Holiday houses in St. Leo

South Brooksville Ave. Bungalow

Welcome to our historic home in Downtown Brooksville! This peaceful unit is located on one of the most historic streets in Brooksville, Florida! We are walking distance to local restaurants, shops, museums, concerts and trails! Sit, relax and enjoy the outdoors from one of the three decks or around the fire pit! Come and visit Florida's Nature Coast! We are near to Weeki Wachee River! Crystal River to visit the manatees and many other springs! Bike from here right to Withlacoochee State Trail!

Location · Family · Backyard

Dade City Restful Retro Retreat

You will be close to everything when you stay at this centrally-located home. Thirty minutes from Tampa and Wesley Chapel, one hour to Disney and minutes to numerous wedding venues and amenities in the Dade City area. Come and enjoy the quaint downtown of Dade City, while still being close to all the action. The apartment has TVs and cable, in each bedroom and living room, kitchen with all amenities, washer and dryer and garage. We ask for dogs to be under 30lbs for reservations over 30 days.

Value · Family · Parks

Relaxing Howard Hideaway

Welcome to our charming 3-bed, 1.5 bath home nestled in the picturesque town of Dade City, where comfort meets convenience! A perfect blend of modern living and recreational amenities, making it the ideal retreat for your getaway. As you step in, you'll be greeted by a spacious, inviting living area. The open-concept seamlessly connects the living room, dining area and kitchen, perfect for relaxation & socializing. Only 20 min. from Epperson Lagoon, 30 min from the Krate’s and Outlet Shopping.

Location · Family · Nearby

Dade City Farm Stay

A prime location for bikers and cycling with some of the only rolling hills in Florida. 30 minutes from Tampa attractions: Busch Gardens, Tampa Premium Outlets, Straz Center, ZooTampa. Local attractions: Giraffe Ranch, Kumquat Festival. Down the road is Snow Cat Ridge, Tree Hoppers, Scream-a-geddon. A rural place with a charming downtown scattered with unique eats and antique shops. Get away from it all while making memories on our farm. Enjoy our animals on your stay! Camel, ostrich and more!

Family · Value · Quiet

Eco-Luxurious Lakefront haven (Fire pit & Hot Tub)

Experience the perfect blend of an eco-friendly retreat and modern luxury of our lakefront container home. Nestled in the heart of nature, this stylish oasis promises an unforgettable experience where you can immerse yourself amidst the beauty of the countryside without sacrificing comfort. Plus, enjoy the opportunity to interact with our farm animals, adding a touch of rural charm to your agritourism escape. Also, feel free to check out my other listing, Casa de Elvira on my host profile.

Family · Location · Backyard

Elegant 3BR Lake Jovita Golf Villa • St. Leo Acces

Stay in elegance at Lake Jovita Golf & Country Club in this upscale 3BR/2BA villa overlooking the 18th green. Enjoy sweeping golf course views, modern comforts including a golf cart & a flexible guest room w/Twin XLs that convert to a King. Perfect for golfers, couples, families, and St. Leo visitors. This is the only villa rental offering the rare chance to golf Black Diamond Ranch’s private, members-only courses, including the world-famous Quarry Course, for an unforgettable experience.

Location · Family · Amenities

The Palm Tree Getaway

Ever stayed the night in the woods? Cross it off the bucket list with our ‘Tiny-Home’ style stay near the Hillsborough State Park. Rated #7 on PureWow as one of the 20 Best Airbnb Cabins. This Modern Luxury tiny home was thoughtfully crafted to capture the natural beauty of its old Florida virgin forest surroundings. Glamping at its finest with the best modern conveniences like a full gourmet kitchen, spa like shower, 5G FiberWi-Fi Internet, TV, and a super quiet Mini SplitAC & Heating.

Location · Value · Barbecue

Lake Jovita Golf Course Villa

Golfer's dream getaway in Lake Jovita! This upscale 3 bedroom, 2 bathroom villa sleeps 8 and overlooks the 18th hole of the South Course, pond, and clubhouse. Fully remodeled with a screened patio and grill for post-round relaxation. Golf cart for transportation is included with the home. Enjoy luxury living just a short drive from beaches, theme parks, and Metro Lagoons. St. Leo University is 2 miles away. Perfect for golf trips, tournaments, or a premium stay for the family on the green.

Family · Location · Backyard

Peaceful Home Retreat w/Pool Near St. Leo & Mirada

Comfortable 2BR/1BA home in a residential neighborhood, great for family visits or local events. Includes a dedicated workspace and internet (best effort; speeds not guaranteed). Enjoy a large screened-in lanai with an outdoor kitchen and a private yard with an in-ground pool (seasonally closed November through February; no heater). Dogs are welcome with prior approval (pet fee applies). Cats are not permitted. Owners live nearby and are available if needed while respecting guest privacy.

Value · Family · Outdoor spaces

Cute farmhouse in a park like setting on 10 acres

Come relax away from it all, in the middle of it all. Our super cute farm house is located on 10 peaceful acres in Wesley Chapel where you can sit on the covered porches and watch our abundant assortment of wildlife including deer, tortoises, and rabbits ALL while having your coffee or wine. You can see all of the stars in the night sky, yet you are 5 mins from shopping, dining and entertainment and a mere 15 mins from Tampa. 5 mins from I-75. Complete privacy, but centrally located.

Family · Value · Biking

King Lake Hideaway

Experience something different Our Tiny house with the amenities of home. Enjoy our very private spot in nature. Beautiful lake view. This is a tiny house. 280 sq feet including the loft. Lots of natural light. It’s perfect for relaxing. We are close to beaches, Sporting venues, museums the aquarium and Busch Gardens in Tampa. Situated between Epperson and Mirada lagoons. Wesley Chapel has movie theaters, mini golf, shopping and restaurants within a short drive.

Location · Value · Wi-Fi

Hickory Breeze Guest House

We invite you to come and enjoy our little piece of country in north Pasco County, Florida! Not fancy, but comfortable is our objective for our guests! We are not a business (nor are we owned by a business) therefore we do not conduct our hospitality like a business, but rather as hosts looking to meet and make new friends! We do all our own cleaning and set-up in the guesthouse so that we know it is done the way we would do it for our own family.

Family · Location · Backyard