Family-friendly vacation rentals in Holiday

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!

Paradise!Renovated waterfront pool home.Sunsets!

No hurricane damage!Sunsets to die for! Completely remodeled in 2023 pool house on the Anclote River with access to the Gulf of America.Imagine fishing,kayaking in the backyard &sometimes you can spot dolphins!Watch birds, ducks, manatees. All new appliances and granite countertops.New quartz bathroom cabinets!New tiles throughout the house including Florida room. Cooler,chairs&umbrella, kids beach toys that you can take to the beach.Bonfire pit.Grill.Heated pool for a fee. Come,relax&enjoy

Heated & Screened in Pool/Coffee Bar/Fully Stocked

🏡 Private Pool House with Large Covered & Screened-In Porch Relax and unwind in this inviting private pool home, featuring a large covered and screened-in porch—perfect for enjoying the outdoors without the bugs. 🌊 Heated Pool Take a dip in the private pool, heated year-round with an electric heat pump (weather permitting), offering comfort no matter the season. Whether you're sipping coffee on the porch or enjoying a swim, this cozy retreat is ideal for a peaceful and private getaway.

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)

Warmth In Holiday

Tiny Living In Holiday offers a delightful and peaceful ambiance, ideal for a serene getaway. Conveniently located near stunning beaches, guests can revel in the beauty of the coast. The room creates a warm and homely atmosphere, ensuring guests feel snug and content during their stay. Furthermore, the room features a handy air fryer microwave oven combo, allowing guests to effortlessly prepare meals at their convenience. Listing does not accommodate infants/toddlers.

Screened Lanai /Clear Kayak / Waterfront / Fire Pi

Funky Flamingo River Cottage is a hidden gem on the Weeki Wachee River, designed for fun, relaxation, and adventure. Enjoy a no-see-um screened lanai, a comfy king bed, Smart TVs in every room, and a fully stocked kitchen. Paddle with manatees in our clear kayak, float on the lily pad mat, or unwind by the fire pit. With games inside and out, a hammock, and direct water access, it's the perfect escape—just off the main river, between the State Park and Roger’s Park.

Cozy Private Apt near beach/2 parking

Private & cozy apartment with independent entrance and free parking for two vehicles. Located in a quiet and safe area just minutes from the beach and Tarpon Springs (“Little Greece”) and just minutes from Fred Howard Park Beach.Enjoy a fully equipped kitchen, comfortable bedroom with work desk, Smart TV, fast WiFi, spacious bathroom, and outdoor terrace. Perfect for couples, small families, or remote workers Scan the QR in the last photo for a full video tour

*NEW* Riverside Retreat w/Pool

Take it easy at this unique and tranquil getaway. Welcome to our Riverside Retreat where you will enjoy incredibly relaxing peaceful days, and sunset views. Recently renovated 2 Bedroom, 2 Full Bathroom, pool home with dock and privacy fenced backyard on the Anclote River. This home is fully equipped and is ready for you to enjoy. Conveniently located and only a 9-minute drive to the World-famous Sponge Docks and minutes from our award winning beaches…

A perfect Lake House get away

Make some memories at this unique and family-friendly slice of paradise. Located on 100-acre Lake Anne. 20 minutes from beautiful Gulf of Mexico beaches. Enjoy breathtaking sunsets around the fire pit. Kayak, paddle board (included) or fish from the dock. Or sit and relax on the screened patio with your favorite beverage at the outdoor bar. Or venture to beautiful downtown Tampa and enjoy the Buccaneers, Tampa Bay Lightning, or the Rays baseball team

Private 3 Bedroom House w/ Heated SaltWater Pool

Spend your holidays in HOLIDAY, FL! We welcome you to our cozy, fully renovated house with a large, heated private in-ground, SALTWATER pool. The house has three bedrooms and enough room for 7 guests, along with two full bathrooms. The kitchen is stocked with all cookware essentials needed. The house has everything you need for vacations, so you may kick back and relax. It is centrally located to many attractions if you're up for a drive.

Private pool home near Tarpon Springs 5 mi

🌴 Private pool home near Tarpon Springs, Gulf beaches, restaurants, and local attractions—perfect for a relaxing Florida getaway. Enjoy a fenced patio, BBQ area, fast WiFi, workspace, fully equipped kitchen, 24/7 self check-in, and on-site parking. Easy access to Dunedin, Clearwater, Tampa, and nearby beaches. ✨ Note: pool heat is available Nov–Mar, weather permitting. ⏳ Last-minute promos active—book and lock in your dates!

Relaxing Lake House

Take it easy at our tranquil getaway. Observe local and migrating birds right from the backyard, fish from the dock, or just relax and enjoy the view from the screened in porch. Minutes from New Port Richey and Tarpon Springs famous Sponge Docks and less than an hour from all the Tampa attractions and Clearwater Beach. Take a day hike at Honeymoon Island Osprey and Pelican Trail and end the hike with a swim at the beach.