Siesta Key All inclusive Vacations 2026

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

$556

per person

Dec 5 - Dec 10

found 1 day ago

Roundtrip flight included

Boston (BOS) to Tampa (TPA)

8.6/10 Excellent! (931 reviews)

Wonderful Stay with Exceptional Staff! We absolutely loved our stay at SkyBeach Resort! The property was beautiful, the atmosphere was fantastic, and we really enjoyed our time there. A special shoutout to the front desk staff, who were absolutely amazing! Everyone was incredibly friendly, welcoming, and helpful. They truly made us feel taken care of and deserve special recognition for their outstanding hospitality. The only two things that could have been better were the shower in our room, which wasn’t working properly, and the shuffleboard area. We would have loved to play, but we couldn’t figure out where or how to get the sticks and pucks. Some clearer instructions would have been helpful! Aside from those minor inconveniences, we had a wonderful experience and would absolutely consider staying here again. Thank you to the fantastic team for making our visit so enjoyable!

Reviewed on Oct 24, 2026

The Westin Sarasota

Central Sarasota

Save 100% on your flight

$1,133

per person

Dec 2 - Dec 8

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Tampa (TPA)

9.2/10 Wonderful! (1,178 reviews)

La Tortuga Historic Downtown Pass A Grille

Pass-a-Grille

$1,043

per person

Jan 13 - Jan 19

found 20 hours ago

Roundtrip flight included

Boston (BOS) to Tampa (TPA)

8.8/10 Excellent! (36 reviews)

Such a beautiful place!!! My only recommendation is they need to lock the gates at the pool! We left at 3:30 am and there were 3 people swimming in the pool… they took off running away when they saw us, so definitely not guests!!! The property is so beautiful and well cared for that I’d hate to see someone destroy something!

Reviewed on Oct 18, 2026

Ocean Club Treasure Island Hotel

Sunshine Beach

Save 100% on your flight

$757

per person

Jan 7 - Jan 11

found 1 day ago

Roundtrip flight included

Boston (BOS) to Tampa (TPA)

9.6/10 Exceptional! (1,282 reviews)

Nice hotel

Reviewed on Oct 25, 2026

Hotel Flor Tampa Downtown, Tapestry Collection by Hilton

Downtown Tampa

$977

per person

Dec 7 - Dec 12

found 1 day ago

Roundtrip flight included

Boston (BOS) to Tampa (TPA)

8.6/10 Excellent! (943 reviews)

The wide site isn’t clear on parking. Plan on paying for parking, whether it’s a parking lot nearby or valet. There are walkable eateries and bars nearby.

Reviewed on Oct 23, 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

$845

per person

Dec 7 - Dec 12

found 1 day ago

Roundtrip flight included

Boston (BOS) to Tampa (TPA)

9.6/10 Exceptional! (75 reviews)

Clean and a great location. Very noisy as you can hear the guest conversations in the units next to you. Tons of Amazon packages at the front door can make it hard to access. Hangers in the closet would be nice. Bathroom was clean but so small the tp kept getting wet when you showered.

Reviewed on Oct 18, 2026

The Gemma by Brightwild

$2,165

per person

Dec 10 - Dec 13

found 1 day ago

Roundtrip flight included

Boston (BOS) to Tampa (TPA)

9.8/10 Exceptional! (7 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

$1,829

per person

Dec 14 - Dec 20

found 15 hours ago

Roundtrip flight included

Minneapolis (MSP) 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.

Ocean Club Treasure Island Hotel

Sunshine Beach

$542

per person

Jan 5 - Jan 8

found 1 day ago

Roundtrip non-stop flight included

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

9.6/10 Exceptional! (1,282 reviews)

Nice hotel

Reviewed on Oct 25, 2026

CW Resort

$1,481

per person

Dec 30 - Jan 2

found 1 day ago

Roundtrip flight included

Boston (BOS) to Tampa (TPA)

9.4/10 Exceptional! (255 reviews)

Everything was new inside, views were great and staff was pleasant.

Reviewed on Oct 25, 2026

Hotel Flor Tampa Downtown, Tapestry Collection by Hilton

Downtown Tampa

$564

per person

Jan 6 - Jan 9

found 1 day ago

Roundtrip flight included

Boston (BOS) to Tampa (TPA)

8.6/10 Excellent! (943 reviews)

The wide site isn’t clear on parking. Plan on paying for parking, whether it’s a parking lot nearby or valet. There are walkable eateries and bars nearby.

Reviewed on Oct 23, 2026

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4 Night All inclusive vacations in Siesta Key

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

Ocean Club Treasure Island Hotel

Sunshine Beach

Save 100% on your flight

$757

per person

Jan 7 - Jan 11

found 1 day ago

Roundtrip flight included

Boston (BOS) to Tampa (TPA)

9.6/10 Exceptional! (1,282 reviews)

Nice hotel

Reviewed on Oct 25, 2026

Cedar Cove Resort and Cottages

Save 100% on your flight

$795

per person

Dec 6 - Dec 10

found 1 day ago

Roundtrip flight included

Boston (BOS) to Tampa (TPA)

9.2/10 Wonderful! (604 reviews)

Awesome resort, highly recommend if visiting AMI. Great location and can use free island trolley to go anywhere you want.

Reviewed on Oct 24, 2026

CW Resort

Save 100% on your flight

$764

per person

Jan 8 - Jan 12

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Tampa (TPA)

9.4/10 Exceptional! (255 reviews)

Everything was new inside, views were great and staff was pleasant.

Reviewed on Oct 25, 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 $542. 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.