Vacation rentals in Howey-in-the-Hills

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Top-rated vacation rentals in Howey-in-the-Hills

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Guest favorite

A compact laundry area is visible, featuring two stacked front-loading washers and dryers. A white laundry basket sits on top, with a shelf above displaying laundry supplies. The space is illuminated by overhead lighting, and a waste bin is placed to the side.

Farm stay in Howey-in-the-Hills

4.95 out of 5 average rating, 110 reviews

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.

Top guest favorite

A sparkling blue pool is the focal point of the outdoor area, surrounded by a spacious patio. A wooden pergola offers shaded seating alongside lush greenery and a koi pond, creating a serene environment. Black patio chairs are visible near the pool's edge.

Home in Lady Lake

4.96 out of 5 average rating, 312 reviews

Cozy Lady Lake Guest House

Private guesthouse in a quiet, rural area of Lady Lake. 1 bedroom, 1 bath, furnished with pool privileges. Kitchen, dining bar, living room and sunroom. Sunroom opens to the pool deck and sparkling blue pool, which is completely privacy-fenced in a common area shared with the owners. Suitable for 1 or 2 adults. Central heat and air, 40” Smart Television , WiFi, washer and dryer. Bed linens and bath towels provided. Kitchen with full sized refrigerator/freezer ice maker and electric stove.

Top guest favorite

Guesthouse in Leesburg

4.98 out of 5 average rating, 387 reviews

Silver Lake Guest Pool House

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

Top guest favorite

The exterior corner of the building is illuminated by soft lights, highlighting the lush greenery and decorative lanterns. An American flag is prominently displayed, while a charming, light-adorned house can be seen in the distance, creating a welcoming nighttime atmosphere.

Guesthouse in Tavares

4.98 out of 5 average rating, 115 reviews

The Landing Pad+Short Stroll to Heart of Tavares!

LOW CLEANING FEES!!! We are located in heart of Taveras where everything is walking distance-restaurants, pubs, the seaport, Wooton Park & the history museum! Sit on the patio while using the electric grill. Bring your boat! Plenty of off street park with easy access using the alleyway. Bathroom has a rain shower with 2 speeds. Full kitchen including all the basic amenities+kureig with refillable cups. Come & relax at this fun little spot & enjoy all we have to offer thanks for landing here!

Top guest favorite

A welcoming front porch features two white rocking chairs positioned on a wooden deck. The entrance is accentuated by a brown front door with a classic window design and a welcome mat placed centrally at the threshold, inviting guests inside.

Home in Tavares

4.96 out of 5 average rating, 151 reviews

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.

Guest favorite

A serene landscape is captured at sunset, showcasing vibrant hues of orange and purple reflecting on a still pond. The surrounding area features tall grasses and trees lining the horizon, creating a peaceful natural setting.

Tiny home in Howey-in-the-Hills

4.96 out of 5 average rating, 144 reviews

Horse Farm-Two Tiny Homes 33mi from Orlando

Rest & Relaxation at its finest! This Tiny Home is set to impress! Add on the natural beauty of the rolling hills of Howey, with some of Thee most impressive sunsets over the water & this becomes an Incredible Unique Stay! After sunset, enjoy a nice campfire in your firepit, as you STARGAZE into the night! This Tiny Home is fully equipped with ALL of your needs. Located on the back 3 acres of property, from which you will have your own Golf Cart to travel to/from our Designate Parking Area.

Top guest favorite

An outdoor patio area features a screened enclosure with a private swimming pool. Comfortable seating is arranged around the pool, and lush greenery surrounds the space, providing a serene environment. Potted plants add a touch of color, enhancing the tranquil setting.

Guesthouse in Deer Island

4.95 out of 5 average rating, 117 reviews

Sapphire Cottage - sleeps 6, on 5 acres with canal

On 5 beautiful wooded acres with a boat dock on the canal. Relax by the shared pool, enjoy a BBQ by the firepit, fish from the boat dock, enjoy nature, or simply read a book in the gazebo. Sapphire Cottage has a Master with a queen size bed, a fully equipped kitchen, 2 full size sofa-beds, dinning area for 6, and a full size bathroom. Whether you are looking to relax, enjoy the farm animals, or a bit of adventure we have the perfect location. We live in the main house across the cottage.

Guest favorite

A circular fire pit surrounded by wooden Adirondack chairs is illuminated by a warm glow. The brick patio is partially covered with fallen leaves, creating a cozy outdoor space for gatherings. Soft shadows play across the scene, complementing the inviting atmosphere.

Home in Minneola

4.98 out of 5 average rating, 123 reviews

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.

Superhost

Home in Howey-in-the-Hills

4.78 out of 5 average rating, 72 reviews

Howey in the hills Home next to Howey Mansion

Looking for a 5-star stay with a less than 1 mile walk to the Howey Mansion and Mission inn? Our centrally located 3 bedroom Howey In The Hills House with a large fully fenced yard will be just that. Immaculately clean with fresh linens this home away from home will be everything you wanted and more. Bring the whole family to our lovely home with lots of room for fun. Located close to The Harris chain of lakes, Tavares, Mount Dora, The Villages, Disney, and the list goes on!

Top guest favorite

Treehouse in St. Cloud

4.96 out of 5 average rating, 979 reviews

TreeHouse in the Cloud, (Close toTheme Parks

The treehouse is a private getaway for a couple that want to experience the magic. Check out video tours on U-Tube. Type in Treehouse in the Cloud. There have been several movie and other photo shoots done on property. Please text request and details, and we can negotiate fees. Our other AirBnB is just next door; Country gem horses close to Theme parks [link] Which is 1,000 sq ft and sleeps six.

Top guest favorite

Apartment in Minneola

4.95 out of 5 average rating, 111 reviews

Spacious Apartment In Minneola

This spacious 1 bedroom / 1 bathroom apartment is located West of Orlando in the beautiful town of Minneola right next to Clermont in the heart of Central Florida and is perfect for a short or long term stay. Features a large bedroom & bathroom, comfortable couch w/ dual recliners, plenty of closet space & storage, and a Smart TV. Kitchen is stocked with all the essentials and has a dishwasher, gas stove, refrigerator w/ ice maker, coffee maker, microwave and crockpot.

Guest favorite

The expansive property is situated on a lush green lawn, highlighted by well-maintained pathways leading to a charming firepit area surrounded by seating. The residence showcases a classic architectural style with multiple levels, framed by mature trees under a colorful sky at dusk.

Home in Leesburg

4.91 out of 5 average rating, 119 reviews

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.

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Popular amenities for Howey-in-the-Hills vacation rentals

Gym

BBQ grill

Laptop-friendly workspace

Wifi

Air conditioning

Other great vacation rentals in Howey-in-the-Hills

Top guest favorite

A decorative sign welcomes guests to Spring House, featuring a tennis racket emblem. The sign is mounted on a black pole, positioned in a landscaped area with green shrubs and yellow flowers, creating a welcoming entryway.

Home in The Villages

5 out of 5 average rating, 31 reviews

SpringHouse - 3 Bdrm Patio Villa in The Villages

ZitaRating, 5 stars2 weeks ago

Walt’s place is absolutely perfect! We have been wanting to check out the Villages and the Spring House was perfectly located to see everything. The home is immaculate, well decorated, and had everything we needed plus! We even used the golf cart and had a wonderful time! Thank you Walt for being such a good host!

Superhost

A fire pit is prominently placed on a stone circle, with flames visible. In the background, a gazebo with wooden beams and a darker seating area can be seen. Lush greenery surrounds the area, including palm trees, contributing to the serene lake view.

Cabin in Leesburg

4.71 out of 5 average rating, 14 reviews

Lakefront Magic Wilderness Cabin

LisaRating, 5 stars1 month ago

We had a truly relaxing and peaceful stay at Bob’s beautiful lakeside property. The setting was perfect — quiet, scenic, and surrounded by nature. I especially loved spending time by the water and photographing the wildlife. Bob and Melanie were wonderful hosts, making sure everything was comfortable and easy. If you’re looking for a peaceful and pet friendly getaway to reconnect with nature, this is the perfect spot. We can’t wait to come back!

Superhost

Home in Tavares

4.81 out of 5 average rating, 88 reviews

Retreat withbike/full kitch/near pavilion/fenceyrd

TracieRating, 5 stars2 weeks ago

Our stay was short and sweet. The place was clean, comfortable, and exactly as described. Check in was easy, home fully stocked, and host was responsive and easy to communicate with. Would definitely stay here again.

Top guest favorite

An open floor plan showcases a bright living area that transitions into a fully equipped kitchen. Natural light filters through large windows, illuminating the polished wooden floors. Comfortable seating is arranged in the living space, while the kitchen features modern appliances and a central island.

Home in Eustis

5 out of 5 average rating, 27 reviews

Lakeside Retreat

RobinRating, 5 stars1 week ago

My husband and I were in the area for a Jr. EYBL basketball tournament for my son. We stayed in the house along with 2 other families and their boys. It was PERFECT!!! So spacious, clean, and well equipped. The lake view was incredibly beautiful! The patio was a nice space for the boys to hang out between games. There were tons of board and card games to keep them busy. There was a nice office space that one of the dads used daily since he had some work to do. The beds were big and so comfortable! I loved the MIL house. It was well furnished and spacious as well. Great for the early to bed people… ME! Richard and Braden were very nice and allowed us a late checkout since our game was a little later on Sunday. I had only 1 question while there and I got a quick response. We have traveled a lot together and everyone agreed this is definitely in our top houses and we’ve stayed in and if ever in the area again, we will be back!

Guest favorite

A spacious outdoor area features two wicker chairs positioned on a patio overlooking a wide canal. Lush green grass leads toward the water, where a dock is visible. Multiple boats are seen in the distance, and trees line the peaceful waterway.

Home in Tavares

4.93 out of 5 average rating, 83 reviews

3 Bed, 2 Bath, Waterfront, Dock, Large Driveway

SabinaRating, 5 stars6 months ago

Exactly like the pictures, clean, good appliances, quiet neighborhood.

Guest favorite

A two-story establishment with a spacious outdoor seating area, featuring colorful tables and umbrellas for shade. The balcony offers additional seating, while large windows provide views of the surroundings. The building is surrounded by greenery and has a clear blue sky overhead.

Home in Leesburg

4.92 out of 5 average rating, 71 reviews

Lakefront home chain of lakes & near Mount Dora

Michelle ARating, 5 stars1 day ago

What an absolutely wonderful place! We really loved and experienced 4 days of bass fishing, and a very peaceful vacation. Patsy’s home is immaculate, beautiful, wide open and modern. She is an amazing host and very responsive, proactive and provides many ideas for restaurants, attractions, stores etc . We enjoyed it so much- we stayed an extra day! Can’t wait to come back!

Top guest favorite

An outdoor view of the home's exterior is presented, featuring a silver golf cart parked on a concrete driveway. The well-maintained front yard includes a white picket fence and landscaped areas with shrubs. A spacious garage is visible in the background under a clear blue sky.

Home in The Villages

4.9 out of 5 average rating, 50 reviews

Stunning Villa 2B/2B With Golf Cart

RhondaRating, 5 stars2 weeks ago

We loved staying at Nicole’s house. The house was beautifully decorated and very clean. Nicole was very responsive to any questions. I highly recommend staying here.

Guest favorite