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3 BR
3.5 BA
8 Guests

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WELCOME TO ALMOST HEAVEN IN SEASIDE, FL!PRIVATE, OPEN AIR TOWER WITH GULF AND TOWN VIEWSTASTEFUL INTERIOR, SLEEPS 8, OPEN, AIRY FLOOR PLANTUPELO ST LOCATION, SHORT STROLL TO BEACH, TOWN, AND MORESCREENED FRONT PORCH WITH SEATING AND BED SWINGPRIVATE, FENCED YARD WITH OUTDOOR GRILLPERFECT MORNING COFFEE SPOT ON FRONT PORCHBED SWING ON SCREENED PORCHOPEN, COASTAL, AIRY FIRST LEVEL SPACIOUS LIVING AREA WITH SLIPCOVER SEATINGOPEN LIVING ROOM WITH QUEEN SLEEPER SOFALIVING WITH MOUNTED FLATSCREEN TVLIVING AREA WITH ALL DESIGNER FURNITUREDINING AREA ON FIRST STORYMODERN, TASTEFUL, FULLY EQUIPPED KITCHEN KITCHEN ALTERNATE VIEW WITH STAINLESS STEEL APPLIANCESKITCHEN WITH BARTOP SEATING FOR THREEKITCHEN ALTERNATE VIEWHALF BATH ON FIRST FLOORKING MASTER ON SECOND LEVELKING W/ FLAT SCREEN TVKING ALTERNATE VIEW WITH LARGE WINDOW AND SEATINGKING MASTER PRIVATE BATH WITH SHOWER AND SINGLE VANITYENSUITE, FULL BATH ALTERNATE VIEWQUEEN ROOM QUEEN ROOM ALTERNATE VIEWQUEEN ROOM WITH BAY WINDOW FULL BATH WITH TUB SHOWER COMBO AND SINGLE VANITYTHIRD BEDROOM UP WITH TWO TWIN BEDSTWIN ROOM WITH MOUNTED FLATSCREENFULL BATH WITH SHOWER AND SINGLE VANITYWASHER DRYER OFF QUEENPRIVATE TOWER W/ BENCH SEATING AND SWEEPING VIEWSROOF TOP AND GULF VIEWS FROM TOWERGULF VIEWS FROM TOWERTOWER VIEWS FROM ATOP TUPELO CIRCLEOUTDOOR SHOWER ON SIDE OF COTTAGEPRIVATE SIDE YARD AREAGUEST WELCOME COOLER SET UP UPON ARRIVALALMOST HEAVEN ON TUPELO CIRCLEPRIVATE RESIDENTIAL SEASIDE BEACH ACCESS AT TUPELO PAVILION SEASIDE BEACH AT TUPELO PAVILIONWALK TO OVER 35 SHOPS & RESTAURANTS STEPS FROM YOUR DOORSEASIDE FARMER'S MARKET EVERY SATURDAYWALK TO MODICA MARKET GOURMET GROCERY STEPS FROM HOMEACCESS TO 3 COMMUNITY POOLS, HEATED IN WINTERLARGEST PRIVATE RESIDENTIAL BEACHES ON 30ASEASIDE, FL, LARGEST PRIVATE BEACH ON 30ASEASIDE, FL SUNSETWALK TO RUSKIN SHOPSTAKE A SUNRISE STROLL
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Description

99 TUPELO STREET

1 KING, 1 QUEEN, 2 TWIN, QUEEN SLEEPER SOFA

Featured in The Cottage Journal – Summer 2020

Tucked just off Tupelo Circle in the heart of Seaside, Florida, this beautifully renovated beach cottage blends relaxed coastal living with elevated Boho beach style. Thoughtfully curated with natural textures and calming tones, the home features floor-to-ceiling white tongue-and-groove paneling, light wood floors, matte black fixtures, sisal rugs, and crisp white linens—creating an atmosphere that feels effortlessly stylish yet deeply inviting.

Coastal Design Meets Everyday Comfort

The recently updated kitchen and primary bathroom showcase a fresh, modern coastal aesthetic with farmhouse sinks, floating shelves, shell stone flooring, and warm teak accents. Carefully selected furnishings and lighting reinforce the home’s laid-back, bohemian charm while maintaining a polished, magazine-worthy feel.

Outdoor living spaces include a screened-in front porch with a classic Southern swing and a private gazebo, offering peaceful spots to relax, read, or enjoy the coastal breeze.

Open Living & Entertaining Spaces

Inside, the main living area offers generous seating, a 72-inch flat-screen TV, and a queen sleeper sofa, providing flexibility for additional guests. The dining room centers around a farmhouse table with bench seating for eight, beautifully illuminated by oversized sea-grass pendant lights. Additional seating at the bay window and kitchen bar makes this space ideal for family meals or casual gatherings. A newly renovated half bath with shell stone floors and glass pendant lighting is conveniently located on the first floor.

Three Private Bedroom Suites

Upstairs, the home features three bedrooms, each with its own en-suite bathroom, offering comfort and privacy for all guests.

  • Primary Suite: Vaulted ceilings, a king bed, abundant natural light, flat-screen TV, walk-in closet, and a spa-inspired bath with a glass shower and teak finishes
  • Queen Bedroom: Bright and welcoming with bay windows and a private bath with shower/tub combination
  • Twin Bedroom: Two twin beds, private bath, and flat-screen TV—perfect for additional guests

A hallway washer and dryer, storage closet, and luggage rack add everyday convenience.

Iconic Tower Views

One of the home’s most memorable features is the third-level tower, accessed via a ship ladder. From this elevated perch, enjoy sweeping views of the Gulf of Mexico and the charming rooftops of Seaside. Whether catching a golden sunset or listening to the waves roll in, this special space delivers unforgettable moments in one of Florida’s most beloved beach communities.

No children under 10

* 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

  • 1,783 square feet
  • 352 yards / 4-minute walk to Tupelo Beach Pavilion
  • Seaside Private Residential Beach – largest private beach on 30A
  • Washer & dryer
  • Peacock Alley Linens – fresh, luxurious towels and sheets throughout
  • Access to Seaside amenities: 3 swimming pools, 5 clay tennis courts, 3 pickleball courts (court fees apply), and a fitness center
  • Welcome tote with 2 beach towels, complimentary bottle of wine, and 2 rental bikes for pickup at the Seaside Transit Authority
  • Personalized service throughout your stay with starter amenities provided
  • Two parking passes issued (Golf carts are considered vehicles. Golf carts are prohibited for non-homeowners (permits required for medical needs))
  • No pets

 STR23-002039

Amenities

Activities

  • Church
  • playground
  • restaurants
  • fitness center
  • 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
  • Apple TV

Outdoor

  • outdoor shower
  • Parking
  • Balcony
  • Deck / Patio
  • Outdoor Grill
  • Porch
  • Tower

Beds and Baths

  • combination tub/shower
  • king bed
  • sleep sofa /futon
  • tub

Geographic

  • East Side

Availability

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

Get Directions

Reviews

Almost Heaven Indeed!

Reviewed on2025-06-15 by from Fernandina Beach, FL United States
Updated on 2025-06-15
5
Services from rental manager
5
Cleanliness
5
Location
5
Property condition
5
We absolutely loved our stay at Almost Heaven in beautiful Seaside, FL! The house is gorgeously decorated in a boho chic style. Everything is clean and well-appointed. We enjoyed many a glass of wine on the comfy swing on the lovely screened-in porch. The location is a quick couple minute bike ride to town yet on such a peaceful and serene street. Cant wait to be back!
Jessica, hello! Thank you for such a sweet overall description of your stay in Seaside, Almost Heaven Cottage & Homeowners Collection.
Cool that you enjoyed the boho chic style, porch side glass of wine and conveniences of all the fun spots.
We are happy you are happy and hope to welcome you back!

One of our favorite homes in Seaside!

Reviewed on2025-05-03 by from Aspen, CO US
Updated on 2025-05-03
5
Services from rental manager
5
Cleanliness
5
Location
5
Property condition
5
We had such an amazing 3 weeks in Almost Heaven and it was absolutely perfect for our family of four. The walk to the beach was 2 minutes, the house was very well equiped, the beds were comfortable, the kitchen had everything we needed as we cook a lot while in Seaside, the front porch was lovely in the mornings and evenings, and most importantly, the communication was so nice while we were down there. We had one minor issue with the TV and that day they installed a brand new one. We are already trying to book it again next year!
Hello Molly, Thank you for taking the time with such great feedback of Almost Heaven Cottage. We also appreciate your positive review of Homeowners Collection services.
We are delighted your amazing 3 weeks with us was an encouragement to already plan for another Emerald Coast vacay! We look forward to welcoming you next time. Take care..

Peaceful

Reviewed on2024-12-15 by from Houston, TX United States
Updated on 2024-12-15
5
Services from rental manager
5
Cleanliness
5
Location
5
Property condition
5
Very well decorated and well-located.
Hello Precious, Peaceful is a perfect experience. We are delighted you enjoyed Almost Heaven Cottage and Homeowners Collection services met your expectations.Thank you for taking the time to review. We do hope to welcome you back to Seaside! Take care..

Peaceful

Reviewed on2024-12-15 by from Houston, TX United States
Updated on 2024-12-15
5
Services from rental manager
5
Cleanliness
5
Location
5
Property condition
5
Very well decorated and well-located.
Hello Precious, Peaceful is a perfect experience. We are delighted you enjoyed Almost Heaven Cottage and Homeowners Collection services met your expectations.Thank you for taking the time to review. We do hope to welcome you back to Seaside! Take care..

Perfect Cottage

Reviewed on2024-06-21 by from Overland Park, KS United States
Updated on 2024-06-21
5
Services from rental manager
5
Cleanliness
5
Location
5
Property condition
5
We have rented Almost Heaven twice. Our first stay was so great, we wanted it a second time. The home is perfectly supplied, you can't get a better location, and it is a cozy place to relax after a day at the beach! If you have a small family or group, this is where you want to stay! we will be back!
Julie, thank you so much for taking the time to share your review of ALMOST HEAVEN. Glad to have you back for the 2nd time and still appears to be a great choice. Our team of Homeowners Collection are delighted you enjoyed for getaway and hope to welcome you back on any return visits to Seaside!

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