Title: Florida Keys Luxury Vacations 2026 | Expedia.com ![](https://images.trvl-media.com/place/6246822/f00ad239-b8ad-4f0c-b162-acc6426db1e2.jpg?impolicy=fcrop&w=1200&h=300&q=medium) # Florida Keys Luxury Vacations ## Book a Luxury Hotel + Flight or Car together to unlock savings - ## Plan, book, travel with confidence - ### Better together Save up to $1,045 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 ## Top Luxury vacation packages in Florida Keys Price found within the past 48 hours. Click for updated prices. ![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 Save 100% on your flight $616 per person May 31 - Jun 2 found 1 day ago Roundtrip non-stop flight included Detroit (DTT) to Miami (MIA) 9.2/10 Wonderful! (1,308 reviews) The staff was friendly and laid back. The resort was absolutely beautiful! Reviewed on Mar 27, 2026 ![Hawks Cay Resort](https://images.trvl-media.com/lodging/1000000/10000/6100/6068/8671ba74_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Hawks Cay Resort Save 100% on your flight $779 per person Apr 29 - May 3 found 1 day ago Roundtrip flight included Houston (HOU) to Miami (MIA) 8/10 Very Good! (1,015 reviews) Staff were friendly and helpful. My family enjoyed the pools and Lagoon. We also enjoyed the marina and the restaurants on the resort. Reviewed on Mar 30, 2026 ![Tranquility Bay Beachfront Hotel and Resort](https://images.trvl-media.com/lodging/1000000/120000/117100/117099/854776a0_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Tranquility Bay Beachfront Hotel and Resort Save 100% on your flight $936 per person May 30 - Jun 3 found 1 day ago Roundtrip non-stop flight included Steamboat Springs (HDN) to Miami (MIA) 8.8/10 Excellent! (1,000 reviews) All 3 pools were beautiful, I loved the surrounding landscape. The two bedroom / 2.5 bath villa was wonderful. I loved sitting on the villas deck each morning to drink my coffee and enjoy the palm tree ocean view. The kitchen had everything we needed to make our meals! I would definitely recommend. Reviewed on Mar 21, 2026 ![Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort](https://images.trvl-media.com/lodging/1000000/20000/11900/11864/4671ebc2_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort $904 per person May 31 - Jun 4 found 1 day ago Roundtrip non-stop flight included Steamboat Springs (HDN) to Miami (MIA) 9/10 Wonderful! (165 reviews) No breakfast bar at this resort. Many onsite options for purchase. I did miss having a microwave. Reviewed on Mar 27, 2026 ![Oceans Edge Key West Resort, Hotel & Marina](https://images.trvl-media.com/lodging/17000000/16210000/16203000/16202992/f7424907_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Oceans Edge Key West Resort, Hotel & Marina $839 per person May 30 - Jun 2 found 1 day ago Roundtrip non-stop flight included Allentown (ABE) to Key West (EYW) 9/10 Wonderful! (1,825 reviews) Overall we enjoyed our stay and would stay again. Our room was a good size however there were some stains in the carpet and once we had to ask for washcloths that housekeeping forget to replace. although when we reach out to get more they brought them up to us The water pressure in the shower was weak. At times we had to go look for towels at the pool and the service at the pool was hit or miss for those reasons we give 4 stars vs 5 stars. The shuttle to downtown Key West was great and the drivers were fantastic! Reviewed on Mar 28, 2026 Don't see what you're looking for? See all available trips from Columbus to Florida Keys [View all trips](https://expedia.com/go/package/search/FlightHotel/2026-04-30/2026-05-07/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=MIA&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## 5\* Luxury vacations in Florida Keys Price found within the past 48 hours. Click for updated prices. ![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 Save 100% on your flight $616 per person May 31 - Jun 2 found 1 day ago Roundtrip non-stop flight included Detroit (DTT) to Miami (MIA) 9.2/10 Wonderful! (1,308 reviews) The staff was friendly and laid back. The resort was absolutely beautiful! Reviewed on Mar 27, 2026 Don't see what you're looking for? See all available trips from Columbus to Florida Keys [View all trips](https://expedia.com/go/package/search/FlightHotel/2026-04-30/2026-05-07/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=MIA&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## 3 Night Luxury vacations in Florida Keys Price found within the past 48 hours. Click for updated prices. ![Tranquility Bay Beachfront Hotel and Resort](https://images.trvl-media.com/lodging/1000000/120000/117100/117099/854776a0_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Tranquility Bay Beachfront Hotel and Resort Save 100% on your flight $712 per person Jun 5 - Jun 8 found 1 day ago Roundtrip flight included Newark Liberty Intl. Airport (EWR) to Miami (MIA) 8.8/10 Excellent! (1,000 reviews) All 3 pools were beautiful, I loved the surrounding landscape. The two bedroom / 2.5 bath villa was wonderful. I loved sitting on the villas deck each morning to drink my coffee and enjoy the palm tree ocean view. The kitchen had everything we needed to make our meals! I would definitely recommend. Reviewed on Mar 21, 2026 ![Hawks Cay Resort](https://images.trvl-media.com/lodging/1000000/10000/6100/6068/8671ba74_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Hawks Cay Resort $1,535 per person May 31 - Jun 3 found 11 hours ago Roundtrip non-stop flight included Norfolk (ORF) to Miami (MIA) 8/10 Very Good! (1,015 reviews) Staff were friendly and helpful. My family enjoyed the pools and Lagoon. We also enjoyed the marina and the restaurants on the resort. Reviewed on Mar 30, 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 Save 100% on your flight $968 per person Jun 5 - Jun 8 found 1 day ago Roundtrip flight included Newark Liberty Intl. Airport (EWR) to Miami (MIA) 9.2/10 Wonderful! (1,308 reviews) The staff was friendly and laid back. The resort was absolutely beautiful! Reviewed on Mar 27, 2026 Don't see what you're looking for? See all available trips from Columbus to Florida Keys [View all trips](https://expedia.com/go/package/search/FlightHotel/2026-04-30/2026-05-07/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=MIA&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## 4 Night Luxury vacations in Florida Keys 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 $497 per person Apr 29 - May 3 found 1 day ago Roundtrip flight included Houston (HOU) to Miami (MIA) 7.8/10 Good! (1,027 reviews) The staff, place, everything was great. Just some irrationals guest let children play and screening around …3 am.. believe me 3:00 am.. l couldn’t believe. Children under 11-10 years old play and yelling around 3:00 am.. ridiculous !! Reviewed on Mar 29, 2026 ![Lime Tree Bay Resort](https://images.trvl-media.com/lodging/1000000/890000/882300/882254/55bf0b8b_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Lime Tree Bay Resort Save 100% on your flight $697 per person Apr 29 - May 3 found 1 day ago Roundtrip flight included Houston (HOU) to Miami (MIA) 9.2/10 Wonderful! (1,194 reviews) The room was spacious and had a feather bed that was almost too soft. A/C was good, and we really liked having a ceiling fan too. Shower was huge! But not a shelf or place to put a bar of soap or hang a washcloth. The laminate floors were very dirty, which we didn't notice until after taking showers and then getting into bed, had to get soap & water and wash them bedside, after that we just kept sandals on while in the room. The pool at Dockside (off site building) was wonderful and the pool at the main building was zero depth entry and oceanside and provided gorgeous sunset views! The on site restaurant was good and we had appetizers; drinks and breakfast there. Sadly we didn't use the offered kayaks; bikes; and paddle boards as we didn't have enough time! Still excellent to have them available to use. Highly recommend. Reviewed on Mar 30, 2026 ![Oceans Edge Key West Resort, Hotel & Marina](https://images.trvl-media.com/lodging/17000000/16210000/16203000/16202992/f7424907_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Oceans Edge Key West Resort, Hotel & Marina $862 per person May 30 - Jun 3 found 1 day ago Roundtrip non-stop flight included Allentown (ABE) to Key West (EYW) 9/10 Wonderful! (1,825 reviews) Overall we enjoyed our stay and would stay again. Our room was a good size however there were some stains in the carpet and once we had to ask for washcloths that housekeeping forget to replace. although when we reach out to get more they brought them up to us The water pressure in the shower was weak. At times we had to go look for towels at the pool and the service at the pool was hit or miss for those reasons we give 4 stars vs 5 stars. The shuttle to downtown Key West was great and the drivers were fantastic! Reviewed on Mar 28, 2026 Don't see what you're looking for? See all available trips from Columbus to Florida Keys [View all trips](https://expedia.com/go/package/search/FlightHotel/2026-04-30/2026-05-07/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=MIA&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## All you need to know about luxury vacations in Florida Keys #### What can I expect from a luxury Florida Keys vacation? Luxury means the very finest of the things you enjoy most. Indulge your every waking moment—and restful night—with a luxury Florida Keys vacation. Sip handcrafted cocktails by an infinity pool, sink into bliss at a full-service spa with a massage cabana on the beach, and chat, cheers, and laugh through exquisite breakfasts, lunches, and dinners with spectacular views. #### How can I find all-inclusive luxury vacation packages in Florida Keys? By refining your filters, the most opulent all-inclusive vacation packages will appear before your eyes. Check the 5\* filter to find truly sensational stays. You barely need to lift a finger. #### Can I book a cheap Florida Keys luxury vacation? Affordable luxury is only ever a few clicks away. Enter your travel dates and sort the grandiose getaways on offer by price to see the most fiscally friendly retreats first. Filter by budget, too, to find your perfect balance of luxury. Right now, luxury vacations start at $497\. Prices and availability are subject to change. Additional terms may apply. #### How can I book a luxury family vacation in Florida Keys? Tailor your luxury family escape by checking the filters that set the whole family’s hearts a-flutter. Whether that’s wet and wild water parks, heavenly hot tubs, or the kid-quieting magic of free Wi-Fi. #### Can I book a package in Florida Keys with a luxury vacation home? A private paradise is true luxury! Filter by property type for houses, villas, and apartments. For an amazingly affordable all-in-one luxury experience, book your accommodation, airfare, and car rental as a package. #### How can I find the best luxury vacation deals in Florida Keys? Find absolute delight in the dropdown! Simply sort your tempting search results by deals to find that lean-budget luxury. For a budget conscious stay, consider booking a stay away from big cities or outside the peak months. #### Can I book a luxury holiday in Florida Keys with free cancellation and/or flexible dates? Freedom and flexibility are the greatest luxuries of all. Get both when you filter by payment option and book a trip with free cancellation or on a buy now, pay later plan. #### Why should I book my luxury trip to Florida Keys with Expedia? A luxurious trip follows a stress-free booking experience. Find, build, and book the most glorious of getaways in seconds—with ATOL protection for added peace of mind. ## Top Luxury Florida Keys Hotels ![Oceans Edge Key West Resort, Hotel & Marina](https://images.trvl-media.com/lodging/17000000/16210000/16203000/16202992/f7424907_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Oceans Edge Key West Resort, Hotel & Marina 5950 Peninsular Avenue Key West FL - 10 min drive from Duval Street Pamper yourself with a luxury stay at Oceans Edge Key West Resort, Hotel & Marina, where you can enjoy amenities like Egyptian cotton sheets, plush bedding, ... 9/10 Wonderful! (1,846 reviews) All was great Reviewed on Mar 29, 2026 [](https://expedia.com/Key-West-Hotels-Oceans-Edge-Key-West-Resort.h16202992.Hotel-Information) ![The Marker Key West Harbor Resort](https://images.trvl-media.com/lodging/10000000/9150000/9148400/9148379/821176b1_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### The Marker Key West Harbor Resort 200 William Street Key West FL - 10 min walk from Duval Street Be treated to a grand stay at The Marker Key West Harbor Resort, where you'll find deep soaking bathtubs and premium bedding. The 3 outdoor pools, poolside bar, ... 9.2/10 Wonderful! (1,003 reviews) Loved the location! Has parking available and is walking distance to everything!!! Great pools and extremely friendly staff as well! We had a great all around experience! Reviewed on Mar 27, 2026 [](https://expedia.com/Key-West-Hotels-The-Marker-Key-West-Harbor-Resort.h9148379.Hotel-Information) ![Cheeca Lodge & Spa](https://images.trvl-media.com/lodging/1000000/10000/5800/5780/4608d7e2_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Cheeca Lodge & Spa 81801 Overseas Highway, Mile Marker 82 Islamorada FL - 3 hours drive from Duval Street Cheeca Lodge & Spa is a Islamorada luxury 5-star beach property where you can treat yourself to Champagne service, massage services, and more. The 2 poolside ... 9.2/10 Wonderful! (1,303 reviews) N/A Reviewed on Mar 29, 2026 [](https://expedia.com/Islamorada-Hotels-Cheeca-Lodge-Spa.h5780.Hotel-Information) [See all 8,317 properties in Florida Keys](https://expedia.com/Hotel-Search?rfrrid=TG.LP.Hotels.Package®ionId=6023765) 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.com/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.com/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) Kid Friendly Vacations [](https://expedia.com/lp/theme-vacations/kid-friendly-vacations?rfrr=editorial.Kid_Friendly%20Vacations.click) 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](https://expedia.com/Florida-Keys-Vacation-Rentals.d6023765.Travel-Guide-VacationRentals)[ Car Rentals in Florida Keys ](https://expedia.com/Car-Rentals-In-Florida-Keys.d6023765.Car-Rental-Guide)[ Florida Keys Vacations ](https://expedia.com/Florida-Keys.d6023765.Destination-Travel-Guides)[ Things to do in Florida Keys ](https://expedia.com/Things-To-Do-In-Florida-Keys.d6023765.Travel-Guide-Activities) \* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.