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2 BR
3 BA
8 Guests

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WELCOME TO VILLA WHIMSEYFIRST FLOOR FRONT SCREENED IN PORCHUPSTAIRS FURNISHED BALCONY OFF LIVING ROOMLIVING/KITCHEN VIEWMASTER QUEEN BEDROOM WITH PRIVATE PORCHPRIVATE DRIVEWAYFRONT SCREENED IN PORCH ALTERNATE VIEWBREAKFAST BAR IN KITCHENBREAKFAST BAR/KITCHEN ALTERNATE VIEWKITCHEN BAR AREAKITCHEN NOOK DINING AREADINING AREALIVING AREALIVING AREA ALTERNATE VIEWPRIMARY QUEEN WITH PRIVATE BATHPRIMARY BATHROOMPRIVATE SCREENED IN PORCH OFF PRIMARY BEDROOM2ND BEDROOM QUEEN FIRST FLOOR2ND BEDROOM QUEEN WITH WINDOW SEATFIRST FLOOR SHARED BATHUPSTAIRS BALCONY ALTERNATE VIEWADDITIONAL SIDE PORCH UPSTAIRSSTAIRCASE TO LOFTTHIRD FLOOR BONUS LOFT WITH TWIN TRUNDLES THIRD FLOOR TWIN LOFT ALTERNATE VIEWTWIN LOFT PRIVATE BATHROOMCLAWFOOT TUBOUTDOOR SHOWERGRILL AREAREAR VIEW OF VILLA WHIMSEYAERIAL VIEWSEASIDE PRIVATE RESIDENTIAL BEACH ACCESS AT TUPELO PAVILIONSEASIDE FARMER'S MARKETSEASIDE WEST SIDE POOL AND GRILLHEAVENLY'S ICE CREAMTHE FAMOUS BUD AND ALLEY'S BEACHFRONT RESTAURANTGOURMET GROCERY MODICA MARKETSEASIDE'S AIRSTREAM ROW RESTAURANTSSEASIDE CENTRAL SQUARE SHOPS AND CONDOMINIUMSBLACK BEAR BREAD CO. IN THE HEART OF SEASIDESEASIDE'S ICONIC POST OFFICEGUEST COOLER BAG SET UP UPON ARRIVALWALK TO THE FAMOUS PICKLES FOR LUNCHPICKLES SANDBAR ON THE BEACH SIDEWALK TO OVER 40 SHOPS AND LOCAL EATS IN TOWNWALK TO RUSKIN SHOPS AND PARKSEASIDE, FL LARGEST PRIVATE BEACH ON 30AMANY DESSERT OPTIONS IN TOWN WITHIN WALKING DISTANCEENJOY A SEASIDE, FL BEACH SUNSETAIRSTREAM ROW WITH SEVERAL FOOD TRUCK OPTIONS IN TOWNSTUNNING VIEWS FROM SEASIDE, FL BEACH
407 people have considered this property in the last 24 hours.

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Description

119 Tupelo Street

2 QUEEN BEDS, 2 TWINS WITH TRUNDLES (Twin trundles accommodate smaller children)

Reminiscent of a classic Victorian-style cottage, Villa Whimsey offers a whimsical escape in the heart of Seaside, combining comfort, privacy, and an unbeatable location. A welcoming screened wraparound porch invites you to relax, dine al fresco, or simply enjoy the art of Seaside people-watching.

On the ground floor, you'll find a queen primary suite adorned in tropical décor, along with a cozy queen guest room featuring a charming window seat. This level also includes a full bath and a private screened porch—perfect for quiet moments outdoors.

Upstairs, the main living area showcases vaulted ceilings and pastel tones that enhance the home’s airy and relaxed atmosphere. Comfortable furnishings, a desk, and a television make it a perfect space to unwind. The well-equipped kitchen includes an island for extra prep space or casual dining, while the built-in dining nook is bathed in natural light. Two decks off this floor invite you to take in the coastal breeze—or a stunning sunset.

The third-floor sleeping loft features twin trundle beds and a full bath with character, including a claw-foot tub beneath a crescent-shaped stained glass window. An interior balcony overlooks the living room below, enhancing the open, whimsical layout.

Just two doors down from the beloved Tupelo Street Gazebo and a short stroll to the beach, boutique shops, and restaurants, Villa Whimsey is ideally located to enjoy everything Seaside has to offer.

Must be 25 years of age to rent and sign the registration. 5-night minimum Spring, Spring Break, and Summer | 3-night minimum Fall and Winter

FEATURES

  • Features 1,439 square feet
  • Seaside Private Residential Beach at Tupelo Pavilion
  • 3-minute, 176-yard walk to beach access
  • Two doors down from the Tupelo Street Gazebo
  • Peacock Alley Linens - Fresh and luxurious Peacock Alley towels and sheets throughout the home
  • Access to 3 swimming pools, 5 Clay tennis courts (court fees apply), 3 Pickleball courts (court fees apply), and a fitness center
  • Welcome tote with 2 beach towels and a complimentary bottle of wine
  • Two complimentary rental bikes are included with your stay for pickup at the Seaside Transit Authority
  • Personalized service throughout your stay
  • Starter amenities provided
  • Only 1 parking pass per one-bedroom cottage and 2 parking passes for two-bedroom and larger homes are issued. A golf cart is considered a car.
  • Golf carts for non-homeowners visiting Seaside are prohibited. Special circumstances and medical needs requests require a golf cart permit.   
  • No pets

STR23-002234

Amenities

Activities

  • Church
  • playground
  • restaurants
  • fitness center
  • Bicycles
  • Communal Pool
  • Heated Pool
  • basketball court
  • cycling
  • fishing
  • golf
  • swimming
  • tennis
  • Massage
  • Paddle Boarding
  • Shuffleboard
  • Shopping

General

  • Satellite / Cable
  • Internet
  • Staff

Comforts of Home

  • Iron & Board
  • Linens Provided

Outdoor

  • outdoor shower
  • Parking
  • Balcony
  • Outdoor Grill
  • Porch

Beds and Baths

  • combination tub/shower
  • tub

Geographic

  • East Side
  • Town View

Availability

Key
#Night Available#Night Unavailable#Arrive Only#Depart Only
November 2025
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Location

Get Directions

Reviews

Great location

Reviewed on2025-07-12 by from White Oak, TX US
Updated on 2025-07-12
5
Services from rental manager
5
Cleanliness
5
Location
5
Property condition
5
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!
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!

Villa Whimsey stay

Reviewed on2025-06-10 by from Sikeston, MO United States
Updated on 2025-06-10
5
Services from rental manager
5
Cleanliness
5
Location
5
Property condition
5
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.
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..

Adorable town to visit

Reviewed on2024-06-20 by from FOLSOM, CA United States
Updated on 2024-06-20
5
Services from rental manager
5
Cleanliness
5
Location
5
Property condition
5
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, 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!

Girls's Weekend

Reviewed on2024-05-21 by from Covington, LA United States
Updated on 2024-05-21
5
Services from rental manager
5
Cleanliness
5
Location
5
Property condition
5
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, 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!

Another Weekend In Paradise

Reviewed on2023-10-18 by from Wildwood, MO United States
Updated on 2023-10-18
5
Services from rental manager
5
Cleanliness
5
Location
5
Property condition
5
Perfect place, perfect location, perfect vacation!
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!

Great rental with fantastic location!

Reviewed on2022-07-17 by from Griffin, GA United States
Updated on 2022-07-17
5
Services from rental manager
5
Cleanliness
5
Location
5
Property condition
5
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!
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!

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