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3 BR
3 BA
8 Guests

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IT'S ALWAYS SUNNY IN SEASIDE FL, FEATURING TOWER W/GULF VIEWSWELCOME TO IT'S ALWAYS SUNNY IN SEASIDE, FLORIDA!FIRST FLOOR LIVING AREA BY BEDROOMS DOWNLIVING AREA FEATURING FLATSCREEN TV AND SEATINGLIVING AREA W/QUEEN SLEEPER SOFA FOR YOUNG KIDSFIRST BEDROOM, KING MASTER W/PRIVATE BATH DOWNKING MASTER ALTERNATE VIEWMASTER FACING PRIVATE PORCHPRIVATE PORCH OFF MASTER W/SWINGMASTER SCREENED PORCH ALTERNATE VIEWMASTER FULL BATH SHOWER ONLYMASTER SHOWER ONLYSECOND BEDROOM DOWN, TWO TWINSFULL BATH OFF LIVING & TWIN BEDR ROOM SHOWER ONLYSECOND STORY LIVING AREA FACING KITCHENLIVING ROOM W/FLAT SCREEN TV & PRIVATE PORCH ACCESSDINING AREA SEATS SIX TO SEVENDINING TABLE SEATS SIX TO SEVENRENOVATED KITCHEN WITH QUARTZ COUNTERS & FARMHOUSE SINKALL STAINLESS STEEL APPLIANCESKITCHEN WITH NATURAL LIGHT AND COASTAL COLORS KITCHEN ALTERNATE VIEW TO DINING & LIVING AREASSCREENED OFF BALCONY OFF LIVING W/ADIRONDACK SEATING FOR 4BALCONY ALTERNATE VIEWTHIRD BEDROOM QUEEN W/PRIVATE BATH ON 2ND FLOORQUEEN ALTERNATE VIEWQUEEN ROOM FEATURING FLATSCREENQUEEN W/PRIVATE BATH, SINGLE VANITYQUEEN ROOM PRIVATE BATH WITH TUB SHOWER COMBOTHIRD STORY GLASS ENCLOSED TOWER W/OUTDOOR BALCONYTOWER AREA ALTERNATE VIEW WITH NATURAL LIGHTOPEN AIR COVERED BALCONY W/BARTOP ADIRONDACK SEATINGTOWER BALCONY ALTERNATE VIEW WITH GULF VIEWS STUNNING GULF & SUNSET VIEWS FROM THE TOWERTOWER VIEWS OF TOWN AND GULF REAR VIEW OF COTTAGE, PRIVATE PORCHES UP AND DOWNSIDE WALKWAY AREA OF COTTAGE FACING BACKYARD, VERY PRIVATESIDE AREA OF COTTAGE WASHER AND DRYER ON FIRST STORYGUEST WELCOME COOLER SET UP UPON ARRIVALPRIVATE RESIDENTIAL SEASIDE BEACH ACCESS AT TUPELO PAVILIONTUPELO PAVILION SEASIDE BEACH VIEWSEARLY MORNING SEASIDE BEACH VIEWS FROM TUPELO PAVILION
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Description

10 ROBERT'S WAY

1 KING, 1 QUEEN, 2 TWINS, 1 QUEEN SLEEPER SOFA

First-Block Location on Roberts Way

Perfectly positioned on the first block to the beach, this inviting Seaside family retreat sits on a large, shaded corner lot along the quiet charm of Roberts Way. With the Gulf of Mexico just seven houses away, the home offers a peaceful setting paired with exceptional proximity to the beach. One of its most beloved features is the third-floor open-air tower, where Adirondack bar seating for four creates the ultimate sunset perch as golden light melts into the Gulf beyond Seaside’s iconic rooftops.

First Floor Living & Private Primary Suite

The first level welcomes guests with a secondary living room, ideal for family gatherings, movie nights, or a relaxed hangout space for those staying in the downstairs bedrooms. This level features a king primary bedroom with a private bathroom (shower only) and access to a screened-in front porch with a swing, offering tranquil, park-like views beneath mature shade trees—perfect for slow mornings with coffee in hand. A second bedroom with two twin beds is also located on this floor, along with a nearby full bathroom with a shower.

Second Floor Open Living & Kitchen

Upstairs, the second floor showcases a recently renovated kitchen outfitted with stainless steel appliances, a large double-door refrigerator, farmhouse sink, and striking art glass pendant lighting. The kitchen opens seamlessly into a bright dining and living area designed for togetherness. The dining table seats six comfortably, while the adjacent living space features a flat-screen TV for easy entertaining. Just beyond, a screened-in second-floor porch with Adirondack seating for four provides a private outdoor retreat surrounded by lush greenery—an ideal spot for evening cocktails or quiet conversation. The third bedroom, located on this level, features a queen bed, a mounted flat-screen TV, and a private en-suite bathroom with a tub/shower combination.

Third Floor Tower & Gulf Views

The crown jewel of the home awaits on the third floor. An enclosed interior tower offers cozy seating for three, making it a peaceful escape for reading or relaxing on rainy afternoons. Step outside to the open-air tower deck, where Gulf breezes, Adirondack bar seating for four, and sweeping views set the stage for unforgettable Seaside sunsets. Whether enjoyed at sunrise or dusk, this elevated space captures the true magic of coastal living.

With its unbeatable beach proximity, multiple living spaces, and signature tower views, this home is destined to become a Seaside favorite for families seeking a relaxed yet memorable Florida getaway.

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

FEATURES

  • 1,370 square feet
  • 176 yards or a 3-minute walk to beach access
  • Private Seaside residential beach at Tupelo Pavilion, the largest private residential beach on 30A
  • Tower with Gulf views
  • Private parking
  • Peacock Alley Linens, featuring 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 two complimentary rental bikes for pickup at the Seaside Transit Authority
  • Personalized service throughout your stay, with starter amenities provided
  • Two parking passes 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 allowed

STR23-001888

Amenities

Activities

  • Church
  • playground
  • restaurants
  • fitness center
  • Communal Pool
  • Heated Pool
  • basketball court
  • tennis
  • Paddle Boarding
  • Shopping

General

  • Satellite / Cable
  • Internet

Comforts of Home

  • Iron & Board
  • Linens Provided

Outdoor

  • outdoor shower
  • Parking
  • Balcony
  • Porch
  • Tower

Beds and Baths

  • combination tub/shower
  • king bed
  • tub

Availability

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

Get Directions

Reviews

Very nice property close to town sqaure

Reviewed on2025-02-19 by from Tallahassee, FL United States
Updated on 2025-02-19
5
Services from rental manager
5
Cleanliness
5
Location
5
Property condition
5
Third consecutive stay at It's Always Sunny. We've been coming to Seaside since 2015 for the Seaside Half Marathon/5K. Up until 3 years ago, we stayed at a hotel and shuttled in. We decided to try a house in Seaside and it made all the difference for race day and other activities. Yes, it's more expensive than staying at a hotel, but there's more room (there are 4 of us) to lounge around and the kitchen has everything you need. 2 screened in porches-- 1 up and 1 down--are nice to sit and have morning coffee. Town Square is a short walk away, complete with food trucks, restaurants, and shops.
Hello Jennifer! We are delighted you chose to return to our Seaside Village & It's Always Sunny cottage.
Thank you for taking the time to share a positive review of your accommodations & our Homeowners Collection team. We always hope to welcome your future Half Marathon/5K returns! Take care.

Very nice property close to town sqaure

Reviewed on2025-02-19 by from TALLAHASSEE, FL US
Updated on 2025-02-19
5
Services from rental manager
5
Cleanliness
5
Location
5
Property condition
5
Third consecutive stay at It's Always Sunny. We've been coming to Seaside since 2015 for the Seaside Half Marathon/5K. Up until 3 years ago, we stayed at a hotel and shuttled in. We decided to try a house in Seaside and it made all the difference for race day and other activities. Yes, it's more expensive than staying at a hotel, but there's more room (there are 4 of us) to lounge around and the kitchen has everything you need. 2 screened in porches-- 1 up and 1 down--are nice to sit and have morning coffee. Town Square is a short walk away, complete with food trucks, restaurants, and shops.
Hello Jennifer! We are delighted you chose to return to our Seaside Village & It's Always Sunny cottage.
Thank you for taking the time to share a positive review of your accommodations & our Homeowners Collection team. We always hope to welcome your future Half Marathon/5K returns! Take care.

Birds Eye View

Reviewed on2024-10-21 by from North Fort Myers, FL United States
Updated on 2024-10-21
5
Services from rental manager
5
Cleanliness
5
Location
5
Property condition
5
My husband and I had a wonderful stay at It's Always Sunny in Seaside. The view of the gulf was amazing from the top of this enchanting home! We loved being able to walk to the beach, shops and restaurants.
Hi Michelle, thank you for sharing a positive review of It's Always Sunny and Homeowner's Collection.. We are happy you enjoyed your stay and can hold those gulf view memories till the next visit! We hope to welcome you back to Seaside. Take care..

Great vacation!

Reviewed on2024-07-16 by from Baton Rouge, LA United States
Updated on 2024-07-16
5
Services from rental manager
5
Cleanliness
5
Location
5
Property condition
5
Beautiful home in Seaside! We loved it! Close to beach. Nice view of ocean from top porch. Several screened in porches perfect for morning coffee. Highly recommend!
Hello Timmy, thanks for sharing a positive review on Its Always Sunny & our Homeowners Collection team. We are pleased you enjoyed your stay, recommend it and hope we will welcome you back to Seaside in the future! Happy summer.

Great house

Reviewed on2024-07-02 by from Meridian, MS United States
Updated on 2024-07-02
5
Services from rental manager
5
Cleanliness
5
Location
5
Property condition
5
Our stay was perfect. Being farther away from 30a and the center of seaside makes this a quiet location. House has a fun layout.
Hi David, thank you for taking the time to write a positive review of IT"S ALWAYS SUNNY & Homeowners Collection team! We are so delighted you enjoyed your stay and hope we can always welcome your return to Seaside in the future! Take care..

Nice place for a get away

Reviewed on2023-10-14 by from Starkville, MS United States
Updated on 2023-10-14
5
Services from rental manager
5
Cleanliness
5
Location
5
Property condition
5
We brought our daughter and five friends to celebrate her birthday. They loved biking around Seaside. The beach was impeccable, this house is an easy elk to the Tupelo pavilion. We used the upstairs bedroom for us to give the girls the bottom floor. That room was a little tight for two grown ups , but doable for a few days. Kitchen was missing a few essentials but eating out was so easy. Loved the rental process and the homeowners collection. A very positive experience and I'd take the smaller space for the convenience of this house.
Thank you so much for taking the time to write this positive review of It's Always Sunny and the Homeowner’s Collection team. We always appreciate feedback and will absolutely pass yours on to our owners and operations team. We are so pleased you enjoyed your stay, and we hope to welcome you back on your next visit to Seaside!

Well appointed cottage to stay in...

Reviewed on2021-11-29 by from Atlanta, GA United States
Updated on 2021-11-29
5
Property condition
5
Location
5
Cleanliness
5
Services from rental manager
5
Homeowners staff was wonderful. Cottage better than expected. Stay was delightful!!!
Thank you for taking the time to write this positive review of It's Always Sunny 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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