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.

Legacy Hotel at IMG Academy

Save 100% on your flight

$727

per person

Oct 31 - Nov 5

found 1 day ago

Roundtrip flight included

Boston (BOS) to Tampa (TPA)

9/10 Wonderful! (1,003 reviews)

Ocean Club Treasure Island Hotel

Sunshine Beach

Save 100% on your flight

$756

per person

Oct 6 - Oct 13

found 1 day ago

Roundtrip flight included

Boston (BOS) to Tampa (TPA)

9.6/10 Exceptional! (1,173 reviews)

Place is very clean and well maintained, the premium room was really nice worked out perfectly for us with 2 bedrooms ,If there was one thing i could recommend would be more comfortable couch / chair in living room but don't let that take away from the very comfortable beds , pool and hot tub were nice and clean also, front desk staff were friendly… parking was never a problem to have a spot… overall nice place to stay!

Reviewed on Aug 31, 2026

The Hotel Zamora

Save 100% on your flight

$812

per person

Oct 17 - Oct 24

found 1 day ago

Roundtrip flight included

Boston (BOS) to Tampa (TPA)

8.8/10 Excellent! (391 reviews)

Highly recommend, friendly staff great hotel.

Reviewed on Aug 31, 2026

The Westin Sarasota

Central Sarasota

Save 100% on your flight

$820

per person

Nov 5 - Nov 11

found 1 day ago

Roundtrip flight included

Boston (BOS) to Tampa (TPA)

9/10 Wonderful! (1,150 reviews)

Great location excellent view front 19 floor from the pool

Reviewed on Aug 31, 2026

CW Resort

Save 100% on your flight

$812

per person

Nov 1 - Nov 7

found 1 day ago

Roundtrip flight included

Boston (BOS) to Tampa (TPA)

9.4/10 Exceptional! (117 reviews)

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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

$633

per person

Nov 7 - Nov 10

found 14 hours ago

Roundtrip flight included

Boston (BOS) to Tampa (TPA)

9.6/10 Exceptional! (74 reviews)

The Gemma by Brightwild

Save 100% on your flight

$2,910

per person

Oct 8 - Oct 12

found 1 day ago

Roundtrip non-stop 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

$1,629

per person

Nov 9 - Nov 12

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Tampa (TPA)

9.8/10 Exceptional! (90 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

$552

per person

Nov 18 - Nov 21

found 19 hours ago

Roundtrip flight included

Boston (BOS) to Tampa (TPA)

9.6/10 Exceptional! (1,173 reviews)

Reviewed on Aug 31, 2026

La Tortuga Historic Downtown Pass A Grille

Pass-a-Grille

Save 100% on your flight

$613

per person

Nov 7 - Nov 10

found 1 day ago

Roundtrip flight included

Boston (BOS) to Tampa (TPA)

8.8/10 Excellent! (36 reviews)

A six page contract with a ton of strict rules can’t move furniture, can’t touch tv, can’t leave sand in any place, leave a/c at 78 degrees etc etc., all these subject to fines. My a/c was pouring water all night and was fixed next morning. There is nobody at the hotel you can reach, that’s why everything is virtual. I don’t recommend it if you are looking for a relax vacation.

Reviewed on Jun 18, 2026

Wyndham Grand Clearwater Beach

Save 100% on your flight

$605

per person

Oct 31 - Nov 3

found 1 day ago

Roundtrip flight included

Boston (BOS) to Tampa (TPA)

9.4/10 Exceptional! (3,767 reviews)

First time visiting the resort and Clearwater. Great service, cleanliness and amenities. Will definitely be back!

Reviewed on Aug 30, 2026

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4 Night All inclusive vacations in Siesta Key

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

Hibiscus Suites - Gateway to Siesta Key

$547

per person

Oct 15 - Oct 19

found 21 hours ago

Roundtrip flight included

New York (JFK) to Tampa (TPA)

8.6/10 Excellent! (2,425 reviews)

Property looks to be recently renovated. Nice pool, room is large and has a kitchenette. Only drawbacks I can think of were very minor. Blinds in bedroom could use black out curtains or something darker. So bring an eye mask. Pool closes at dusk which is a shame. Location is a few minutes drive to the main beaches. Great value, clean, and service from front desk and house keeping were very good.

Reviewed on Aug 29, 2026

Cedar Cove Resort and Cottages

Save 100% on your flight

$1,062

per person

Oct 16 - Oct 20

found 14 hours ago

Roundtrip flight included

Boston (BOS) to Tampa (TPA)

9.2/10 Wonderful! (579 reviews)

Crystal Palms Beach Resort

Sunshine Beach

Save 100% on your flight

$560

per person

Nov 11 - Nov 15

found 22 hours ago

Roundtrip flight included

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

8.8/10 Excellent! (2,394 reviews)

I was misled, and very disappointed, this is not a real resort, it’s a motel with a pool and hot tub only. Not on the beach a street over. Check in at a sister location. My place wasn’t that clean because I kept my shoes on at all times. Dirty towels was left on top of the washer. I’m not sure why I’m paying resort fees of $16+ a day. There was no one round until the day I checked out. But overall, I enjoyed the beautiful island and will visit again and explore other options that suit my needs.😢

Reviewed on Aug 29, 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 $547. 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.