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.

Saddlebrook Resort

Wesley Chapel South

Save 100% on your flight

$752

per person

Jan 12 - Jan 17

found 20 hours ago

Roundtrip flight included

Boston (BOS) to Tampa (TPA)

8/10 Very Good! (172 reviews)

Nice place, just that when i arrived to my room the Air Conditionea didnt work, i had to wait until next date fir someone to fix it. Also the toilet paper dispenser was falling off the wall.

Reviewed on Oct 25, 2026

CW Resort

$997

per person

Jan 4 - Jan 11

found 1 day ago

Roundtrip flight included

Boston (BOS) to Tampa (TPA)

9.4/10 Exceptional! (255 reviews)

We enjoyed the location and the property. Very new and clean. Beds were comfortable. We would definitely stay at the CW again.

Reviewed on Oct 26, 2026

La Tortuga Historic Downtown Pass A Grille

Pass-a-Grille

$1,043

per person

Jan 13 - Jan 19

found 1 day 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

The Avalon Club

$1,324

per person

Jan 4 - Jan 11

found 1 day ago

Roundtrip flight included

Boston (BOS) to Tampa (TPA)

9.4/10 Exceptional! (608 reviews)

Much more spacious than we expected. Very clean, entire staff were very friendly and knowledgeable. A nice scent was all over the hotel, a nice touch. Definitely would recommend this hotel.

Reviewed on Oct 23, 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)

Huge suite with 2 bedrooms and 2 bathrooms. Large kitchen area with all the appliances, dishes, etc. Beautiful balcony area that has a great view of the ocean and sunsets. Very clean property with an excellent staff who were extremely friendly and helpful. Great location that has many dining options in the immediate vicinity. We highly recommend this property and will definitely be back!

Reviewed on Oct 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

$1,083

per person

Jan 15 - Jan 19

found 22 hours 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

$1,653

per person

Nov 30 - Dec 4

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 1 day 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)

Reviewed on Oct 26, 2026

Legacy Hotel at IMG Academy

$710

per person

Jan 7 - Jan 10

found 12 hours ago

Roundtrip non-stop flight included

Minneapolis (MSP) to Tampa (TPA)

9/10 Wonderful! (1,004 reviews)

CW Resort

$557

per person

Jan 5 - Jan 8

found 1 day ago

Roundtrip non-stop flight included

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

9.4/10 Exceptional! (255 reviews)

We enjoyed the location and the property. Very new and clean. Beds were comfortable. We would definitely stay at the CW again.

Reviewed on Oct 26, 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)

Reviewed on Oct 26, 2026

Cedar Cove Resort and Cottages

$940

per person

Dec 1 - Dec 5

found 15 hours ago

Roundtrip flight included

Boston (BOS) to Tampa (TPA)

9.2/10 Wonderful! (604 reviews)

Everything was perfect. Clean rooms Great Beach

Reviewed on Oct 25, 2026

CW Resort

Save 100% on your flight

$1,577

per person

Dec 28 - Jan 1

found 1 day ago

Roundtrip flight included

Boston (BOS) to Tampa (TPA)

9.4/10 Exceptional! (255 reviews)

We enjoyed the location and the property. Very new and clean. Beds were comfortable. We would definitely stay at the CW again.

Reviewed on Oct 26, 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.