Siesta Key All inclusive Vacations 2026

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Top All inclusive vacation packages in Siesta Key

Price found within the past 48 hours. Click for updated prices.

SkyBeach Resort

Greater Pinellas Point

Save 100% on your flight

$804

per person

Oct 17 - Oct 24

found 1 day ago

Roundtrip flight included

Boston (BOS) to Tampa (TPA)

8.6/10 Excellent! (889 reviews)

Ocean Club Treasure Island Hotel

Sunshine Beach

Save 100% on your flight

$1,383

per person

Dec 2 - Dec 9

found 1 day ago

Roundtrip flight included

Boston (BOS) to Tampa (TPA)

9.6/10 Exceptional! (1,190 reviews)

Enjoyed everything

Reviewed on Sep 14, 2026

The Westin Sarasota

Central Sarasota

Save 100% on your flight

$1,068

per person

Dec 1 - Dec 6

found 1 day ago

Roundtrip flight included

Boston (BOS) to Tampa (TPA)

9.2/10 Wonderful! (1,150 reviews)

Legacy Hotel at IMG Academy

Save 100% on your flight

$1,056

per person

Dec 2 - Dec 5

found 13 hours ago

Roundtrip flight included

Newark Liberty Intl. Airport (EWR) to Tampa (TPA)

9/10 Wonderful! (1,003 reviews)

Nice place to stay.

Reviewed on Sep 16, 2026

DoubleTree by Hilton Sarasota Bradenton Airport

Save 100% on your flight

$861

per person

Nov 17 - Nov 22

found 1 day ago

Roundtrip flight included

Boston (BOS) to Tampa (TPA)

8.8/10 Excellent! (1,767 reviews)

Great hotel. It was very clean and the staff was friendly. There was a restaurant on the premises that offered a delicious breakfast buffet. It was a bit pricey ($20/p) so I highly recommend choosing a room rate that has it included. And don't forget to request your free yummy daily cookie!

Reviewed on Sep 16, 2026

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5* All inclusive vacations in Siesta Key

Price found within the past 48 hours. Click for updated prices.

The Adaline

Hyde Park

$953

per person

Oct 21 - Oct 26

found 1 day ago

Roundtrip flight included

Boston (BOS) to Tampa (TPA)

9.6/10 Exceptional! (74 reviews)

Indian Rocks Escape

Save 100% on your flight

$3,403

per person

Nov 23 - Nov 30

found 1 day ago

Roundtrip flight included

Newark Liberty Intl. Airport (EWR) to Tampa (TPA)

No reviews

The Gemma by Brightwild

$1,994

per person

Dec 1 - Dec 5

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Tampa (TPA)

9.8/10 Exceptional! (6 reviews)

The Jade House is in an excellent location only a block from the beach and short walk to restaurants, shops, and bars. Communication with the management company was difficult through Expedia. Even when I called directly, one of the three client service agents was not helpful whatsoever. However, once I was given the number to text, communication was much better. The pool/ hot tub area is perfect. The house is very comfortable. Only decks are narrow (only stand); ocean view is from one of theses.

Reviewed on Jul 30, 2026

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3 Night All inclusive vacations in Siesta Key

Price found within the past 48 hours. Click for updated prices.

CW Resort

$437

per person

Oct 31 - Nov 3

found 1 day ago

Roundtrip flight included

Boston (BOS) to Tampa (TPA)

9.4/10 Exceptional! (132 reviews)

The property is in an amazing location we enjoyed being able to walk to the beach, restaurants, and shops, especially since it costs $42 per day to park your car. We tried the restaurant onsite for breakfast the food was okay, not great, for the price. The service was super slow as they only had one server working in a packed restaurant. We had seven people in our group most of them children it would have been nice to have had more seating in the living area. Another thing I would recommend for larger groups is to ask for more toilet paper and towels up front we ran out about half way through our stay. Overall, we had a great trip and a wonderful stay at this beautiful property.

Reviewed on Sep 17, 2026

Ocean Club Treasure Island Hotel

Sunshine Beach

$562

per person

Nov 19 - Nov 22

found 1 day ago

Roundtrip non-stop flight included

Newark Liberty Intl. Airport (EWR) to Tampa (TPA)

9.6/10 Exceptional! (1,190 reviews)

Enjoyed everything

Reviewed on Sep 14, 2026

Legacy Hotel at IMG Academy

Save 100% on your flight

$1,056

per person

Dec 2 - Dec 5

found 13 hours ago

Roundtrip flight included

Newark Liberty Intl. Airport (EWR) to Tampa (TPA)

9/10 Wonderful! (1,003 reviews)

Nice place to stay.

Reviewed on Sep 16, 2026

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4 Night All inclusive vacations in Siesta Key

Price found within the past 48 hours. Click for updated prices.

The Fold Hotels Indian Shores

Save 100% on your flight

$481

per person

Nov 28 - Dec 2

found 1 day ago

Roundtrip flight included

Minneapolis (MSP) to Tampa (TPA)

9.2/10 Wonderful! (1,014 reviews)

Such a nice place! Walking distance to the beach. The staff are very friendly and responsive. Our room was very clean and modern. Great stay!!

Reviewed on Sep 10, 2026

Cedar Cove Resort and Cottages

Save 100% on your flight

$872

per person

Nov 17 - Nov 21

found 1 day ago

Roundtrip flight included

Boston (BOS) to Tampa (TPA)

9.2/10 Wonderful! (591 reviews)

Un lugar muy bonito y cómodo para disfrutar en familia lo único es que los sofácama no son cómodos yo tuve que comprar un colchón y solo hay un parqueo por habitación el personal es muy amable la pasamos bien

Reviewed on Sep 16, 2026

voco Sarasota by IHG

Central Sarasota

Save 100% on your flight

$625

per person

Dec 8 - Dec 12

found 13 hours ago

Roundtrip non-stop flight included

Newark Liberty Intl. Airport (EWR) to Tampa (TPA)

9/10 Wonderful! (1,004 reviews)

The staff was very helpful and friendly. Room was available for early check in which was so convenient. Personal touches were appreciated, thanks Tiffany.

Reviewed on Sep 16, 2026

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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 $437. 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.