Title: Beach Vacations in Chokoloskee Island 2026/2026 | 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 Beach 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 Beach 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 $824 per person Jan 8 - Jan 11 found 1 day ago Roundtrip flight included Toronto (YTO) to Fort Myers (RSW) 9.6/10 Exceptional! (477 reviews) No real breakfast, a coffee shop with limited menu. Reviewed on Dec 4, 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 $1,869 per person Jan 10 - Jan 17 found 1 day ago Roundtrip non-stop flight included Toronto (YYZ) to Fort Myers (RSW) 9.8/10 Exceptional! (527 reviews) El personal súper amable y todo muy limpio,la habitación excelente Reviewed on Nov 24, 2025 ![Wiggins Pass Chalet](https://images.trvl-media.com/lodging/59000000/58120000/58115200/58115199/d32fc7b1_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Wiggins Pass Chalet CA $1,889 per person Feb 13 - Feb 20 found 1 day ago Roundtrip non-stop flight included Detroit (DTW) to Fort Myers (RSW) 9.6/10 Exceptional! (236 reviews) Clean and comfortable Reviewed on Nov 23, 2025 ![Hilton Naples](https://images.trvl-media.com/lodging/1000000/450000/448200/448199/29d5d584_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Hilton Naples Central Naples CA $2,337 per person Feb 13 - Feb 20 found 1 day ago Roundtrip non-stop flight included Detroit (DTW) to Fort Myers (RSW) 9.2/10 Wonderful! (1,312 reviews) Close to beach and 5th Ave Reviewed on Dec 2, 2025 ![Marriott Sanibel Harbour Resort & Spa](https://images.trvl-media.com/lodging/1000000/10000/3100/3079/ac9a3a07_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Marriott Sanibel Harbour Resort & Spa Punta Rassa CA $1,724 per person Feb 17 - Feb 24 found 1 day ago Roundtrip flight included Hamilton (YHM) to Fort Myers (RSW) 8.4/10 Very Good! (1,005 reviews) The staff was extremely friendly. Property is beautiful. Reviewed on Nov 25, 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/2026-01-04/2026-01-11/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=MRK&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## 5\* Beach holidays in Chokoloskee Island Price found within the past 48 hours. Click for updated prices. ![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 $1,395 per person Jan 8 - Jan 11 found 1 day ago Roundtrip flight included Toronto (YTO) to Fort Myers (RSW) 9.4/10 Exceptional! (609 reviews) Very clean, amazing restaurants to choose fr I highly recommend! Reviewed on Nov 30, 2025 ![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 $2,469 per person Feb 17 - Feb 24 found 1 day ago Roundtrip flight included Hamilton (YHM) 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 $7,610 per person Feb 13 - Feb 20 found 1 day ago Roundtrip non-stop flight included Detroit (DTW) to Fort Myers (RSW) 6/10 (2 reviews) 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/2026-01-04/2026-01-11/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=MRK&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## 3 Night Beach holidays in Chokoloskee Island Price found within the past 48 hours. Click for updated prices. ![Wiggins Pass Chalet](https://images.trvl-media.com/lodging/59000000/58120000/58115200/58115199/d32fc7b1_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Wiggins Pass Chalet CA $690 per person Jan 8 - Jan 11 found 1 day ago Roundtrip flight included Toronto (YTO) to Fort Myers (RSW) 9.6/10 Exceptional! (236 reviews) Clean and comfortable Reviewed on Nov 23, 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 $824 per person Jan 8 - Jan 11 found 1 day ago Roundtrip flight included Toronto (YTO) to Fort Myers (RSW) 9.6/10 Exceptional! (477 reviews) No real breakfast, a coffee shop with limited menu. Reviewed on Dec 4, 2025 ![Naples Grande Beach Resort](https://images.trvl-media.com/lodging/1000000/20000/15900/15898/65da812e_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Naples Grande Beach Resort Park Shore CA $849 per person Jan 8 - Jan 11 found 1 day ago Roundtrip flight included Toronto (YTO) to Fort Myers (RSW) 9/10 Wonderful! (1,914 reviews) The property was very beautiful and well maintain. Staff were great and helpful. Reviewed on Dec 3, 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/2026-01-04/2026-01-11/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=MRK&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## 4 Night Beach holidays in Chokoloskee Island Price found within the past 48 hours. Click for updated prices. ![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 $760 per person Jan 26 - Jan 30 found 1 day ago Roundtrip flight included Toronto (YYZ) to Fort Myers (RSW) 9.2/10 Wonderful! (704 reviews) Clean, modern and amenities were top notch. The pools, gym, saunas and entire facility was very relaxing. Definitely will visit again. Reviewed on Dec 4, 2025 ![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 $869 per person Jan 19 - Jan 23 found 18 hours ago Roundtrip flight included Montreal (YUL) to Fort Myers (RSW) 9.2/10 Wonderful! (1,001 reviews) The staff-Erika and Penny, were so wonderful and attentive to our requests! The clean room, the beautiful grounds and the restaurant manager, Raymond, so friendly. Just a perfect stay and memories made. Thank you. Catherine & Ernie K Reviewed on Nov 28, 2025 ![Hilton Garden Inn Ft Myers](https://images.trvl-media.com/lodging/1000000/850000/848800/848740/d8bd559a_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Hilton Garden Inn Ft Myers Villas CA $926 per person Feb 17 - Feb 21 found 8 hours ago Roundtrip non-stop flight included Detroit (DTW) to Fort Myers (RSW) 8.6/10 Excellent! (1,002 reviews) In general, excellent service. Reviewed on Nov 30, 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/2026-01-04/2026-01-11/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=MRK&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## Find the best beach vacations in Chokoloskee Island #### What are some benefits when booking beach vacations in Chokoloskee Island? When you travel to the beach in Chokoloskee Island, soft sands and inviting waters, warm sun and gentle breezes will help you relax. This applies to the whole family, as kids and adults can find something fun to do, so family beach vacations are the quintessential family trip. #### How can I book the best beach vacations in Chokoloskee Island? To find the best beach vacation, you'll need to book the right accommodations for your family. What the best is depends on what you want from your Chokoloskee Island trip. Fortunately, you can use various filters combined with the beach filter to sort for what you want. Additionally, you'll need to consider the time of year you visit. #### Can I book cheap beach vacations in Chokoloskee Island? There are quite a few things you can do to get cheap beach vacations in Chokoloskee Island. Prices range from CA $690, and if you want to keep yours on the lower side, you may want to consider just how close to the beach you are. If you don't mind a bit of a walk, further away is typically cheaper. Additionally booking something with a kitchen can help you save by avoiding dining out. #### Can I book beach packages? Yes, and you'll find quite a few beach packages available in Chokoloskee Island. These package deals let you save by booking your accommodation and your flight together with savings of up to 36\. #### Why should I book family beach vacations? When you're travelling with the family to Chokoloskee Island, booking your vacation by the beach is one of the best ways to keep everyone happy. There's a reason why some of the most memorable family trips for kids are family beach vacations. You'll be just steps away from the water, and you can often enjoy stunning views of the shore from your room. #### How can I find a beachfront vacation in Chokoloskee Island? It's easy to find a beachfront vacation accommodation in Chokoloskee Island using the search filter. You can filter for waterfront properties specifically that will only show you results that have beautiful views of the shoreline. #### How can I book last-minute beach vacations? Travelling at the last minute doesn't mean you're out of luck to have a dream beach vacation. Last-minute beach vacations may even offer a nice discount as the owners of hotels or other accommodations try to fill their remaining vacancies. All you have to do is input your travel dates and Chokoloskee Island as your destination and see what's available. #### Can I find all-inclusive beach vacations ? Yes, all you have to do to find all-inclusive beach vacations in Chokoloskee Island is to use the search filter. It will automatically restrict your results to all-inclusive deals that allow you to plan the entire trip in advance. #### Can I book a beach trip that's fully refundable? Any fully refundable booking can bring peace of mind, and we're happy to offer this feature in several packages and locations throughout Florida. All you have to do to find them is check the policies section on each accommodation page. Of course, you can filter for fully-refundable results specifically, too. #### Why should I book beach vacations with Expedia? When you book with Expedia, you'll find a one-stop shop for all your planning needs. You can book your flight and accommodation at the same place and potentially get a discount for booking these together. You can also take advantage of the Expedia Rewards program. Becoming a member is free, and when you do, you'll earn points with every booking will add discounts on subsequent trips. ## Beach Hotels in Chokoloskee Island ![Deep Water Access with a Panoramic View of Chokoloskee Bay](https://images.trvl-media.com/lodging/30000000/29630000/29623500/29623408/a4bd5fde_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Deep Water Access with a Panoramic View of Chokoloskee Bay Chokoloskee FL - 4 min walk from Smallwood Store Book a stay at this beach vacation home in Chokoloskee. Enjoy free WiFi, a beach locale, and a garden. Popular attractions Smallwood Store and Chokoloskee Bay ... 9.8/10 Exceptional! (55 reviews) Awesome place! Very clean, private, beautiful area. We definitely plan on coming back! Reviewed on Oct 21, 2025 [](https://expedia.ca/Chokoloskee-Hotels-Deep-Water-Access-With-A-Panoramic-View-Of-Chokoloskee-Bay.h29623408.Hotel-Information) [See all 245 properties in Chokoloskee Island](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Package®ionId=553248635976468286) 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 Beach Vacation Destinations > - [Myrtle beach vacations ](https://www.expedia.ca/lp/theme-vacations/beach-vacations/601685/Myrtle-Beach) > - [Miami beach vacations ](https://www.expedia.ca/lp/theme-vacations/beach-vacations/8833/Miami-Beach) > - [Florida beach vacations ](https://www.expedia.ca/lp/theme-vacations/beach-vacations/211/Florida) > - [Barbados beach vacations ](https://www.expedia.ca/lp/theme-vacations/beach-vacations/16/Barbados) > - [South beach vacations ](https://www.expedia.ca/lp/theme-vacations/beach-vacations/6138745/South-Beach) > - [Palm beach vacations ](https://www.expedia.ca/lp/theme-vacations/beach-vacations/9061/Palm-Beach) > - [Daytona beach vacations ](https://www.expedia.ca/lp/theme-vacations/beach-vacations/6023995/Daytona-Beach) > - [Newport beach vacations ](https://www.expedia.ca/lp/theme-vacations/beach-vacations/8111/Newport-Beach) > - [Vero beach vacations ](https://www.expedia.ca/lp/theme-vacations/beach-vacations/6023660/Vero-Beach) > - [India beach vacations ](https://www.expedia.ca/lp/theme-vacations/beach-vacations/80/India) > - [Laguna beach vacations ](https://www.expedia.ca/lp/theme-vacations/beach-vacations/6298668/Laguna-Beach) > - [Ontario beach vacations ](https://www.expedia.ca/lp/theme-vacations/beach-vacations/2680/Ontario) > - [Canada beach vacations ](https://www.expedia.ca/lp/theme-vacations/beach-vacations/31/Canada) > - [Barcelona beach vacations ](https://www.expedia.ca/lp/theme-vacations/beach-vacations/179992/Barcelona) > - [Fort Myers beach vacations ](https://www.expedia.ca/lp/theme-vacations/beach-vacations/7194/Fort-Myers-Beach) > - [Portugal beach vacations ](https://www.expedia.ca/lp/theme-vacations/beach-vacations/147/Portugal) > - [Italy beach vacations ](https://www.expedia.ca/lp/theme-vacations/beach-vacations/86/Italy) > - [Thailand beach vacations ](https://www.expedia.ca/lp/theme-vacations/beach-vacations/178/Thailand) > - [France beach vacations ](https://www.expedia.ca/lp/theme-vacations/beach-vacations/59/France) ## 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