Vacation Rentals in Seaside, Florida – 30A

Vacation Rentals in Seaside, Florida

By: Ali Diamond | Posted Nov 6, 2021

Seaside, Florida, is a vibrant, energetic town filled with new adventures around every corner. Founded in 1981 by Robert and Daryl Davis, Seaside has become the poster child for the New Urbanism architecture movement.

A gorgeous, walkable community, filled with civic spaces that host movie nights and farmer’s markets, it’s the perfect place to stay with your family and friends.

Seaside has also become the unofficial “downtown” to the 30A community, with people flocking to more than 50 retail and restaurant locations. With the delicious restaurants, exciting events hosted nightly, and convenient beach access, it’s no wonder that Seaside is one of the most popular communities to stay in on 30A.

To experience all the fun and action that Seaside has to offer, here are five, beach-approved rentals located within the beautiful community.



1. Monday’s Child

Cottage Rental Agency

If Monday’s Child’s bright pink exterior isn’t enough to make you smile, then the stunning Gulf views surely will! Located on Savannah Street in Seaside, this gorgeous home is directly across from the beach access, and just steps away from the sandy white beaches and green Gulf waters. This home features three bedrooms, two bathrooms, can sleep up to 6 comfortably, and is located within walking distance to Seaside’s famous Airstream Row. Pick up a grilled cheese from The Meltdown on 30A, and enjoy it on the spacious front porch. This property also features a cozy living area, a fully-equipped kitchen, complimentary WiFi, a second-floor balcony with incredible Gulf views, and an in-unit washer/dryer. Book Monday’s Child with a starting rate of $400/ night and for additional rooms, the one-bedroom guesthouse, Sea for Two, can be rented as well.

2. Love Me Tender

Cottage Rental Agency

The view from Love Me Tender. Photo credit: Cottage Rental Agency.

First time to the beach, and you’re looking for something with gorgeous Gulf views? Well, look no further than Love Me Tender.

Located directly on the water, this cozy, one-bed, one-bath cottage features stunning Gulf views and an expansive, covered balcony to enjoy the morning sunrises and late-night sunsets.

Love Me Tender also features complimentary WiFi, soaring ceilings, and a newly-updated interior. The cottage sleeps up to four comfortably and has a starting rate of $300/ night. Located on the main strip of Seaside, and just steps away from the iconic East Ruskin Beach Pavilion and local eateries such as Great Southern Cafe and Pickles. Bring an evening cocktail back from Bud & Alleys to enjoy the sunset on your gorgeous Gulf-front balcony.



3. Bella Vista

Benchmark 30A

Feel like you’re back in Old Florida with Bella Vista, an original Seaside cottage. Built in 1981, this beach cottage is located right by the iconic Tupelo Street Gazebo. The property features adorable beach decor, an oversize screen porch, and is also located just steps away from the Seaside beach pavilion. Bella Vista features 2 bedrooms, 2 bathrooms and can sleep up to 6 comfortably. This adorable property also features incredible amenities. Guests can enjoy a free credit toward rental gear with each booking to use on various items such as bikes, beach bonfires, tours/experiences, and much more. Certain restrictions, exclusions, and limitations apply. Make Bella Vista a family favorite destination with a starting rate of only $265/ night.

4. Mocean

Cottage Rental Agency

Mocean. Photo credit: Cottage Rental Agency.

Located on Seaside’s quaint East Ruskin Place, Mocean is actually two homes in one: “Slow Mocean” and “Seasuite.” With 6 bedrooms and 6.5 bathrooms, this home is great for big groups of family and friends as this gorgeous property can sleep up to 14 comfortably. Slow Mocean is the main house with beautiful, luxury furnishings. The main house features several large living spaces, a large kitchen with a dining table that seats 12, three additional bedrooms and a bunk room, an outdoor shower, and more. Seasuite, the detached bungalow cottage, features a gorgeous queen bedroom with a full bath, a kitchenette with beautiful glass-tile countertops, and an in-unit washer/dryer. With a starting rate of $2,250/ night, Mocean is the perfect option for your next family and friends reunion!

5. Breakers + Carriage House

Paradise Properties

Another fantastic option for large parties, the Breakers and Carriage House can sleep up to 13 guests comfortably. Located in the heart of historic Seaside, this property is perfectly located a block away from beach access, a few blocks from the community pools, and only a couple blocks from the town center.

With four bikes included with your reservation, you’ll have a great time exploring Seaside’s adorable shops, delicious restaurants, and the rest of Scenic 30A.

This property features a main house and a carriage house; and also features four bedrooms, three bathrooms, gorgeous Gulf views from the balconies, complimentary WiFi, a screened-in front and back porch, community amenities and has a starting rate of $675/ night. As Paradise Properties says: “come and fix yourself a Mint Julep, and sit on the porch bed under the fans, listening to the palm trees and birdsongs.”

To discover more beach homes in Seaside, check out 30A Rentals.

Ali Diamond is a local, 30A-based freelance writer who enjoys working and living at the beach. Ali also works in real estate on 30A. When she’s not writing or working, she enjoys watching the sunrise on early-morning paddle boards, or ending the day while watching the sunset on the beach.