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.

Hotel Flor Tampa Downtown, Tapestry Collection by Hilton

Downtown Tampa

$651

per person

Nov 27 - Dec 2

found 2 days ago

Roundtrip flight included

Boston (BOS) to Tampa (TPA)

8.6/10 Excellent! (943 reviews)

Ocean Club Treasure Island Hotel

Sunshine Beach

Save 100% on your flight

$1,002

per person

Dec 19 - Dec 24

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

$877

per person

Dec 21 - Dec 26

found 14 hours ago

Roundtrip flight included

Boston (BOS) to Tampa (TPA)

9.2/10 Wonderful! (1,178 reviews)

We had a great stay at this hotel. It was in a convenient location, and we really enjoyed the amenities. The shuttle service was especially helpful and made it easy to get to many places around the city. We’d happily stay here again!

Reviewed on Oct 17, 2026

Bali Hai Beachfront Resort and Spa

Save 100% on your flight

$1,227

per person

Nov 19 - Nov 22

found 1 day ago

Roundtrip flight included

Boston (BOS) to Tampa (TPA)

8.6/10 Excellent! (769 reviews)

Excellent location. Professional staff. Clean and comfy rooms.

Reviewed on Oct 16, 2026

Tropic Isle at Anna Maria Island Inn

$874

per person

Nov 19 - Nov 22

found 1 day ago

Roundtrip flight included

Boston (BOS) to Tampa (TPA)

9/10 Wonderful! (724 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

$813

per person

Jan 7 - Jan 10

found 1 day ago

Roundtrip flight included

Boston (BOS) to Tampa (TPA)

9.6/10 Exceptional! (75 reviews)

The best part about this apartment is its location: right by Bayshore, 10 min walking distance from Hyde Park, and in short driving distance from everything S Tampa. The apartment is cute, spacious, quiet, and well equipped. The host provided comprehensive info ahead of check-in so getting in the apartment was smooth.

Reviewed on Oct 11, 2026

The Gemma by Brightwild

Save 100% on your flight

$2,134

per person

Nov 28 - Dec 2

found 2 days 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

$2,112

per person

Nov 18 - Nov 24

found 16 hours ago

Roundtrip flight included

Boston (BOS) 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

Save 100% on your flight

$602

per person

Dec 17 - Dec 20

found 22 hours ago

Roundtrip flight included

Minneapolis (MSP) to Tampa (TPA)

9.6/10 Exceptional! (1,252 reviews)

Bali Hai Beachfront Resort and Spa

Save 100% on your flight

$1,227

per person

Nov 19 - Nov 22

found 1 day ago

Roundtrip flight included

Boston (BOS) to Tampa (TPA)

8.6/10 Excellent! (769 reviews)

Excellent location. Professional staff. Clean and comfy rooms.

Reviewed on Oct 16, 2026

Hotel Flor Tampa Downtown, Tapestry Collection by Hilton

Downtown Tampa

$658

per person

Jan 7 - Jan 10

found 1 day ago

Roundtrip flight included

Boston (BOS) to Tampa (TPA)

8.6/10 Excellent! (943 reviews)

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See all available trips from Columbus to Siesta Key

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4 Night All inclusive vacations in Siesta Key

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

Westwinds Waterfront Resort

Save 100% on your flight

$538

per person

Dec 5 - Dec 9

found 18 hours ago

Roundtrip flight included

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

9/10 Wonderful! (737 reviews)

Excellent time at this property. Only thing I wish was a little bit later checkout time as our flight wasn’t until 9pm at night and we had to be out by 10am. I understand it was most likely due to cleaning for incoming guest so we made it work. Overall I would definitely stay at this property again if we ever returned to Clearwater.

Reviewed on Oct 15, 2026

The Avalon Club

Save 100% on your flight

$1,391

per person

Dec 26 - Dec 30

found 1 day ago

Roundtrip non-stop flight included

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

9.4/10 Exceptional! (608 reviews)

Anna Maria Beach Resort

Save 100% on your flight

$1,480

per person

Dec 4 - Dec 8

found 15 hours ago

Roundtrip flight included

Boston (BOS) to Tampa (TPA)

9.4/10 Exceptional! (423 reviews)

We loved the Anna Maria Beach Resort and plan on returning for another vacation!

Reviewed on Oct 15, 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 $538. 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.