Guide)[ Islamorada Vacations ](https://expedia.ca/Islamorada.d10768.Destination-Travel-Guides)[ Things to do in Islamorada ](https://expedia.ca/Things-To-Do-In-Islamorada.d10768.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 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