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

Top rated by guests
WELCOME TO VILLA WHIMSEY
LIVING/KITCHEN VIEW
BREAKFAST BAR IN KITCHEN
BREAKFAST BAR/KITCHEN ALTERNATE VIEW
KITCHEN BAR AREA
review stars
9.6Outstanding
(51 Ratings)
"Great location. Great communication."
Ashley H.
Don't miss out! Price and availability may change
9.6 / 10
Outstanding(51 Ratings)

House in Seaside, FL

8 guests · 2 bedrooms · 3 baths

Reasons to book

Guests love it hereGuests give this property a top rating
Top-tier experienceA high end property in this area
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About this house rental

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 beach home 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

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

Non-smoking
No pets allowed
Family friendly

Map of Seaside, FL


Ratings and reviews

9.6 / 10
Outstanding(51 Ratings)
10 / 10Outstanding·Aug 2025
Great location. Great communication.
10 / 10Outstanding·Jul 2025
Rating Details: The vacation rental was spotless. I was very happy with the location. I was very satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: As Described.
10 / 10Outstanding·Jul 2025
Rating Details: The property manager was very helpful. The vacation rental was spotless. I was very happy with the location. I was very satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: Villa Whimsy was the perfect house for our week at Seaside! The house was clean, had everything we needed, plus is located in a great spot! Easy walk to the beach, or to the main square. We loved it!
6 / 10Average·Dec 2021
Rating Details: The property manager was adequately helpful. The vacation rental was spotless. I was very happy with the location. I was more than satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: The AC was either working incredibly well or it wasn’t because the bottom floor with all the beds was freezing. We had to sleep with all the blankets. We told the rental company but they kept saying “heat rises”. Yes that’s true, the bunk room was incredibly hot but the rest of the house was freezing. By the end of the trip we all slept on the couch or in the loft. We were grateful they let us spent two extra nights but next time I’ll bring warm long underwear.

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FAQs

Is parking included with this house?

Parking is not specified as an available amenity at Updated 2-Bedroom W/Loft in Seaside 1 Block to Beach, 2 Adult Bikes, Sleeps 8. For more information, we encourage you to contact the property about where to park.

Is there a pool at this house?

We didn’t find pool listed as an amenity for this house. It may be worth double checking if a pool is important for your stay.

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

Unfortunately, this house is not pet-friendly. Try searching again and filter for "Pets Allowed"

What amenities are available at Updated 2-Bedroom W/Loft in Seaside 1 Block to Beach, 2 Adult Bikes, Sleeps 8?

We found 3 amenities for this rental. This includes non-smoking, no pets allowed, and family friendly.