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.

Legacy Hotel at IMG Academy

$470

per person

Oct 6 - Oct 10

found 1 day ago

Roundtrip flight included

Boston (BOS) to Tampa (TPA)

9/10 Wonderful! (1,003 reviews)

The Westin Sarasota

Central Sarasota

Save 100% on your flight

$960

per person

Oct 24 - Oct 31

found 1 day ago

Roundtrip flight included

Boston (BOS) to Tampa (TPA)

9/10 Wonderful! (1,151 reviews)

Ocean Club Treasure Island Hotel

Sunshine Beach

Save 100% on your flight

$772

per person

Nov 12 - Nov 17

found 1 day ago

Roundtrip flight included

Boston (BOS) to Tampa (TPA)

9.6/10 Exceptional! (1,165 reviews)

CW Resort

Save 100% on your flight

$502

per person

Sep 30 - Oct 3

found 1 day ago

Roundtrip flight included

Boston (BOS) to Tampa (TPA)

9.6/10 Exceptional! (99 reviews)

Excellent experience! The resort apartment was very clean, spacious, and comfortable. Everything was in great condition, and we had a wonderful and relaxing stay. I highly recommend it and would definitely stay here again!

Reviewed on Aug 24, 2026

SkyBeach Resort

Greater Pinellas Point

$669

per person

Sep 23 - Sep 28

found 11 hours ago

Roundtrip flight included

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

8.6/10 Excellent! (876 reviews)

Don't see what you're looking for?

See all available trips from Columbus to Siesta Key

View all trips

5* All inclusive vacations in Siesta Key

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

The Adaline

Hyde Park

$1,120

per person

Oct 31 - Nov 7

found 1 day ago

Roundtrip flight included

Boston (BOS) to Tampa (TPA)

9.6/10 Exceptional! (73 reviews)

The Gemma by Brightwild

Save 100% on your flight

$3,188

per person

Oct 8 - Oct 11

found 1 day ago

Roundtrip 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

Save 100% on your flight

$4,930

per person

Nov 7 - Nov 14

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Tampa (TPA)

9.8/10 Exceptional! (88 reviews)

Great staff and close attention to detail. Helpful all around. Great restaurants.

Reviewed on Aug 14, 2026

Don't see what you're looking for?

See all available trips from Columbus to Siesta Key

View all trips

3 Night All inclusive vacations in Siesta Key

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

CW Resort

Save 100% on your flight

$502

per person

Sep 30 - Oct 3

found 1 day ago

Roundtrip flight included

Boston (BOS) to Tampa (TPA)

9.6/10 Exceptional! (99 reviews)

Reviewed on Aug 24, 2026

Ocean Club Treasure Island Hotel

Sunshine Beach

$543

per person

Oct 31 - Nov 3

found 8 hours ago

Roundtrip flight included

Boston (BOS) to Tampa (TPA)

9.6/10 Exceptional! (1,165 reviews)

The Hotel Zamora

$542

per person

Oct 31 - Nov 3

found 8 hours ago

Roundtrip flight included

Boston (BOS) to Tampa (TPA)

8.8/10 Excellent! (388 reviews)

The hotel is beautiful and very clean. Great amenities, close to great restaurants and beautiful stretch of the beach. Lovely service, staff weee friendly and very helpful. Rachel at the hotel restaurant was amazing. We had a beautiful weekend. Will definitely visit again.

Reviewed on Aug 21, 2026

Don't see what you're looking for?

See all available trips from Columbus to Siesta Key

View all trips

4 Night All inclusive vacations in Siesta Key

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

GALAXY HOTEL

Downtown St. Petersburg

Save 100% on your flight

$456

per person

Sep 27 - Oct 1

found 5 hours ago

Roundtrip flight included

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

8.4/10 Very Good! (963 reviews)

没有停车位

Reviewed on Aug 24, 2026

Cedar Cove Resort and Cottages

Save 100% on your flight

$881

per person

Oct 6 - Oct 10

found 1 day ago

Roundtrip flight included

Boston (BOS) to Tampa (TPA)

9.2/10 Wonderful! (568 reviews)

The beach view was great. Just steps away. Our room was very clean and smelled refreshing when entering. Staff was very helpful. We will be back

Reviewed on Aug 22, 2026

Ocean Club Treasure Island Hotel

Sunshine Beach

Save 100% on your flight

$633

per person

Nov 12 - Nov 16

found 10 hours ago

Roundtrip non-stop flight included

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

9.6/10 Exceptional! (1,165 reviews)

Don't see what you're looking for?

See all available trips from Columbus to Siesta Key

View all trips

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 $456. 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.