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2 BR
1 BA
4 Guests

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WELCOME TO HAPPILY EVER AFTER TOWER IN SEASIDE, FL! LIVING SPACE NEAR MASTER WITH SOFA & KITCHENETTEBONUS ROOM, RENOVATED AND SPACIOUSKING PRIMARY BEDROOM WITH FLATSCREEN TVSECOND BEDROOM ON 2ND FLOOR, CUSTOM BUILT IN BUNKKING PRIMARY LIVING ALTERNATE VIEW FACING MASTERKITCHENETTE AREA WITH MICROWAVE, SINK, ETC.TWO SINGLE BUNKS, ONE SOFA AND A FLATSCREEN TVFULL BATH W/GLASS ENCLOSED SHOWERREAR GUEST COTTAGE FROM MAIN HOME HAPPILY EVER AFTERTOWER WITH GULF VIEWSBAR TOP ADIRONDACK CHAIRS FOR TWO & BUILD IN SEATING TOWER DECK WITH GULF AND TOWN VIEWSGULF VIEWS FROM TOWERINCREDIBLE SUNSET & SEASIDE TOWN VIEWSGUEST WELCOME COOLER SET UP UPON ARRIVALSEASIDE PRIVATE RESIDENTIAL BEACH ACCESS AT TUPELO PAVILIONTUPELO PAVILION ENTRANCE VIEWS FAMOUS SEASIDE POST OFFICESEASIDE, FL, LARGEST PRIVATE BEACH ON 30AENJOY STUNNING SEASIDE SUNSETSBUD AND ALLEY'S RESTAURANT AND BAR ON THE BEACH SIDEKRIER PLAZA NEXT TO BUD AND ALLEYSBUD AND ALLEYS PIZZA BAR UNDER BUDSBUD AND ALLEYS TACO BAR BY PIZZA BARMANY DESSERT OPTIONS IN TOWN WITHIN WALKING DISTANCEWALK TO RUSKIN SHOPSNIGELS FANCY BANANAS IN RUSKIN PARKBLACK BEAR BREAD CO. JUST STEPS FROM YOUR COTTAGETHE SEASIDE CHAPEL ON FOREST STWALK TO OVER 40 SHOPS AND LOCAL EATS IN TOWNA GORGEOUS SEASIDE SUNSET FROM PRIVATE BEACHWALK TO THE FAMOUS PICKLES FOR LUNCHENJOY THE OPEN AIR SCENE AT THE SANDBARSUNDOG BOOKSTORE AND CENTRAL SQUARE RECORDSTHE SHRIMP SHACK BAR WITH FABULOUS GULF VIEWSSTUNNING PRIVATE BEACH VIEWSWALK TO MODICA MARKET FOR GROCERIESAIRSTREAM ROW IN TOWN W SEVERAL FOOD TRUCK OPTIONSTAKE A STROLL THROUGH RUSKIN PARKDOWNTOWN SEASIDE, FL VIEWTHE SEASIDE AMPHITHEATER W EVENTS EVENING VIEW OF SEASIDE AMPHITHEARERSEASIDE WEST SIDE POOL AND GRILLSEASIDE TRANSIT BIKE RENTAL IN POP UP DISTRICTSEASIDE BASKETBALL COURTS AND AMENITIES NEARBYTHE DAYTRADER TIKI BAR AND RESTAURANT GRAB A DRINK AT C BAR NEXT TO GREAT SOUTHERN CAFETAKE A WALK ON BEACH AT DUSKAMAVIDA DONUT TRUCK IN CENTRAL SQUARE
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Description

56 TUPELO STREET

KING, 1 BUNK 

A Newly Reimagined Guest Cottage in Seaside Proper

Happily Ever After has recently undergone a thoughtful renovation and has been beautifully redesigned as a charming two-bedroom guest cottage that comfortably sleeps up to four guests. One of the rare two-bedroom guest cottages in Seaside, Florida, this home offers lovely Gulf views and an unbeatable location just five houses back from the beach on scenic Tupelo Street in the heart of Seaside proper.

Prime Location Near the Beach & Town Center

Perfectly positioned near Seaside’s sugar-white sands, Happily Ever After allows guests to enjoy effortless access to the beach while remaining just a short stroll from Seaside’s iconic town center, boutique shopping, dining, and coastal attractions. This prime Tupelo Street setting offers both convenience and a peaceful retreat feel.

Thoughtfully Designed Interior Living

The newly reimagined interior showcases custom details and efficient use of space throughout. On the main level, the built-in king bedroom serves as a serene retreat, featuring abundant custom storage, a wall-mounted flat-screen smart TV, and a cozy sitting area filled with natural light. Just outside the bedroom is a stylish full bathroom with a sleek single vanity and a glass-enclosed walk-in shower.

Also on the first floor is a newly added kitchenette designed for both function and style. It includes an under-counter mini refrigerator, refrigerator and freezer drawers, microwave, coffee maker, and custom built-in shelving—ideal for light meals, snacks, and morning coffee before the beach.

Second Bedroom & Cozy Upper-Level Retreat

Up the spiral staircase, the second bedroom offers a custom built-in twin bunk, making it perfect for children. This inviting space includes built-in bunk storage, a mini closet, a large flat-screen TV, and a loveseat for lounging or winding down after a day in the sun.

Open-Air Rooftop Tower with Gulf Views

The true highlight of Happily Ever After is the open-air rooftop tower, accessed by a private staircase. This elevated escape features Adirondack seating for two and delivers breathtaking panoramic views of the Gulf of Mexico, Seaside’s iconic rooftops, and unforgettable sunsets—an ideal spot for evening relaxation or morning coffee with a view.

A Rare & Charming Seaside Escape

Whether you’re planning a family beach getaway, a parents-and-kids retreat, or a cozy Seaside vacation for four, Happily Ever After offers a unique blend of charm, location, and elevated design. With Gulf views, thoughtful renovations, and a prime Seaside setting, this guest cottage is a truly special place to relax, recharge, and enjoy the magic of 30A.

This home can also be rented as a 3-bedroom lock-off Happily Ever 3 or the whole house, Happily Ever After, a five-bedroom home.

Must be 25 years of age to rent and sign the registration. 3-night minimum Spring, Spring Break | 5-night minimum Summer | 3-night minimum Fall | 2-night minimum Winter

FEATURES

  • 475 square feet
  • Private Seaside residential beach access at Tupelo Pavilion
  • 308 feet or a 1-minute walk to beach access
  • Shared washer and dryer accessed from the outdoor walkway between the street and the tower
  • Kitchenette with no dishwasher
  • 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, a complimentary bottle of wine, and 2 complimentary rental bikes for pickup at the Seaside Transit Authority
  • Personalized service throughout your stay with starter amenities provided
  • One parking pass issued for Happily Tower. 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 allowed

Amenities

Activities

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

General

  • Satellite / Cable
  • Internet
  • Staff

Comforts of Home

  • Iron & Board
  • Linens Provided
  • Mini Fridge

Outdoor

  • Parking
  • Outdoor Grill
  • Porch
  • Tower

Beds and Baths

  • king bed

Geographic

  • East Side

Availability

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

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Reviews

Clean, cozy, excellent location

Reviewed on2023-06-19 by from United States
Updated on 2023-06-19
5
Services from rental manager
5
Cleanliness
5
Location
5
Property condition
5
Drove 10 hours to arrive at Seaside, found that original location had been double booked by Airbnb. The other rental agency and Airbnb resolution was to cancel my stay and say sorry but please rates us good because we can only put you up 3 miles away from where you want to stay. Thank you to Homeowners collection agency for stepping up after the angel Ashley at Shrimp Shack heard us talking and said we Seaside will fix this. HCA is the absolute best and amenities you get along side with renting through them is amazing. Free parking permit, private beach access, free bike rentals, wine, cooler, towels, and a spirit of caring about you! There is no need to book through anyone else EVER because their places are spotless and their employees will always take care of you.
Wow! Thank you so much for taking the time to write this positive review of Happily Ever After Tower 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 weekend getaway!

Reviewed on2021-09-27 by from Suwanee, GA United States
Updated on 2021-09-27
5
Services from rental manager
5
Cleanliness
5
Location
5
Property condition
5
We had a great time at this cottage tower for a long weekend getaway. Our only issue was the AC only blasted in the bathroom directly over the toilet. It got hot upstairs where we slept and the bathroom was freezing. Everything else was great and we really enjoyed this unit!

Terrific stay, will be back

Reviewed on2020-11-24 by
Updated on 2020-11-24
5
My wife and I just finished a terrific vacation to Seaside at the Happily Ever After Tower cottage. We could not be more pleased with the house itself. The grounds were well-maintained. The interior of the home was beautiful and kitchen was equipped with everything we needed. The rooms were spacious and the beds were comfortable. We really enjoyed the views from the Tower! The pictures sold us but the real thing was even better! We will definitely use the Homeowners Collection after using them for our rental this trip. Their customer service was top-notch. They were very helpful from beginning to end, not to mention the cost savings. Thank you for helping us find this wonderful GEM in such an amazing location! We can not wait to come back!

Comfort and Class

Reviewed on2020-10-13 by from Dallas, TX United States
Updated on 2020-10-13
5
Services from rental manager
5
Cleanliness
5
Location
5
Property condition
5
All aspects of the property met or exceeded expectations. The views from the tower were, as advertised, amazing. The 2nd floor bedroom was large and comfortable. The 1st floor sitting area was well-furnished. Importantly, it was super clean on arrival. Homeowners Collection was very responsive, even over the weekend, to any questions I had.
Thank you for taking the time to provide this review and for your kind comments on the Happily Ever After Tower and your experience with Homeowner's Collection. We hope to welcome you back to Seaside again very soon!

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