Title: Luxury 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 Luxury 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 Luxury 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 $1,240 per person Jan 25 - Jan 30 found 17 hours ago Roundtrip flight included Toronto (YYZ) to Miami (MIA) 8.6/10 Excellent! (1,000 reviews) Clean, spacious room. Property was beautiful. Staff friendly. Nice to be able to go to the sister resorts as well. Reviewed on Dec 15, 2025 ![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 $3,605 per person Feb 22 - Feb 28 found 1 day ago Roundtrip flight included Toronto (YYZ) to Miami (MIA) 9.2/10 Wonderful! (1,262 reviews) Ate dinner at the Asian restaurant Nikki- the Chilean Seabass was delicious andmelted with every bite. And service was good Reviewed on Dec 18, 2025 ![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 $1,740 per person Jan 23 - Jan 27 found 7 hours ago Roundtrip non-stop flight included Ottawa (YOW) to Miami (MIA) 9/10 Wonderful! (108 reviews) Overall it was a nice stay. They didn’t have elevators so it was rough carrying up full suitcases and we did find a couple of fish hooks in our rooms as those the maids only did what they must did. It wasn’t a thorough cleaning of the room. The staff was nice and very friendly. Food was good We would probably stay again Reviewed on Dec 15, 2025 ![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 $1,581 per person Jan 23 - Jan 27 found 7 hours ago Roundtrip non-stop flight included Ottawa (YOW) to Miami (MIA) 8.8/10 Excellent! (1,252 reviews) I would give this hotel one the highest ratings for my most recent stays in the area. The views were spectacular. All of the staff were very friendly and helpful. Very very minor thing was the condition of the furniture and electrical sockets weren't the best quality but I just loved everything else so much that it would not deter me from returning. Reviewed on Dec 16, 2025 ![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 $2,163 per person Feb 22 - Feb 28 found 1 day ago Roundtrip flight included Toronto (YYZ) to Miami (MIA) 9.2/10 Wonderful! (1,005 reviews) The resort was perfect Everyone from checking in and during our stay could not have been nicer and helpful Reviewed on Dec 17, 2025 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/2026-01-19/2026-01-26/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=MIA&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## 5\* Luxury 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 $3,605 per person Feb 22 - Feb 28 found 1 day ago Roundtrip flight included Toronto (YYZ) to Miami (MIA) 9.2/10 Wonderful! (1,262 reviews) Ate dinner at the Asian restaurant Nikki- the Chilean Seabass was delicious andmelted with every bite. And service was good Reviewed on Dec 18, 2025 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/2026-01-19/2026-01-26/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=MIA&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## 4 Night Luxury 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 $1,077 per person Feb 19 - Feb 23 found 10 hours ago Roundtrip non-stop flight included Ottawa (YOW) to Miami (MIA) 8/10 Very Good! (1,005 reviews) The room was nice, but walking out to the pier from door was excellent Reviewed on Dec 16, 2025 ![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 $1,740 per person Jan 23 - Jan 27 found 7 hours ago Roundtrip non-stop flight included Ottawa (YOW) to Miami (MIA) 9/10 Wonderful! (108 reviews) Overall it was a nice stay. They didn’t have elevators so it was rough carrying up full suitcases and we did find a couple of fish hooks in our rooms as those the maids only did what they must did. It wasn’t a thorough cleaning of the room. The staff was nice and very friendly. Food was good We would probably stay again Reviewed on Dec 15, 2025 ![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 $1,439 per person Feb 7 - Feb 11 found 5 hours ago Roundtrip flight included Ottawa (YOW) to Miami (MIA) 8.6/10 Excellent! (1,000 reviews) Clean, spacious room. Property was beautiful. Staff friendly. Nice to be able to go to the sister resorts as well. Reviewed on Dec 15, 2025 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/2026-01-19/2026-01-26/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=MIA&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## Plan the perfect luxury Islamorada vacation with Expedia #### What are some benefits when booking luxury Islamorada vacations? When you book a luxury Islamorada vacation, you get to enjoy some of the best amenities and special features available. Luxury vacation options often feature spa facilities right in your accommodation, along with room service and an on-site restaurant. The quality of the bedding and even the water pressure tends to be better, so it's the perfect solution for travellers looking to put their feet up and relax. #### How can I find all-inclusive luxury vacations in Islamorada? If you're looking for something luxurious in Islamorada, all you have to do is take advantage of our search filters. You can implement a filter to only show 5-star accommodations as well as some amenities you may be interested in, like spa facilities and hot tubs. When you opt for an all-inclusive package, you can enjoy luxury alongside a potential discount for booking your accommodation and flight together. #### Can I book a cheap luxury vacation? While luxury vacations tend to be on the more costly end of the spectrum, ranging from CA $1,077, there are a few methods you can try to lower the price as much as possible. When booking a flight and accommodation together, you can enjoy savings of up to 29\. After implementing filters for luxury features, you can also sort by price to list the cheapest luxury packages first. #### Are there luxury spa vacations? Yes, luxury spa vacations are available and quite popular in Islamorada. When you book one of these experiences, it's easier than ever to relax, unwind and recharge in between excursions. Either way, you can easily find spa vacations by implementing the spa filter in your search. #### What should I look for in a luxury family vacation in Islamorada? When booking something for the whole family, it's important to consider exactly what kind of experience your family will want.Luxury packages make it easy to keep everyone happy with creature comforts. Kids especially enjoy features like pools, a delicious breakfast and plenty of space. Suites tend to offer your family members a bit more privacy and comfort compared to simple rooms throughout Islamorada. #### Can I book last-minute luxury vacations? Yes, last-minute bookings are often available in Islamorada. All you have to do is enter your travel dates to see what's available. Sometimes, you'll even find additional discounts for booking last-minute, as accommodations are desperate to fill their last remaining spaces. #### What can help me find the best luxury vacation deals in Islamorada? You can use a few strategies to find the best deals on luxury vacation packages. Consider travelling during the off-season to take advantage of the typically lower overall prices. Additionally, staying in the less popular parts of Islamorada or travelling to more obscure destinations altogether can often lead to lower prices. #### Can I book a luxury vacation that is fully refundable? Yes, fully refundable reservations are sometimes available on luxury vacation packages in Islamorada. You can implement a filter for it specifically or check out the policy section on any one of your search results. It should clearly state what's necessary to qualify for a fully refundable booking. #### Why should I book my luxury vacation with Expedia? When you book with Expedia, you can enjoy a one-stop shop for all your travel planning needs. We offer accommodations as well as flights, and you may even be able to enjoy discounts by booking them together. Of course, Expedia Rewards members will find even more discounts and earn points that can be put toward discounts on future bookings. ## Luxury 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! (1,267 reviews) Everything was awsome Reviewed on Dec 7, 2025 [](https://expedia.ca/Islamorada-Hotels-Cheeca-Lodge-Spa.h5780.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! (1,263 reviews) I would give this hotel one the highest ratings for my most recent stays in the area. The views were spectacular. All of the staff were very friendly and helpful. Very very minor thing was the condition of the furniture and electrical sockets weren't the best quality but I just loved everything else ... Reviewed on Dec 16, 2025 [](https://expedia.ca/Islamorada-Hotels-Amara-Cay-Resort.h61976.Hotel-Information) ![Drop Anchor](https://images.trvl-media.com/lodging/5000000/4290000/4287400/4287368/7fd0f78d_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Drop Anchor 84959 Overseas Highway, 222 Islamorada FL - 8 min walk from Theater of the Sea Stay at this hotel in Islamorada. Enjoy free WiFi, free parking, and free bicycles on site. Our guests praise the helpful staff and the clean rooms in our reviews. ... 8.6/10 Excellent! (1,000 reviews) Had a wonderful stay at Drop Anchor! Very adorable and super clean. Loved the amenities and the hotel staff were amazing! Reviewed on Dec 7, 2025 [](https://expedia.ca/Islamorada-Hotels-Drop-Anchor.h4287368.Hotel-Information) [See all 2,221 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 Luxury Vacation Destinations > - [Luxury vacations in India ](https://www.expedia.ca/lp/theme-vacations/luxury-vacations/80/India) > - [Luxury vacations in France ](https://www.expedia.ca/lp/theme-vacations/luxury-vacations/59/France) > - [Luxury vacations in Switzerland ](https://www.expedia.ca/lp/theme-vacations/luxury-vacations/174/Switzerland) > - [Luxury vacations in Canada ](https://www.expedia.ca/lp/theme-vacations/luxury-vacations/31/Canada) > - [Luxury vacations in Jamaica ](https://www.expedia.ca/lp/theme-vacations/luxury-vacations/88/Jamaica) > - [Luxury vacations in Italy ](https://www.expedia.ca/lp/theme-vacations/luxury-vacations/86/Italy) > - [Luxury vacations in New Zealand ](https://www.expedia.ca/lp/theme-vacations/luxury-vacations/133/New-Zealand) > - [Luxury vacations in the Maldives ](https://www.expedia.ca/lp/theme-vacations/luxury-vacations/109/Maldives) > - [Luxury vacations in Costa Rica ](https://www.expedia.ca/lp/theme-vacations/luxury-vacations/42/Costa-Rica) > - [Luxury vacations in Florida Keys ](https://www.expedia.ca/lp/theme-vacations/luxury-vacations/6023765/Florida-Keys) > - [Luxury vacations in Mexico ](https://www.expedia.ca/lp/theme-vacations/luxury-vacations/117/Mexico) > - [Luxury vacations in the Caribbean ](https://www.expedia.ca/lp/theme-vacations/luxury-vacations/6022969/Caribbean) > - [Luxury vacations in Zanzibar ](https://www.expedia.ca/lp/theme-vacations/luxury-vacations/4186/Zanzibar) > - [Luxury vacations in Cancun ](https://www.expedia.ca/lp/theme-vacations/luxury-vacations/179995/Cancun) > - [Luxury vacations in Kerala ](https://www.expedia.ca/lp/theme-vacations/luxury-vacations/602187/Kerala) > - [Luxury vacations in Australia ](https://www.expedia.ca/lp/theme-vacations/luxury-vacations/10/Australia) > - [Luxury vacations in Puglia ](https://www.expedia.ca/lp/theme-vacations/luxury-vacations/6048562/Puglia) > - [Luxury vacations in Cuba ](https://www.expedia.ca/lp/theme-vacations/luxury-vacations/44/Cuba) > - [Luxury vacations in Cyprus ](https://www.expedia.ca/lp/theme-vacations/luxury-vacations/45/Cyprus) ## 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