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.

The Hotel Zamora

Save 100% on your flight

$729

per person

Dec 2 - Dec 6

found 8 hours ago

Roundtrip flight included

Boston (BOS) to Tampa (TPA)

8.8/10 Excellent! (417 reviews)

Ocean Club Treasure Island Hotel

Sunshine Beach

Save 100% on your flight

$893

per person

Nov 7 - Nov 13

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Tampa (TPA)

9.6/10 Exceptional! (1,190 reviews)

Had a wonderful stay, everything was very clean and well maintained, staff was very friendly, convenient parking at the property, dog friendly and walking path right of the property,

Reviewed on Sep 27, 2026

The Don CeSar

Save 100% on your flight

$1,372

per person

Nov 14 - Nov 21

found 1 day ago

Roundtrip flight included

Boston (BOS) to Tampa (TPA)

9/10 Wonderful! (1,334 reviews)

Clean room, attentive staff worth the money!

Reviewed on Sep 26, 2026

SkyBeach Resort

Greater Pinellas Point

Save 100% on your flight

$952

per person

Dec 5 - Dec 12

found 22 hours ago

Roundtrip flight included

New York (JFK) to Tampa (TPA)

8.6/10 Excellent! (911 reviews)

The outside is the best part of the hotel ! If you’re plan is to do outside things there- it’s worth it. The rooms themselves, are just ok. You have half the room that has entered 2026, and the bathroom that is still in 1986. It’s kind of gross. Overall, the hotel is fine, and the location is good.

Reviewed on Sep 26, 2026

Wyndham Grand Clearwater Beach

Save 100% on your flight

$1,038

per person

Nov 7 - Nov 13

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Tampa (TPA)

9.4/10 Exceptional! (3,817 reviews)

Staff, property and location were all great!

Reviewed on Sep 26, 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

$875

per person

Oct 29 - Nov 3

found 1 day ago

Roundtrip flight included

Boston (BOS) to Tampa (TPA)

9.6/10 Exceptional! (74 reviews)

Fantastic property. The area was quiet and it felt very safe and private. Friendly owners and staff.

Reviewed on Sep 21, 2026

The Gemma by Brightwild

Save 100% on your flight

$2,026

per person

Nov 1 - Nov 5

found 1 day ago

Roundtrip 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

Indian Rocks Escape

$1,116

per person

Nov 6 - Nov 8

found 9 hours ago

Roundtrip non-stop flight included

Boston (BOS) to Tampa (TPA)

No reviews

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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

$588

per person

Dec 11 - Dec 14

found 1 day ago

Roundtrip flight included

Boston (BOS) to Tampa (TPA)

9.4/10 Exceptional! (132 reviews)

Staff were terrible. Not helpful at all

Reviewed on Sep 26, 2026

Legacy Hotel at IMG Academy

Save 100% on your flight

$973

per person

Dec 4 - Dec 7

found 10 hours ago

Roundtrip non-stop flight included

Islip (ISP) to Tampa (TPA)

9/10 Wonderful! (1,003 reviews)

Room was clean and staff were welcoming. I needed a late check out and was accommodated thank you

Reviewed on Sep 26, 2026

Ocean Club Treasure Island Hotel

Sunshine Beach

$1,014

per person

Nov 27 - Nov 30

found 1 day ago

Roundtrip flight included

New York (JFK) to Tampa (TPA)

9.6/10 Exceptional! (1,190 reviews)

Had a wonderful stay, everything was very clean and well maintained, staff was very friendly, convenient parking at the property, dog friendly and walking path right of the property,

Reviewed on Sep 27, 2026

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4 Night All inclusive vacations in Siesta Key

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

Hibiscus Suites - Gateway to Siesta Key

Save 100% on your flight

$556

per person

Dec 11 - Dec 15

found 1 day ago

Roundtrip flight included

Boston (BOS) to Tampa (TPA)

8.8/10 Excellent! (2,452 reviews)

Everything was as advertised

Reviewed on Sep 24, 2026

Cedar Cove Resort and Cottages

Save 100% on your flight

$959

per person

Nov 11 - Nov 15

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Tampa (TPA)

9.2/10 Wonderful! (591 reviews)

voco Sarasota by IHG

Central Sarasota

Save 100% on your flight

$680

per person

Dec 11 - Dec 15

found 1 day ago

Roundtrip flight included

Boston (BOS) to Tampa (TPA)

9/10 Wonderful! (1,000 reviews)

It was very comfortable. I love the fact you have transportation to go to the beach and that you gave us the umbrella, towels and chairs. The front desk personnel were very nice and helpful. Thanks

Reviewed on Sep 23, 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 $556. 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.