Family-friendly holiday rentals in Wesley Chapel

Poolside Paradise Retreat-spacious 4 bedroom home!

Welcome to The Poolside Retreat! Bring the family, unwind, & have fun at our modern Tampa home, located just a short distance away from beautiful downtown Tampa and other local attractions. If you are looking for a spacious place to stay that incorporates the perfect mix of indoor and outdoor fun, look no further. 4 bedrooms to accommodate 8 guests with fully stocked kitchen and outdoor bar/grilling area. Outside you will find a pool (heated during winter), outdoor seating and covered patio.

Entire House with Game Room in Lutz - near Tampa

Entire house with a Game Room equipped with a pool table and a foosball table. Designated working area in Master Bedroom. One King Bed, one Queen Bed and two Twin Beds to accommodate a group of up to six people. A TV in each bedroom, living room and game room. Easy access to USF, Busch Gardens, restaurants, malls and beaches. Short distance to Tampa Premium Outlets and Advent Health Center Ice. Playground, Community Pool, Basketball and Tennis Courts are conveniently located across the street.

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!

Breathtaking Sunset - Renovated Studio Saddlebrook

Relax in this fully Renovated large Studio, in the highly desirable SADDLEBROOK Golf & Tennis RESORT. The sudio features a beautiful terrace just on the lake with AMAZING VIEWS of the lake and golf green. For your comfort, a Queen bed with new mattress, a nice size kitchenette with: Refrigirator, Microwave, Large toaster-oven, coffee maker and sink. The Studio also offers a dining area, work space, and walk-in closet, as well as Wifi & Cable TV. In the Resort local restaurants and Pub.

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.

Cozy Home Historic Zephyrhills

Escape to our 2-bedroom midcentury gem in Zephyrhills! Relax on the Santorini-inspired outdoors and patio, minutes from bars and parks. Sofa bed for extra guests’ flexibility, fully stocked kitchen with coffee and spices, and touch-free entry for a seamless stay. Explore nearby attractions: Zephyr Park, Sky Dive City, Dade City, Wesley Chapel, and Tampa. Easy drive to Busch Gardens, Tampa Premium Outlet, Disney World, and more. Your ideal retreat, blending style, comfort, and convenience!

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.

J&M Homestead

Relax with the whole family at this peaceful place to stay. Close to I-75 and Suncoast Parkway in Pasco County. Located north of Land O Lakes, Florida, in Pasco Trails, a gated community of acreage and horses. Outlet mall, many eating establishments and sports complexes within half-hour drive. We have had to institute a policy of "no smoking. To be clear, we are retired couple who live in the main house. The apartment is attached but has its own entrance and is self contained.

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)

Why stay at a hotel when you can stay at a Resort!

Come enjoy this gorgeous Villa, completely renovated into a comfy cozy cottage atmosphere with lots of character. One bedroom with a king bed, it’s own full bath and large screen tv? Short and long terms welcome. Tons of restaurants nearby. A half hour in one direction takes you to Busch Gardens, an hour in the other takes you to Universal Studios, Disney World and Seaworld. The beach is about an hour west or enjoy sitting on the back patio where it is quiet and peaceful!

Forest Theme Oasis | Peaceful Retreat Near Tampa

Escape to your own private forest-inspired retreat in Wesley Chapel 🌿✨ This beautifully designed 2-bedroom home blends comfort, tranquility, and convenience — located in one of the most desirable and growing areas near Tampa. Enjoy fast WiFi, free parking, a fully equipped kitchen, and peaceful garden views. Perfect for couples, small families, traveling professionals, or long stays. Just minutes from Tampa Premium Outlets, restaurants, shopping, hospitals, and I-75.

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.