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

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WELCOME TO VILLA WHIMSEY
FIRST FLOOR FRONT SCREENED IN PORCH
UPSTAIRS  FURNISHED BALCONY OFF LIVING ROOM
LIVING/KITCHEN VIEW
MASTER QUEEN BEDROOM WITH PRIVATE PORCH

Reviews

9.6 out of 10
Exceptional
2 bedrooms3 bathroomsSleeps 81439 sq ft

Popular amenities

  • Parking available
  • Dryer
  • Pool
  • Washer
  • Air conditioning
  • Outdoor space

Explore the area

Map
Seaside, FL
  • Seaside Beach
    ‪3 min walk‬
  • Grayton Beach State Park
    ‪7 min drive‬
  • Blue Mountain Beach
    ‪11 min drive‬
  • Fort Walton Beach, FL (VPS-Northwest Florida Regional)
    ‪67 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

2 Queens, 2 Twins with Trundles (twin trundles accommodate smaller children)

Seaside is a place of whimsey 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 Spring, Spring Break and Summer | 3 night minimum Fall | 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 and 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 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

Property manager

Homeowners Collection
Premier Host

Languages

English

Add dates for prices

Amenities

Pool
Kitchen
Washer
Dryer
Free WiFi
Air conditioning

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House Rules

Check in after 4:00 PM
Minimum age to rent: 25
Check out before 10:00 AM
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Children

Children allowed: ages 0–17
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Events

No events allowed
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Pets

No pets allowed
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Smoking

Smoking is not permitted

Important information

You need to know

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. The area's natural beauty can be seen at Grayton Beach State Park and Seaside Beach. 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.
Map
Seaside, FL

What's nearby

  • Seaside Beach - 3 min walk - 0.3 km
  • Seagrove Beach East - 6 min walk - 0.6 km
  • Grayton Beach State Park - 7 min drive - 2.1 km
  • Grayton Beach - 9 min drive - 5.6 km
  • Blue Mountain Beach - 11 min drive - 8.4 km

Getting around

  • Panama City, FL (ECP-Northwest Florida Beaches Intl.) - 43 min drive

Restaurants

  • ‪Amavida Coffee Roasters - ‬6 min walk
  • ‪Pickle's Snack Station - ‬6 min walk
  • ‪Surfing Deer - ‬8 min walk
  • ‪Bud & Alley's Waterfront Restaurant & Bar - ‬6 min walk
  • ‪AJ's Grayton Beach - ‬6 min drive

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.

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.

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 mi (2 km) of Seaside Beach and Grayton Beach State Park. Seagrove Beach West and Seaside Repertory Theatre are also within 5 minutes.

Reviews

9.6

Exceptional

Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labelled.
Learn moreOpens in a new window
Rating 10 - Excellent. 38 out of 48 reviews
Rating 8 - Good. 7 out of 48 reviews
Rating 6 - Okay. 2 out of 48 reviews
Rating 4 - Poor. 1 out of 48 reviews
Rating 2 - Terrible. 0 out of 48 reviews

9.8/10

Cleanliness

10/10

Check-in

9.8/10

Communication

10/10

Location

9.8/10

Listing accuracy

Reviews

This review comes from a trusted partner site and has not been verified.

10/10 Excellent

Donald M.

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.
This review comes from a trusted partner site and has not been verified.

10/10 Excellent

Jill S.

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!
This review comes from a trusted partner site and has not been verified.

10/10 Excellent

Sherry C.

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.

10/10 Excellent

Juli R.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great week in Seaside with family

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!
Stayed 8 nights in Aug 2024

10/10 Excellent

Nicole R.

Great vacation!

This house worked perfectly for our group of 4! Very clean, very convenient, and wonderful overall!
Stayed 7 nights in Apr 2019

10/10 Excellent

Kara F.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Seaside escape

Villa Whimsey was perfect for our Seaside Escape! Everyone had a great time!
Stayed 7 nights in Jul 2021

10/10 Excellent

Susan R.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Seaside stay

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!
Stayed 4 nights in Jun 2024

10/10 Excellent

Homeowner's C., Santa Rosa Beach, Florida

Wonderful

Could not ask for a better location. House was spacious enough for all of us. Would definitely return.
This review comes from a trusted partner site and has not been verified.

10/10 Excellent

Jessica C.

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!
This review comes from a trusted partner site and has not been verified.

10/10 Excellent

Stephanie d.

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!
This review comes from a trusted partner site and has not been verified.

10/10 Excellent

Chris A.

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!
This review comes from a trusted partner site and has not been verified.

10/10 Excellent

John C.

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.
This review comes from a trusted partner site and has not been verified.

10/10 Excellent

Stephanie A.

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!!
This review comes from a trusted partner site and has not been verified.

10/10 Excellent

Berkeley D.

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!
Stayed 5 nights in Mar 2022
This review comes from a trusted partner site and has not been verified.

10/10 Excellent

Margaret C.

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!!!

8/10 Good

Roger T.

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.
Stayed 6 nights in May 2019
This review comes from a trusted partner site and has not been verified.

10/10 Excellent

Doug G., Knoxville

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!
This review comes from a trusted partner site and has not been verified.

10/10 Excellent

Stephanie S.

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!
This review comes from a trusted partner site and has not been verified.

10/10 Excellent

Cynthia R., Mobile

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!
This review comes from a trusted partner site and has not been verified.

10/10 Excellent

Greg M.

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.
This review comes from a trusted partner site and has not been verified.

10/10 Excellent

Rachael W.

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.
This review comes from a trusted partner site and has not been verified.

10/10 Excellent

Sarah M.

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.
This review comes from a trusted partner site and has not been verified.

10/10 Excellent

Gerry C.

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.
This review comes from a trusted partner site and has not been verified.

8/10 Good

Karen H.

Quaint Villa in Seaside

Rating Details: The property manager was more than helpful. The vacation rental was 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: Seaside is a hidden gem and glad we found. This is the best street and pavilion for getting on beach. Quiet but only a few streets away from good food and shops. The house was open airy and nicely decorated. However wishi was a little cleaner. Was dusty, and had a lot of fine black hairs on couch and chairs and even a few in the master bed. Both queen beds were very uncomfortable as our backs hurt every morning. They definitely need to be changed. Other than that house was very nice and kitchen was fully stocked. We did have a hard time getting a hold of a Homeowners representative for questions we needed answered after checking in. I would highly recommend staying on Tupelo street in this villa or another property for ideal location. The beaches and sand are like none other and we will be back!
This review comes from a trusted partner site and has not been verified.

4/10 Poor

Cortney J.

Could be a total gem

Rating Details: The property manager was very unhelpful. The vacation rental was very dirty. I was very 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: House has a great location and is super cute. Found the Homeowners’ Collection staff to be surprisingly surly and the rental not to be ready for us upon arrival. The cleanliness of the rental was poor, and we asked for the cleaners to return to sweep the floor, clean mildew and conditioner out of the shower, and vacuum an excessive amount of pet hair off the rugs. We changed the air filter ourselves as they were so filthy. For the amount of special cleaning fees we paid for during coronavirus, we were shocked that basic cleaning was incomplete. We had a great trip anyway. The beach is fabulous and the town is so fun, but this house has a bunch of deferred maintenance that should be addressed.
Stayed 7 nights in Jun 2020

About the host

Hosted by Homeowners Collection

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Languages:

English

Premier Host

They consistently provide great experiences for their guests