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. ![Saddlebrook Resort](https://images.trvl-media.com/lodging/1000000/10000/8200/8126/3a68ae49_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Saddlebrook Resort Wesley Chapel South Save 100% on your flight $606 per person Mar 27 - Apr 1 found 1 day ago Roundtrip flight included Boston (BOS) to Tampa (TPA) No reviews The resort is doing 90 million dollars in upgrades. Our 2-bedroom suite was upgraded and was very nice. I had the pork at Rare and it was delicious, highly recommend. We went off site for dinner at Cooper's Hawk and it was amazing. The tennis camp was a lot of fun and also played pickleball. The pool area was just updated as well. They did plant all new vegetation but the 2 week cold spell killed everything unfortunately and must be redone. They are going to open the spa in March 2026 and there is a sports bar that is going to open. This was a great resort.. Had a blast. Reviewed on Feb 16, 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 Save 100% on your flight $766 per person Apr 7 - Apr 14 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 $978 per person Apr 7 - Apr 14 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 ![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 $783 per person Apr 7 - Apr 14 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 ![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 Save 100% on your flight $858 per person May 6 - May 10 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/2026-03-24/2026-03-31/?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 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 Save 100% on your flight $2,720 per person Apr 7 - Apr 14 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 ![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 $4,637 per person May 16 - May 23 found 1 day ago Roundtrip flight included Newark Liberty Intl. Airport (EWR) 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 ![Indian Rocks Escape](https://images.trvl-media.com/lodging/118000000/117150000/117146500/117146493/9b1574d5_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Indian Rocks Escape $4,686 per person Apr 3 - Apr 9 found 6 hours ago Roundtrip flight included New York (LGA) to Tampa (TPA) No reviews 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/2026-03-24/2026-03-31/?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 $380 per person May 12 - May 15 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 ![SeaSpray Resort](https://images.trvl-media.com/lodging/115000000/114190000/114189500/114189452/62be52d5_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### SeaSpray Resort Save 100% on your flight $648 per person May 12 - May 15 found 1 day ago Roundtrip flight included Boston (BOS) to Sarasota (SRQ) 9.4/10 Exceptional! (67 reviews) Everything was great all the staff was very helpful the room was very clean Victoria and Pricilla helped us out on changing rooms to one that fit our situation would definitely recommend!!! Reviewed on Feb 17, 2026 ![Hotel Alba, Tapestry Collection by Hilton](https://images.trvl-media.com/lodging/1000000/20000/13800/13705/2714044c_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Hotel Alba, Tapestry Collection by Hilton Westshore Save 100% on your flight $738 per person Apr 26 - Apr 29 found 24 hours ago Roundtrip flight included Boston (BOS) to Tampa (TPA) 8.8/10 Excellent! (2,363 reviews) Staff were very friendly and the room was cozy and clean. The hot water from the sink does have a sulfur smell though initially. Reviewed on Feb 18, 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/2026-03-24/2026-03-31/?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. ![Kompose Boutique Hotel](https://images.trvl-media.com/lodging/39000000/38220000/38215400/38215316/e948f2e5_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Kompose Boutique Hotel Save 100% on your flight $447 per person Apr 29 - May 3 found 1 day ago Roundtrip flight included Boston (BOS) to Tampa (TPA) 9.2/10 Wonderful! (4,624 reviews) Room was clean and the staff was friendly. Reviewed on Feb 24, 2026 ![Captiva Beach Resort](https://images.trvl-media.com/lodging/2000000/1170000/1163600/1163507/3fe58375_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Captiva Beach Resort South Village Save 100% on your flight $568 per person Apr 29 - May 3 found 1 day ago Roundtrip flight included Boston (BOS) to Sarasota (SRQ) 9/10 Wonderful! (1,156 reviews) Upon arriving at the resort, found this place to be charming. Our room had a kitchenette with small dining table and 4 chairs, 2 queen beds - which were very comfortable and a nice bathroom. The court yard was lovely! The pool was nice as well! Beach access about a 3-4 minute walk away from the resort. Lastly, I want to give a shoutout to the staff in the office. They could not have been nicer! Plan on booking another stay at Captive Beach resort next year. Reviewed on Feb 21, 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 Save 100% on your flight $685 per person Apr 14 - Apr 18 found 1 day ago Roundtrip non-stop 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 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/2026-03-24/2026-03-31/?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 $380\. 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) ![](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.com/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.com/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.com/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.com/lp/theme-vacations/ski-vacations?rfrr=editorial.Ski_Vacations.click) ![LGBTQ+ Vacation Packages](https://forever.travel-assets.com/flex/flexmanager/images/2023/01/23/352703_320x320_32517_Miami_LGBTQ.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) LGBTQ+ Vacations [](https://expedia.com/lp/theme-vacations/gay-friendly-vacations?rfrr=editorial.LGBTQ+_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2017/07/05/170615_Adventure_1320_2.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Adventure Vacations [](https://expedia.com/lp/theme-vacations/adventure-vacations?rfrr=editorial.Adventure_Vacations.click) ![Where to go when](https://forever.travel-assets.com/flex/flexmanager/images/2023/05/10/mesog-34434-card-venice.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Where to go when [](https://www.expedia.com/lp/b/where-to-go-when?rfrr=editorial.Where_to go when.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2024/05/21/honeymoon_hawaii.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Honeymoon Vacations [](https://expedia.com/lp/theme-vacations/honeymoon-vacations?rfrr=editorial.Honeymoon_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2024/05/23/Mountain-vacations.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Mountain Vacations [](https://expedia.com/lp/theme-vacations/mountain-vacations?rfrr=editorial.Mountain_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2024/05/23/fishing-vacations-2.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Fishing Vacations [](https://expedia.com/lp/theme-vacations/fishing-vacations?rfrr=editorial.Fishing_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2019/05/16/Hyatt%20Zilara%20Cancun%20-%20All%20Inclusive%20-%20Adults%20Only.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Adults Only Vacations [](https://expedia.com/lp/theme-vacations/adults-only-vacations?rfrr=editorial.Adults_Only%20Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2024/05/23/waterpark-vacations.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Waterpark Vacations [](https://expedia.com/lp/theme-vacations/waterpark-vacations?rfrr=editorial.Waterpark_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2024/05/08/Caribean_scuba_diving.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Scuba Diving Vacations [](https://expedia.com/lp/theme-vacations/scuba-diving-vacations?rfrr=editorial.Scuba_Diving%20Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2024/05/08/aruba_yoga.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Yoga Vacations [](https://expedia.com/lp/theme-vacations/yoga-vacations?rfrr=editorial.Yoga_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2023/04/04/EPS-RBC-SummerBeachVacations-AdobeStock_206356322.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Cheap Vacations [](https://expedia.com/lp/theme-vacations/cheap-vacations?rfrr=editorial.Cheap_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2024/06/26/1175883311.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Solo Vacations [](https://expedia.com/lp/b/vacations/solo-vacations?rfrr=editorial.Solo_Vacations.click) ### Top All inclusive Vacation Destinations > - [Puerto Rico All Inclusive Vacation Packages ](https://www.expedia.com/lp/theme-vacations/all-inclusive-vacations/148/Puerto-Rico) > - [USA All Inclusive Vacation Packages ](https://www.expedia.com/lp/theme-vacations/all-inclusive-vacations/201/United-States-Of-America) > - [Maldives All Inclusive Vacation Packages ](https://www.expedia.com/lp/theme-vacations/all-inclusive-vacations/109/Maldives) > - [Fiji All Inclusive Vacation Packages ](https://www.expedia.com/lp/theme-vacations/all-inclusive-vacations/57/Fiji) > - [Aruba All Inclusive Vacation Packages ](https://www.expedia.com/lp/theme-vacations/all-inclusive-vacations/9/Aruba) > - [Thailand All Inclusive Vacation Packages ](https://www.expedia.com/lp/theme-vacations/all-inclusive-vacations/178/Thailand) > - [Bahamas All Inclusive Vacation Packages ](https://www.expedia.com/lp/theme-vacations/all-inclusive-vacations/13/Bahamas) > - [Cancun All Inclusive Vacation Packages ](https://www.expedia.com/lp/theme-vacations/all-inclusive-vacations/179995/Cancun) > - [Mexico All Inclusive Vacation Packages ](https://www.expedia.com/lp/theme-vacations/all-inclusive-vacations/117/Mexico) > - [Bora Bora All Inclusive Vacation Packages ](https://www.expedia.com/lp/theme-vacations/all-inclusive-vacations/602861/Bora-Bora) > - [Hawaii All Inclusive Vacation Packages ](https://www.expedia.com/lp/theme-vacations/all-inclusive-vacations/213/Hawaii) > - [Jamaica All Inclusive Vacation Packages ](https://www.expedia.com/lp/theme-vacations/all-inclusive-vacations/88/Jamaica) > - [Florida All Inclusive Vacation Packages ](https://www.expedia.com/lp/theme-vacations/all-inclusive-vacations/211/Florida) > - [Costa Rica All Inclusive Vacation Packages ](https://www.expedia.com/lp/theme-vacations/all-inclusive-vacations/42/Costa-Rica) > - [Las Vegas All Inclusive Vacation Packages ](https://www.expedia.com/lp/theme-vacations/all-inclusive-vacations/178276/Las-Vegas) > - [Punta Cana All Inclusive Vacation Packages ](https://www.expedia.com/lp/theme-vacations/all-inclusive-vacations/601906/Punta-Cana) > - [Cabo San Lucas All Inclusive Vacation Packages ](https://www.expedia.com/lp/theme-vacations/all-inclusive-vacations/180032/Cabo-San-Lucas) > - [Dominican Republic All Inclusive Vacation Packages ](https://www.expedia.com/lp/theme-vacations/all-inclusive-vacations/50/Dominican-Republic) > - [Puerto Vallarta All Inclusive Vacation Packages ](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