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.

Saddlebrook Resort

Wesley Chapel South

Save 100% on your flight

$464

per person

Oct 31 - Nov 5

found 1 day ago

Roundtrip flight included

Boston (BOS) to Tampa (TPA)

8/10 Very Good! (143 reviews)

Very nice and quiet, staff were helpful, will come back

Reviewed on Aug 8, 2026

Ocean Club Treasure Island Hotel

Sunshine Beach

Save 100% on your flight

$821

per person

Sep 9 - Sep 16

found 1 day ago

Roundtrip flight included

Boston (BOS) to Tampa (TPA)

9.6/10 Exceptional! (1,128 reviews)

Great location. Rooms are spacious and clean.

Reviewed on Aug 9, 2026

CW Hotel

Save 100% on your flight

$907

per person

Oct 10 - Oct 17

found 1 day ago

Roundtrip flight included

Boston (BOS) to Tampa (TPA)

9.6/10 Exceptional! (48 reviews)

Super clean, staff was very friendly.

Reviewed on Aug 9, 2026

The Westin Sarasota

Central Sarasota

$803

per person

Oct 17 - Oct 23

found 1 day ago

Roundtrip flight included

Boston (BOS) to Tampa (TPA)

9/10 Wonderful! (1,163 reviews)

Wyndham Grand Clearwater Beach

Save 100% on your flight

$831

per person

Oct 2 - Oct 6

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Tampa (TPA)

9.4/10 Exceptional! (3,672 reviews)

Loved it !!

Reviewed on Aug 8, 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

$992

per person

Oct 23 - Oct 28

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Tampa (TPA)

9.6/10 Exceptional! (72 reviews)

The Gemma by Brightwild

$2,405

per person

Oct 24 - Oct 28

found 1 day ago

Roundtrip flight included

Boston (BOS) to Tampa (TPA)

10/10 Exceptional! (5 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

$2,457

per person

Sep 17 - Sep 22

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Tampa (TPA)

9.8/10 Exceptional! (86 reviews)

Excellent stay in every way a must try

Reviewed on Aug 8, 2026

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3 Night All inclusive vacations in Siesta Key

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

Legacy Hotel at IMG Academy

$469

per person

Nov 2 - Nov 5

found 6 hours ago

Roundtrip non-stop flight included

New York (NYC) to Tampa (TPA)

9/10 Wonderful! (1,009 reviews)

The Westin Sarasota

Central Sarasota

$607

per person

Oct 15 - Oct 18

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Tampa (TPA)

9/10 Wonderful! (1,163 reviews)

Ocean Club Treasure Island Hotel

Sunshine Beach

$645

per person

Oct 12 - Oct 15

found 1 day ago

Roundtrip flight included

New York (JFK) to Tampa (TPA)

9.6/10 Exceptional! (1,128 reviews)

Great location. Rooms are spacious and clean.

Reviewed on Aug 9, 2026

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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.

Ocean Club Treasure Island Hotel

Sunshine Beach

Save 100% on your flight

$718

per person

Oct 22 - Oct 26

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Tampa (TPA)

9.6/10 Exceptional! (1,128 reviews)

Great location. Rooms are spacious and clean.

Reviewed on Aug 9, 2026

Cedar Cove Resort and Cottages

Save 100% on your flight

$826

per person

Oct 22 - Oct 26

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Tampa (TPA)

9.2/10 Wonderful! (563 reviews)

Lovely stay, perfect for our family!!

Reviewed on Aug 8, 2026

St Pete Beach Suites

Save 100% on your flight

$724

per person

Oct 22 - Oct 26

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Tampa (TPA)

9.2/10 Wonderful! (1,003 reviews)

Excellent

Reviewed on Aug 8, 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 $464. 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.