Title: Luxury Vacations in Southwest Coast Florida 2026 | Expedia.ca ![](https://images.trvl-media.com/place/7194/a3a41af4-04ff-4ed9-8a12-4ad5a2acfee2.jpg?impolicy=fcrop&w=1200&h=300&q=medium) # Southwest Coast Florida Luxury 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 Luxury hotel deals in Southwest Coast Florida Price found within the past 48 hours. Click for updated prices. ![Casey Key Resorts - Mainland](https://images.trvl-media.com/lodging/7000000/6620000/6619300/6619300/93021f2f_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Casey Key Resorts - Mainland CA $708 per person May 21 - May 24 found 1 hour ago Roundtrip flight included Toronto (YYZ) to Sarasota (SRQ) 8.8/10 Excellent! (1,151 reviews) Friendly staff and great food Reviewed on Mar 21, 2026 ![Sundial Beach Resort & Spa](https://images.trvl-media.com/lodging/1000000/10000/2000/1939/f4e5c65a_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Sundial Beach Resort & Spa Mid Island CA $1,734 per person Apr 30 - May 5 found 1 day ago Roundtrip flight included Detroit (DTW) to Fort Myers (RSW) 8.6/10 Excellent! (2,605 reviews) Room was incorrect and not what we booked .. wrong bed selection Reviewed on Mar 13, 2026 ![Inn on Fifth](https://images.trvl-media.com/lodging/1000000/90000/85000/84910/6086381e_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Inn on Fifth Old Naples CA $1,934 per person May 22 - May 29 found 6 hours ago Roundtrip non-stop flight included Toronto (YTO) to Fort Myers (RSW) 9.4/10 Exceptional! (1,004 reviews) Great hotel in a perfect location right on 5th Avenue in Naples, Florida, surrounded by some of the best restaurants in the area. The property was extremely clean and well maintained. The rooftop pool was awesome and a great place to relax, and the food was very good for a hotel restaurant. The staff was attentive and friendly throughout the stay. Another big plus is that the beach is only about a half mile away, making it an easy walk. The only drawback for me is that I’m a big gym person, and the fitness center felt a bit tired and could use an update. Other than that, it was a great stay and I would definitely come bac Reviewed on Mar 17, 2026 ![Naples Bay Resort & Marina](https://images.trvl-media.com/lodging/2000000/1600000/1599000/1598931/fa0bc766_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Naples Bay Resort & Marina Oyster Bay CA $1,567 per person May 22 - May 29 found 6 hours ago Roundtrip non-stop flight included Toronto (YTO) to Fort Myers (RSW) 9.4/10 Exceptional! (1,004 reviews) The food was over priced. some front desk staff not so nice. had to to pay for parking even though room rate was high. there was an oven but not dish/tray to put in there so it was useless and staff could not supply anything. Reviewed on Mar 21, 2026 ![Wyvern Hotel, an Ascend Collection Hotel](https://images.trvl-media.com/lodging/3000000/2200000/2193300/2193202/75be6006_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Wyvern Hotel, an Ascend Collection Hotel Downtown Punta Gorda CA $1,208 per person May 22 - May 28 found 3 hours ago Roundtrip flight included Ottawa (YOW) to Fort Myers (RSW) 9/10 Wonderful! (1,005 reviews) Rooftop bartenders and wait stay , ignored us. They stood around talking to each other. Had to wave at them for service It was me and my husband we ordered food , I had to ask for silverware and napkins. The girl brought one it took 5 mins to get anyone attention to get a 2nd set. Overall the rooftop busy and not busy very bad service. Reviewed on Mar 21, 2026 Don't see what you're looking for? See all available trips from Columbus to Southwest Coast Florida [View all trips](https://expedia.ca/go/package/search/FlightHotel/2026-04-21/2026-04-28/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=FMY&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## 5\* Luxury holidays in Southwest Coast Florida 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/f4e5c65a_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Sundial Beach Resort & Spa Mid Island CA $1,734 per person Apr 30 - May 5 found 1 day ago Roundtrip flight included Detroit (DTW) to Fort Myers (RSW) 8.6/10 Excellent! (2,605 reviews) Room was incorrect and not what we booked .. wrong bed selection Reviewed on Mar 13, 2026 ![The Ritz-Carlton Naples, Tiburón](https://images.trvl-media.com/lodging/1000000/790000/788300/788295/a653a1be_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### The Ritz-Carlton Naples, Tiburón CA $2,804 per person May 13 - May 18 found 3 hours ago Roundtrip non-stop flight included Montreal (YUL) to Fort Myers (RSW) 9.4/10 Exceptional! (620 reviews) Very nice accomodations. Reviewed on Jan 12, 2026 ![The Ritz-Carlton, Sarasota](https://images.trvl-media.com/lodging/1000000/810000/806200/806101/90558b2d_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### The Ritz-Carlton, Sarasota Central Sarasota CA $5,018 per person Jun 12 - Jun 14 found 24 hours ago Roundtrip non-stop flight included Buffalo (BUF) to Tampa (TPA) 9.2/10 Wonderful! (1,006 reviews) Classic Rittz, but could use a few updates so it doesn't start looking like a Marriott. Reviewed on Mar 4, 2026 Don't see what you're looking for? See all available trips from Columbus to Southwest Coast Florida [View all trips](https://expedia.ca/go/package/search/FlightHotel/2026-04-21/2026-04-28/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=FMY&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## 3 Night Luxury holidays in Southwest Coast Florida Price found within the past 48 hours. Click for updated prices. ![Casey Key Resorts - Mainland](https://images.trvl-media.com/lodging/7000000/6620000/6619300/6619300/93021f2f_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Casey Key Resorts - Mainland CA $708 per person May 21 - May 24 found 1 hour ago Roundtrip flight included Toronto (YYZ) to Sarasota (SRQ) 8.8/10 Excellent! (1,151 reviews) Friendly staff and great food Reviewed on Mar 21, 2026 ![The Ritz-Carlton, Sarasota](https://images.trvl-media.com/lodging/1000000/810000/806200/806101/90558b2d_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### The Ritz-Carlton, Sarasota Central Sarasota CA $2,678 per person May 15 - May 18 found 1 day ago Roundtrip non-stop flight included Toronto (YYZ) to Tampa (TPA) 9.2/10 Wonderful! (1,006 reviews) Classic Rittz, but could use a few updates so it doesn't start looking like a Marriott. Reviewed on Mar 4, 2026 Don't see what you're looking for? See all available trips from Columbus to Southwest Coast Florida [View all trips](https://expedia.ca/go/package/search/FlightHotel/2026-04-21/2026-04-28/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=FMY&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## 4 Night Luxury holidays in Southwest Coast Florida Price found within the past 48 hours. Click for updated prices. ![The Lighthouse Resort Inn & Suites](https://images.trvl-media.com/lodging/1000000/810000/800800/800715/d9487eb4_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### The Lighthouse Resort Inn & Suites CA $965 per person May 2 - May 6 found 1 day ago Roundtrip non-stop flight included Syracuse (SYR) to Fort Myers (RSW) 8.6/10 Excellent! (1,613 reviews) Clean room that could use an update. Convenient location to beach and had tiki bar with live music. Reviewed on Mar 18, 2026 ![Tween Waters Island Resort & Spa](https://images.trvl-media.com/lodging/1000000/180000/170800/170769/a5c54d2c_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Tween Waters Island Resort & Spa CA $1,675 per person May 14 - May 18 found 11 hours ago Roundtrip non-stop flight included Ottawa (YOW) to Fort Myers (RSW) 8.6/10 Excellent! (1,008 reviews) We are repeat visitors and we're amazed at how beautiful the resort is this year! Proud of the staff for rebounding after the hurricane. Love the pool and all the staff. Nothing is better than being able to walk across the street to a beautiful beach. Amazing. Reviewed on Mar 19, 2026 ![Naples Bay Resort & Marina](https://images.trvl-media.com/lodging/2000000/1600000/1599000/1598931/fa0bc766_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Naples Bay Resort & Marina Oyster Bay CA $1,063 per person May 11 - May 15 found 1 hour ago Roundtrip non-stop flight included Toronto (YTO) to Fort Myers (RSW) 9.4/10 Exceptional! (1,004 reviews) The food was over priced. some front desk staff not so nice. had to to pay for parking even though room rate was high. there was an oven but not dish/tray to put in there so it was useless and staff could not supply anything. Reviewed on Mar 21, 2026 Don't see what you're looking for? See all available trips from Columbus to Southwest Coast Florida [View all trips](https://expedia.ca/go/package/search/FlightHotel/2026-04-21/2026-04-28/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=FMY&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## Plan the perfect luxury Southwest Coast Florida vacation with Expedia #### What are some benefits when booking luxury Southwest Coast Florida vacations? When you book a luxury Southwest Coast Florida vacation, you get to enjoy some of the best amenities and special features available. Luxury vacation options often feature spa facilities right in your accommodation, along with room service and an on-site restaurant. The quality of the bedding and even the water pressure tends to be better, so it's the perfect solution for travellers looking to put their feet up and relax. #### How can I find all-inclusive luxury vacations in Southwest Coast Florida? If you're looking for something luxurious in Southwest Coast Florida, all you have to do is take advantage of our search filters. You can implement a filter to only show 5-star accommodations as well as some amenities you may be interested in, like spa facilities and hot tubs. When you opt for an all-inclusive package, you can enjoy luxury alongside a potential discount for booking your accommodation and flight together. #### Can I book a cheap luxury vacation? While luxury vacations tend to be on the more costly end of the spectrum, ranging from CA $708, there are a few methods you can try to lower the price as much as possible. When booking a flight and accommodation together, you can enjoy savings of up to 9\. After implementing filters for luxury features, you can also sort by price to list the cheapest luxury packages first. #### Are there luxury spa vacations? Yes, luxury spa vacations are available and quite popular in Southwest Coast Florida. When you book one of these experiences, it's easier than ever to relax, unwind and recharge in between excursions. Either way, you can easily find spa vacations by implementing the spa filter in your search. #### What should I look for in a luxury family vacation in Southwest Coast Florida? When booking something for the whole family, it's important to consider exactly what kind of experience your family will want.Luxury packages make it easy to keep everyone happy with creature comforts. Kids especially enjoy features like pools, a delicious breakfast and plenty of space. Suites tend to offer your family members a bit more privacy and comfort compared to simple rooms throughout Southwest Coast Florida. #### Can I book last-minute luxury vacations? Yes, last-minute bookings are often available in Southwest Coast Florida. All you have to do is enter your travel dates to see what's available. Sometimes, you'll even find additional discounts for booking last-minute, as accommodations are desperate to fill their last remaining spaces. #### What can help me find the best luxury vacation deals in Southwest Coast Florida? You can use a few strategies to find the best deals on luxury vacation packages. Consider travelling during the off-season to take advantage of the typically lower overall prices. Additionally, staying in the less popular parts of Southwest Coast Florida or travelling to more obscure destinations altogether can often lead to lower prices. #### Can I book a luxury vacation that is fully refundable? Yes, fully refundable reservations are sometimes available on luxury vacation packages in Southwest Coast Florida. You can implement a filter for it specifically or check out the policy section on any one of your search results. It should clearly state what's necessary to qualify for a fully refundable booking. #### Why should I book my luxury vacation with Expedia? When you book with Expedia, you can enjoy a one-stop shop for all your travel planning needs. We offer accommodations as well as flights, and you may even be able to enjoy discounts by booking them together. Of course, Expedia Rewards members will find even more discounts and earn points that can be put toward discounts on future bookings. ## Luxury Hotels in Southwest Coast Florida ![Wyvern Hotel, an Ascend Collection Hotel](https://images.trvl-media.com/lodging/3000000/2200000/2193300/2193202/75be6006_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Wyvern Hotel, an Ascend Collection Hotel 101 E Retta Esplanade Punta Gorda FL - 1 hour drive from Siesta Key Beach Book a stay at this luxury hotel in Punta Gorda. Enjoy free WiFi, free parking, and 2 restaurants. Our guests praise the helpful staff and the clean rooms in ... 8.8/10 Excellent! (1,003 reviews) Rooftop bartenders and wait stay , ignored us. They stood around talking to each other. Had to wave at them for service It was me and my husband we ordered food , I had to ask for silverware and napkins. The girl brought one it took 5 mins to get anyone attention to get a 2nd set. Overall the rooftop ... Reviewed on Mar 21, 2026 [](https://expedia.ca/Port-Charlotte-Charlotte-Harbor-Hotels-Wyvern-Hotel.h2193202.Hotel-Information) ![Naples Grande Beach Resort](https://images.trvl-media.com/lodging/1000000/20000/15900/15898/018506a5_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Naples Grande Beach Resort 475 Seagate Drive Naples FL - 3 hours drive from Siesta Key Beach Book a stay at this luxury resort in Naples. Enjoy 3 outdoor pools, a full-service spa, and 4 restaurants. Our guests praise the pool and the helpful staff in ... 9/10 Wonderful! (2,037 reviews) Staff was so friendly and acomodating. Rooms, beds and common areas are spacious, bright and comfortable. The beach is gorgeous and magical for collecting shells in the morning. This hotel has been a favorite of ours for years and we look forward to returning. Reviewed on Mar 20, 2026 [](https://expedia.ca/Naples-Hotels-Naples-Grande-Beach-Resort.h15898.Hotel-Information) ![The Ritz-Carlton, Sarasota](https://images.trvl-media.com/lodging/1000000/810000/806200/806101/90558b2d_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### The Ritz-Carlton, Sarasota 1111 Ritz Carlton Dr Sarasota FL - 12 min drive from Siesta Key Beach Book a stay at this luxury hotel in Sarasota. Enjoy free WiFi, 2 outdoor pools, and a full-service spa. Our guests praise the helpful staff in our reviews. Popular ... 9.2/10 Wonderful! (1,000 reviews) Classic Rittz, but could use a few updates so it doesn't start looking like a Marriott. Reviewed on Mar 4, 2026 [](https://expedia.ca/Sarasota-Hotels-The-Ritz-Carlton.h806101.Hotel-Information) [See all 46,885 properties in Southwest Coast Florida](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Package®ionId=6048100) 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 Luxury Vacation Destinations > - [Luxury vacations in India ](https://www.expedia.ca/lp/theme-vacations/luxury-vacations/80/India) > - [Luxury vacations in France ](https://www.expedia.ca/lp/theme-vacations/luxury-vacations/59/France) > - [Luxury vacations in Switzerland ](https://www.expedia.ca/lp/theme-vacations/luxury-vacations/174/Switzerland) > - [Luxury vacations in Canada ](https://www.expedia.ca/lp/theme-vacations/luxury-vacations/31/Canada) > - [Luxury vacations in Jamaica ](https://www.expedia.ca/lp/theme-vacations/luxury-vacations/88/Jamaica) > - [Luxury vacations in Italy ](https://www.expedia.ca/lp/theme-vacations/luxury-vacations/86/Italy) > - [Luxury vacations in New Zealand ](https://www.expedia.ca/lp/theme-vacations/luxury-vacations/133/New-Zealand) > - [Luxury vacations in the Maldives ](https://www.expedia.ca/lp/theme-vacations/luxury-vacations/109/Maldives) > - [Luxury vacations in Costa Rica ](https://www.expedia.ca/lp/theme-vacations/luxury-vacations/42/Costa-Rica) > - [Luxury vacations in Florida Keys ](https://www.expedia.ca/lp/theme-vacations/luxury-vacations/6023765/Florida-Keys) > - [Luxury vacations in Mexico ](https://www.expedia.ca/lp/theme-vacations/luxury-vacations/117/Mexico) > - [Luxury vacations in the Caribbean ](https://www.expedia.ca/lp/theme-vacations/luxury-vacations/6022969/Caribbean) > - [Luxury vacations in Zanzibar ](https://www.expedia.ca/lp/theme-vacations/luxury-vacations/4186/Zanzibar) > - [Luxury vacations in Cancun ](https://www.expedia.ca/lp/theme-vacations/luxury-vacations/179995/Cancun) > - [Luxury vacations in Kerala ](https://www.expedia.ca/lp/theme-vacations/luxury-vacations/602187/Kerala) > - [Luxury vacations in Australia ](https://www.expedia.ca/lp/theme-vacations/luxury-vacations/10/Australia) > - [Luxury vacations in Puglia ](https://www.expedia.ca/lp/theme-vacations/luxury-vacations/6048562/Puglia) > - [Luxury vacations in Cuba ](https://www.expedia.ca/lp/theme-vacations/luxury-vacations/44/Cuba) > - [Luxury vacations in Cyprus ](https://www.expedia.ca/lp/theme-vacations/luxury-vacations/45/Cyprus) ## More Vacations Ideas [Flights to Southwest Coast Florida ](https://expedia.ca/Cheap-Flights-To-Southwest-Coast-Florida.d6048100.Travel-Guide-Flights)[ Southwest Coast Florida Hotels ](https://expedia.ca/Southwest-Coast-Florida-Hotels.d6048100.Travel-Guide-Hotels)[ Southwest Coast Florida Vacation Rentals ](https://expedia.ca/Southwest-Coast-Florida-Vacation-Rentals.d6048100.Travel-Guide-VacationRentals)[ Southwest Coast Florida Car Rentals ](https://expedia.ca/Car-Rentals-In-Southwest-Coast-Florida.d6048100.Car-Rental-Guide)[ Southwest Coast Florida Vacations ](https://expedia.ca/Southwest-Coast-Florida.d6048100.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