Title: Romantic Vacations in Chokoloskee Island 2026 | Expedia.ca ![](https://images.trvl-media.com/place/3000430940/6a686070-6a7c-41a9-b800-f0b3cf385f24.jpg?impolicy=fcrop&w=1200&h=300&q=medium) # Chokoloskee Island Romantic Vacations ## Book a Hotel + Flight or Car together to unlock savings Photo by Noel Benadom - ## 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 Chokoloskee Island Price found within the past 48 hours. Click for updated prices. ![The Perry Hotel Naples](https://images.trvl-media.com/lodging/103000000/102390000/102386400/102386398/0ad2742c_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### The Perry Hotel Naples CA $1,488 per person Feb 5 - Feb 11 found 1 day ago Roundtrip flight included Detroit (DTW) to Fort Myers (RSW) 9.6/10 Exceptional! (477 reviews) Food quality was excellent, staff was very polite, professional, and accommodating especially Reuben at the front desk, the hotel is under a year old so very current with technology, and lastly it's a beautiful hotel! Reviewed on Dec 15, 2025 ![Innovation Hotel](https://images.trvl-media.com/lodging/83000000/82990000/82988300/82988281/61b55ef1_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Innovation Hotel CA $1,652 per person Feb 5 - Feb 11 found 1 day ago Roundtrip flight included Detroit (DTW) to Fort Myers (RSW) 9.8/10 Exceptional! (527 reviews) We had a great time! Modern design, great service and friendly. Reviewed on Dec 14, 2025 ![Hyatt Vacation Club at Coconut Cove, Bonita Springs](https://images.trvl-media.com/lodging/1000000/1000000/991200/991114/fedffc57_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Hyatt Vacation Club at Coconut Cove, Bonita Springs CA $2,196 per person Feb 3 - Feb 10 found 1 day ago Roundtrip non-stop flight included Toronto (YTO) to Fort Myers (RSW) 9.2/10 Wonderful! (704 reviews) The place was fabulous!!! Everyone was fabulous! Only issue was that the adult pool was not just adults. Parents would leave their kids in it and they would yell and splash. Reviewed on Dec 18, 2025 ![Landing Apartments Fort Myers near Olympia Pointe](https://images.trvl-media.com/lodging/119000000/118250000/118241800/118241745/2104d438_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Landing Apartments Fort Myers near Olympia Pointe CA $1,524 per person Feb 18 - Feb 25 found 1 day ago Roundtrip flight included Detroit (DTW) to Fort Myers (RSW) 10/10 Exceptional! (2 reviews) This property is beautiful! We were thoroughly impressed with how nice our room was and how amazing the facilities were. The pool is incredible and made our stay that much better! We would definitely come back again and recommend to others. Reviewed on Oct 7, 2025 ![Inn on Fifth](https://images.trvl-media.com/lodging/1000000/90000/85000/84910/7138f29c_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Inn on Fifth Old Naples CA $4,707 per person Feb 5 - Feb 11 found 1 day ago Roundtrip flight included Detroit (DTW) to Fort Myers (RSW) 9.4/10 Exceptional! (1,000 reviews) This was described as a boutique hotel. It is dated and hasn't been updated since the '90s, with a 90s contemporary style of artwork, flooring and decor. The rooms are tiled so bring slippers or you're walking on cold tile. There's no magnifying mirror in the bathroom, no mini bar, the gift shop is minuscule, the size of a closet.. My room overlooked the parking garage. Check in is 4 pm. I was told I'd get a text when my room is ready, waited and by 4:00 I went to the front desk and asked why I didn't get a text even though it was obvious my room had been ready for a while. The staff is friendly and the place is clean but the only good thing about this hotel is the location. Reviewed on Dec 17, 2025 Don't see what you're looking for? See all available trips from Columbus to Chokoloskee Island [View all trips](https://expedia.ca/go/package/search/FlightHotel/2026-01-19/2026-01-26/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=MRK&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## 5\* Romantic holidays in Chokoloskee Island Price found within the past 48 hours. Click for updated prices. ![Sundial Beach Resort & Spa](https://images.trvl-media.com/lodging/1000000/10000/2000/1939/5481c209_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Sundial Beach Resort & Spa Mid Island CA $1,584 per person Jan 29 - Feb 3 found 1 day ago Roundtrip non-stop flight included Toronto (YTO) to Fort Myers (RSW) 8.6/10 Excellent! (2,581 reviews) Very clean, fun activities for the kids. Reviewed on Nov 29, 2025 ![Naples Beach Club, A Four Seasons Resort](https://images.trvl-media.com/lodging/1000000/10000/9800/9786/e6518097_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Naples Beach Club, A Four Seasons Resort Coquina Sands CA $4,433 per person Feb 18 - Feb 22 found 6 hours ago Roundtrip flight included Toronto (YTO) to Fort Myers (RSW) 6/10 (2 reviews) ![The Ritz-Carlton Naples, Tiburón](https://images.trvl-media.com/lodging/1000000/790000/788300/788295/75f45fbf_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### The Ritz-Carlton Naples, Tiburón CA $2,992 per person Feb 18 - Feb 22 found 6 hours ago Roundtrip flight included Toronto (YTO) to Fort Myers (RSW) 9.4/10 Exceptional! (609 reviews) The staff overall was very nice! The only small issue we had was that a lot of times we couldn't reqch valet, were transferred to the front desk, asked for our car, and then they never communicated with valet to get our car. The rooms were okay, nothing spectacular, and the beds weren't comfortable at all. We specifically won't stay here again because of the bed discomfort. Reviewed on Dec 7, 2025 Don't see what you're looking for? See all available trips from Columbus to Chokoloskee Island [View all trips](https://expedia.ca/go/package/search/FlightHotel/2026-01-19/2026-01-26/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=MRK&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## 3 Night Romantic holidays in Chokoloskee Island Price found within the past 48 hours. Click for updated prices. ![Doubletree by Hilton Fort Myers at Bell Tower Shops](https://images.trvl-media.com/lodging/1000000/20000/12400/12375/704cf90c_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Doubletree by Hilton Fort Myers at Bell Tower Shops Villas CA $533 per person Feb 3 - Feb 6 found 10 hours ago Roundtrip flight included Detroit (DTW) to Fort Myers (RSW) 8.8/10 Excellent! (1,004 reviews) In a plaza with a lot of options! Staff was great! Reviewed on Dec 12, 2025 ![Inn on Fifth](https://images.trvl-media.com/lodging/1000000/90000/85000/84910/7138f29c_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Inn on Fifth Old Naples CA $2,106 per person Mar 4 - Mar 7 found 1 day ago Roundtrip flight included Toronto (YYZ) to Fort Myers (RSW) 9.4/10 Exceptional! (1,000 reviews) This was described as a boutique hotel. It is dated and hasn't been updated since the '90s, with a 90s contemporary style of artwork, flooring and decor. The rooms are tiled so bring slippers or you're walking on cold tile. There's no magnifying mirror in the bathroom, no mini bar, the gift shop is minuscule, the size of a closet.. My room overlooked the parking garage. Check in is 4 pm. I was told I'd get a text when my room is ready, waited and by 4:00 I went to the front desk and asked why I didn't get a text even though it was obvious my room had been ready for a while. The staff is friendly and the place is clean but the only good thing about this hotel is the location. Reviewed on Dec 17, 2025 ![LaPlaya Beach & Golf Resort - A Noble House Resort](https://images.trvl-media.com/lodging/1000000/30000/25200/25199/d2442103_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### LaPlaya Beach & Golf Resort - A Noble House Resort Vanderbilt Beach CA $2,964 per person Feb 12 - Feb 15 found 1 day ago Roundtrip non-stop flight included Detroit (DTW) to Fort Myers (RSW) 9/10 Wonderful! (1,000 reviews) Loved everything about this property. Beautiful rooms, loved the beach, pools, and dining. Staff went above expectations. Great location. We will be back! Reviewed on Dec 11, 2025 Don't see what you're looking for? See all available trips from Columbus to Chokoloskee Island [View all trips](https://expedia.ca/go/package/search/FlightHotel/2026-01-19/2026-01-26/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=MRK&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## 4 Night Romantic holidays in Chokoloskee Island Price found within the past 48 hours. Click for updated prices. ![Matanzas Inn Bayside Resort and Marina](https://images.trvl-media.com/lodging/3000000/2670000/2665100/2665085/fc463bf9_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Matanzas Inn Bayside Resort and Marina CA $1,006 per person Feb 18 - Feb 22 found 1 day ago Roundtrip flight included Toronto (YTO) to Fort Myers (RSW) 9.2/10 Wonderful! (1,010 reviews) got the 2 bdr unit next to office. rooms were great, check inn easy, pool and hot tub made it very enjoyable. my only complaint was i only booked for 1 night. will be my stop when return Reviewed on Dec 18, 2025 ![Innovation Hotel](https://images.trvl-media.com/lodging/83000000/82990000/82988300/82988281/61b55ef1_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Innovation Hotel CA $1,351 per person Feb 18 - Feb 22 found 6 hours ago Roundtrip flight included Toronto (YTO) to Fort Myers (RSW) 9.8/10 Exceptional! (527 reviews) We had a great time! Modern design, great service and friendly. Reviewed on Dec 14, 2025 ![The Perry Hotel Naples](https://images.trvl-media.com/lodging/103000000/102390000/102386400/102386398/0ad2742c_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### The Perry Hotel Naples CA $1,111 per person Feb 18 - Feb 22 found 6 hours ago Roundtrip flight included Toronto (YTO) to Fort Myers (RSW) 9.6/10 Exceptional! (477 reviews) Food quality was excellent, staff was very polite, professional, and accommodating especially Reuben at the front desk, the hotel is under a year old so very current with technology, and lastly it's a beautiful hotel! Reviewed on Dec 15, 2025 Don't see what you're looking for? See all available trips from Columbus to Chokoloskee Island [View all trips](https://expedia.ca/go/package/search/FlightHotel/2026-01-19/2026-01-26/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=MRK&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## Plan unforgettable romantic Chokoloskee Island vacations #### What are some of the benefits of booking a romantic Chokoloskee Island vacation? When booking a romantic Chokoloskee Island 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 Florida. #### 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 Chokoloskee Island 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 Chokoloskee Island? Yes, there are several options for booking cheap romantic vacations that don't break the bank. You'll find prices as low as CA $533 and can enjoy savings of up to 38 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 Chokoloskee Island? 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 Chokoloskee Island 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 Chokoloskee Island. #### Can I book a romantic Chokoloskee Island 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 Chokoloskee Island search. #### Can I book a romantic trip to Chokoloskee Island that is fully refundable? Several romantic Chokoloskee Island 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. ## 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 Chokoloskee Island ](https://expedia.ca/Cheap-Flights-To-Chokoloskee-Island.d553248635976468286.Travel-Guide-Flights)[ Chokoloskee Island Hotels ](https://expedia.ca/Chokoloskee-Island-Hotels.d553248635976468286.Travel-Guide-Hotels)[ Chokoloskee Island Vacation Rentals ](https://expedia.ca/Chokoloskee-Island-Vacation-Rentals.d553248635976468286.Travel-Guide-VacationRentals)[ Chokoloskee Island Car Rentals ](https://expedia.ca/Car-Rentals-In-Chokoloskee-Island.d553248635976468286.Car-Rental-Guide)[ Chokoloskee Island Vacations ](https://expedia.ca/Chokoloskee-Island.d553248635976468286.Destination-Travel-Guides) \* 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