Holiday rentals in Howey-in-the-Hills

Fun Getaway Ranch Lake Pool Soccer 6 Bed 3 Bath

Relax and have fun on our beautiful 5 acres Ranch located only 30 Min From Disney and most attractions. We offer many activities inside the Ranch like: Kayak, Paddle Boards, fishing,Soccer, Pool,hottub, Ping Pong, Pool, air hokey,drums, huge 75’ Tv to watch movies . You will enjoy Mother Nature with all birds that constantly visit us. Perfect location for bicycle riding also we are a mile away from Sugarloaf famous for the hills to train. Your UTVs are welcome we have a track that you can ride.

Eden Escape Suite, Lake Harris, Florida

Settling into this luxuriously curated boutique suite, you may come to agree with lore that the original Garden of Eden was nearby. Bask in the rejuvenating spring waters flowing through all taps and feeding the pool just a three minute stroll to Lake Harris, a premier bass fishing lake in a chain that leads to the Atlantic. From the comforts of your private efficiency immerse in the outdoor privacy of your patio garden soaking up serenity in your vintage claw-foot tub, ah the perfect choice.

Sapphire Cottage - sleeps 6, on 5 acres with canal

Escape to Sapphire Cottage, a 5-acre wooded retreat with a private canal boat dock. Relax by the shared pool, fish from the dock, or enjoy a BBQ at the firepit. Our cozy cottage features a queen master, 2 sofa-beds, a full kitchen, and dining for 6. From meeting our farm animals, biking, kayaking, or reading in the gazebo, there is something for everyone! We live in the main house across the way and are happy to help while ensuring you have a peaceful stay. Come make lasting memories with us!

Country Chic Cottage with Private Boat Parking

Beautifully remodeled historic home combines up-to-date amenities with charming southern style. 4 bedroom, 3 full bath home located in friendly Tavares, America’s Seaplane City. Only a half mile from downtown Tavares restaurants and shops, 10 minutes to Downtown Mount Dora, 15 minutes to Howey in the Hills and centralized between Lake Dora, Lake Eustis, and Lake Harris with lakeside activities, seaplane rides, boat rentals, and festivals. Less than an hour to Disney, Universal, and Sea World.

Modern Brick Rural Home

Newly renovated ranch- style home, this stunning 4 bedrooms 3 bath single story home has been updated and newly furnished. Featuring a full size kitchen and granite counter top open to finish dining and living areas. The floor is updated with high end vinyl plank. Fully fenced and features an outdoor area. Pet fee applied. The total size of the property is approximately 5 acres of land. Very unique and peaceful property where you can appreciate the outdoor and beautiful oak trees.

Island life on the lakes

Escape to the island life (yes, an actual island!) located on the Clermont and Groveland chain of lakes where an endless amount of exploration awaits and you choose your own adventure…kayaks, paddle boards, pedal boat, fishing! Bring your boat and enjoy the lakes or sit on the dock in solitude with the sunsets and wildlife. This rustic slice of paradise is secluded yet within a short driving distance to local hot spots, Orlando attractions, the beach, and everything in between.

Adorable Downtown Lakeview Home 1105

Experience unparalleled comfort and charm in our distinctive Lakeview home, ideally located in downtown Clermont's vibrant heart. This bright and captivating property exudes an inviting aura with its scenic lake views and exceptional decor. Start your day with a refreshing cup of coffee on the serene back porch, take a stroll to the nearby park, or enjoy the array of amenities in the vicinity. Families and athletes alike will enjoy the convenient proximity to key attractions.

Charming Downtown Apartment - Walk to Everything

Stay in the heart of historic downtown Clermont- steps from the lakefront, breweries, shops, & dining. This light-filled, stylish apartment above our garage offers cozy aesthetics, comfy beds, a double shower, two spacious bedrooms, and a smart TV. Thoughtfully stocked for a stress-free stay, with garage storage for your bikes or paddle gear upon request. More than a stay—we proudly offer a distinct Clermont experience. We hope you love our charming town just as much as we do!

The Faith Estate - A Lakefront Storybook House

Welcome to The Faith Estate, a historic 5-bedroom, 3.5-bathroom lake house in Leesburg, FL, near The Villages, Eustis, and Mount Dora. Perfect for reunions, retreats, or a relaxing getaway. Ideal for boaters, with space for multiple boats and trailers—great for Harris Chain of Lakes events. The estate also allows approved events. Submit details via Airbnb for approval before check-in. Unapproved events are not permitted. Event setups must respect property guidelines.

Peaceful, adorable, guest cottage on Apopka Canal.

This special place with an "out in the country" feel is actually close to everything, making it easy to plan your visit. It is close to the cute shops and restaurants of Mt. Dora and Tavares, yet only an hour from all the attractions in the Orlando area. This 15 acre peace of paradise is right on the Apopka Canal with easy access to the Harris Chain of Lakes. Launch your boat from the boat ramp just across the canal from The Acorn at Lake Jem park.

Private Country House | 16 Guests | Gatherings

Bring the whole family to this private 5-acre retreat, situated in one of the few hilly regions of Florida. Enjoy privacy, nature, spectacular sunsets, and starry nights—perfect for relaxing or enjoying outdoor activities. ⚠️ Gatherings require prior approval—please contact us before booking. Note: There is another house on the property that may be rented by other guests. Both are completely private, with no shared areas or parking.

The Lake Harris Bungalow

The newly finished Lake Harris Bungalow offers fun, sun & relaxation! Sitting directly on Lake Harris this in-law suite offers amazing views from its 2 beds (queen & twin XL), full bathroom, kitchen w/ full size appliances, WiFi/TV, covered parking (with power for boat/EV charging) and furnished screened in back porch overlooking the lake (with bbq grill). We promise a relaxing & peaceful stay. You're going to love it here!