A Tropical Travel Blog
by Cate Lincoln

Seaside Florida Vacation Rentals

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Ahh Seaside. One of my favorite places in Florida! The beaches are just the best (blue water, white sand!) and the town is SO CUTE. There aren’t many hotels in this area (none at all in Seaside proper) so if you want to stay here you’ll be doing a vacation rental.

Seaside has the most charming colorful cottages you’ll find anywhere, but there are so many that it can be kind of overwhelming narrowing it down. So I’ve rounded up some of my favorite Seaside vacation rentals plus general tips that I always use when booking condos/vacation rentals.

First things first…before you start looking around for specific rentals, it’s best to have a general idea of where you want to stay. Presumably, if you’re reading this post, you’re wanting to stay in Seaside, but if you’re not terribly familiar with the area, or you’re just wanting to stay somewhere on 30a in general, read this post first for a breakdown of the whole area. Also, read up on 7 swoon worth Rosemary Beach vacation rentals here.

My Tips for Booking a Seaside Vacation Rental

Consider what you need. What’s important to you? Are you looking for something right on the beach? Do you need a full kitchen? Reliable Wi-Fi? A full house or just studio? Something pet friendly? Be clear about what you want before you start searching.

Read reviews. Before you even consider staying at a property, you should read up on what people who have stayed there have to say. Remember, you’ll only hear the good points from the host but reviews usually give a much more honest story. And when I’m weeding through listings, I also put a lot of weight into the photographs provided. If the photos look professional, it probably means that the owner runs their vacation rental in a professional manner and that is an indication that it’s a good place to stay.

Ask plenty of questions. When you’re seriously considering staying at a specific property, you should correspond with the owner and ask them any questions you may have.
Count the extra costs. Be sure to factor in any security deposits, cleaning fees, and booking fees.
Know the cancellation policy. Each property and owner may have different terms so know what they are before you commit.

Where I Book My Seaside Vacation Rentals

So now that you know what you’re looking for…how do you find it?

I think the best place to find (and book) Seaside/30a vacation rentals is Vrbo. They’ve been around forever and are probably the most reputable booking platform online (with owners and vacationers alike), which means that you’ll find more quality properties listed on Vrbo than anywhere else online. I used to book more often with Airbnb, but I’ve begun to find that they often don’t have what I’m looking for (plus I had a less than great experience dealing with corporate last time I used them).

Overall on Vrbo you’re going to find properties listed by owners who take their rental business very seriously and are committed to providing you the best accommodations possible.
How does it work? By doing a simple search by specific area (in this case Seaside/30a), you’ll be able to find a wide (price and type) range of accommodations. You can refine your search to fit certain criteria (price, space, style, etc.) before you start weeding through specific properties.

The number of search results you’ll find can be extremely overwhelming, so I would suggest putting as many filters as possible (especially price and number of bedrooms) and then viewing the results on a map so you can get an idea for where everything is located.
I know what people are looking for specifically varies greatly, but I often get asked for the best (i.e. cheapest, nicest, cleanest) beachfront rentals, so I’ve rounded up a few specific properties that I like the looks of:

My Favorite Seaside Vacation Rentals

Seaside Florida Vacation Rentals

Luxurious 5 Bedroom Beachfront Stunner! Yowzer…I know what I’ll be booking for our next extended family vacation. Sleeps 18!

Seaside Florida Vacation Rentals

Cozy 2 Bedroom with a Big Deck! The inside of this one is suuuuper cute. Quiet location close to town and the beach. Price starts at $108/night.

Seaside Florida Vacation Rentals

Coastal Cottage with Ocean Views! Cozy little coastal cottage interior with views out over the ocean. Right above the town center. Price starts at $252/night.

Seaside Florida Vacation Rentals

Dog Friendly 1 Bedroom Cottage! Comes with a shared pool. Price starts at $153/night.

Seaside Florida Vacation Rentals

Family & Dog Friendly 4 Bedroom/3 Bath! Super cool architecture on the inside plus amazing porch. Very southern. Price starts at $228/night.

Seaside Florida Vacation Rentals

One Bedroom “Dreamboat” Across from Beach! The house is called the “Dreamboat.” Enough said. Price starts at $200/night.

Seaside Florida Vacation Rentals

Three Bedroom Beach House of My DREAMS! There’s just no way to describe it. Check out the pictures! Sleeps 9. Price starts at $468/night.

All photos are from individual property listings on Vrbo.

All of the cottages/rentals I’ve linked to above are in what’s considered Seaside “proper” (which a lot of the listings tout). This means they’re in the official township of Seaside (which isn’t very big). It’s kind of like being in an exclusive club. Real estate in Seaside is finite and it’s a real bragging point to be “in Seaside” instead of Seagrove or Watercolor (which could just be a block or two away). Aside from it being a “thing,” there’s not necessarily much benefit from staying “in” Seaside or “in” Seagrove. But if you’re wanting to mostly walk, definitely check the distances to Seaside’s town square (where all the shops and restaurants are) as Seagrove is MUCH more spreadout than Seaside and you could end up being several miles away. I’ll do another post with my favorite rentals in Seagrove.

Also, these rates are also STARTING rates, meaning that’s the cheapest rate you’ll find during the slow season (usually September through April) so if you’re putting in dates for high season (summer months and spring break), the rates may be higher.

These are just 7 dreamy Seaside vacation rentals but THERE. ARE. SO. MANY. Hundreds. So click here and put in your search parameters (price, # of bedrooms, etc.) and I guarantee that you will find something PERFECT for you!

RELATED: My 30a Favorites