Happily Ever After Tower

56 TUPELO STREET

A Newly Reimagined Guest Cottage in Seaside Proper

Happily Ever After has recently undergone a thoughtful renovation and has been beautifully redesigned as a charming two-bedroom guest cottage that comfortably sleeps up to four guests. One of the rare two-bedroom guest cottages in Seaside, Florida, this home offers lovely Gulf views and an unbeatable location just five houses back from the beach on scenic Tupelo Street in the heart of Seaside proper.

Prime Location Near the Beach & Town Center

Perfectly positioned near Seaside’s sugar-white sands, Happily Ever After allows guests to enjoy effortless access to the beach while remaining just a short stroll from Seaside’s iconic town center, boutique shopping, dining, and coastal attractions. This prime Tupelo Street setting offers both convenience and a peaceful retreat feel.

Thoughtfully Designed Interior Living

The newly reimagined interior showcases custom details and efficient use of space throughout. On the main level, the built-in king bedroom serves as a serene retreat, featuring abundant custom storage, a wall-mounted flat-screen smart TV, and a cozy sitting area filled with natural light. Just outside the bedroom is a stylish full bathroom with a sleek single vanity and a glass-enclosed walk-in shower.

Also on the first floor is a newly added kitchenette designed for both function and style. It includes an under-counter mini refrigerator, refrigerator and freezer drawers, microwave, coffee maker, and custom built-in shelving—ideal for light meals, snacks, and morning coffee before the beach.

Second Bedroom & Cozy Upper-Level Retreat

Up the spiral staircase, the second bedroom offers a custom built-in twin bunk, making it perfect for children. This inviting space includes built-in bunk storage, a mini closet, a large flat-screen TV, and a loveseat for lounging or winding down after a day in the sun.

Open-Air Rooftop Tower with Gulf Views

The true highlight of Happily Ever After is the open-air rooftop tower, accessed by a private staircase. This elevated escape features Adirondack seating for two and delivers breathtaking panoramic views of the Gulf of Mexico, Seaside’s iconic rooftops, and unforgettable sunsets—an ideal spot for evening relaxation or morning coffee with a view.

A Rare & Charming Seaside Escape

Whether you’re planning a family beach getaway, a parents-and-kids retreat, or a cozy Seaside vacation for four, Happily Ever After offers a unique blend of charm, location, and elevated design. With Gulf views, thoughtful renovations, and a prime Seaside setting, this guest cottage is a truly special place to relax, recharge, and enjoy the magic of 30A.

This home can also be rented as a 3-bedroom lock-off Happily Ever 3 or the whole house, Happily Ever After, a five-bedroom home.

Must be 25 years of age to rent and sign the registration. 3-night minimum Spring, Spring Break | 5-night minimum Summer | 3-night minimum Fall | 2-night minimum Winter

FEATURES

• 475 square feet
• Private Seaside residential beach access at Tupelo Pavilion
• 308 feet or a 1-minute walk to beach access
• Shared washer and dryer accessed from the outdoor walkway between the street and the tower
• Kitchenette with no dishwasher
• Peacock Alley Linens – fresh and luxurious Peacock Alley towels and sheets throughout the home
• Access to 3 swimming pools, 5 clay tennis courts (court fees apply), 3 pickleball courts (court fees apply), and a fitness center
• Welcome tote with 2 beach towels, a complimentary bottle of wine, and 2 complimentary rental bikes for pickup at the Seaside Transit Authority
• Personalized service throughout your stay with starter amenities provided
• One parking pass issued for Happily Tower. A golf cart is considered a car. Golf carts for non-homeowners visiting Seaside are prohibited. Special circumstances and medical needs requests require a golf cart permit
• No pets allowed