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/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 $738 per person May 16 - May 23 found 2 days 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 ![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 $1,046 per person May 16 - May 23 found 2 days ago Roundtrip 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 ![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 $1,039 per person May 16 - May 23 found 2 days ago Roundtrip 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 ![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 $810 per person May 3 - May 8 found 1 day ago Roundtrip 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 ![Crystal Palms Beach Resort ](https://images.trvl-media.com/lodging/116000000/115920000/115915100/115915092/a65b8935_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Crystal Palms Beach Resort Sunshine Beach Save 100% on your flight $941 per person May 2 - May 9 found 20 hours ago Roundtrip flight included Boston (BOS) to Tampa (TPA) 9/10 Wonderful! (2 reviews) Staff was kind and accommodating Reviewed on Feb 17, 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/2026-04-02/2026-04-09/?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 $1,101 per person May 12 - May 17 found 16 hours 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 $3,585 per person Apr 19 - Apr 23 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 $1,700 per person Apr 17 - Apr 20 found 2 days ago Roundtrip non-stop 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/2026-04-02/2026-04-09/?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 $546 per person May 16 - May 19 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 ![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 $710 per person May 21 - May 24 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 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 $1,571 per person Apr 8 - Apr 11 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 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/2026-04-02/2026-04-09/?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 $489 per person May 3 - May 7 found 1 day ago Roundtrip non-stop flight included Boston (BOS) 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 ![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 $533 per person Apr 9 - Apr 13 found 8 hours ago Roundtrip non-stop flight included Newark Liberty Intl. Airport (EWR) to Tampa (TPA) 8.6/10 Excellent! (60 reviews) Staff was very responsive although we did not meet in person. Very old but clean Florida Motel which is all we needed for the night and the price was good! Reviewed on Feb 26, 2026 ![Cedar Cove Resort and Cottages](https://images.trvl-media.com/lodging/9000000/8100000/8099700/8099611/0a89d66d_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Cedar Cove Resort and Cottages Save 100% on your flight $957 per person Apr 13 - Apr 17 found 1 day ago Roundtrip flight included Boston (BOS) to Sarasota (SRQ) 9.2/10 Wonderful! (492 reviews) Everything was perfect cant wait to go back Reviewed on Feb 10, 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/2026-04-02/2026-04-09/?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 $489\. 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