Title: Romantic Vacations in Florida Keys 2025/2026 | 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 Stay added Flight added Car - Economy - Premium economy - Business class - First class Leaving from Going to Dates Travellers ## Room 1 Adults ChildrenAges 2 to 17 InfantsYounger than 2 I only need accommodation for part of my trip - ## 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 ## 3 Night Romantic holidays in Florida Keys Price found within the past 48 hours. Click for updated prices. ![Pier House Resort & Spa](https://images.trvl-media.com/lodging/1000000/20000/19400/19307/ed076ab9_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Pier House Resort & Spa Key West Historic District CA $1,695 per person Dec 4 - Dec 7 found 1 day ago Roundtrip non-stop flight included Toronto (YTO) to Key West (EYW) 9/10 Wonderful! (1,005 reviews) Loved the property and location! Will definitely stay again! Reviewed on Sep 24, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2025-12-04/2025-12-07/?FromAirport=YTO&Destination=EYW&NumRoom=1&NumAdult=2&NumChild=0&hotelId=19307&paandie=true&HotelClass=40&dealMarker=lZEHMHO0zLZQj6pnOWlSYOvRzMLiqbwDJ0VTRs2o2bWJnwpFcDwLKF_rUDdzjZ7J) ![Southernmost Beach Resort and Guesthouses](https://images.trvl-media.com/lodging/1000000/870000/863400/863329/026f10af_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Southernmost Beach Resort and Guesthouses Old Town Key West CA $1,710 per person Dec 4 - Dec 7 found 1 day ago Roundtrip non-stop flight included Toronto (YTO) to Key West (EYW) 8.6/10 Excellent! (2,750 reviews) The three pools were amazing. We particularly enjoyed the tranquility pool for a quieter or relaxed experience. Lots of great activities and good communication via text from the hotel throughout the stay. Walkable to many of the must see Key West destinations. Reviewed on Sep 27, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2025-12-04/2025-12-07/?FromAirport=YTO&Destination=EYW&NumRoom=1&NumAdult=2&NumChild=0&hotelId=863329&paandie=true&HotelClass=40&dealMarker=bYeZ0zNbyuTEHYoqBgyX5zKpKjUWdThg9zo_L4depRbVUuivf7I01R_Pv6c5Sk3A) ![The Reach Key West, Curio Collection by Hilton](https://images.trvl-media.com/lodging/1000000/460000/457900/457821/888fac6b_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### The Reach Key West, Curio Collection by Hilton Old Town Key West CA $1,849 per person Dec 4 - Dec 7 found 1 day ago Roundtrip non-stop flight included Toronto (YTO) to Key West (EYW) 8.4/10 Very Good! (1,005 reviews) Beach was a little disappointing Reviewed on Sep 26, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2025-12-04/2025-12-07/?FromAirport=YTO&Destination=EYW&NumRoom=1&NumAdult=2&NumChild=0&hotelId=457821&paandie=true&HotelClass=40&dealMarker=bYeZ0zNbyuTEHYoqBgyX5zKpKjUWdThg9zo_L4depRZyhj8cwaa1TusAbF8J8V6u) 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/2025-10-28/2025-11-04/?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. ![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 $650 per person Nov 2 - Nov 6 found 11 hours ago Roundtrip flight included Boston (BOS) to Miami (MIA) 9.2/10 Wonderful! (1,201 reviews) It was nice and peacful Reviewed on Sep 20, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2025-11-02/2025-11-06/?FromAirport=BOS&Destination=MIA&NumRoom=1&NumAdult=2&NumChild=0&hotelId=5780&paandie=true&dealMarker=vCJ_-WAfKaSPWdQS4ZiMalLojJUJLiVf9fLaQkKHDh0QOGgTLMuntu2sMaqfUrNd) ![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 $1,378 per person Nov 2 - Nov 6 found 11 hours ago Roundtrip flight included Boston (BOS) to Miami (MIA) 8/10 Very Good! (1,007 reviews) Never used spa and didn't have a pet. Interaction with staff was not good. On check in the receptionist did upgrade our room without our requesting it. It turns out there were very few guests. The staff did not make up our room on day 2 and said they needed 24 hours notice. The front desk folks agreed to replace the towels and coffee pods but never did. The room had a tv that only showed snow on the screen and the front desk said they would send up help to take care of it. The help arrived next morning 15 minutes prior to checkout time. When we checked out of the resort our invoice included a daily self parking $25 fee along with a plethora of other fees not previously known. Room was nice and the property was well taken care of but otherwise we would not recommend this resort Reviewed on Sep 26, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2025-11-02/2025-11-06/?FromAirport=BOS&Destination=MIA&NumRoom=1&NumAdult=2&NumChild=0&hotelId=6068&paandie=true&dealMarker=vCJ_-WAfKaSPWdQS4ZiMall6w3GbdUX9z1XotcDvkqciiO-WWPXLx1GLYpod-gpi) ![Tranquility Bay Beachfront Hotel and Resort](https://images.trvl-media.com/lodging/1000000/120000/117100/117099/a50ca43c_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Tranquility Bay Beachfront Hotel and Resort CA $1,026 per person Nov 2 - Nov 6 found 11 hours ago Roundtrip flight included Boston (BOS) to Miami (MIA) 8.8/10 Excellent! (1,005 reviews) Me encantó en todos los sentidos. Volvería con toda seguridad. Reviewed on Sep 25, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2025-11-02/2025-11-06/?FromAirport=BOS&Destination=MIA&NumRoom=1&NumAdult=2&NumChild=0&hotelId=117099&paandie=true&dealMarker=vCJ_-WAfKaSPWdQS4ZiMall6w3GbdUX9z1XotcDvkqeBHZE4QY61pKakfLzqjNg1) 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/2025-10-28/2025-11-04/?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 $650 and can enjoy savings of up to 24 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/1000000/870000/863400/863329/026f10af_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Southernmost Beach Resort and Guesthouses 1319 Duval Street, Key West, FL - 11 min walk from Duval Street Stay at this 4-star beach hotel in Key West. Enjoy free WiFi, 3 outdoor pools, and a full-service spa. Our guests praise the pool and the bar in our reviews. ... 8.6/10 Excellent! (2,785 reviews) "The three pools were amazing. We particularly enjoyed the tranquility pool for a quieter or relaxed experience. Lots of great activities and good communication via text from the hotel throughout the stay. Walkable to many of the must see Key West destinations." Reviewed on Sep 27, 2025 [](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/b83a5985_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! (1,100 reviews) "Really liked the 4 pools, the restaurant and the chickens walking around." Reviewed on Sep 23, 2025 [](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/ed076ab9_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Pier House Resort & Spa 1 Duval St, Key West, FL - 11 min walk from Duval Street Stay at this 4-star beach resort in Key West. Enjoy a full-service spa, a private beach, and 2 bars/lounges. Our guests praise the pool and the bar in our reviews. ... 9/10 Wonderful! (1,011 reviews) "Loved the property and location! Will definitely stay again!" Reviewed on Sep 24, 2025 [](https://expedia.ca/Key-West-Hotels-Pier-House-Resort-Spa.h19307.Hotel-Information) [See all 8,389 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 Ontario](https://www.expedia.ca/lp/theme-vacations/romantic-vacations/2680/Ontario) > - [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 ![QR code to download the app](data:image/png;base64,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)