Title: Wing South Vacation Packages | Holiday Packages & Trips 2026/2027 from CA $699 Expedia.ca [Hotels in Wing South](https://expedia.ca/Wing-South-Naples-Hotels.0-n553248635976481348-0.Travel-Guide-Filter-Hotels)[Flights to Naples](https://expedia.ca/Cheap-Flights-To-Naples.d602724.Travel-Guide-Flights)[Things to do in Naples](https://expedia.ca/Things-To-Do-In-Naples.d602724.Travel-Guide-Activities)[Wing South Car Rentals](https://expedia.ca/Car-Rentals-In-Wing-South.d553248635976481348.Car-Rental-Guide) ![](https://a.travel-assets.com/travel-assets-manager/fallback-images-brand/bex_packages.jpeg?impolicy=fcrop&w=1200&h=300&q=medium) # Wing South Vacation Packages ## 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 ## Top Holiday Package Deals in Wing South Price found within the past 48 hours. Click for updated prices. ![Matanzas Inn Bayside Resort and Marina](https://images.trvl-media.com/lodging/3000000/2670000/2665100/2665085/78d7ce83_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Matanzas Inn Bayside Resort and Marina CA $699 per person Jun 30 - Jul 4 found 14 hours ago Roundtrip non-stop flight included Detroit (DTW) to Fort Myers (RSW) 9.4/10 Exceptional! (1,008 reviews) This place is a gem! Reviewed on Apr 6, 2026 ![The Suites at Fishermen’s Village- 2 Bedroom Suites](https://images.trvl-media.com/lodging/53000000/52080000/52074900/52074809/7bc32ddb_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### The Suites at Fishermen’s Village- 2 Bedroom Suites Punta Gorda Isles CA $931 per person May 15 - May 19 found 13 hours ago Roundtrip non-stop flight included Detroit (DTW) to Fort Myers (RSW) 9.8/10 Exceptional! (1,146 reviews) Absolute hidden Gem!! Loved it Reviewed on Apr 7, 2026 ![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 $1,892 per person May 14 - May 18 found 1 day ago Roundtrip flight included Detroit (DTW) to Fort Myers (RSW) 9/10 Wonderful! (1,002 reviews) Excellent , more than what I expected Reviewed on Apr 5, 2026 ![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 $755 per person Jun 27 - Jul 1 found 6 hours ago Roundtrip flight included Toronto (YTO) to Fort Myers (RSW) 9.6/10 Exceptional! (725 reviews) Very beautiful hotel, everything in great condition Reviewed on Apr 7, 2026 ![Hyatt Vacation Club at Coconut Cove, Bonita Springs](https://images.trvl-media.com/lodging/1000000/1000000/991200/991114/7c494168_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Hyatt Vacation Club at Coconut Cove, Bonita Springs CA $953 per person Jun 30 - Jul 4 found 14 hours ago Roundtrip non-stop flight included Detroit (DTW) to Fort Myers (RSW) 9/10 Wonderful! (821 reviews) Beautiful Grounds! Very comfortable rooms. The pool was a blast! Reviewed on Apr 6, 2026 ## Where to stay in Wing South Find the best Wing South areas and neighborhoods for the activities you enjoy most. [Learn more about Wing South](https://expedia.ca/Naples-Wing-South.dx553248635976481348) ![East Naples](https://images.trvl-media.com/place/6177501/5f861be1-5382-48a5-99ea-10946f7b2f07.jpg?impolicy=fcrop&w=350&h=192&q=medium) ### East Naples 4/5(11 area reviews) Beaches, shopping, and restaurants are just a few things travelers enjoy about East Naples. Check out Fifth Avenue South or Naples Botanical Garden while you're exploring the area. [Find hotel + flight trips in East Naples](https://expedia.ca/go/package/search/FlightHotel/?FromAirport=Downtown%20Columbus,%20Columbus,%20Ohio,%20United%20States%20of%20America&Destination=East%20Naples&DestID=6177511&DaysInFuture=30&StayLength=7&rfrr=TG.LP.Dest.PKG.Neighborhoods) ![walking down the bridge of Baker park in Naples Florida in southwest Florida public park ](https://images.trvl-media.com/place/553248635975749203/5fdacfb7-94ce-4350-9d5b-8788aaea5743.jpg?impolicy=fcrop&w=350&h=192&q=medium) ### Central Naples 1 out of top 10 points of interest in this area If you're spending some time in Central Naples, Naples Zoo at Caribbean Gardens and Naples Grande Golf Club are top sights worth seeing. [Find hotel + flight trips in Central Naples](https://expedia.ca/go/package/search/FlightHotel/?FromAirport=Downtown%20Columbus,%20Columbus,%20Ohio,%20United%20States%20of%20America&Destination=Central%20Naples&DestID=553248635975749203&DaysInFuture=30&StayLength=7&rfrr=TG.LP.Dest.PKG.Neighborhoods) ![old city dock in tropical Naples Florida; Shutterstock ID 155142134](https://images.trvl-media.com/place/6337317/773e6b3f-e6bb-40d2-8271-236a37a0dcaa.jpg?impolicy=fcrop&w=350&h=192&q=medium) ### Old Naples 3 out of top 10 points of interest in this area 5/5(25 area reviews) The stunning beaches and popular shops are just a few highlights of Old Naples. Make a stop by Fifth Avenue South or Naples Beach while you're exploring the area. [Find hotel + flight trips in Old Naples](https://expedia.ca/go/package/search/FlightHotel/?FromAirport=Downtown%20Columbus,%20Columbus,%20Ohio,%20United%20States%20of%20America&Destination=Old%20Naples&DestID=6337317&DaysInFuture=30&StayLength=7&rfrr=TG.LP.Dest.PKG.Neighborhoods) ![Delnor Wiggins State Park - Panoramic aerial view](https://images.trvl-media.com/place/6177550/10d8a15d-ce96-43ef-bf31-e37eb5973c97.jpg?impolicy=fcrop&w=350&h=192&q=medium) ### Naples Park Located in North Naples, Naples Park is bounded by U.S. Route 41 and offers easy access to Vanderbilt Lagoon. Enjoy shopping at the nearby outdoor mall, The Mercato, for a delightful experience. [Find hotel + flight trips in Naples Park](https://expedia.ca/go/package/search/FlightHotel/?FromAirport=Downtown%20Columbus,%20Columbus,%20Ohio,%20United%20States%20of%20America&Destination=Naples%20Park&DestID=6177550&DaysInFuture=30&StayLength=7&rfrr=TG.LP.Dest.PKG.Neighborhoods) ![Vanderbilt Beach](https://images.trvl-media.com/place/6065875/2d1b283b-31ba-4ddc-adeb-36fe90f32f9d.jpg?impolicy=fcrop&w=350&h=192&q=medium) ### Vanderbilt Beach 1 out of top 10 points of interest in this area 4.5/5(4 area reviews) While visiting Vanderbilt Beach, you might make a stop by sights like Vanderbilt Beach and Delnor-Wiggins Pass State Park. [Find hotel + flight trips in Vanderbilt Beach](https://expedia.ca/go/package/search/FlightHotel/?FromAirport=Downtown%20Columbus,%20Columbus,%20Ohio,%20United%20States%20of%20America&Destination=Vanderbilt%20Beach&DestID=553248635977184221&DaysInFuture=30&StayLength=7&rfrr=TG.LP.Dest.PKG.Neighborhoods) ## Wing South Hotel Deals ![Hilton Marco Island Beach Resort and Spa](https://images.trvl-media.com/lodging/1000000/20000/17600/17575/65dd4041_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Hilton Marco Island Beach Resort and Spa 560 S Collier Blvd Marco Island FL Fully refundableReserve now, pay when you stay CA $337 CA $451 total May 3 - May 4 includes taxes & fees 9/10 Wonderful! (1,742 reviews) Overall great property for families . Had to ask housekeeping staff repeatedly to repair shower gel container . Robe never provided Reviewed on Apr 7, 2026 [](https://expedia.ca/Hotel-Search?startDate=03%2F05%2F2026&endDate=04%2F05%2F2026&selected=17575&PinnedHotelID=17575&HadPinnedHotel=true®ionId=553248635976481348) ![Great Wolf Lodge Naples](https://images.trvl-media.com/lodging/113000000/112020000/112014600/112014521/c6e60574_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Great Wolf Lodge Naples 3900 City Gate Blvd N. Naples FL Fully refundableReserve now, pay when you stay CA $221 CA $245 total Apr 22 - Apr 23 includes taxes & fees 9.4/10 Exceptional! (646 reviews) This hotel is amazing!!!! It feels you are in a fairy tail story or even Disney. A lot of activities for kids. Everything easy and without any error. The food was just good compared with the average waterpark resorts and many different options. I definitely recommend this one. I will be back this ... Reviewed on Apr 6, 2026 [](https://expedia.ca/Hotel-Search?startDate=22%2F04%2F2026&endDate=23%2F04%2F2026&selected=112014521&PinnedHotelID=112014521&HadPinnedHotel=true®ionId=553248635976481348) ![La Quinta Inn & Suites by Wyndham Naples Downtown](https://images.trvl-media.com/lodging/1000000/30000/24700/24612/3a0774b2_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### La Quinta Inn & Suites by Wyndham Naples Downtown 1555 5th Ave S Naples FL Fully refundableReserve now, pay when you stay CA $142 CA $158 total May 3 - May 4 includes taxes & fees 8.2/10 Very Good! (1,898 reviews) The overall condition of the property was good. The pool area did not look well kept, needed more chlorine, and needed to be vacuumed. Staff were very friendly. Breakfasts were average. Reviewed on Apr 7, 2026 [](https://expedia.ca/Hotel-Search?startDate=03%2F05%2F2026&endDate=04%2F05%2F2026&selected=24612&PinnedHotelID=24612&HadPinnedHotel=true®ionId=553248635976481348) [See all 10,909 properties in Wing South](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=09%2F04%2F2026&endDate=10%2F04%2F2026®ionId=553248635976481348) 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. ![](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) ## Frequently asked questions ### How much does a Wing South vacation package cost? ### How do I get a cheap travel package to Wing South? ### Where should I stay in Wing South? ### How far in advance should I book my Wing South vacation? ### What does an Expedia Wing South travel package include? ### What should I know before booking a Wing South travel package? ### Can I choose my airline with a Wing South Expedia vacation package? ### If I'm not able to travel, can I cancel my Wing South vacation package? ### Discover the most popular places to visit in Wing South ![Fifth Avenue South](https://images.trvl-media.com/place/6337227/652d7a23-0ecb-418a-b7cc-95f00eef6cc8.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### Fifth Avenue South Enjoy many happy hours exploring the variety of shops, dining options and cultural attractions of this popular shopping district in Naples, Florida. [](https://expedia.ca/Fifth-Avenue-South-Old-Naples.d6337227.Vacation-Attraction) ![Pristine and idyllic beach at sunset in a bright day, Naples, Florida, USA](https://images.trvl-media.com/place/553248621565061337/c3e350a9-2166-42a1-bc09-fe8d70fa80a9.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### Naples Beach Why not spend a carefree afternoon at Naples Beach during your travels in Naples? Stroll along the seaside or visit the shops while you're in the area. [](https://expedia.ca/Naples-Beach-West-Naples.d553248621565061337.Vacation-Attraction) ![Vanderbilt beach in Naples, Florida](https://images.trvl-media.com/place/553248621532652404/2e032eea-d142-4ae9-80c9-a10de88f17a7.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### Vanderbilt Beach If a restful vacation is part of your travel plans, Vanderbilt Beach might be the perfect place to seek out during your trip to North Naples. [](https://expedia.ca/Vanderbilt-Beach-Vanderbilt-Beach.d553248621532652404.Vacation-Attraction) ### Things to do ![Naples Sightseeing Boat Tour](https://mediaim.expedia.com/localexpert/1343716/ac14e815-1432-4873-b606-0821d4890ff8.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### Naples Sightseeing Boat Tour CA $90 per adult **96%** of travellers recommend [](https://expedia.ca/things-to-do/naples-sightseeing-boat-tour.a1343716.activity-details) ![Naples Florida: Downtown Electric Trike Tour](https://mediaim.expedia.com/localexpert/47891159/6efb2442-2dc7-4d4b-aa54-fffa02778569.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### Naples Florida: Downtown Electric Trike Tour - Family Fun CA $96 per adult **100%** of travellers recommend [](https://expedia.ca/things-to-do/naples-florida-downtown-electric-trike-tour-family-fun.a47891159.activity-details) ![Gulf of Mexico Sunset Cruise from Naples](https://mediaim.expedia.com/localexpert/1344546/f630ba30-182b-40d9-a356-41d6167ac3b3.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### Gulf of Mexico Sunset Cruise from Naples CA $101 per adult **88%** of travellers recommend [](https://expedia.ca/things-to-do/gulf-of-mexico-sunset-cruise-from-naples.a1344546.activity-details) [See all activities in Naples](https://expedia.ca/things-to-do/search?rid=553248635976481348) \* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.