Updated 2-Bedroom W/Loft in Seaside 1 Block to Beach, 2 Adult Bikes, Sleeps 8

*Please be advised that neighboring properties may currently be undergoing construction or renovation during your stay. As a result, intermittent noise or construction-related activity may occur at certain times throughout the day. This work is managed by third parties outside of our control, and we appreciate your understanding while enjoying the property. For additional questions or concerns regarding nearby construction activity, please contact Homeowner’s Collection at

Seaside is a place of whimsy and wonder for both adults and children, and Villa Whimsey captures that spirit perfectly. Ideally situated on historic Tupelo Street—Seaside’s very first street—this charming cottage offers easy access to the iconic white sand and shimmering turquoise waters that make Seaside so beloved. The wraparound screened porch on the ground floor immediately invites you to relax with a book, chat with friends, or simply soak in the laid-back beach vibe. Thoughtfully designed for comfort and convenience, the first level includes a queen primary suite with a full bath (shower only) and a private screened porch with a glider, plus an additional queen bedroom and full bath. An essential outdoor shower completes the ground floor.

Upstairs, the open and airy second floor features a sunlit kitchen, dining area, and living room—perfect for gathering with family and friends. Two breezy decks invite you to start your mornings slowly and end your days watching the sun dip behind Seaside’s distinctive rooftops. The third-floor sleeping loft, with twin beds and trundles, offers a cozy retreat beneath the sky. A full bath with a whimsical claw-foot tub and stained-glass window adds a playful touch to the top floor.

Just two doors down from the beloved Tupelo Street Gazebo and a short walk to Seaside’s Children’s and Recreation areas, unforgettable restaurants, and boutique shops, Villa Whimsey is a restful retreat in an ideal location. As they say, “all streets in Seaside lead to the sea,” and Tupelo Street is no exception—your private beach entrance awaits at the Tupelo Street Pavilion.

* 5 night minimum Summer; 3 night minimum Fall, Spring, & Spring Break; 2 night minimum Winter. Must be 25 years of age to rent and sign registration.

Features:
* Features 1,439 square feet
* Private Seaside residential beach at Tupelo Pavilion
* Seaside is the largest private residential beach on 30A
* 3-minute walk, 176 yards to beach access
* Private driveway
* Third-floor loft
* Peacock Alley Linens - Fresh and luxurious Peacock Alley towels and sheets throughout the home
* Access to 3 swimming pools, 5 Clay tennis courts & 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 Seaside Transit Authority
* Personalized service throughout your stay with starter amenities provided.
* 2 parking passes for two-bedroom and larger homes are issued. A golf cart is considered a car, and for non-homeowners visiting Seaside are prohibited. Special circumstances and medical needs requests require a golf cart permit.
* No pets allowed
* Tankless water heater

STR23-002234