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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 AREAALMOST 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 SHOPSGUEST WELCOME COOLER SET UP UPON ARRIVALTAKE 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

Nestled just off Tupelo Circle in the heart of Seaside, Florida, this beautifully renovated beach cottage offers the perfect blend of relaxed coastal living and sophisticated Boho beach style. Thoughtfully designed with natural textures and soothing tones, this home features floor-to-ceiling white tongue-and-groove paneling and light wood flooring, accented with matte black hardware and fixtures. Sisal rugs and crisp white linens complete the aesthetic, creating a welcoming and comfortable space that invites you to slow down and unwind.

The recently updated kitchen and primary bath showcase a breezy, modern coastal design, with elements like a farmhouse sink, floating shelves, shell stone flooring, and natural teak accents. Stylish furniture and light fixtures reinforce the home’s laid-back, Boho-chic vibe. A screened-in front porch with a classic southern-style swing and a private gazebo provide serene outdoor spaces for relaxation.

Inside, the main living area features ample seating, a 72-inch flat-screen TV, and a queen-sized sleeper sofa for additional guests. The dining room centers around a farmhouse table with bench seating for eight, softly illuminated by large sea-grass pendant lights. Additional seating is available at the bay window and kitchen bar, making it a great space for casual gatherings or family meals. A newly renovated half bath with shell stone floors and glass pendant lighting is also located on the first floor for guests’ convenience.

Upstairs, you’ll find three comfortable bedrooms, each with its own en suite bathroom. The primary bedroom boasts a vaulted ceiling, king-sized bed, abundant natural light, flat-screen TV, walk-in closet, and a spa-inspired bathroom featuring a glass shower and teak finishes. A bright queen bedroom offers a cozy retreat with bay windows and a bath featuring a shower/tub combo. The third bedroom is outfitted with two twin beds and its own private bath and TV. A hallway washer and dryer, along with a storage closet and luggage rack, offer added convenience.

One of the home’s most memorable features is the third-level tower, accessible via a ship ladder. From here, take in breathtaking views of the Gulf and the charming town of Seaside. Whether you're soaking in a golden sunset or enjoying the soothing sounds of the waves, this special perch promises 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

  • Features 1,783 square feet
  • 352 yards or 4-minute walk to beach access
  • Tupelo Beach Pavillion Seaside Private Residential Beach; largest private beaches on 30A
  • Washer & Dryer
  • 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, complimentary bottle of wine, and 2 rental bikes for pickup at Seaside Transit Authority
  • Personalized service throughout your stayand starter amenities provided
  • 2 parking passes 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 

 STR23-002039

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

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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