Siesta Key All inclusive Vacations 2026

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

$876

per person

Dec 2 - Dec 9

found 1 day ago

Roundtrip flight included

Boston (BOS) to Tampa (TPA)

9.6/10 Exceptional! (1,252 reviews)

This property was amazing! On the beach and the rooms excellent!! Would absolutely stay here again!

Reviewed on Oct 15, 2026

Bali Hai Beachfront Resort and Spa

Save 100% on your flight

$1,374

per person

Nov 18 - Nov 23

found 1 day ago

Roundtrip flight included

Boston (BOS) to Tampa (TPA)

8.6/10 Excellent! (769 reviews)

This was chosen for the location! The spa was good, we enjoyed a couples massage. The parking was spacious.

Reviewed on Oct 12, 2026

Tropic Isle at Anna Maria Island Inn

Save 100% on your flight

$1,016

per person

Nov 18 - Nov 23

found 1 day ago

Roundtrip flight included

Boston (BOS) to Tampa (TPA)

9/10 Wonderful! (724 reviews)

Arrived 8:30 pm , front desk staff member could not tell me which building my room was in, only that is was on the second floor of the 2 buildings in this property! Being unfamiliar with this area and dark, it seems it would be helpful to others to know this information, a little education of the property should happen to the staff members!

Reviewed on Oct 14, 2026

Landing Palmetto Apartments

Save 100% on your flight

$1,137

per person

Dec 25 - Jan 1

found 1 day ago

Roundtrip flight included

Boston (BOS) to Sarasota (SRQ)

9/10 Wonderful! (71 reviews)

The apartment had everything we needed. The bathroom vanity was a pedestal sink with no counter space for toiletries.

Reviewed on Oct 12, 2026

CW Resort

$1,533

per person

Dec 26 - Dec 30

found 1 day ago

Roundtrip flight included

Boston (BOS) to Tampa (TPA)

9.4/10 Exceptional! (204 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 15 hours 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

$2,702

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 St. Regis Longboat Key Resort

Save 100% on your flight

$7,701

per person

Dec 25 - Jan 1

found 1 day ago

Roundtrip flight included

Boston (BOS) to Tampa (TPA)

9.8/10 Exceptional! (97 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

$674

per person

Dec 17 - Dec 20

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Tampa (TPA)

9.6/10 Exceptional! (1,252 reviews)

This property was amazing! On the beach and the rooms excellent!! Would absolutely stay here again!

Reviewed on Oct 15, 2026

Bali Hai Beachfront Resort and Spa

Save 100% on your flight

$1,103

per person

Nov 20 - Nov 23

found 1 day ago

Roundtrip flight included

Boston (BOS) to Tampa (TPA)

8.6/10 Excellent! (769 reviews)

This was chosen for the location! The spa was good, we enjoyed a couples massage. The parking was spacious.

Reviewed on Oct 12, 2026

The Avalon Club

Save 100% on your flight

$694

per person

Dec 5 - Dec 8

found 1 day ago

Roundtrip flight included

Boston (BOS) to Tampa (TPA)

9.4/10 Exceptional! (608 reviews)

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4 Night All inclusive vacations in Siesta Key

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

The Avalon Club

Save 100% on your flight

$1,473

per person

Dec 31 - Jan 4

found 1 day ago

Roundtrip flight included

Boston (BOS) to Tampa (TPA)

9.4/10 Exceptional! (608 reviews)

Ocean Club Treasure Island Hotel

Sunshine Beach

Save 100% on your flight

$1,662

per person

Dec 26 - Dec 30

found 1 day ago

Roundtrip flight included

Boston (BOS) to Tampa (TPA)

9.6/10 Exceptional! (1,252 reviews)

This property was amazing! On the beach and the rooms excellent!! Would absolutely stay here again!

Reviewed on Oct 15, 2026

Anna Maria Beach Resort

Save 100% on your flight

$3,349

per person

Nov 25 - Nov 29

found 21 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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See all available trips from Columbus to Siesta Key

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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 $674. 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.