Family-friendly holiday rentals in Winter Springs

Tiny Home Near the Springs

Fresh air and back to nature. Imagine a tiny but comfortable hotel room in a rural setting. You'll hear roosters crow as the sun rises. Take a walk on a moonless cloudless night, and you may see stars. This 190 sq. ft. tiny house is a ten minute drive to either Rock Springs or Wekiva Springs, a four minute bike ride to the West Orange Trail which runs for 22 miles, and a 15 minute drive to the Lake Apopka Wildlife Drive. The major theme parks are a 30 to 45 minute drive, depending on traffic.

St.John suite

Luxurious space with PRIVATE ENTRANCE, BATHROOM, and breakfast kitchenette. Located on a large lake front property with amenities that include private dock, pool, large manicured lawns and much more. Ideal for canoeing, watching the sun rise or doing nothing at all. Close to theme parks and beaches. Spring Valley is a peaceful community with age old oak tree lined streets, Ample shopping and award winning restaurants very nearby. Come play or rejuvenate your soul in this picturesque setting.

The Secret Sanctuary in Sanford, 5min from Airport

Welcome to your quiet, spacious, and private sanctuary. Enjoy all new appliances in the full size kitchen, a 50” flat screen TV, and a shaded outdoor area surrounded by greenery. It is located only minutes from the Orlando Sanford International Airport, Historic Downtown Sanford’s restaurants and shops, Lake Monroe’s scenic waterfront, and is centrally located between Florida’s beaches and the amusement parks. **Space is cleaned with EPA approved cleaners, including high touch surfaces**

Suite Retreat

Avoid blah hotels with high prices and stay in this luxe new apartment suite! It’s a perfect retreat in Central Florida. Located a short drive to activities, restaurants, & shops in Lake Mary or downtown Sanford - 45-55 min to Orlando theme parks or the beaches of New Smyrna. Ideal for a couple’s retreat or a getaway for one. Guests use office space designed for comfort & productivity. A cozy chair begs readers to curl up and read. The outdoor canopy hosts breakfast with birdsong!

Stylish & spa like Getaway - peaceful garden suite

Relax and unwind from your busy life in this serene and quiet getaway. We are located 5 minutes to shopping and dining in downtown Lake Mary in a beautiful and safe neighborhood. Enjoy the solar heated saltwater pool and the comfy outdoor lounge area, Enjoy the backyard with its mature trees and tropical flowers. The indoors come with a luxury and modern wellness bathroom. Soak in the oversized tub or reenergize in the stylish rainfall shower with inbuilt bench and mood lighting.

Oviedo Oasis:2/1 attached Guest Suite;Private Pool

Cozy 2 bedroom guest suite connected to host's primary residence but has its own entrance and there is no shared spaces inside. Living room, 2 separate bedrooms and a full size bath. Amenities include a coffee bar, mini fridge, microwave, TV, Wifi and access to non-heated swimming pool. Host primary residence does overlook the pool area. Listing does not include a full kitchen. Central to everything: UCF: 5 miles MCO Airport: 25 miles Sanford Airport: 11 miles Disney: 40 miles

Tiny Tropical House! 🏝

Welcome to life on Tropical ! Our tiny home is located right outside of Oviedo. About 20 mins away from UCF and an hour from Cocoa and most major theme Parks. We live down the street from Lake Mills Park which is a beautiful park with a great lake you are welcome to use our water crafts too! *Please note that the ladder to access the loft above the restroom is not secured to the wall and is moveable. If you proceed to book use at your own risk.

Spacious 3 BR Home Perfect for Orlando Getaway

Relax with friends or family at this peaceful parkside home, while enjoying everything that makes Central Florida so special. From Disney and Universal Studios to Downtown Orlando. Entertainment is just minutes away in either direction with an abundance of shopping and dining options to choose from. Our family absolutely loves this area! We have a recommendation for just about anything and are excited to share this home with you!

Unique and modern airstream near UCF

Our airstream has all the amenities you need. It is located in our one acre property behind our house (very private) the parking is on the side of our house next to our carport and you will go through a gate and follow the path to the airstream. MCO Airport 12 miles Disney parks 25 mil Universal Studios 16 mil beaches 50 mil UCF 2.4 mil Full Sail 2.4 mil Valencia 3.5 mil Dining, Shopping entertainment and much more!