Family-friendly vacation rentals in Brooksville

The Tangerine Apartment - Downtown Brooksville

This 2-bed 1 bath clean home in the PERFECT location in Brooksville! This home tucked away on a peaceful side street yet just minutes by foot to downtown filled with restaurants, events, brewery & more! Cozy stay in the top unit in a 1925’s Victorian home, renovated with the perfect finishes for modern comfort and convenience. Granite Counters, walk in shower, new reclining couch, small office space & more! Near many wedding venues, golf courses, Frisbee Golf, Festivals, restaurants & more

Latitude 28 a little Patch of Paradise!

"Latitude 28" in Floral City is a spacious 2 BR/2BA Mobile Home. Once inside you'll find semi-open living concept with split bedrooms; Ciozy bedding w/Queen Pillowtop & ensuite bath in MBR, GBR offers Full gel-foam topper. Living area has unique design elements from a local artisan. Amenities include 40" Smart TV, Wi-Fi, fully equipped eat-in Kitchen w/Keurig. Large Sun Room overlooking the expansive lawn great for Birdwatching and located just .07 miles from Trail for Cycling Enthusiasts!

Get to the Choppa! One-of-a-kind 2/1 Helicopter!

Experience a truly UNIQUE Stay! “Chinook” is situated on a serene 5-acre compound inside the breathtaking Withlacoochee State Forest and the thrilling Croom Motorcycle Area, outside of Brooksville, FL. This unforgettable vacation experience is sure to take your adventure to new heights! Our one-of-a-kind accommodation, a REAL repurposed Chinook CH-47D helicopter, promises a stay like no other. This iconic “choppa” with the modern amenities of home, can not be found anywhere else in the world!

Private Waterfront Cabin Retreat with Kayaking

Your private retreat on an acre nestled on a canal to the Withlacoochee River, wrapping around 2 sides of the property. Relax on your porch overlooking the water as you watch the birds and deer play. Kids will love the tire swing, toys such as Lego, Lincoln logs, pool table and ski ball. Kayaks available to our guests awaiting adventure. Bond around the fire pit, walk the trails, lounge in the hammocks, and fish on the dock. Setup the big screen to watch a movie. Welcome to your get-a-way!

Private Suite Boutique • Luxurious Spa Bathroom

Discover unmatched luxury and comfort in our private suite. Drift into a queen bed or queen sofa bed, enjoy a 55” TV, or curl up in a comfortable reading chair. The compact kitchen with a full-size fridge adds convenience, while the spa-inspired bathroom enchants with a sculptural freestanding tub beneath an arched window, a double rain shower, dual sinks, and sunlight that warms the space. Step onto your private, fully fenced, tranquil patio and immerse yourself in serene elegance and calm…

Off the Beaten Path

Our home is located on 5 acres in the middle of farms yet we are 10 minutes from shopping and a large variety of restaurants. Tampa International Airport is 50 minutes away so we have the best of both worlds. We enjoy the quiet beauty of the countryside but can be in Tampa for theatre in minutes. Hernando county boasts of some of the best golf courses in the area. We have a walking/biking trail 2 minutes from the house. Two State parks are 10 miles away and are a great way to spend the day.

Weeki Wachee Springs heated pool home retreat

Relax with the whole family at this Weekie Wachee/Springhill Heated pool home. 5 minutes from the crystal clear springs of Weekie Wachee state park and Buccaneer Bay that has spring fed beach with water slides , tiki bars and mermaid shows. It’s also located 10-15 minutes from Rodgers Park located on the river where you can swim, kayak with manatees and enjoy fun family time! Also 15 minutes away is Pine Island Beach Park and SunWest Beach Park for skiing, wake boarding and obstacle course.

HORSE FARM Retreat, Newer Built Private Guesthouse

Escape to our private guesthouse located in our peaceful but lively 7-acre farm with our family of horses, ponies, Guinea hens, ducks, roosters, chickens, bunnies, cats, & very lovable dogs. Enjoy grabbing fresh eggs, giving animals treats, puppies belly rubs, grilling, making s’mores at the fire pit, and enjoying the farm life! PLEASE read entire listing if little ones will be joining :-) NOTE: Our horses are not available for riding (see our guidebook for great alternate options)

Highland House 🐶

Adorable historic small town bungalow with large screened in front porch. Back yard has large deck shaded by an antique Magnolia tree. Fenced in beautiful back yard. Come stay in one of Brooksville's oldest, quantist and most intriguing neighborhoods. Weeki Wachee river only 15 miles away. Chasowistka river 15 miles away. Suncoast bike trail and lots of perserves for hiking. 🐶 This is a a dog friendly space and neighborhood.

Olive Grove Retreat

Relax, unwind and enjoy glamping in a 4 acre olive orchard. Fresh air, fresh eggs , freshly milled olive oil from our orchard. Queen Bed, TV, Wi-Fi , AC and an amazing view. Close to Weeki Wachee River State Park, mermaids, manatees & Chassahawitzka River. Bring your bike-we’re on the SC Bike Path. Hot shower, fire pit, kitchenette. Guinea Fowl, Hens, ducks and Roosters free range the grounds.

Whispers of Country Where your soul will Wander.

The Shebeen – a charming retreat nestled along the Brooksville ridge, on a picturesque working dairy farm. Here, adventure meets relaxation in a space designed for, reflection, and a bit of romance. Let the rhythmic sound of the farm surround you as you step into a world where time slows, and every moment feels like a sweet escape. Book your stay now and find a little magic in every moment.

Independent Guest House - Ideal for Rest

An independent guesthouse with its private fenced space and with 2 available parking spaces conveniently located in front. A newly furnished space with all all full bath, bedroom with double bed and fully stocked kitchen. Enjoy personalized attention for an unforgettable stay, ideal for rest and relaxation. Close park and beaches, near I-75 and Suncoast Parkway in Pasco County.