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.

Hyatt Regency Clearwater Beach Resort and Suites

Save 100% on your flight

$456

per person

Oct 28 - Oct 31

found 1 day ago

Roundtrip flight included

Boston (BOS) to Tampa (TPA)

9.4/10 Exceptional! (2,303 reviews)

Ocean Club Treasure Island Hotel

Sunshine Beach

Save 100% on your flight

$734

per person

Oct 24 - Oct 31

found 1 day ago

Roundtrip flight included

Boston (BOS) to Tampa (TPA)

9.6/10 Exceptional! (1,190 reviews)

Reviewed on Sep 11, 2026

SkyBeach Resort

Greater Pinellas Point

Save 100% on your flight

$996

per person

Nov 4 - Nov 11

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Tampa (TPA)

8.6/10 Excellent! (889 reviews)

Love this hidden gem 💎

Reviewed on Sep 9, 2026

Via Roma Beach Resort

Save 100% on your flight

$549

per person

Dec 4 - Dec 8

found 1 day ago

Roundtrip flight included

Philadelphia (PHL) to Tampa (TPA)

10/10 Exceptional! (13 reviews)

An amazing view. Room 20 beachfront. So relaxing. Steps down to the white sandy beach. Beach is amazing. The gulf was super calm and warm. Saw lots of dolphins turtles and manatees. Room had kitchen with all facilities. Trolley just outside so can get around island easy. Pool was great. Easy parking across the road. An amazing stay. Highly recommended. Will definitely return 😎🏝️

Reviewed on Sep 5, 2026

The Westin Sarasota

Central Sarasota

Save 100% on your flight

$570

per person

Oct 13 - Oct 17

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Tampa (TPA)

9.2/10 Wonderful! (1,150 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

$967

per person

Nov 12 - Nov 17

found 1 day ago

Roundtrip flight included

Boston (BOS) to Tampa (TPA)

9.6/10 Exceptional! (74 reviews)

The Gemma by Brightwild

Save 100% on your flight

$2,366

per person

Oct 28 - Oct 31

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 Ritz-Carlton, Sarasota

Central Sarasota

$1,342

per person

Oct 13 - Oct 17

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Tampa (TPA)

9.2/10 Wonderful! (1,018 reviews)

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3 Night All inclusive vacations in Siesta Key

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

Hyatt Regency Clearwater Beach Resort and Suites

Save 100% on your flight

$456

per person

Oct 28 - Oct 31

found 1 day ago

Roundtrip flight included

Boston (BOS) to Tampa (TPA)

9.4/10 Exceptional! (2,303 reviews)

Ocean Club Treasure Island Hotel

Sunshine Beach

$568

per person

Nov 18 - Nov 21

found 1 day ago

Roundtrip flight included

Boston (BOS) to Tampa (TPA)

9.6/10 Exceptional! (1,190 reviews)

Reviewed on Sep 11, 2026

The Avalon Club

Save 100% on your flight

$663

per person

Oct 17 - Oct 20

found 2 hours ago

Roundtrip non-stop flight included

Boston (BOS) to Tampa (TPA)

9.4/10 Exceptional! (595 reviews)

The Avalon is clean. The staff are amazing and friendly

Reviewed on Sep 9, 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

Save 100% on your flight

$467

per person

Nov 13 - Nov 17

found 1 day ago

Roundtrip non-stop flight included

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

8.6/10 Excellent! (2,434 reviews)

Turtle Beach Resort

Save 100% on your flight

$756

per person

Oct 13 - Oct 17

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Tampa (TPA)

8.8/10 Excellent! (363 reviews)

Great location. Friendly staff and nice amentities.

Reviewed on Sep 9, 2026

Cedar Cove Resort and Cottages

Save 100% on your flight

$959

per person

Nov 21 - Nov 25

found 1 day ago

Roundtrip flight included

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

9.2/10 Wonderful! (591 reviews)

Beautiful private beach. Room was nice. Amenities were great. Housekeeping could have been a little better.

Reviewed on Sep 11, 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 $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.