Title: Luxury Vacations in Windley Key 2026 | Expedia.ca ![](https://images.trvl-media.com/place/553248635997958830/30b22f53-286f-436b-ae7a-d035c9062e6c.jpg?impolicy=fcrop&w=1200&h=300&q=medium) # Windley Key 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 Windley 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/e49031f1_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### The Shelborne By Proper, a Member of Design Hotels South Beach CA $1,163 per person Jan 22 - Jan 25 found 1 day ago Roundtrip flight included Detroit (DTW) to Miami (MIA) 9.4/10 Exceptional! (56 reviews) Incredible staff, very attentive and from start to check out. The hotel is spotless and smells so lovely! Didn't get to use the pool because of the weather but it looked very inviting. Thanks for a lovely stay. Reviewed on Dec 10, 2025 ![Hawks Cay Resort](https://images.trvl-media.com/lodging/1000000/10000/6100/6068/b1845555_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Hawks Cay Resort CA $1,829 per person Feb 20 - Feb 27 found 1 day ago Roundtrip flight included Detroit (DTW) to Miami (MIA) 8/10 Very Good! (1,003 reviews) Beautiful balcony and porch views. Reviewed on Dec 8, 2025 ![Pelican Hotel](https://images.trvl-media.com/lodging/1000000/60000/55100/55046/22b81b04_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Pelican Hotel South Beach CA $1,729 per person Jan 11 - Jan 18 found 1 day ago Roundtrip flight included Detroit (DTW) to Miami (MIA) 9.2/10 Wonderful! (394 reviews) Staff was friendly, room was clean, bed was comfortable, and everything looked as pictured, but down-rated slightly because a couple of little wall fixtures were broken in the room and the chairs in the room were uncomfortable. BEWARE there is a daily resort fee hiding in the fine print that increases the cost of the room and there was no major amenity like a swimming pool or spa that seemed to justify this. Breakfast was not included in the price of stay. Reviewed on Dec 8, 2025 ![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 $7,542 per person Jan 21 - Jan 24 found 5 hours ago Roundtrip flight included Detroit (DTW) to Miami (MIA) 8/10 Very Good! (1 review) ![Miami Downtown Condos](https://images.trvl-media.com/lodging/110000000/109790000/109784700/109784697/w2048h1535x0y1-af4622e2_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Miami Downtown Condos Downtown Miami CA $1,192 per person Feb 20 - Feb 25 found 6 hours ago Roundtrip non-stop flight included Detroit (DTW) to Miami (MIA) 8.6/10 Excellent! (72 reviews) Will for sure book again!! Reviewed on Dec 10, 2025 Don't see what you're looking for? See all available trips from Columbus to Windley Key [View all trips](https://expedia.ca/go/package/search/FlightHotel/2026-01-12/2026-01-19/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=MIA&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## 5\* Luxury holidays in Windley Key Price found within the past 48 hours. Click for updated prices. ![Miami Downtown Condos](https://images.trvl-media.com/lodging/110000000/109790000/109784700/109784697/w2048h1535x0y1-af4622e2_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Miami Downtown Condos Downtown Miami CA $1,192 per person Feb 20 - Feb 25 found 6 hours ago Roundtrip non-stop flight included Detroit (DTW) to Miami (MIA) 8.6/10 Excellent! (72 reviews) Will for sure book again!! Reviewed on Dec 10, 2025 ![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 $7,542 per person Jan 21 - Jan 24 found 5 hours ago Roundtrip flight included Detroit (DTW) to Miami (MIA) 8/10 Very Good! (1 review) ![EAST Miami Residences](https://images.trvl-media.com/lodging/79000000/78580000/78570600/78570563/dca879fa_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### EAST Miami Residences Brickell CA $3,261 per person Jan 18 - Jan 25 found 1 day ago Roundtrip non-stop flight included Hamilton (YHM) to Miami (MIA) 9/10 Wonderful! (84 reviews) Great location and hotel. Reviewed on Dec 8, 2025 Don't see what you're looking for? See all available trips from Columbus to Windley Key [View all trips](https://expedia.ca/go/package/search/FlightHotel/2026-01-12/2026-01-19/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=MIA&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## 3 Night Luxury holidays in Windley Key Price found within the past 48 hours. Click for updated prices. ![Pelican Hotel](https://images.trvl-media.com/lodging/1000000/60000/55100/55046/22b81b04_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Pelican Hotel South Beach CA $501 per person Feb 8 - Feb 11 found 13 hours ago Roundtrip flight included Detroit (DTW) to Miami (MIA) 9.2/10 Wonderful! (394 reviews) Staff was friendly, room was clean, bed was comfortable, and everything looked as pictured, but down-rated slightly because a couple of little wall fixtures were broken in the room and the chairs in the room were uncomfortable. BEWARE there is a daily resort fee hiding in the fine print that increases the cost of the room and there was no major amenity like a swimming pool or spa that seemed to justify this. Breakfast was not included in the price of stay. Reviewed on Dec 8, 2025 ![The Shelborne By Proper, a Member of Design Hotels](https://images.trvl-media.com/lodging/1000000/30000/25500/25451/e49031f1_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### The Shelborne By Proper, a Member of Design Hotels South Beach CA $1,163 per person Jan 22 - Jan 25 found 1 day ago Roundtrip flight included Detroit (DTW) to Miami (MIA) 9.4/10 Exceptional! (56 reviews) Incredible staff, very attentive and from start to check out. The hotel is spotless and smells so lovely! Didn't get to use the pool because of the weather but it looked very inviting. Thanks for a lovely stay. Reviewed on Dec 10, 2025 ![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 $7,542 per person Jan 21 - Jan 24 found 5 hours 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 Windley Key [View all trips](https://expedia.ca/go/package/search/FlightHotel/2026-01-12/2026-01-19/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=MIA&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## 4 Night Luxury holidays in Windley Key Price found within the past 48 hours. Click for updated prices. ![Miami Downtown Condos](https://images.trvl-media.com/lodging/110000000/109790000/109784700/109784697/w2048h1535x0y1-af4622e2_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Miami Downtown Condos Downtown Miami CA $1,100 per person Feb 20 - Feb 24 found 5 hours ago Roundtrip flight included Montreal (YMQ) to Miami (MIA) 8.6/10 Excellent! (72 reviews) Will for sure book again!! Reviewed on Dec 10, 2025 ![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 $8,299 per person Feb 1 - Feb 5 found 10 hours ago Roundtrip flight included Hamilton (YHM) to Miami (MIA) 8/10 Very Good! (1 review) ![The Shelborne By Proper, a Member of Design Hotels](https://images.trvl-media.com/lodging/1000000/30000/25500/25451/e49031f1_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### The Shelborne By Proper, a Member of Design Hotels South Beach CA $2,250 per person Feb 12 - Feb 16 found 1 day ago Roundtrip flight included Montreal (YUL) to Miami (MIA) 9.4/10 Exceptional! (56 reviews) Incredible staff, very attentive and from start to check out. The hotel is spotless and smells so lovely! Didn't get to use the pool because of the weather but it looked very inviting. Thanks for a lovely stay. Reviewed on Dec 10, 2025 Don't see what you're looking for? See all available trips from Columbus to Windley Key [View all trips](https://expedia.ca/go/package/search/FlightHotel/2026-01-12/2026-01-19/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=MIA&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## Plan the perfect luxury Windley Key vacation with Expedia #### What are some benefits when booking luxury Windley Key vacations? When you book a luxury Windley Key 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 Windley Key? If you're looking for something luxurious in Windley Key, 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 $501, 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 53\. 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 Windley Key. 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 Windley Key? 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 Windley Key. #### Can I book last-minute luxury vacations? Yes, last-minute bookings are often available in Windley Key. 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 Windley Key? 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 Windley Key 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 Windley Key. 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. ## 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 Windley Key ](https://expedia.ca/Cheap-Flights-To-Windley-Key.d553248635976197663.Travel-Guide-Flights)[ Windley Key Hotels ](https://expedia.ca/Windley-Key-Hotels.d553248635976197663.Travel-Guide-Hotels)[ Windley Key Vacation Rentals ](https://expedia.ca/Windley-Key-Vacation-Rentals.d553248635976197663.Travel-Guide-VacationRentals)[ Windley Key Car Rentals ](https://expedia.ca/Car-Rentals-In-Windley-Key.d553248635976197663.Car-Rental-Guide)[ Windley Key Vacations ](https://expedia.ca/Windley-Key.d553248635976197663.Destination-Travel-Guides)[ Things to do in Windley Key ](https://expedia.ca/Things-To-Do-In-Windley-Key.d553248635976197663.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