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

$643

per person

Nov 20 - Nov 23

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Tampa (TPA)

9.6/10 Exceptional! (1,190 reviews)

The Westin Sarasota

Central Sarasota

Save 100% on your flight

$929

per person

Nov 12 - Nov 17

found 1 day ago

Roundtrip flight included

Boston (BOS) to Tampa (TPA)

9.2/10 Wonderful! (1,160 reviews)

The Westin was a excellent hotel with many things going for it. The staff was super friendly and helpful in all aspects at our time of stay. Pretty clean property at times could see litter scattered, but nothing bad. The pool chairs on the roof top were very uncomfortable for the most part and difficult to adjust. The chairs were very slippery aswell. Drinks were great but very expensive.

Reviewed on Sep 6, 2026

CW Resort

$749

per person

Nov 28 - Dec 2

found 1 day ago

Roundtrip flight included

Boston (BOS) to Tampa (TPA)

9.4/10 Exceptional! (132 reviews)

They charge you for the cookies and two bottles of water that they leave in your room.

Reviewed on Sep 6, 2026

SkyBeach Resort

Greater Pinellas Point

Save 100% on your flight

$719

per person

Oct 30 - Nov 4

found 23 hours ago

Roundtrip flight included

Boston (BOS) to Tampa (TPA)

8.6/10 Excellent! (889 reviews)

Great hotel for the price - very clean, friendly staff. Great view from room onto the water. Food and drinks were good. Pool was not crowded either day I was there getting chairs in afternoon was very easy. Ava at the front desk was great as was Maria at the sky bar.

Reviewed on Sep 6, 2026

Legacy Hotel at IMG Academy

$767

per person

Nov 12 - Nov 16

found 1 day ago

Roundtrip flight included

Boston (BOS) to Tampa (TPA)

9/10 Wonderful! (1,008 reviews)

The staff are very polite the hotel is clean from the rooms to the pool as well as the fitness center . No complaints at all. I will only stay here when I come

Reviewed on Sep 4, 2026

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5* All inclusive vacations in Siesta Key

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

The Ritz-Carlton, Sarasota

Central Sarasota

$1,884

per person

Nov 12 - Nov 17

found 1 day ago

Roundtrip flight included

Boston (BOS) to Tampa (TPA)

9.2/10 Wonderful! (1,018 reviews)

The Gemma by Brightwild

$2,067

per person

Oct 6 - Oct 9

found 15 hours 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

The St. Regis Longboat Key Resort

Save 100% on your flight

$3,658

per person

Nov 12 - Nov 17

found 1 day ago

Roundtrip flight included

Boston (BOS) to Tampa (TPA)

9.8/10 Exceptional! (90 reviews)

Perfecto

Reviewed on Sep 4, 2026

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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

$643

per person

Nov 20 - Nov 23

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Tampa (TPA)

9.6/10 Exceptional! (1,190 reviews)

The Hotel Zamora

$679

per person

Nov 20 - Nov 23

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Tampa (TPA)

8.8/10 Excellent! (397 reviews)

Wyndham Grand Clearwater Beach

$690

per person

Nov 20 - Nov 23

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Tampa (TPA)

9.4/10 Exceptional! (3,817 reviews)

Would recommend this hotel to others. Plan on going back.

Reviewed on Sep 6, 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

$590

per person

Nov 10 - Nov 14

found 1 day ago

Roundtrip flight included

Boston (BOS) to Tampa (TPA)

9.6/10 Exceptional! (1,190 reviews)

Cedar Cove Resort and Cottages

Save 100% on your flight

$1,051

per person

Nov 23 - Nov 27

found 1 hour ago

Roundtrip flight included

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

9.2/10 Wonderful! (584 reviews)

The room was immaculate and the beds and pillows were the comfiest I have ever slept in. The room had everything we needed to make our stay comfortable. The location is perfect and the beach there is amazing. We have stayed here 4 times now and will be back again. This is a small, locally owned resort and they take great pride in the property. We absolutely love it.

Reviewed on Sep 3, 2026

The Hotel Zamora

Save 100% on your flight

$593

per person

Nov 10 - Nov 14

found 24 hours ago

Roundtrip flight included

Boston (BOS) to Tampa (TPA)

8.8/10 Excellent! (397 reviews)

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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 $590. 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.