Holiday rentals in Howey-in-the-Hills

Private Getaway on the Hilltop

Our small apartment is on a 20 acre tree farm at the top of one of the highest hills in florida. We are perfectly situated in the middle of bicyclist heaven with many challenging hills just outside our gated property. Enjoy all Central Florida has to offer within a short drive... Mt. Dora, with its cute shops, Clermont, Choice of Champions training, Disney is less than 45 minutes away and either coast just over 1 hour. Private, just remodeled, and cozy ground floor entrance w/ 2nd floor living.

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.

Silver Lake Guest Pool House Very Private !

The Silver Lake Pool Guest house Is your home away from home 1400 sq feet plenty of room! The pool house is a peaceful place to relax or take a swim in a large salt water pool . Mt Dora Tavares, Eustis 10 to 15 minutes away from Pool house Forty five minutes Daytona, Tampa Smyrna beach and parks Minutes from grocery stores restaurants malls Full kitchen also grilling. We are happy to help you with your needs ! Home is great for couples families, solo adventurers, and business travelers

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!

Courtland Waterfront at Tavares

Welcome to Courtland Waterfront, a peaceful lakefront house on Lake Dora located in the heart of Florida. This comfortable updated home is a perfect location for a family reunion or weekend retreat & offers a spacious and peaceful experience for your vacation. Bring your boat or rent one nearby to explore the Harris Chain of Lakes by water & cruise the Dora Canal to Lake Eustis. Access the Lake via a private small boat ramp on the property or via one of the many public boat ramps in the area.

1950's Sunnyside Cottage-Boat Parking-Hot tub-Cozy

Refresh and unwind in this stylish and carefully curated cottage, with plenty of parking for your boat, rv, or trailer! Enjoy morning coffee on the deck and an evening soak in the hot tub! The boat ramp and quaint downtown Tavares is only a half mile down the street. A short 11 minute drive to Downtown Mount Dora, this cozy spot is centrally located. Whether you're coming for a weekend getaway or spending an extended season in sunny Florida, this retreat will be one you always come back to!

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.

Private Cedar Hideaway

You won’t regret choosing this peaceful, secluded hidden gem. 40 min. to Disney, 10 min. to downtown Clermont, Waterfront Park, the Howie Mansion and Mission Inn's world class golf courses. 15 min. to National Training Center. Home to some of Florida's only hills, this is a popular cyclist destination! *kitchenette. Not a full kitchen. *this is a private apartment attached to a home occupied by the hosts. All spaces are private. They're are NO shared SPACES, other than the driveway! :)

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 also offer discounted pontoon boat rental prices for guests. We promise a relaxing & peaceful stay. You're going to love it here!

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.

Cozy Studio Near Disney/Universal/Training center

This cozy stylish studio, detached guest house is perfect for short-term or extended stay in the beautiful city of Minneola. Sleeps 2, can accommodate up to 4. Features a large backyard and a fire pit.  Close to Downtown Clermont, National Training Center, and 35 minutes to Disney World and other major attractions. This tranquil space features a queen bed with 3" memory foam mattress topper and a spacious living space that has a Multi-Functional Sofa that converts into a Bed.

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.