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

$900

per person

Nov 7 - Nov 13

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Tampa (TPA)

9.6/10 Exceptional! (1,252 reviews)

The Westin Sarasota

Central Sarasota

Save 100% on your flight

$1,138

per person

Dec 5 - Dec 12

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Tampa (TPA)

9.2/10 Wonderful! (1,162 reviews)

Wyndham Grand Clearwater Beach

Save 100% on your flight

$968

per person

Nov 7 - Nov 13

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Tampa (TPA)

9.4/10 Exceptional! (3,946 reviews)

Great hotel with a fantastic location that offers unobstructed views of the gulf, city, and intercoastal. The amenities are excellent, the pool area is both amazing and fun, and the restaurant is great. However, what truly sets this hotel far apart from the others is the staff, as everyone is willing to help and dedicated to making the stay unforgettable.

Reviewed on Oct 5, 2026

The Avalon Club

Save 100% on your flight

$985

per person

Dec 5 - Dec 11

found 1 day ago

Roundtrip flight included

Boston (BOS) to Tampa (TPA)

9.4/10 Exceptional! (605 reviews)

SkyBeach Resort

Greater Pinellas Point

Save 100% on your flight

$929

per person

Dec 5 - Dec 12

found 24 hours ago

Roundtrip flight included

New York (JFK) to Tampa (TPA)

8.6/10 Excellent! (919 reviews)

We liked quite a bit about the property. There were a lot of amenities and really cool things to do and unique and private places to sit and have serenity and everything was beautifully appointed. The rooms were a bit dated, but we hardly spend any time in the rooms anyway. The restaurant and the coffee shop were delightful and the furniture and fencing and decks and buildings were all in top notch.

Reviewed on Oct 5, 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

$942

per person

Nov 27 - Dec 1

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

$2,916

per person

Dec 5 - Dec 11

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

The Ritz-Carlton, Sarasota

Central Sarasota

$2,453

per person

Dec 5 - Dec 12

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Tampa (TPA)

9.2/10 Wonderful! (1,024 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

$597

per person

Dec 10 - Dec 13

found 1 day ago

Roundtrip flight included

Boston (BOS) to Tampa (TPA)

9.4/10 Exceptional! (204 reviews)

The room Was clean. Very nice layout . If you order from the restaurant make sure all of your condiments and utensils are in the bag. They forgot it every time we order from them, but besides the minor inconveniences we Would definitely stay again.

Reviewed on Oct 5, 2026

Ocean Club Treasure Island Hotel

Sunshine Beach

Save 100% on your flight

$619

per person

Dec 10 - Dec 13

found 1 day ago

Roundtrip flight included

Boston (BOS) to Tampa (TPA)

9.6/10 Exceptional! (1,252 reviews)

Hotel Flor Tampa Downtown, Tapestry Collection by Hilton

Downtown Tampa

Save 100% on your flight

$815

per person

Dec 10 - Dec 13

found 1 day ago

Roundtrip flight included

Boston (BOS) to Tampa (TPA)

8.6/10 Excellent! (938 reviews)

Nice enough place, but the location didn't really support the pricing of this location, plus the bums asking for money etc. Outside the establishments main doors. With that comes with the three guys heckling our beautiful wives, just because we were not with them. Then the walls are thin enough you can hear the lady next door getting railed by her man. Real Classy! Thanks for nothing.

Reviewed on Oct 5, 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

$724

per person

Dec 10 - Dec 14

found 1 day ago

Roundtrip flight included

Boston (BOS) to Tampa (TPA)

9.6/10 Exceptional! (1,252 reviews)

CW Resort

Save 100% on your flight

$1,188

per person

Dec 23 - Dec 27

found 1 day ago

Roundtrip flight included

Boston (BOS) to Tampa (TPA)

9.4/10 Exceptional! (204 reviews)

Reviewed on Oct 5, 2026

Cedar Cove Resort and Cottages

Save 100% on your flight

$1,016

per person

Nov 27 - Dec 1

found 1 day ago

Roundtrip flight included

Boston (BOS) to Tampa (TPA)

9.2/10 Wonderful! (603 reviews)

So clean and anything at all that we needed the staff was more than willing to do great experience

Reviewed on Oct 4, 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 $597. 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.