Holiday rentals in Fleming Island

Beachside Ocean & Pool View- New Listing!

Experience the charm of our beachfront condo, where the ocean's waves greet you. Steps from the white, sandy beach, enjoy ocean views, sunrises, and sunsets from our balcony. Our two-story condo overlooks a large pool and ocean waves in a quiet, family-friendly area. Newly remodeled, king bedrm looks out to the beach, 2 full bathrms, & bright kitchen. Close to historic St. Augustine's exquisite dining, shopping, and the charm of historic streets. Perfect place to stay to visit Nights of Lights!

Tasteful 3/2 vacation rental

This modern and beautiful vacation home offers guest space, comfort, and luxury. The home has a 3 bedrooms 2 full bathrooms, master suite offers a private bathroom. Fully equipped kitchen, living room, and separate family room with a Q size pull out sofa. Features also include WiFi and 2 Samsung 65’ inch smart tv’s with surround sound attached to each. We do our best to make this place cozy so you can have a great and comfortable time with your family. Leather sofas include charging station.

Paradise Retreat*Vilano Beach*Sand & Ocean Breeze

Come and escape to the Florida sun and beaches at Paradise Retreat! This completely renovated home is only a few minute's walk to the beach with access to miles of tranquil, quiet stretches of beautiful sand, abundant sea seashells and a fantastic blue ocean. It is located in a quiet residential neighborhood, perfect for bike riding and evening walks under the stars. Paradise Retreat is your peaceful getaway only minutes to everything Vilano Beach and historic Saint Augustine has to offer.

"The Coastal House" Water Views and a Golf cart!

Coastal home 5 mins from downtown sits on a double lot and has water views from every room! A stone's throw from the intercoastal and just across A1A from an uncrowded beach. This Gorgeous 3-bedroom home is loaded with high-end furnishings and artwork. The Oak trees give this home 3 decks and tons of privacy. 50' Smart TV in every bedroom. Alexa shows in each bedroom. Upstairs on the 3rd floor is the huge master suite built for royalty. Treat yourself to the best and never be disappointed.

Perfect location- Cottage Retreat in historic area

This charming two story gem with a wrap around front porch is perfect for your stay while visiting historic St. Augustine. Situated within walking distance of the Fountain of Youth and the Old Town Trolley Tours, you can easily explore all the city has to offer! It’s in a perfect location near the city’s downtown area featuring Castillo de San Marcos (1 mile away) and many local shops and restaurants. Check out the featured guidebook which references many nearby points of interest.

Updated Cottage in Heart of Town / Park & Walk

Located in the Historic Abbott District of St Augustine, Florida in the heart of it all. Walk to everything, you will never need your car! This 2-bedroom cottage has all the historic charm was lovingly updated with an open floor plan is beautifully decorated and tastefully furnished. Enjoy a five-minute walk through the neighborhood to famed Castillo De San Marcos (the fort) and Historic St. George Street in the ancient “Colonial Quarter”. Extremely clean, and well-maintained.

Sand In My Shoes -1 min to Beach-Close to Downtown

Sand in my Shoes - in just seconds you will be walking on pristine sandy beach & minutes from exploring 17 Century watch towers & history, this 2 bedroom 2.5 bath townhouse condo sleeps 6 and won’t disappoint. Kitchen equipped for any occasion, amenities galore. 3 TV/DVDs. Private keyless entry. Don't miss WORLD FAMOUS "NIGHT OF LIGHT" ranked as one of the top 10 places IN THE WORLD to see Christmas lights, every November 20, 2021 through January 31, 2022.

The Place to Bee. Make your memory with us!

The Place to be🐝 St.Augustine and this condo! Our location is perfect any time of the year. One of kind condo experience: a setting which is a short walk to the beautiful flat beaches or free parking next to the pier. All your beach needs: umbrella,towels, beach chairs...and a beach cart! As a fellow vacationer explains: it’s the 🐝hive to begin your exploration of the most ancient city in America! So many adventures if you choose to partake or not🦄

Perfect location 2 Bedroom Private Hot Tub

Couples retreat, grill out in your own private courtyard while listening to the relaxing water fountain. “Wine” down and watch the sunset. Private brand new 4 person hot tub. Beautiful courtyard night lighting. 0.5 miles walking distance to the bridge of lions and historic downtown. Off-street parking. Food bars and fun within 300 feet location is directly off the downtown boulevard entrance. Special requests are available.