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3 BR
3 BA
8 Guests

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IT'S ALWAYS SUNNY IN SEASIDE FL, 7 HOUSES TO BEACH!TWO ADDITIONAL SCREENED PORCHES OVERLOOKING ROSEWALK PARKTWO LIVING ROOMS; SECONDARY LIVING DOWN3 MINUTE WALK, ONLY 176 YARDS TO PRIVATE BEACH ACCESS IN SEASIDETWO SCREENED PORCHES & TOWER W/STUNNING SUNSET VIEWSWELCOME TO IT'S ALWAYS SUNNY IN SEASIDE, FLORIDA!ENTER TO FIRST FLOOR LIVING AREA DOWNLIVING AREA W/QUEEN SLEEPER SOFA FOR YOUNG KIDSFIRST BEDROOM, KING PRIMARY W/PRIVATE BATH & PRIVATE PORCHKING PRIMARY ALTERNATE VIEWPRIMARY FACING FURNISHED PRIVATE SCREENED PORCHPRIVATE PORCH OFF MASTER W/SWING, PERFECT FOR COFFEEMASTER 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 EIGHTDINING AREA ALTERNATE VIEW, STAIRS TO TOWER ROOMRENOVATED KITCHEN WITH QUARTZ COUNTERS & FARMHOUSE SINKFOUR BURNER ELECTRIC STOVE TOP; UNDER MOUNT MICROWAVEVIEW TO LARGE SUB ZERO FRIDGE, DISHWASHER, FARMHOUSE SINKKITCHEN ALTERNATE VIEW TO DINING & LIVING AREASSCREENED PORCH W/ADIRONDACK SEATING FOR FOUR, OFF LIVINGTHIRD BEDROOM QUEEN W/PRIVATE BATH ON 2ND FLOORQUEEN W/CLOSETQUEEN ROOM FEATURING LARGE MOUNTED FLATSCREENQUEEN W/PRIVATE BATH, SINGLE VANITYQUEEN ROOM PRIVATE BATH WITH TUB SHOWER COMBOENCLOSED TOWER, PERFECT FOR RAINY DAYS; & LARGE TOWER DECKTOWER AREA ALTERNATE VIEW WITH NATURAL LIGHTOPEN AIR COVERED BALCONY W/BARTOP ADIRONDACK SEATINGADIRONDACK SEATING FOR FOUR WITH GULF VIEWS STUNNING GULF & SUNSET VIEWS FROM THE TOWERTOWER VIEWS OF TOWN AND GULF SIDE WALKWAY AREA OF COTTAGE FACING BACKYARD, VERY PRIVATESIDE AREA OF COTTAGE; LARGE FENCED PRIVATE CORNER LOTWASHER AND DRYER ON FIRST STORYGUEST WELCOME COOLER SET UP UPON ARRIVALPRIVATE RESIDENTIAL SEASIDE BEACH ACCESS AT TUPELO PAVILIONEARLY MORNING SEASIDE BEACH VIEWS FROM TUPELO PAVILIONEACH STAY COMES W/TWO COMPLIMENTARY BIKE AT SEASIDE TRANSIT 6 MINUTE WALK TO OVER 40 SHOPS & RESTAURANTS STEPS FROM HOME6 MINUTE WALK TO SEASIDE AMPHITHEATER, FREE EVENTS SEASIDE FARMER'S MARKET EVERY SATURDAY6 MINUTE WALK TO GOURMET GROCER MODICA MARKET6 MINUTE WALK TO 30A AIR STREAM ROW; GOURMET TO GOENJOY PLENTY OF CHARMING BOUTIQUES, WALKING DISTANCE FROM HOMEACCESS TO 3 COMMUNITY POOLS; HEATED IN OFF SEASONSACESS TO 5 CLAY & 3 PICKLEBALL COURTS (ct. fees apply)LARGEST PRIVATE RESIDENTIAL BEACHES ON 30A
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Description

10 ROBERT'S WAY

1 KING, 1 QUEEN, 2 TWINS, 1 QUEEN SLEEPER SOFA; Sleeps 8

Prime Beachside Location

Just one block from the beach in Seaside, this inviting family retreat sits on a spacious, shaded corner lot along quiet Robert’s Way—only seven homes from the Gulf. Combining classic coastal charm with thoughtful updates, the home offers multiple indoor and outdoor living spaces designed for relaxation, gathering, and enjoying every moment of your beach vacation. A standout feature is the third-floor open-air tower, complete with Adirondack bar seating for four and breathtaking sunset views over the rooftops and Gulf.

First Floor Comfort

The first floor features a secondary living area with dual club chairs, a queen sleeper sofa, and a large flat-screen TV—perfect for movie nights or unwinding after a day in the sun. The private king primary suite includes a bathroom with shower, plus a screened porch with a swing and Adirondack seating overlooking peaceful, park-like surroundings—ideal for morning coffee or quiet reflection. A second bedroom with two twin beds and an additional full bath provide convenience and flexibility for families, while the queen sleeper in the living area accommodates extra guests.

Renovated Kitchen & Second-Floor Living

Upstairs, the fully renovated kitchen is equipped with stainless steel appliances, a Sub-Zero refrigerator, quartz countertops, farmhouse sink, and custom cabinetry, with all cookware included for family meals. The open layout flows seamlessly into the dining area, seating 6–8 guests, and the adjacent living space with sofa, club chairs, and mounted TV. A second screened porch overlooks serene tree-lined Rosewalk views—perfect for evening drinks or quiet relaxation. This floor also includes a queen bedroom with a private ensuite bath.

Third-Floor Tower & Sunset Views

The third-floor tower is the crown jewel of the home. An enclosed sitting area provides a cozy space to read or relax, while the outdoor deck offers Gulf breezes, partial water views, and elevated sightlines over Seaside’s iconic rooftops—an ideal spot to watch unforgettable sunsets.

Charming Rosewalk Neighborhood

Located within the historic Rosewalk enclave, designed by Robert Orr and Melanie Taylor, this home combines privacy, character, and walkability. With lush landscaping, pedestrian-friendly paths, and a short walk to the beach, shops, and dining, it captures the essence of a classic Seaside getaway and is perfect for families seeking comfort, charm, and convenience

* 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

  • 1,370 square feet
  • 176 yards or a 3-minute walk to private residential Seaside beach access at Tupelo Pavilion
  • Seaside is the largest private beach on 30A 
  • Tower with Gulf views
  • Private parking for two cars in front of home
  • Peacock Alley Linens, featuring fresh and luxurious Peacock Alley towels and sheets throughout the home
  • Access to 3 swimming pools, 5 clay tennis & 3 Pickleball courts (ct. 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
  • live theater
  • playground
  • restaurants
  • fitness center
  • Communal Pool
  • Heated Pool
  • basketball court
  • cycling
  • fishing
  • golf
  • tennis
  • Massage
  • Paddle Boarding
  • Shopping

General

  • Satellite / Cable
  • Internet
  • Staff

Comforts of Home

  • Iron & Board
  • Linens Provided

Outdoor

  • outdoor shower
  • Parking
  • Balcony
  • Porch
  • Tower

Beds and Baths

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

Availability

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

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Reviews

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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