Family-friendly vacation rentals in Holiday

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 the beautiful Gulf of Mexico beaches. Enjoy breathtaking sunsets around the fire pit. 3 Kayaks and 1 paddle board (included) or fish from the dock. Or sit and relax on the screened patio with your favorite beverage at the outdoor bar, by the fire pit, or on the dock. Or venture to beautiful downtown Tampa and enjoy the Buccaneers, Tampa Bay Lightning, or the Rays baseball team

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.

The Bohemian Studio: Separate Entry & Fenced Patio

🚨 Unbeatable Summer Deal‼️Serene Countryside Escape. Surrounded by nature & near everything. This cozy studio offers total privacy, separate entrance & self check-in Great location, minutes away from hospitals, restaurants, springs & beaches 30 min from Tampa Bay Area 🌳 2 Acres & Fenced Patio 🍳 Fully Equipped Kitchen & bathroom 💻 High-Speed Internet, ethernet & FREE Netflix 🚗 FREE Parkings Perfect for traveling nurses, visiting family or romantic escapes. The best of both worlds!

Downtown Darling

Bring the whole family to this great property with lots of room for fun. 3 king bedrooms with pillow top mattresses, one bunk bed room that sleeps 3 kids. Large kitchen, large laundry room. Home has been completely renovated. Less than a 10 minute walk to all the activities on Main Street, Restaurants, breweries, roof top restaurant, axle throwing bar, sims park with weekly activities and a brand new playground and splash pad for the kids. Walk in the evening down the river boardwalk.

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)

Beachy Holiday Hideaway- 3/2 up to 6 guests

Bring the whole family to this great Florida style home. Centrally located in Holiday, close to beaches, parks & world famous Sponge Docks. Anclote Gulf Park- 6 miles Key Vista Nature Park- 5 miles Tarpon Springs Sponge Docks- 4 miles Anclote Beach- 5 miles Fred Howard Park- 7 miles Innisbrook Golf Resort & Spa- 8 miles Honeymoon Island State Park- 15 miles Clearwater Beach- 23 miles Tampa International Airport- 28 miles Busch Gardens- 31 miles Disney World- 94 miles

Lake access studio near Tarpon Springs.

🌿 Enjoy a quiet private studio for 2 near Tarpon Springs beaches, perfect for a relaxing getaway, work trip, or calm stay close to nature. 🌅 Step through a short hallway to reach the peaceful outdoor lake area, then return to a queen bed, fast WiFi, workspace, fully equipped kitchen, private parking, and 24/7 self check-in. 📍 Close to Fred Howard Park, Sunset Beach, Dunedin, Clearwater, New Port Richey, restaurants, shops, and Tampa. Clean, easy, 5-star stay. ⭐

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

Heated Pool, Hot Tub & Sand Volleyball

Your perfect getaway awaits in this pet-friendly 2BR/2BA retreat! Relax by the in-ground pool and hot tub, play a game of sand volleyball, unwind on the deck or have a BBQ. The fully fenced yard offers privacy, while the covered outdoor seating, pool-side hammock, fire pit, and a variety of games make it fun for all. With WiFi, AC, and a workspace, it’s perfect for both short and long stays. Just minutes from the beach, dining, and entertainment.

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.

Lakefront Paradise with Heated Saltwater Pool

Discover lakeside bliss at this 2-bedroom retreat with a private pool, dock, and outdoor fire pit. Enjoy stunning waterfront views, relax by the pool, or gather around the fire under the stars. The bedrooms offer a cozy haven, and the fully equipped kitchen ensures convenience. Just minutes from pristine beaches, this retreat provides the ideal balance of relaxation and recreation. Your perfect lakefront getaway awaits!