Longboat Key vs Siesta Key vs Anna Maria Island: Which Island Is Best?

If you love the beach and you’re planning a trip to Florida, you’ve undoubtedly heard about the beaches of Sarasota’s famous barrier islands: Anna Maria Island, Longboat Key, and Siesta Key. This chain of islands off Sarasota (between Tampa and Fort Myers on the gulf coast) is well known for its white sand beaches, turquoise waters, and small beach town vibes. People searching for Florida’s best beaches and wanting to avoid the crowded, over touristy beaches of St Pete and Clearwater (to the north) are often drawn here. 

But which island is best??? I wish there was an obvious answer, but unfortunately…”it depends.”

Stay tuned…in this post I’m going to break down the pros and cons of each island so you can decide which one sounds best to you. 

If you’re feeling drawn to Anna Maria Island or Longboat Key, read this post that’s a full guide to the area. 

The Sarasota Area

First off, while these three islands are all very different, they’re all fairly close together in the Sarasota area and have somewhat of a similar vibe. These islands feel like small beach towns. There aren’t very many hotels or resorts. Everything is mostly condos and vacation rentals. Things feel pretty spread out on the islands but there are little hubs where shops and restaurants tend to be centralized. They’re also pretty tropical (Bradenton is where the tropic line is in Florida) which I like. 

While there is plenty built up on these islands, they don’t feel overly commercialized. This area is night and day from the St Pete and Clearwater area just north. You won’t find a Bubba Gump’s or Hooters anywhere in sight. If you like Destin, Panama City Beach, Coco Beach, or Clearwater/St Pete, you’re probably not going to like this area. If you like Sanibel/Captiva and Marco Island then you’ll probably like it. 

Now, onto the specifics…

Anna Maria Island vs Siesta Key vs Longboat Key

30+ miles of white sand beaches stretch along (from north to south) Anna Maria Island, Bradenton Beach, Longboat Key, Lido Key, and Siesta Key. 

Anna Maria Island

The northernmost island is technically one long island, but it’s split into two distinct parts: Anna Maria Island and Bradenton Beach. The southern part of the island is Bradenton Beach (the city of Bradenton is just across on the mainland). There’s a very large public beach access at the southern end of the island (Coquina Beach) and as you go north it’s pretty much one long stretch of “little beach town” vibes. 

The northern end of the island is Anna Maria Island. There’s not really a definitive line that separates one from the other and there’s not a noticeable difference in the types of accommodations (one’s not necessarily nicer than the other). I will say that there’s definitely an attitude that Anna Maria Island is a bit superior to Bradenton Beach, but I think it’s mostly to do with name recognition. I noticed that quite a few restaurants that are located more on the southern end of the island use “Anna Maria Island” in their name or merchandise instead of Bradenton. 

So while there’s a lot of ambiguity about where one ends and the other begins, Holmes Beach and north is definitely considered Anna Maria Island. If you’re wanting to be in the center of the action (close proximity to restaurants, shops, etc.) Pine Avenue is definitely the main drag on the north end of the island. It cuts the island from west to east (there’s a public beach access on the west and Anna Maria Island City Pier on the east) and it’s lined with cute shops and restaurants. If you’re staying on the north end of Anna Maria Island, it’s definitely doable to get around mostly by walking, biking, or by golf cart (bike and golf cart rentals are available at several places in town). 

Overall, the vibe on Anna Maria island is pretty laid back but there can be a lot of traffic (especially around Bradenton Beach). It’s your typical small beach town in most ways. Think: small inns/motels, ice cream shops, beach shops, cozy restaurants, etc. The main road up the island is more or less lined with these things. It’s not an idyllic preplanned feel (like Seaside or Rosemary Beach on the 30a), but it’s also not overly commercialized with a lot of chain restaurants or stores. It’s just slowly been built up throughout the years and has that kind of charmingly ramshackle look that’s usually the result of a small beach town being “discovered.”

My pick on this island is to stay at the north end somewhere within walking distance to places along Pine Avenue. Also it would be ideal to rent a golf cart. If you stay on the north end of the island, you’ll avoid a lot of the traffic that comes through Bradenton Beach (where there’s a huge public beach access) and there’s a Publix on the north end as well as a bridge over to Bradenton. 

Bali Hai Beach Resort: Next time I’m on Anna Maria Island, this is probably where I’ll stay. It’s a small boutique hotel right on the beach and it looks so cute! The property is in the process of being completely renovated, and I think the key to having a perfect stay here is definitely booking one of the newly renovated rooms (I believe the beachfront rooms haven’t been renovated yet). Pricing starts at $230/night. Click here to check pricing and availability during your stay. 

Anna Maria Island Condos & Vacation Rentals: Click here to find the best condos in Anna Maria Island. You can filter for your wishlist (exact location, price, # of rooms, pet friendly, etc.). And if you’re on a tight budget, you’ll be pleased to find many options under $100/night. Search for Anna Maria Island condos and vacation rentals here

Longboat Key

Just south of Anna Maria Island (and connected by a bridge) is Longboat Key. I’m partial to Longboat because my family used to start every summer with a trip to Longboat over Memorial Day weekend when I was a kid. 

Longboat Key is by far the most mellow place to stay in this whole area. The 10-mile long island is almost entirely residential. Think vacation homes, small condos and inns, upscale complexes (but still on the smaller side) plus a couple of beach resorts. There are very few shops and restaurants on the island and besides golf and tennis, you won’t find much to do. There’s a Publix and a CVS and a few restaurants and that’s about it. 

But that’s kind of what I like about Longboat Key. There’s 0 traffic. Like it just doesn’t exist. There are a lot of beach front accommodations (in a wide range of prices and styles) but none of the places are very big so the beaches are never crowded. And no matter where you stay on the island you’re a very quick drive from either Bradenton/Anna Maria Island to the north (plenty of shops, restaurants, things to do, etc.) or St Armand’s Circle and Sarasota to the south which is heavily concentrated with shopping, dining, and attractions. 

You definitely need a car if you’re staying on Longboat Key (anywhere in this area really), but staying on Longboat gives you the best of both worlds getting a peaceful and quiet beach experience but with nearby areas and attractions being easily accessible. 

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At the south end of Longboat Key, there’s a bridge over to St Armand’s Key (where you’ll find St Armand’s Circle and TONS of shopping and dining) and Lido Key and from there you’ve got the bridge to Sarasota on the mainland. 

It’s a long skinny island and I’m not sure there’s a bad place to stay, but I do have one observation: the sand seems to be a little softer and whiter at the southern and northern ends of the island. We always used to stay on the south end (the old Colony Beach and Tennis Resort) and stayed more in the middle on this trip and the sand seemed a little coarser and more full of shells. Of course it’s all relative though. The sand is still pretty great. 

The overall vibe on Longboat Key is interesting. You’ll notice a pretty dramatic difference between it and Bradenton/Anna Maria Island. Overall, I think the people who stay on Longboat Key tend to be older and in general I would say everything is just a little more upscale. 

So where exactly should you stay?

We always stayed at the Colony Beach and Tennis Resort when I was a kid and it was absolutely perfect but sadly it is no more. After many years of sitting abandoned, the property has recently been cleared to make way for a St Regis resort. And I’m not exactly mad about it. Honestly, when the St Regis finally opens, I think it’s going to make Longboat Key a REAL destination. This whole area is severely lacking a super nice place to stay. And the St Regis is definitely going to fill that void. I think it will ultimately draw people to this area that hadn’t considered it before. But alas, that looks like it’s still probably a couple of years away. So for now…

The Resort at Longboat Key Club: This is where I would stay next time. It’s pretty much the only beachfront resort in this whole area (not a condo complex). It’s been recently renovated and it’s a pretty large property with full amenities (plus amazing golf, tennis, spa, etc.). Pricing starts at $350/night. Click here to check pricing and availability during your stay.

On my last trip to Longboat, we stayed at the Zota Beach Resort (former Hilton), and it was fairly disappointing. I definitely wouldn’t go back. I’ve written up a full review in this post

Longboat Key Condos & Vacation Rentals: Click here to find the best condos and rentals on Longboat Key. You can filter for your wishlist (exact location, price, # of rooms, pet friendly, etc.). And if you’re on a tight budget, you’ll be pleased to find many options under $100/night. Search for Longboat Key condos and vacation rentals here

Siesta Key

After years of hearing of its famed sugar white sand beaches, I finally made it down to Siesta Key recently. I honestly was not expecting to be suuuuper impressed. I mean, the whole gulf coast of Florida is pretty renowned for its white sand beaches. Is Siesta Key really that special? Yes. Yes it is. 

Come to find out…the sand is actually quartz so that’s why it feels so squeaky clean and fine. 

So about the island as a whole…Siesta Key feels more like Anna Maria Island than Longboat, but it’s still different. 

For starters, it’s separate from the other islands. You can’t get from Longboat Key/St Armand’s without going across the bridge to Sarasota, down the coast a ways and then across the bridge to Siesta Key. There’s actually two bridges from Sarasota to Siesta Key, one in the middle of the island and one at the very northern end. There’s a small collection of restaurants (and maybe a couple of shops) around the bridge at Midnight Pass (the middle of the island), but by far the majority of everything else is concentrated up at the northern end on Ocean Blvd. It’s the area that feels most like a “town” on the island. Whereas Anna Maria Island/Bradenton is pretty much one long stretch of shops, restaurants, and businesses, everything on Siesta is pretty concentrated into those two areas. 

Most of the accommodations are around the Midnight Pass bridge or north of it. Driving south along the island, things are mainly residential (and not necessarily the kind of places you rent-I think people actually live there). There are a TON of condo complexes, small inns, and vacation rentals on Siesta Key. The thing you have to be aware of is even if a place is on the beach side of the main road, it still may be a WAYS from the actual beach. The island is fairly wide in one stretch and it looks like there are 2-3 condo complexes deep between the road and the beach so just watch out to make sure you’re getting something actually on the beach if that’s something important to you. 

Back to the beaches…while there’s a continuous stretch of sand along the whole island depending on where you stay you may or may not have access right at your place or need to use a public beach access. WELL…the public access at Siesta Beach is seriously impressive. I’m not exaggerating. Siesta Beach is the nicest public beach (facilities included) that I’ve ever seen. Anywhere. 

After years of getting attention for “America’s best beach” and winning countless awards, it’s nice to see that they’ve invested in infrastructure that makes visiting it a pleasant experience. There was a ton of parking (I’m sure not enough during high season but you only have so much!), drop off and loading zones, clean restrooms with a ton of stalls, a snack bar, shop with essentials like sunscreen, inflatables, beach toys, hats, etc., picnic tables and MORE. 

Also there’s an accessible entrance (and I read that they also had beach wheelchair rentals available) which I had never seen before. There was a 5-6 foot wide industrial cloth/walkway from the facilities where you park down close to the edge of the water. It’s an extremely wide beach (it seemed like ¼ mile plus from the parking lot to the water) so it’s amazing being able to walk (or push a wheelchair, pull a wagon, etc) to the shoreline without having to slug through thick, hot sand. 

My pick on this island would be to stay towards the northern end of the island at a place that’s within walking distance to all of the shops and restaurants on Ocean Blvd. There’s so little parking in the area (and so few restaurants compared to how many rooms are on the island) that it would be nice not to have to worry about a car every time you want to go eat. 

Tropical Breeze Resort: This little collection of bungalows would be the perfect place to stay. They’re right near a beach access point and within walking distance to all the spots on Ocean Blvd (without being right in the middle of everything). Pricing starts at $169/night. Click here to check pricing and availability during your stay. 

If you want more of a hotel set up, this Hyatt looks pretty nice. 

Which Island Is Best? 

Now that you’ve read up on all three islands, you’ve probably got a feeling as to which one sounds best to you. But in case you’re still having a tough time making a decision, here’s some more info: 

Best Beach? Anna Maria Island, Longboat Key or Siesta Key?

Siesta Key has the best beach (sand!!!) hands down UNLESS you like to shelling. The sand is like white sugar (quartz) and it’s because it has 0 shells in it. That’s why it’s so beautiful but you might be disappointed if you’re hoping to stroll the beach looking for shells. 

Siesta Key is also has the best public beach access. If you’re not staying somewhere right on the beach that could be important. Longboat Key has virtually no public beach access (there’s some but it’s usually pretty hidden and parking is super limited). Bradenton/Anna Maria Island has good access (Coquina Beach in particular has parking and some amenities), but there can be a lot of traffic. Siesta Beach is 100% set up for people coming for the day (whether it’s from across the bridge on the mainland or from a condo that’s not right on the beach). Once you get there, it’s pretty easy to set up camp and they have everything you’ll need (restrooms, showers, snack bar, picnic tables, a small shop, etc.). 

Best Shelling? Anna Maria Island, Longboat Key or Siesta Key?

Longboat Key has the best shelling. As I mentioned above, Siesta beaches have no shells. Anna Maria Island is decent but Longboat seems to be the best. Maybe it’s because there’s fewer people to pick over them. 

Best Oceanfront Restaurants? Anna Maria Island, Longboat Key or Siesta Key?

Anna Maria Island definitely has the best beachfront restaurants. It actually might be the only island with restaurants on the beach. Longboat has a few on the bay and Siesta Key doesn’t seem to have many on the water at all. But Anna Maria has quite a few spots where you can literally sit at your table with your feet in the sand. That’s pretty rare in this area where most beachfront property is taken up by condos and vacation rentals. 

Quietest Beaches? Anna Maria Island, Longboat Key or Siesta Key?

Definitely Longboat Key. It’s the quietest area. There’s virtually no traffic.  There’s also not much to do besides the beach, golf, and tennis. But it’s super close to St Armand’s Circle if you want to get out. 

Best Grocery Store? Anna Maria Island, Longboat Key or Siesta Key?

Longboat Key has a SUPER nice Publix (the prepared food section is amazing). Anna Maria Island also has a Publix on the north end, but there’s not a major grocery store on Siesta Key. 

Best Resorts or Hotels? Anna Maria Island, Longboat Key or Siesta Key?

Longboat Key is really the only island with what I would consider a true resort…the Resort at Longboat Key Club. Otherwise, you’re looking at condos and vacation rentals pretty much everywhere.