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

Santa Rosa Beach, Florida
$728 avg/night Minimum Stay 1 Nights
Bed 2

Bed

Bath 3

Bath

Home Private Vacation Home

Property Type

Sleep 8

Max Sleeps

Night 1 nights

Min Stay

*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

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  • Feature Features
  • Map Map
  • School District Rates & Availability
  • Review Review

Feature Features

  • PETS

    No Pets Allowed
  • BEACH

    Near The Beach
  • DINING

    Dining Table
  • SAFETY

    Carbon Monoxide Detector Not Reported (host Has Not Indicated Whether There Is A Carbon Monoxide Detector On The Property; Consider Bringing A Portable Detector) Fire Extinguisher Smoke Detector Installed (host Has Indicated There Is A Smoke Detector On The Property)
  • BEDROOM

    2 Bedrooms Bed Sheets Provided
  • GENERAL

    Unit Size: 1439 Sq Ft (134 Sq M)
  • KITCHEN

    Coffee/tea Maker Cookware/dishes/utensils Dishwasher Microwave Oven Refrigerator Stovetop Toaster
  • LAUNDRY

    Laundry Facilities Washing Machine And Dryer
  • PARKING

    Onsite Parking
  • INTERNET

    Free WiFi, With Speed Of 100+ Mbps (good For 1–2 People Or Up To 6 Devices)
  • OUTDOORS

    Balcony Barbecue Grill
  • POOL/SPA

    Heated Pool Massages Shared/communal Pool
  • BATHROOMS

    3 Bathrooms Hair Dryer Shower Towels Provided
  • LANGS SPOKEN

    English
  • THINGS TO DO

    Basketball Nearby Bicycle On Site Cycling Nearby Fishing Nearby Fitness Facilities Nearby Golf Nearby Golfing On Site Snorkeling Nearby Swimming Nearby
  • ENTERTAINMENT

    TV With Cable/satellite Service
  • CLIMATE CONTROL

    Air Conditioning
  • LOCATION HIGHLIGHTS

    Near A Hospital Near The Sea
  • SERVICES AND CONVENIENCES

    Concierge Services Iron/ironing Board
  • SUITABILITY/ACCESSIBILITY

    Smoke-free Property

CheckIn Check-in : 04:00 PM CheckOut Check-out : 10:00 AM
No Wheelchair No smoking No pets Children allowed
Occupancy Max occupancy : 8

Map Map

School District Rates & Availability

Review Review

  • Ashley H.

    Submitted Aug 4, 2025

    Stayed Jul 31, 2025

    Great location. Great communication.

  • Donald M.

    Submitted Jul 20, 2025

    Stayed Jul 12, 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.

  • Jill S.

    Submitted Jul 12, 2025

    Stayed Jul 5, 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!

  • Sherry C.

    Submitted Jun 10, 2025

    Stayed Jun 6, 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: Great weekend getaway with my family. Cottage had perfect set up for us. Liked that it had 3 bathrooms. Very clean. Nice location. Great communication from Homeowners Collection Co.

  • Juli R.

    Submitted Aug 11, 2024

    Stayed Aug 3, 2024

    Very smooth booking with clear and timely communication. Check in was easy as well. The cottage had everythingwe needed for a relaxing and comfortable stay. We would definitely stay here again!

  • Susan R.

    Submitted Jun 22, 2024

    Stayed Jun 7, 2024

    Location! Location! Location! Wonderful location to the beach and to the shopping areas! Beautiful home and we felt spoiled by the hosting company. They were wonderful with communicating and making sure we had all of our needs ! Would definitely book again!

  • Rachael W.

    Submitted Jun 21, 2024

    Stayed Dec 31, 1969

    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: We stayed in Villa Whimsey and loved it. It is a 3 min walk to the beach, 4 min walk to town center and 1 min to fitness. All much faster on bikes. The management team was so helpful and responsive. The loft is a tub only and bathroom for kiddos or tiny adults as the ceiling is low. We had a great time and loved beach time, pool time and dinners at home with the grill and full kitchen. The town at night was the place to be! We hope to return and loved everything about Seaside.

  • Stephanie d.

    Submitted May 22, 2024

    Stayed Dec 31, 1969

    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: I love this place! The house was adorable. I stayed at this vacation home for three nights with a friend. The space was excellent and the walk to the beach and other activities was short. Great location!

  • Jessica C.

    Submitted Oct 19, 2023

    Stayed Dec 31, 1969

    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: Perfect place, perfect location, perfect vacation!

  • Margaret C.

    Submitted Aug 20, 2023

    Stayed Dec 31, 1969

    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: I loved everything about this house! The location was perfect to the beach, the square and anywhere else you’d want to go. Homeowners went above and beyond to make sure our stay was seamless and they were always available for any questions I had. I’ll definitely be staying at Villa Whimsey next year!!!

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Total

Includes taxes and fees
$728+
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