At iTrip St. Augustine, we’re passionate about helping guests experience the very best of our charming coastal city — from its historic cobblestone streets to its sun-soaked beaches and scenic waterways. Each month, we handpick a few standout homes that capture the heart of St. Augustine living. Whether you’re planning a peaceful getaway, a family vacation, or a trip with friends, these homes offer all the comfort, beauty, and character you need to make your stay unforgettable.
Whether you’re dreaming of oceanfront views or river sunsets, these seven St. Augustine getaways are our favorite homes of the month to relax, unwind, and make memories. Each one offers something special — from peaceful pools and ocean breezes to cozy family spaces and unbeatable locations.
BeachTime – Ocean Views and Easy Living
Perched in the heart of St. Augustine Beach, BeachTime is a sun-soaked escape with ocean and pool views from the private balcony. This updated condo is perfect for anyone who loves being steps from the sand but still wants the comfort of home. The soothing coastal décor, open layout, and bright master suite make it the ideal spot to slow down, sip your coffee with a sunrise view, and let the sound of the waves set your pace for the day.
ParadiSea – Riverfront Bliss with a Private Pool
Tucked between the beach and the river, ParadiSea lives up to its name. This home is all about family time and outdoor fun — lounge by the private pool, take the boat out from your own dock, or gather for movie nights and backyard games. With space for everyone (plus a detached cottage for extra privacy), this home is a slice of riverfront paradise just minutes from the ocean and Old City attractions.
Ocean & Racquet 8208 – Classic Beach Vibes, Perfect Location
If convenience is key, Ocean & Racquet 8208 puts everything at your fingertips. This freshly remodeled condo combines comfort and style with ocean views, resort-style amenities, and walkability to restaurants, the pier, and the beach. Relax by the pool, play tennis, or stroll to dinner. It’s the perfect home base for a carefree St. Augustine vacation.
Sunshine Daydream – Endless Views, Family Comfort
True to its name, Sunshine Daydream is the kind of home that makes every day feel like a perfect beach day. With stunning views of the ocean and Matanzas Inlet, multiple decks for sunrise coffee or sunset cocktails, and plenty of space for families, this home was made for connection and relaxation. The downstairs den gives the kids their own hangout, while the upstairs living area opens up to sweeping ocean breezes.
Four Winds D-08 – Oceanfront Serenity
At Four Winds D-08, every detail invites you to slow down and soak in the coastal calm. Newly renovated and just steps from Crescent Beach, this condo offers a private balcony for morning coffee, resort amenities for fun-filled afternoons, and a quiet atmosphere that makes it easy to truly unwind. Whether you’re strolling the dunes or watching the sunset, this is beachside simplicity at its best.
The House of Shells – Coastal Charm Meets Backyard Oasis
Between the beach and the Intracoastal, The House of Shells blends coastal charm with modern comfort. The backyard is a private oasis — complete with a hot tub, fire pit, grill, and tropical garden — perfect for unwinding after a day exploring Vilano Beach or the historic downtown. Walk to the sand, enjoy dinner at a local restaurant, or relax under the pergola and listen to the palm trees sway.
Casa Ola – A Spacious Haven Near Vilano Beach
Just a short walk from Vilano Beach, Casa Ola is made for families and groups looking for space, comfort, and a little luxury. The large backyard features a sparkling pool, fire pit, and plenty of seating for long Florida evenings. Inside, two master suites, a fully stocked kitchen, and a breezy second-floor living space make it easy to settle in and feel at home. Whether you’re kayaking at sunset or exploring historic St. Augustine, this home is the perfect base for your beach getaway.
Ready to plan your next coastal escape?
Each of these homes is available for your next St. Augustine stay — so whether you crave peaceful mornings by the waves or lively afternoons by the pool, your perfect retreat is waiting. To learn more or book your stay, reach out to our friendly team at iTrip St. Augustine — we’re happy to help you find the home that fits your dream vacation.
Text or call us at 904-824-9974
Or email us at [email protected]
Your next beach getaway is just a message away!