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.

Ocean Club Treasure Island Hotel

Sunshine Beach

Save 100% on your flight

$869

per person

Sep 19 - Sep 26

found 1 day ago

Roundtrip flight included

Boston (BOS) to Tampa (TPA)

9.6/10 Exceptional! (1,128 reviews)

Everything was good

Reviewed on Aug 17, 2026

CW Hotel

Save 100% on your flight

$871

per person

Sep 19 - Sep 26

found 1 day ago

Roundtrip flight included

Boston (BOS) to Tampa (TPA)

9.6/10 Exceptional! (48 reviews)

Everyone was friendly. Great views from our room. Amazing location, walkable to pier/beach. Parking was $40 I think, reasonable for the area. Resort fee of $40, had access to pool we didn’t use. Didn’t really get any value out of resort fee. $300 security deposit seems a bit high but was removed from credit card in a couple days. Just one elevator for 8 floors so sometimes a wait/full. Would stay there again.

Reviewed on Aug 18, 2026

The Avalon Club

Save 100% on your flight

$1,553

per person

Oct 31 - Nov 7

found 1 day ago

Roundtrip flight included

Boston (BOS) to Tampa (TPA)

9.4/10 Exceptional! (581 reviews)

Wyndham Grand Clearwater Beach

Save 100% on your flight

$1,172

per person

Oct 31 - Nov 7

found 1 day ago

Roundtrip flight included

Boston (BOS) to Tampa (TPA)

9.4/10 Exceptional! (3,672 reviews)

Reviewed on Aug 18, 2026

The Gemma by Brightwild

Save 100% on your flight

$4,088

per person

Oct 31 - Nov 7

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

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5* All inclusive vacations in Siesta Key

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

Little Harbor Resort at Bahia Beach

$985

per person

Oct 2 - Oct 9

found 1 day ago

Roundtrip flight included

Boston (BOS) to Tampa (TPA)

9.4/10 Exceptional! (27 reviews)

Loved the rental. Quiet neighbors.

Reviewed on Apr 27, 2026

The Gemma by Brightwild

Save 100% on your flight

$4,088

per person

Oct 31 - Nov 7

found 1 day ago

Roundtrip flight included

Boston (BOS) to Tampa (TPA)

9.8/10 Exceptional! (6 reviews)

Reviewed on Jul 30, 2026

Indian Rocks Escape

Save 100% on your flight

$1,075

per person

Sep 28 - Oct 1

found 20 hours ago

Roundtrip flight included

Philadelphia (PHL) 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

$470

per person

Nov 3 - Nov 6

found 8 hours ago

Roundtrip non-stop flight included

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

9.6/10 Exceptional! (1,128 reviews)

Everything was good

Reviewed on Aug 17, 2026

Wyndham Grand Clearwater Beach

$630

per person

Oct 18 - Oct 21

found 17 hours ago

Roundtrip non-stop flight included

Boston (BOS) to Tampa (TPA)

9.4/10 Exceptional! (3,672 reviews)

Reviewed on Aug 18, 2026

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4 Night All inclusive vacations in Siesta Key

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

ChartHouse Clearwater Beach Marina Hotel

Save 100% on your flight

$640

per person

Sep 17 - Sep 21

found 1 day ago

Roundtrip flight included

Boston (BOS) to Tampa (TPA)

9.6/10 Exceptional! (1,341 reviews)

Cedar Cove Resort and Cottages

Save 100% on your flight

$941

per person

Oct 28 - Nov 1

found 1 day ago

Roundtrip flight included

Boston (BOS) to Tampa (TPA)

9.2/10 Wonderful! (568 reviews)

The room we were staying in was simple, had 1 window out to the back and the parking lot of the property, it doesnt have any ocean view directly from that room. I think thats important to know. The property has other rooms with direct view to the Gulf which is fyi. The property is well kept, clean, simple and friendly. The beach is spectacular, very quiet, not crowded at all, the ocean was unbelievable clear and beautiful. Anna Maria is a dream to visit with many restaurants on the water

Reviewed on Aug 18, 2026

Ocean Club Treasure Island Hotel

Sunshine Beach

Save 100% on your flight

$727

per person

Nov 4 - Nov 8

found 1 day ago

Roundtrip non-stop flight included

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

9.6/10 Exceptional! (1,128 reviews)

Everything was good

Reviewed on Aug 17, 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 $470. 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.