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. ![The Sarasota Modern, a Tribute Portfolio Hotel](https://images.trvl-media.com/lodging/28000000/27710000/27704600/27704596/3763f29c_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### The Sarasota Modern, a Tribute Portfolio Hotel Central Sarasota Save 100% on your flight $618 per person Apr 5 - Apr 10 found 1 day ago Roundtrip flight included Boston (BOS) to Tampa (TPA) 8.2/10 Very Good! (530 reviews) All of those and the wonderful, helpful staff Reviewed on Feb 19, 2026 ![Ocean Club Treasure Island Hotel](https://images.trvl-media.com/lodging/97000000/96160000/96150700/96150639/a3e54a35_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Ocean Club Treasure Island Hotel Sunshine Beach Save 100% on your flight $1,052 per person May 21 - May 27 found 1 day ago Roundtrip non-stop flight included Boston (BOS) to Tampa (TPA) 9.6/10 Exceptional! (837 reviews) Beautiful property with stunning beach views . Very modern and clean units with all Possible amenities you could need. Very nice pool area and a stunning rooftop bar to watch the sunsets . Reviewed on Mar 2, 2026 ![The Westin Sarasota](https://images.trvl-media.com/lodging/17000000/16820000/16819000/16818933/2384a13f_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### The Westin Sarasota Central Sarasota Save 100% on your flight $757 per person Apr 5 - Apr 10 found 1 day ago Roundtrip flight included Boston (BOS) to Tampa (TPA) 9/10 Wonderful! (1,185 reviews) Helpful staff; room was very humid and smelled a bit. Reviewed on Mar 2, 2026 ![Island Grand at TradeWinds](https://images.trvl-media.com/lodging/1000000/10000/2000/1914/6ca26be4_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Island Grand at TradeWinds Save 100% on your flight $880 per person May 21 - May 27 found 1 day ago Roundtrip non-stop flight included Boston (BOS) to Tampa (TPA) 7.4/10 Good! (1,005 reviews) Impressive property, great amenities, very helpful staff Reviewed on Mar 1, 2026 ![RumFish Beach at TradeWinds](https://images.trvl-media.com/lodging/1000000/10000/8600/8544/37eb40ec_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### RumFish Beach at TradeWinds Save 100% on your flight $847 per person May 21 - May 27 found 1 day ago Roundtrip non-stop flight included Boston (BOS) to Tampa (TPA) 8.2/10 Very Good! (1,516 reviews) A little dirty and dated in area but overall a lot of fun Reviewed on Mar 2, 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/2026-04-04/2026-04-11/?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. ![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 $1,998 per person Apr 6 - Apr 9 found 6 hours ago Roundtrip flight included Boston (BOS) to Tampa (TPA) No reviews ![The St. Regis Longboat Key Resort](https://images.trvl-media.com/lodging/1000000/10000/5500/5487/6b2968af_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### The St. Regis Longboat Key Resort $3,398 per person Apr 17 - Apr 20 found 1 day ago Roundtrip non-stop flight included Boston (BOS) to Sarasota (SRQ) 9.8/10 Exceptional! (63 reviews) great property great service expensive but worth it in my opinion Reviewed on Feb 20, 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/2026-04-04/2026-04-11/?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. ![The Westin Sarasota](https://images.trvl-media.com/lodging/17000000/16820000/16819000/16818933/2384a13f_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### The Westin Sarasota Central Sarasota Save 100% on your flight $594 per person Apr 29 - May 2 found 1 day ago Roundtrip flight included Boston (BOS) to Tampa (TPA) 9/10 Wonderful! (1,185 reviews) Helpful staff; room was very humid and smelled a bit. Reviewed on Mar 2, 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 Save 100% on your flight $1,184 per person May 14 - May 17 found 1 day ago Roundtrip flight included Boston (BOS) to Tampa (TPA) 9.4/10 Exceptional! (481 reviews) Gym was well equipped and spacious, rooms were clean, kitchenette had all the things you would need, staff was super friendly and accommodating, and they have beach stuff that you can check out for free which was such a nice surprise. Plus the location is minutes from the beach with a rooftop view you can’t beat! Reviewed on Mar 2, 2026 ![Hotel Tampa Riverwalk](https://images.trvl-media.com/lodging/1000000/30000/22400/22354/8517839d_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Hotel Tampa Riverwalk Downtown Tampa Save 100% on your flight $718 per person May 14 - May 17 found 9 hours ago Roundtrip non-stop flight included Boston (BOS) to Tampa (TPA) 7/10 Good! (1,804 reviews) Room was good, only thing was the air conditioning was a little warm. Reviewed on Mar 3, 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/2026-04-04/2026-04-11/?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. ![Captiva Beach Resort](https://images.trvl-media.com/lodging/2000000/1170000/1163600/1163507/3d46ab53_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Captiva Beach Resort South Village Save 100% on your flight $636 per person Apr 13 - Apr 17 found 1 day ago Roundtrip flight included Newark Liberty Intl. Airport (EWR) to Sarasota (SRQ) 9/10 Wonderful! (1,206 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 ![voco Sarasota by IHG](https://images.trvl-media.com/lodging/2000000/1580000/1577400/1577382/6f2696b7_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### voco Sarasota by IHG Central Sarasota Save 100% on your flight $652 per person May 21 - May 25 found 17 hours ago Roundtrip non-stop flight included Boston (BOS) to Tampa (TPA) 9.2/10 Wonderful! (1,002 reviews) Location and friendly staff.. Reviewed on Mar 1, 2026 ![The Sarasota Modern, a Tribute Portfolio Hotel](https://images.trvl-media.com/lodging/28000000/27710000/27704600/27704596/3763f29c_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### The Sarasota Modern, a Tribute Portfolio Hotel Central Sarasota Save 100% on your flight $662 per person May 21 - May 25 found 17 hours ago Roundtrip non-stop flight included Boston (BOS) to Tampa (TPA) 8.2/10 Very Good! (530 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/2026-04-04/2026-04-11/?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 $594\. 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