You're never far from where you need to be with this convenient location.
Discover nearby landmarks
Walk to Seaside Beach
2 bedrooms3 bathroomsSleeps 8
Popular amenities
Massages in spa
Balcony
Swimming pool
Barbecue
Air-conditioning
Refrigerator
Explore the area
Santa Rosa Beach, FL
Seaside Beach
Place, Seaside Beach
3 min walk
Central Square
Place, Central Square
5 min walk
Seagrove Beach East
Place, Seagrove Beach East
6 min walk
Fort Walton Beach, FL (VPS-Northwest Florida Regional)
Airport, Fort Walton Beach, FL (VPS-Northwest Florida Regional)
61 min drive
Rooms & beds
2 bedrooms (sleeps 8)
Bedroom 1
1 Queen Bed
Bedroom 2
1 Queen Bed
Other Space 1
2 Single Beds
3 bathrooms
Bathroom 1
Bathtub · Toilet
Bathroom 2
Bathtub · Toilet
Bathroom 3
Toilet · Shower only
Spaces
Deck or patio
Porch or lanai
Kitchen
Balcony
About this property
Updated 2-Bedroom W/Loft in Seaside 1 Block to Beach, 2 Adult Bikes, Sleeps 8
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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Extra-person charges may apply and vary depending on property policy
Government-issued photo identification and a credit card, debit card or cash deposit may be required at check-in for incidental charges
Special requests are subject to availability upon check-in and may incur additional charges; special requests cannot be guaranteed
On-site parties or group events are strictly prohibited
Host has not indicated whether there is a carbon monoxide detector on the property; consider bringing a portable detector with you on the trip
Host has indicated that there is a smoke detector on the property
Safety features at this property include a fire extinguisher
About the area
Santa Rosa Beach
Located near the beach, this holiday home is in Seaside, a neighbourhood in Santa Rosa Beach. Shoppers can check out Grand Boulevard at Sandestin, while everyone can enjoy the natural beauty of Seaside Beach and Grayton Beach State Park. Sundog Books and Eden Gardens State Park are also worth visiting. Snorkelling, fishing and swimming offer great chances to get out on the surrounding water, or you can seek out an adventure with cycling nearby.
Panama City, FL (ECP-Northwest Florida Beaches Intl.) - 49 min drive
Restaurants
Bud & Alley's Waterfront Restaurant & Bar - 6 min walk
Pickles - 5 min walk
Seagrove Village Market Cafe - 8 min walk
Boggy Boys Pizza - 5 min drive
Scratch Biscuit Kitchen - 14 min walk
Frequently asked questions
Does Updated 2-Bedroom W/Loft in Seaside 1 Block to Beach, 2 Adult Bikes, Sleeps 8 have a pool?
Yes, this property has a pool. Pool types include heated pools.
How much does it cost to stay at Updated 2-Bedroom W/Loft in Seaside 1 Block to Beach, 2 Adult Bikes, Sleeps 8?
As of 16 June 2026, prices found for a 1-night stay for 2 adults at Updated 2-Bedroom W/Loft in Seaside 1 Block to Beach, 2 Adult Bikes, Sleeps 8 on 18 August 2026 start from NZ$1,586, including taxes and fees. This price is based on the lowest nightly price found in the last 24 hours for stays in the next 30 days. Prices are subject to change. Choose your dates for more accurate prices.
Is Updated 2-Bedroom W/Loft in Seaside 1 Block to Beach, 2 Adult Bikes, Sleeps 8 pet-friendly?
No, pets are not allowed at this property.
How much is parking at Updated 2-Bedroom W/Loft in Seaside 1 Block to Beach, 2 Adult Bikes, Sleeps 8?
On-site parking is available at the property.
What time is check-in at Updated 2-Bedroom W/Loft in Seaside 1 Block to Beach, 2 Adult Bikes, Sleeps 8?
Check-in begins at 4:00 PM.
What time is check-out at Updated 2-Bedroom W/Loft in Seaside 1 Block to Beach, 2 Adult Bikes, Sleeps 8?
Checkout is at 10:00 AM.
Where is Updated 2-Bedroom W/Loft in Seaside 1 Block to Beach, 2 Adult Bikes, Sleeps 8 located?
Located in Seaside, this holiday home is within 1 mile (2 km) of Seagrove Beach West, Seaside Beach and Grayton Beach State Park. Seaside Repertory Theatre and Sundog Books are also within 5 minutes.
Reviews
9.4
Exceptional
Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labelled.
Thank you so much for taking the time to write this positive review of your cottage and the Homeowner’s Collection team. We are so pleased you enjoyed your stay, and we hope to welcome you back on your next visit to Seaside!
From a partner site
6/10 Okay
30 March 2026
Peek a Boo / Villa Whimsey
Rating Details:
The property manager was very helpful.
The vacation rental was very clean.
I was happy with the location.
I was somewhat dissatisfied with the condition of the vacation rental.
Overall, I do not recommend this vacation rental.
Reviewer Comments:
Disappointing.Peek a Boo is not a functional property.Villa Whimsey appears to be close to needing a complete makeover or tear down.
Response from VrboOwner on 31 March 2026
Hi there, We extend a sincere apology for your disappointment with Peek a Boo and Villa Whimsey.
I will share your comments with the Quality Control Manager and Property Owner right away.
A team member in Customer Relations will reach out to you soon to discuss more in detail, offline..
We do hope you will consider giving us another opportunity with special care, and accommodate your expectations.
Homeowners Collection appreciates the positive review of our services. Thank you....
From a partner site
10/10 Excellent
Donald M.
20 July 2025
Villa Whimsey
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.
Donald M.
Response from VrboOwner on 22 July 2025
Hello Donald, thank you for taking time to share a positive review of Villa Whimsey Cottage and Homeowners Collection.
We do hope to welcome you back and thankful you enjoyed Seaside. Take care...
Verified
10/10 Excellent
Nicole R.
23 April 2019
Great vacation!
This house worked perfectly for our group of 4! Very clean, very convenient, and wonderful overall!
Nicole R.
Stayed 7 nights in Apr 2019
Response from VrboOwner on 30 March 2020
Thanks for the positive review, we hope to host you again soon.
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!
Juli R.
Stayed 8 nights in Aug 2024
Response from VrboOwner on 4 September 2024
Juli, thank you so much for taking the time to write this positive review of Villa Whimsey and the Homeowner’s Collection team. We are so pleased you enjoyed your stay and we hope to welcome you back on your next visit to Seaside!
Villa Whimsey was perfect for our Seaside Escape! Everyone had a great time!
Kara F.
Stayed 7 nights in Jul 2021
Response from VrboOwner on 11 August 2021
Thank you so much for taking the time to write this positive review of Villa Whimsey and the Homeowner's Collection team. We are so pleased you enjoyed your stay and we hope to welcome you back on your next visit to Seaside
From a partner site
10/10 Excellent
Jill S.
12 July 2025
Great location
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!
Jill S.
Response from VrboOwner on 15 July 2025
Hi Jill, We are happy that you were happy with Villa Whimsey & our Homeowners Collection team.
We so appreciate the positive review and do hope to welcome you back again & again. We also hope many great memories were made.
Take care!
Verified
10/10 Excellent
Homeowner's C.
14 March 2018
Wonderful
Could not ask for a better location. House was spacious enough for all of us.
Would definitely return.
Homeowner's C.
Response from VrboOwner on 10 June 2020
Thanks for the great review!
From a partner site
10/10 Excellent
Jessica C.
19 October 2023
Another Weekend In Paradise
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!
Jessica C.
Response from VrboOwner on 3 November 2023
Thank you so much for taking the time to write this positive review of Villa Whimsey and the Homeowner’s Collection team. We are so pleased you enjoyed your stay, and we hope to welcome you back on your next visit to Seaside!
From a partner site
10/10 Excellent
Sherry C.
10 June 2025
Villa Whimsey stay
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.
Sherry C.
Response from VrboOwner on 11 June 2025
Hi Sherry, we are happy to hear you had a great weekend stay with us in Seaside.
Thanks for taking time to share a positive review of Villa Whimsey Cottage and Homeowners Collection.
We do hope to welcome your next visit to our beautiful Emerald Coast..
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!
Susan R.
Stayed 4 nights in Jun 2024
Response from VrboOwner on 23 July 2024
Susan, thank you so much for taking the time to write this positive review of Villa Whimsey and the Homeowner’s Collection team. We are so pleased you enjoyed your stay, and we hope to welcome you back on your next visit to Seaside!
From a partner site
10/10 Excellent
Chris A.
24 October 2021
Great last minute find
Rating Details:
The property manager was more than 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:
Property was just as described and we had a terrific time in Seaside!
Chris A.
Response from VrboOwner on 26 October 2021
Thank you so much for taking the time to write this positive review of Villa Whimsey and the Homeowner's Collection team. We are so pleased you enjoyed your stay and we hope to welcome you back on your next visit to Seaside!
From a partner site
10/10 Excellent
John C.
15 August 2023
Just Awesome
Rating Details:
The property manager was very 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:
Great location. Fun house layout for a family of five. Couldn’t have drawn up a better vacation.
John C.
Response from VrboOwner on 25 August 2023
Thank you so much for taking the time to write this positive review of Villa Whimsey and the Homeowner’s Collection team. We are so pleased you enjoyed your stay, and we hope to welcome you back on your next visit to Seaside!
From a partner site
10/10 Excellent
Stephanie A.
28 June 2022
Awesome!!
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 Whimsey was a wonderful beach house! It was roomy, yet cozy, and had everything we needed and wanted!! Highly reommend!!
Stephanie A.
Response from VrboOwner on 29 June 2022
Thank you so much for taking the time to write this positive review of Villa Whimsey and the Homeowner's Collection team. We are so pleased you enjoyed your stay and we hope to welcome you back on your next visit to Seaside!
From a partner site
10/10 Excellent
Stephanie d.
22 May 2024
Girls's Weekend
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!
Stephanie d.
Response from VrboOwner on 6 June 2024
Stephanie, thank you so much for taking the time to write this positive review of Villa Whimsey and the Homeowner’s Collection team. We are so pleased you enjoyed your stay, and we hope to welcome you back on your next visit to Seaside!
From a partner site
10/10 Excellent
Berkeley D.
19 March 2022
Villa whimsey was lovely!
Rating Details:
The property manager was very helpful.
The vacation rental was clean.
I was very happy with the location.
I was satisfied with the condition of the vacation rental.
Overall, I recommend this vacation rental.
Reviewer Comments:
We had a great time staying at the Villa Whimsey! Seaside is a magical town and the house was perfect for our needs. Homeowners collection was great with assisting with any questions and accommodating us I would definitely recommend staying here!
Berkeley D.
Stayed 5 nights in Mar 2022
Response from VrboOwner on 21 March 2022
Thank you so much for taking the time to write this positive review of Villa Whimsey and the Homeowner's Collection team. We are so pleased you enjoyed your stay and we hope to welcome you back on your next visit to Seaside!
Verified
8/10 Good
Roger T.
12 May 2019
Overall good vacation
The mattress in the master bedroom needs to be replaced. Older people might have a hard time going up and down stairs to kitchen and den.
Roger T.
Stayed 6 nights in May 2019
Response from VrboOwner on 30 March 2020
Thank you for taking the time to provide this review and for your constructive feedback. We will advise the owener of your concerns regarding the mattress.
From a partner site
10/10 Excellent
Margaret C.
20 August 2023
Can’t wait to go back next year......
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!!!
Margaret C.
Response from VrboOwner on 29 August 2023
Thank you so much for taking the time to write this positive review of Villa Whimsey and the Homeowner’s Collection team. We are so pleased you enjoyed your stay, and we hope to welcome you back on your next visit to Seaside!
From a partner site
10/10 Excellent
Doug G.
8 September 2021
Nice getaway for my family
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:
It was so nice to walk into a nice clean vacation rental and immediately greeted with gifts! I really appreciate the text check ins and everyone we talked to was so accommodating! The house was perfect for our family and we had a great time. We will book again most definitely!
Doug G.
Response from VrboOwner on 12 May 2022
Thank you so much for taking the time to write a positive review of Villa Whimsey and the Homeowner's Collection team. We are so happy you enjoyed your stay and we hope to welcome you back on your next visit to Seaside!
From a partner site
10/10 Excellent
Stephanie S.
18 July 2022
Great rental with fantastic location!
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 location - close to adult and family pool! Also, it is a quick walk to the beach and Seaside Shopping. Great loft area for kids! The kitchen is well stocked with a coffee pot, Keurig, and all you need to cook! There is a charcoal grill which we enjoyed using one night! Overall, we loved this rental for our family!
Stephanie S.
Response from VrboOwner on 19 July 2022
Thank you so much for taking the time to write this positive review of Villa Whimsey and the Homeowner's Collection team. We are so pleased you enjoyed your stay and we hope to welcome you back on your next visit to Seaside!
From a partner site
10/10 Excellent
Greg M.
3 August 2022
Bigger Than Expected
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:
Immediately when walking in, the house was bigger than expected and had everything we needed. We had a baby and a 5 year old which accommodated everything perfectly. Everything was kept nicely, and it's not too far of a walk from the square or the beach.
Greg M.
Response from VrboOwner on 11 August 2022
Thank you so much for taking the time to write this positive review of Villa Whimsey and the Homeowner's Collection team. We are so pleased you enjoyed your stay and we hope to welcome you back on your next visit to Seaside!
From a partner site
10/10 Excellent
Cynthia R.
12 July 2023
Family Vacation
Rating Details:
The property manager was very 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:
Thoroughly enjoyed our adult family stay at Villa Whimsy! Kitchen was well stocked for meal prep. Plenty of space for family of 6. Location is near adult pool & fitness center. The house stayed nice and cool. Lovely cottage is gently used and quintessential Seaside. Highly recommend!
Cynthia R.
Response from VrboOwner on 28 July 2023
Thank you so much for taking the time to write this positive review of Villa Whimsey and the Homeowner’s Collection team. We are so pleased you enjoyed your stay, and we hope to welcome you back on your next visit to Seaside!
From a partner site
10/10 Excellent
Sarah M.
4 January 2023
The perfect home for a family
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 staying here. It was perfect for our family of 5. It's nice enough without being too nice where you are afraid your kids will mess something up. I truly loved our time here. If you have a kid in a pack n play, the primary bathroom is large enough for your pack n play. The second guest room doesn't get too much morning light and so our kids miraculously slept in.
Sarah M.
Response from VrboOwner on 4 January 2023
Thank you so much for taking the time to write this positive review of Villa Whimsey and the Homeowner's Collection team. We are so pleased you enjoyed your stay and we hope to welcome you back on your next visit to Seaside!
From a partner site
10/10 Excellent
Gerry C.
22 January 2023
Winter Get Away to Seaside
Rating Details:
The property manager was very helpful.
The vacation rental was very clean.
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:
It's always a good day when in Seaside. Staying at Villa Whimsey, an older property, allowed us to experience the charm of what Seaside was, and is. The layout is very conducive to relaxation and fun. From the wrap around porch, to the decks in the back, and the open concept living area, it's a great place to leave all of the stresses and worries of life behind. It's in walking distance to all of the amenities that Seaside has to offer.
Gerry C.
Response from VrboOwner on 24 February 2023
Thank you so much for taking the time to write this positive review of Villa Whimsey and the Homeowner's Collection team. We are so pleased you enjoyed your stay and we hope to welcome you back on your next visit to Seaside!
From a partner site
10/10 Excellent
Rachael W.
21 June 2024
Adorable town to visit
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.
Rachael W.
Response from VrboOwner on 27 June 2024
Rachael, Thanks for sharing such great detail and positive comments about VILLA WHIMSEY and our team of Homeowners Collection! We are delighted your time was enjoyable and are hopeful you and your family can return. We will always welcome you back on any future visits to Seaside!
About the host
Hosted by Homeowners Collection
Languages:
English
Premier Host
They consistently provide great experiences for their guests