Title: Romantic Vacations in Florida Keys 2026 | Expedia.ca ![](https://images.trvl-media.com/place/6246822/f00ad239-b8ad-4f0c-b162-acc6426db1e2.jpg?impolicy=fcrop&w=1200&h=300&q=medium) # Florida Keys 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 Florida Keys Price found within the past 48 hours. Click for updated prices. ![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 CA $1,601 per person Jun 6 - Jun 12 found 1 day ago Roundtrip flight included Toronto (YTO) to Miami (MIA) 8/10 Very Good! (1,015 reviews) Avoid Angler and Ale restaurant, the food is terrible and the service also terrible, we wait one hour and 20 minutes for our drinks and 2 hours for our food. We had to return most of the dishes because of the terrible taste and presentation. AVOID eating at this place at any cost. Overall the hotel is great and the villas are very nice and comfortable. Reviewed on Apr 2, 2026 ![The Gardens Hotel](https://images.trvl-media.com/lodging/1000000/30000/20800/20796/a4035487_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### The Gardens Hotel Old Town Key West CA $2,436 per person May 14 - May 18 found 1 day ago Roundtrip non-stop flight included Nashville (BNA) to Key West (EYW) 9.8/10 Exceptional! (1,000 reviews) A little slice of heaven nestled amongst quaint downtown location. Quiet and relaxing atmosphere perfect Key West getaway. Reviewed on Mar 21, 2026 ![Casa Marina Key West, Curio Collection by Hilton](https://images.trvl-media.com/lodging/1000000/20000/12400/12346/14292c62_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Casa Marina Key West, Curio Collection by Hilton Old Town Key West CA $1,983 per person Jun 6 - Jun 13 found 4 hours ago Roundtrip flight included Toronto (YTO) to Key West (EYW) 8.4/10 Very Good! (595 reviews) I had an ocean front suite is was wonderful. The room was very clean and well presented. I ate the restaurant a few times during my stay and it was perfect everytime. I also used the fitness center and valet and everything was wonderful. Reviewed on Apr 3, 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 CA $2,471 per person Jun 6 - Jun 13 found 4 hours ago Roundtrip flight included Toronto (YTO) to Miami (MIA) 8.8/10 Excellent! (1,000 reviews) Pools closed earlier than advertised. You can’t bring outside food or drink onto the public areas of the property but it took an hour to get one sandwich at the Tiki Bar. Once it came, we had a total of three drinks and shared the sandwich. $90\. I reduced it because it took an hour but they still tried to bill me full with non-negotiable , automatic tip even though I reduced it when I signed. Reviewed on Apr 2, 2026 ![The Reach Key West, Curio Collection by Hilton](https://images.trvl-media.com/lodging/1000000/460000/457900/457821/bc3021c3_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### The Reach Key West, Curio Collection by Hilton Old Town Key West CA $1,670 per person Jun 6 - Jun 12 found 1 day ago Roundtrip flight included Toronto (YTO) to Key West (EYW) 8.6/10 Excellent! (1,013 reviews) The beach was perfect except when a wedding was going on it was limited and no warnings for this. There was only 1 waitress fir beach and pool orders. Also waitress didnt even knowledge us over 10 when we tried to go for breakfast so we left . The culture is wonderful except wasnt informed roosters would wake u at 4am so earplugs would have been nice . Other than that It was beautiful and enjoyable Reviewed on Mar 29, 2026 Don't see what you're looking for? See all available trips from Columbus to Florida Keys [View all trips](https://expedia.ca/go/package/search/FlightHotel/2026-05-03/2026-05-10/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=MIA&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## 3 Night Romantic holidays in Florida Keys Price found within the past 48 hours. Click for updated prices. ![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 CA $1,388 per person Jun 26 - Jun 29 found 20 hours ago Roundtrip flight included Montreal (YUL) to Miami (MIA) 8/10 Very Good! (1,015 reviews) Avoid Angler and Ale restaurant, the food is terrible and the service also terrible, we wait one hour and 20 minutes for our drinks and 2 hours for our food. We had to return most of the dishes because of the terrible taste and presentation. AVOID eating at this place at any cost. Overall the hotel is great and the villas are very nice and comfortable. Reviewed on Apr 2, 2026 ![Pier House Resort & Spa](https://images.trvl-media.com/lodging/1000000/20000/19400/19307/c9267f77_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Pier House Resort & Spa Key West Historic District CA $1,867 per person May 17 - May 20 found 1 hour ago Roundtrip non-stop flight included Calgary (YYC) to Key West (EYW) 9/10 Wonderful! (1,073 reviews) My husband and I had a spectacular time at this resort. Looking forward to coming back real soon! The food and location were perfect! Reviewed on Apr 2, 2026 ![Casa Marina Key West, Curio Collection by Hilton](https://images.trvl-media.com/lodging/1000000/20000/12400/12346/14292c62_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Casa Marina Key West, Curio Collection by Hilton Old Town Key West CA $1,527 per person May 25 - May 28 found 10 hours ago Roundtrip non-stop flight included Toronto (YTO) to Key West (EYW) 8.4/10 Very Good! (595 reviews) I had an ocean front suite is was wonderful. The room was very clean and well presented. I ate the restaurant a few times during my stay and it was perfect everytime. I also used the fitness center and valet and everything was wonderful. Reviewed on Apr 3, 2026 Don't see what you're looking for? See all available trips from Columbus to Florida Keys [View all trips](https://expedia.ca/go/package/search/FlightHotel/2026-05-03/2026-05-10/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=MIA&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## 4 Night Romantic holidays in Florida Keys Price found within the past 48 hours. Click for updated prices. ![Hyatt Vacation Club at Beach House, Key West](https://images.trvl-media.com/lodging/1000000/860000/858000/857962/864ce9f9_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Hyatt Vacation Club at Beach House, Key West CA $1,783 per person May 11 - May 15 just found Roundtrip non-stop flight included Toronto (YYZ) to Key West (EYW) 9.4/10 Exceptional! (1,004 reviews) These are recently renovated “condos” with 2 beds/2 baths, full kitchen, dining, and living area. Master bath is very nicely done with a giant shower for two. Very large deck/porch off each unit. The A/C went out but the friendly front desk and maintenance crew repaired it quickly. Resort has a large pool and large sand beach area with plenty of chairs and cabanas. New gas grills are near the pool area. There is a tiki bar on site with food. No complaints about this property whatsoever. There is a kayak tour guide right next door and I highly recommend their night kayak tour. The property is at the opposite end of the island to Old town/Duvall street. It’s about a 20 min bike ride to Duvall, and a 9 minute bike ride to Publix. Reviewed on Apr 1, 2026 ![The Gardens Hotel](https://images.trvl-media.com/lodging/1000000/30000/20800/20796/a4035487_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### The Gardens Hotel Old Town Key West CA $2,436 per person May 14 - May 18 found 1 day ago Roundtrip non-stop flight included Nashville (BNA) to Key West (EYW) 9.8/10 Exceptional! (1,000 reviews) A little slice of heaven nestled amongst quaint downtown location. Quiet and relaxing atmosphere perfect Key West getaway. Reviewed on Mar 21, 2026 ![Southernmost Beach Resort and Guesthouses](https://images.trvl-media.com/lodging/1000000/870000/863400/863329/546caf1e_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Southernmost Beach Resort and Guesthouses Old Town Key West CA $2,069 per person May 11 - May 15 just found Roundtrip non-stop flight included Toronto (YYZ) to Key West (EYW) 8.8/10 Excellent! (3,162 reviews) Great beach view, very clean Reviewed on Apr 3, 2026 Don't see what you're looking for? See all available trips from Columbus to Florida Keys [View all trips](https://expedia.ca/go/package/search/FlightHotel/2026-05-03/2026-05-10/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=MIA&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## Plan unforgettable romantic Florida Keys vacations #### What are some of the benefits of booking a romantic Florida Keys vacation? When booking a romantic Florida Keys 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 United States of America. #### 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 Florida Keys 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 Florida Keys? Yes, there are several options for booking cheap romantic vacations that don't break the bank. You'll find prices as low as CA $1,388 and can enjoy savings of up to 32 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 Florida Keys? 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 Florida Keys 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 Florida Keys. #### Can I book a romantic Florida Keys 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 Florida Keys search. #### Can I book a romantic trip to Florida Keys that is fully refundable? Several romantic Florida Keys 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 Florida Keys ![Southernmost Beach Resort and Guesthouses](https://images.trvl-media.com/lodging/1000000/870000/863400/863329/546caf1e_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Southernmost Beach Resort and Guesthouses 1319 Duval Street Key West FL - 10 min walk from Duval Street Book a stay at this beach hotel in Key West. Enjoy free WiFi, 3 outdoor pools, and a full-service spa. Our guests praise the pool and the helpful staff in our ... 8.8/10 Excellent! (3,167 reviews) Great beach view, very clean Reviewed on Apr 3, 2026 [](https://expedia.ca/Key-West-Hotels-Southernmost-Beach-Resort.h863329.Hotel-Information) ![Parrot Key Hotel & Villas](https://images.trvl-media.com/lodging/1000000/30000/24700/24615/cf132c1e_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Parrot Key Hotel & Villas 2801 N Roosevelt Blvd Key West FL - 5 min drive from Duval Street Book a stay at this beach hotel in Key West. Enjoy free WiFi, 4 outdoor pools, and breakfast (surcharge). Our guests praise the pool and the bar in our reviews. ... 9/10 Wonderful! (1,329 reviews) The shower has poor water pressure and couldn’t regulate the temp. Reviewed on Mar 31, 2026 [](https://expedia.ca/Key-West-Hotels-Parrot-Key-Hotel-Villas.h24615.Hotel-Information) ![Pier House Resort & Spa](https://images.trvl-media.com/lodging/1000000/20000/19400/19307/c9267f77_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Pier House Resort & Spa 1 Duval St Key West FL - 11 min walk from Duval Street Book a stay at this beach resort in Key West. Enjoy a full-service spa, a private beach, and 2 bars/lounges. Our guests praise the pool and the helpful staff ... 9/10 Wonderful! (1,071 reviews) My husband and I had a spectacular time at this resort. Looking forward to coming back real soon! The food and location were perfect! Reviewed on Apr 2, 2026 [](https://expedia.ca/Key-West-Hotels-Pier-House-Resort-Spa.h19307.Hotel-Information) [See all 8,085 properties in Florida Keys](https://expedia.ca/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.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 Florida Keys ](https://expedia.ca/Cheap-Flights-To-Florida-Keys.d6023765.Travel-Guide-Flights)[ Florida Keys Hotels ](https://expedia.ca/Florida-Keys-Hotels.d6023765.Travel-Guide-Hotels)[ Florida Keys Vacation Rentals ](https://expedia.ca/Florida-Keys-Vacation-Rentals.d6023765.Travel-Guide-VacationRentals)[ Florida Keys Car Rentals ](https://expedia.ca/Car-Rentals-In-Florida-Keys.d6023765.Car-Rental-Guide)[ Florida Keys Vacations ](https://expedia.ca/Florida-Keys.d6023765.Destination-Travel-Guides)[ Things to do in Florida Keys ](https://expedia.ca/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. ![](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