Title: Siesta Key All inclusive Vacations 2026 | Expedia.com ![](https://images.trvl-media.com/place/6066003/d186efac-4013-4501-b81a-fe907f268f8f.jpg?impolicy=fcrop&w=1200&h=300&q=medium) # Siesta Key All inclusive Vacations ## Book a All inclusive Hotel + Flight or Car together to unlock savings - ## Plan, book, travel with confidence - ### Better together Save up to $1,045 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 All inclusive vacation packages in Siesta Key Price found within the past 48 hours. Click for updated prices. ![Legacy Hotel at IMG Academy](https://images.trvl-media.com/lodging/23000000/22890000/22882300/22882236/80dcbca1_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Legacy Hotel at IMG Academy Save 100% on your flight $573 per person Apr 30 - May 5 found 1 day ago Roundtrip flight included Boston (BOS) to Sarasota (SRQ) 9/10 Wonderful! (913 reviews) Very convenient to athletic fields Reviewed on Jan 12, 2026 ![The Sarasota Modern, a Tribute Portfolio Hotel](https://images.trvl-media.com/lodging/28000000/27710000/27704600/27704596/f22dde90_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### The Sarasota Modern, a Tribute Portfolio Hotel Central Sarasota $685 per person Apr 27 - May 2 found 1 day ago Roundtrip flight included Boston (BOS) to Tampa (TPA) 8.2/10 Very Good! (515 reviews) All of those and the wonderful, helpful staff Reviewed on Feb 19, 2026 ![The Westin Sarasota](https://images.trvl-media.com/lodging/17000000/16820000/16819000/16818933/7ee146c3_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### The Westin Sarasota Central Sarasota Save 100% on your flight $787 per person Apr 30 - May 5 found 1 day ago Roundtrip flight included Boston (BOS) to Tampa (TPA) 9/10 Wonderful! (1,131 reviews) Clean rooms great staff smells great Reviewed on Feb 8, 2026 ![The Avalon Club](https://images.trvl-media.com/lodging/68000000/67580000/67572800/67572769/a97427b8_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### The Avalon Club $1,675 per person Mar 27 - Mar 30 found 1 day ago Roundtrip non-stop flight included Boston (BOS) to Tampa (TPA) 9.4/10 Exceptional! (481 reviews) Everything was great except having to carry beach chairs to the beach. Awkward and heavy.. They need a cabana person to set up for a fee. Reviewed on Feb 23, 2026 ![Ocean Club Treasure Island Hotel](https://images.trvl-media.com/lodging/97000000/96160000/96150700/96150639/3e4355d4_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Ocean Club Treasure Island Hotel Sunshine Beach $675 per person May 15 - May 18 found 1 day ago Roundtrip flight included Boston (BOS) to Tampa (TPA) 9.6/10 Exceptional! (712 reviews) The room was positively spotless and beds and bathrooms so clean. Very well stocked with dishes and cookware too! Reviewed on Feb 23, 2026 Don't see what you're looking for? See all available trips from Columbus to Siesta Key [View all trips](https://expedia.com/go/package/search/FlightHotel/2026-03-25/2026-04-01/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=SRQ&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## 5\* All inclusive vacations in Siesta Key Price found within the past 48 hours. Click for updated prices. ![The Adaline](https://images.trvl-media.com/lodging/97000000/96050000/96044100/96044015/2cb71c62_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### The Adaline Hyde Park $1,605 per person Apr 14 - Apr 19 found 1 day ago Roundtrip flight included Boston (BOS) to Tampa (TPA) 9.6/10 Exceptional! (53 reviews) A perfect stay with incredible attention to detail! "We had a fantastic experience at The Adaline. From the moment we entered it was clear that the hosts/staff prioritize guest comfort. The rooms were impeccably clean with all the amenities of being at home. The kitchen had every utensil you would need to satisfy your hunger. Whether you want to prepare a gourmet meal or late night snack (less food). We particularly loved the comfort of the bedding.The mattress was super comfortable and it was obvious there was little expense spared in choosing the linens. The location was ideal for our trip (Soccer Tournament); it was quiet enough for a relaxing night's sleep but only a shot drive to the Soccer Fields. Additionally, it’s only a short walk to the Riverwalk, Hyde Park Village and lots more! Our complements to Brightwild Team for providing such comfortable and clean accommodations. We would highly recommend this stay to anyone looking for a high-quality getaway with a convenient location!? Reviewed on Jan 14, 2026 ![The St. Regis Longboat Key Resort](https://images.trvl-media.com/lodging/1000000/10000/5500/5487/1e787841_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### The St. Regis Longboat Key Resort Save 100% on your flight $3,544 per person May 6 - May 11 found 1 day ago Roundtrip flight included Boston (BOS) to Sarasota (SRQ) 9.8/10 Exceptional! (56 reviews) great property great service expensive but worth it in my opinion Reviewed on Feb 20, 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 $1,886 per person Apr 27 - May 2 found 1 day ago Roundtrip flight included Boston (BOS) to Tampa (TPA) 9.2/10 Wonderful! (1,001 reviews) Staff were very friendly and helpful. Valet parking staff was extremely accomodating. Loved the ocean club. Bar was wonderful. Beach was great. Amenities were fantastic. Room was somewhat dated but very clean. Reviewed on Feb 22, 2026 Don't see what you're looking for? See all available trips from Columbus to Siesta Key [View all trips](https://expedia.com/go/package/search/FlightHotel/2026-03-25/2026-04-01/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=SRQ&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## 3 Night All inclusive vacations in Siesta Key Price found within the past 48 hours. Click for updated prices. ![Legacy Hotel at IMG Academy](https://images.trvl-media.com/lodging/23000000/22890000/22882300/22882236/80dcbca1_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Legacy Hotel at IMG Academy $442 per person May 18 - May 21 found 1 day ago Roundtrip flight included Boston (BOS) to Sarasota (SRQ) 9/10 Wonderful! (913 reviews) Very convenient to athletic fields Reviewed on Jan 12, 2026 ![The Avalon Club](https://images.trvl-media.com/lodging/68000000/67580000/67572800/67572769/a97427b8_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### The Avalon Club $1,675 per person Mar 27 - Mar 30 found 1 day ago Roundtrip non-stop flight included Boston (BOS) to Tampa (TPA) 9.4/10 Exceptional! (481 reviews) Everything was great except having to carry beach chairs to the beach. Awkward and heavy.. They need a cabana person to set up for a fee. Reviewed on Feb 23, 2026 ![Ocean Club Treasure Island Hotel](https://images.trvl-media.com/lodging/97000000/96160000/96150700/96150639/3e4355d4_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Ocean Club Treasure Island Hotel Sunshine Beach $675 per person May 15 - May 18 found 1 day ago Roundtrip flight included Boston (BOS) to Tampa (TPA) 9.6/10 Exceptional! (712 reviews) The room was positively spotless and beds and bathrooms so clean. Very well stocked with dishes and cookware too! Reviewed on Feb 23, 2026 Don't see what you're looking for? See all available trips from Columbus to Siesta Key [View all trips](https://expedia.com/go/package/search/FlightHotel/2026-03-25/2026-04-01/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=SRQ&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## 4 Night All inclusive vacations in Siesta Key Price found within the past 48 hours. Click for updated prices. ![Hibiscus Suites - Gateway to Siesta Key](https://images.trvl-media.com/lodging/2000000/1220000/1213000/1212924/6ff58e07_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Hibiscus Suites - Gateway to Siesta Key Save 100% on your flight $397 per person May 5 - May 9 found 1 day ago Roundtrip flight included Boston (BOS) to Tampa (TPA) 8.6/10 Excellent! (2,193 reviews) Great place to stay. Like a mini condo. Casey is the best - super friendly & helpful. Very convenient location & easy to get around. We’re definitely staying here again. Reviewed on Feb 19, 2026 ![Mar Bay Motel &Suites](https://images.trvl-media.com/lodging/24000000/23610000/23608800/23608750/d8e0ef7d_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Mar Bay Motel &Suites Save 100% on your flight $475 per person May 22 - May 26 found 1 day ago Roundtrip non-stop flight included New York (NYC) to Tampa (TPA) 8.6/10 Excellent! (60 reviews) Older property but very well maintained. It was clean and had everything we needed for our stay. Great communication with the host. Reviewed on Feb 10, 2026 ![voco Sarasota by IHG](https://images.trvl-media.com/lodging/2000000/1580000/1577400/1577382/dc3c2bf5_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### voco Sarasota by IHG Central Sarasota Save 100% on your flight $430 per person May 5 - May 9 found 1 day ago Roundtrip flight included Boston (BOS) to Tampa (TPA) 9.2/10 Wonderful! (1,001 reviews) Staff was friendly. Room was clean. My main complaintcis NO COMPLIMENTARY coffee. I,ve never been to a hotel that does not provide coffee. Paid 4.00 each. Also more towels needed upon check in. Only 2 large. Need 4. Reviewed on Feb 23, 2026 Don't see what you're looking for? See all available trips from Columbus to Siesta Key [View all trips](https://expedia.com/go/package/search/FlightHotel/2026-03-25/2026-04-01/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=SRQ&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## All-inclusive Siesta Key vacations: everything you need to know #### Can I book a Siesta Key vacation with airfare and meals? On an all-inclusive vacation, your mind and body can wander far from your wallet. Pay one simple price when you bundle your accommodation and airfare, and you avoid all those yucky bills after conversation-starting cocktails or decadent dinners. #### How can I find Siesta Key all-inclusive vacations that are adults only? All the best all-inclusive, all-adult vacations are a click of a filter or two away. Choose from great grown-up features. Say, a spa for a couple’s massage, a hot tub to soak away the stresses of the day, or a swim-up bar to get the party started. #### How much is an all-inclusive trip to Siesta Key? Affordable all-inclusive is yours, whatever your budget. Packages start tempting you from just $397\. Prices and availability are subject to change. Additional terms may apply. #### How can I book cheap all-inclusive trips to Siesta Key? Whenever you book your travel, sorting by price and filtering by budget shows you what’s out there in your price range. #### What are the benefits of all-inclusive Siesta Key vacations with airfare? Create your dream getaway by bundling your flight and hotel and you get delightful deals and discounts. Add your car rental, too, and you save on all three. #### What should I think about when I book an all-inclusive Siesta Key family vacation package? With little tummies taken care of, you just need to put smiles on their faces. Easy! Book an all-inclusive vacation with a full-on water park or epic pools—or book your stay near the world’s biggest theme parks and attractions. #### Why should I book an all-inclusive honeymoon package in Siesta Key? You can start your married life how you mean to go on with an all-inclusive honeymoon package. Eat and drink to your heart’s content, waltz around in happy harmony, and have your fill of delights. Together, you can book up adventure excursions and return to a pool-side cabana for cocktails at sunset. #### Can I book an all-inclusive Siesta Key package with free cancellation and/or flexible dates? When you’re searching for your all-inclusive getaway, filter your results by payment option to find free cancellation and buy now, pay later options. That way, you can rebook without worry, should your plans change. #### Why should I book an all-inclusive Siesta Key package vacation with Expedia? Book amazing all-inclusive adventures, all in one place. Choose from a vast inventory of deals, adding every little extra to build your brilliant break in minutes. ## 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.com/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.com/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) Kid Friendly Vacations [](https://expedia.com/lp/theme-vacations/kid-friendly-vacations?rfrr=editorial.Kid_Friendly%20Vacations.click) 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](https://www.expedia.com/lp/theme-vacations/all-inclusive-vacations/180016/Puerto-Vallarta) ## More Vacation Ideas [Flights to Siesta Key ](https://expedia.com/Cheap-Flights-To-Siesta-Key.d6881.Travel-Guide-Flights)[ Siesta Key Hotels ](https://expedia.com/Siesta-Key-Hotels.d6881.Travel-Guide-Hotels)[ Vacation Rentals in Siesta Key ](https://expedia.com/Siesta-Key-Vacation-Rentals.d6881.Travel-Guide-VacationRentals)[ Car Rentals in Siesta Key ](https://expedia.com/Car-Rentals-In-Siesta-Key.d6881.Car-Rental-Guide)[ Siesta Key Vacations ](https://expedia.com/Siesta-Key.d6881.Destination-Travel-Guides)[ Things to do in Siesta Key ](https://expedia.com/Things-To-Do-In-Siesta-Key.d6881.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 even more - get up to 20% on select hotels 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