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

$636

per person

Apr 26 - May 1

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

![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

$758

per person

Apr 26 - May 1

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Tampa (TPA)

9/10 Wonderful! (1,131 reviews)

Clean rooms great staff smells great

Reviewed on Feb 8, 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

$646

per person

Apr 11 - Apr 16

found 1 day ago

Roundtrip flight included

Boston (BOS) to Tampa (TPA)

8.2/10 Very Good! (1,516 reviews)

Very clean room, a surprise upgrade, wonderful stafg

Reviewed on Feb 23, 2026

![The Don CeSar](https://images.trvl-media.com/lodging/1000000/20000/16700/16658/2e9ef8e3_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### The Don CeSar

Save 100% on your flight

$1,491

per person

Apr 30 - May 5

found 1 day ago

Roundtrip flight included

Boston (BOS) to Tampa (TPA)

9/10 Wonderful! (1,044 reviews)

Staff was exceptional, Especially Kim at the front desk and Denis at the car valet service. Room was very nice & clean. Small issue with the A/C but that was fixed quickly after alerting the front desk.

Reviewed on Feb 24, 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

$783

per person

May 4 - May 8

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 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 5 hours 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

Save 100% on your flight

$3,635

per person

Mar 29 - Apr 5

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

![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 18 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 1 day 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

![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

$463

per person

Apr 29 - May 3

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

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. 

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## 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.

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