Oliver's & Oliver's Too

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5 BR
5.5 BA
16 Guests
Welcome to Oliver's + Oliver's Too; Private Pool - Gulf Views- Sleeps 16 Welcome to Oliver's + Oliver's Too; Private Pool - Gulf Views- Sleeps 16Private Pool Private PoolGulf Views from Main House and Carriage Gulf Views from Main House and CarriageOutdoor Firepit Outdoor FirepitFreshly Remodeled Freshly RemodeledFront Porch at Oliver's with Gulf Views Front Porch at Oliver's with Gulf ViewsFront Porch at Oliver's with Gulf Views Front Porch at Oliver's with Gulf ViewsFront Porch at Oliver's with Gulf Views Front Porch at Oliver's with Gulf ViewsLiving Room at Oliver's Living Room at Oliver'sLiving Room at Oliver's Living Room at Oliver'sDining + Kitchen at Oliver's Dining + Kitchen at Oliver'sDining + Kitchen at Oliver's Dining + Kitchen at Oliver'sDining + Kitchen at Oliver's Dining + Kitchen at Oliver'sDining + Kitchen at Oliver's Dining + Kitchen at Oliver'sDining + Kitchen at Oliver's Dining + Kitchen at Oliver'sLiving Room at Oliver's Living Room at Oliver'sPrimary King Bedroom at Oliver's with En Suite Primary King Bedroom at Oliver's with En SuitePrimary King Bedroom at Oliver's with En Suite Primary King Bedroom at Oliver's with En SuitePrimary King Bedroom at Oliver's with En Suite Primary King Bedroom at Oliver's with En SuitePrimary King Bedroom at Oliver's with En Suite Primary King Bedroom at Oliver's with En SuitePrimary King Bedroom at Oliver's with En Suite Primary King Bedroom at Oliver's with En Suite2nd Floor Bedroom with Two King Beds and En Suite 2nd Floor Bedroom with Two King Beds and En Suite2nd Floor Bedroom with Two King Beds and En Suite 2nd Floor Bedroom with Two King Beds and En Suite2nd Floor Bedroom with Two King Beds and En Suite 2nd Floor Bedroom with Two King Beds and En Suite2nd Floor Bedroom with Two King Beds and En Suite 2nd Floor Bedroom with Two King Beds and En Suite2nd Floor Bedroom with Two King Beds and En Suite 2nd Floor Bedroom with Two King Beds and En Suite2nd Floor Porch at Oliver's with Gulf Views 2nd Floor Porch at Oliver's with Gulf Views2nd Floor Porch at Oliver's with Gulf Views 2nd Floor Porch at Oliver's with Gulf Views2nd Floor Queen Bedroom at Oliver's with En Suite 2nd Floor Queen Bedroom at Oliver's with En Suite2nd Floor Queen Bedroom at Oliver's with En Suite 2nd Floor Queen Bedroom at Oliver's with En Suite2nd Floor Queen Bedroom at Oliver's with En Suite 2nd Floor Queen Bedroom at Oliver's with En Suite2nd Floor Queen Bedroom at Oliver's with En Suite 2nd Floor Queen Bedroom at Oliver's with En Suite2nd Floor Queen Bedroom at Oliver's with En Suite 2nd Floor Queen Bedroom at Oliver's with En SuitePrivate Pool Private PoolPrivate Pool Private PoolPrivate Pool Private PoolOliver's Too Carriage House Oliver's Too Carriage HousePrivate Pool Private PoolOliver's Too Living Area with Sleeper Sofa Oliver's Too Living Area with Sleeper SofaOliver's Too Living Area with Sleeper Sofa Oliver's Too Living Area with Sleeper SofaOliver's Too Living Area with Sleeper Sofa Oliver's Too Living Area with Sleeper SofaOliver's Too Kitchen Oliver's Too KitchenOliver's Too Kitchen Oliver's Too KitchenOliver's Too Kitchen Oliver's Too KitchenOliver's Too Kitchen Oliver's Too KitchenOliver's Too 2nd Floor King Bedroom with Gulf Views and En Suite Oliver's Too 2nd Floor King Bedroom with Gulf Views and En SuiteOliver's Too 2nd Floor King Bedroom with Gulf Views and En Suite Oliver's Too 2nd Floor King Bedroom with Gulf Views and En SuiteOliver's Too 2nd Floor King Bedroom with Gulf Views and En Suite Oliver's Too 2nd Floor King Bedroom with Gulf Views and En SuiteOliver's Too 2nd Floor King Bedroom Porch with Gulf Views Oliver's Too 2nd Floor King Bedroom Porch with Gulf ViewsOliver's Too 2nd Floor King Bedroom with Gulf Views and En Suite Oliver's Too 2nd Floor King Bedroom with Gulf Views and En SuiteOliver's Too 2nd Floor King Bedroom with Gulf Views and En Suite Oliver's Too 2nd Floor King Bedroom with Gulf Views and En SuiteOliver's Too Full over Full Bunk Bed and Bathroom Oliver's Too Full over Full Bunk Bed and BathroomOliver's Too Full over Full Bunk Bed and Bathroom Oliver's Too Full over Full Bunk Bed and BathroomOliver's Too Full over Full Bunk Bed and Bathroom Oliver's Too Full over Full Bunk Bed and BathroomAerial View of Oliver's + Oliver's Too. Beach Access is 1 minute walk. Aerial View of Oliver's + Oliver's Too. Beach Access is 1 minute walk.Outdoor Shower and Clean Your Fresh Catch! Outdoor Shower and Clean Your Fresh Catch!
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Description

Oliver's and Oliver's Too
Inlet Beach Community – Winston Lane

Home Highlights
5 total bedrooms (Room configurations available under the “Room Details” tab)
5 total full baths, 1 half baths
Sleeps up to 16
Main House and Carriage sleep 8 people each
1 minute walk to beach access
Gulf views from every porch
Private Pool and Lounge Area
Spacious Parking
Fish Cleaning Station
Two Full Kitchens 
Two Washer & Dryers
Six 26” adult bikes included seasonally (Not included Dec–Feb; additional rentals available)

The Space
Welcome to Oliver’s — a lovingly restored historic Inlet Beach retreat named after the home’s original owner and filled with the timeless charm of Old Florida. Set on a rare oversized property with gulf views, expansive porches, and a large private pool, this one-of-a-kind estate offers the perfect blend of classic coastal character and modern comfort. Thoughtfully renovated while preserving the soul of the original cottage, Oliver’s exudes warmth, charm, and relaxed beach living at every turn. From the breezy porches with gulf views to the beautifully curated interiors, the home was designed to honor its history while creating an elevated and comfortable getaway experience.

The main house, Oliver’s, comfortably sleeps 8 guests and features inviting living spaces, charming coastal décor, and beautifully updated finishes throughout. Just steps away, the spacious carriage house — Oliver’s Too — also sleeps 8 guests and includes a full kitchen and private laundry, making it ideal for extended family, friends, or multiple families vacationing together.

Outside, guests will love the private courtyard and large pool, creating a peaceful oasis just moments from the sugar-white sand and emerald waters of the Gulf. Spend mornings sipping coffee on the porch with salty breezes, afternoons lounging poolside, and evenings gathering together after sunset beach walks.

Located in the heart of Inlet Beach and directly next door to Rosemary Beach, the home offers easy biking and walking access to Rosemary Beach, Alys Beach, Seacrest Beach, and 30Avenue for dining, shopping, coffee shops, and entertainment. Beach access is just 350 feet away — approximately a 1-minute walk from the property. Rich with history, full of character, and perfectly located along Scenic 30A, Oliver’s and Oliver’s Too offer a truly special beach experience that feels both nostalgic and effortlessly welcoming.

Gulf Views & Prime Inlet Beach Location
Enjoy sweeping Gulf views from nearly every level of the home. You're just a short walk from the community pool and private beach access, with Inlet Beach’s peaceful charm and close proximity to Rosemary, Seacrest, and Alys Beach—all just minutes away.

Outdoor Living on 30A
Enjoy Gulf breezes from three spacious balconies—perfect for morning coffee, afternoon relaxation, or sunset cocktails. Seasonal bikes are included for exploring the best of 30A. A large private pool, outdoor dining and spacious entertaining space.

Amenities You’ll Love
Beach access just steps away
Private Pool & Outdoor entertaining area with grill and wood burning fire pit
6 adult bikes (seasonal)
Main House & Carriage House perfect for large families, multi generational or families traveling together who want additional privacy

Community Amenities
Inlet Beach offers a true “local” feel from the moment you arrive. Enjoy one of the largest public beach accesses in South Walton, fish from the Gulf, explore new dining and shopping options. Walk or bike to Rosemary Beach, Seacrest, 30Avenue or Alys Beach for world-class shopping and dining.

Parking
This home includes parking spaces for 5 vehicles. No on street parking allowed.

Reservation & Booking Policies
The cancelation policy and terms in the 30A Cottages & Concierge Vacation Rental Agreement override those from third-party booking sites (VRBO, HomeAway, Airbnb).
We cannot reimburse third-party booking service fees.
No Smoking
No Pets Allowed (except certified service animals with advance notice and documentation)
50% deposit due at booking
Remaining balance due 60 days prior to arrival
Optional travel insurance available (must be purchased before final payment or at time of full payment)
Check-in: 4:00 PM (CST) | Check-out: 10:00 AM (CST)
Primary renter must be 25+ and remain on the premises for the entire stay

Amenities

  • No Pets Allowed
  • Private Pool
  • Outdoor Gas Grill
  • Flat Screen Televisions
  • Free Wireless Internet
  • Linens Provided
  • Washer/ Dryer

Room Details

Room DetailsBedsRoom DetailsBathroomComments
King Master Bedroom Oliver'sKingTVFull Bath with Shower, Double vanityKing Bed
King Guest Bedroom Oliver's2 King BedsTVFull Bath with Shower, Double vanity2 King Beds
Queen Guest Bedroom Oliver'sQueenTVFull Bath with Tub/Shower combo, Double vanityQueen Bed
King Master Bedroom Oliver's TooKingTVFull Bath with Shower, Double vanityKing Bed
Guest Bedroom Oliver's Too2 Sets of Bunk Beds (4 Full)Full Bath with Tub/Shower comboBunkroom
Half Bathroom Oliver's

Availability

Key
#Night Available#Night Unavailable#Arrive Only#Depart Only
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30A COTTAGES
497 Serenoa Rd Suite 2
Santa Rosa Beach, Florida 32459
850.468.0006

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