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, 113 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!

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 Orlando Two Tiny Homes

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

A screened patio area is shown, featuring a private pool surrounded by an expansive deck. Comfortable seating arrangements are visible, along with lush plants and natural light streaming in from large windows overlooking the wooded landscape.

Guesthouse in Deer Island

4.95 out of 5 average rating, 116 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.

Top guest favorite

A modern bathroom features dual vessel sinks on a wooden vanity, surrounded by turquoise accents. Natural light illuminates through the windows. Textured stone walls add depth, while a small seating area is visible in the corner. Clean lines and neutral tones create a calming environment.

Apartment in Minneola

4.97 out of 5 average rating, 74 reviews

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! :)

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

A treehouse is illuminated by warm string lights, nestled among large branches under a deep blue sky. The structure features large windows allowing views of the surrounding greenery, with a cozy seating area visible inside. A wooden walkway leads to the entrance.

Treehouse in St. Cloud

4.96 out of 5 average rating, 976 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

A modern kitchen featured with a large island, complemented by bar stools. Rustic wooden beams hang above, adding an element of design. Stainless steel appliances and a unique tiled backsplash enhance the functional cooking space. Natural light enters through windows, creating an open atmosphere.

Cottage in Clermont

4.9 out of 5 average rating, 110 reviews

Beautiful country house

Take the whole family to this fantastic place with many areas for fun. we have 5 acres of land just for you, beautiful country house in the only hills of the state of Florida, you will enjoy the tranquility, privacy, connection with nature and witness a beautiful sunset unparalleled, stay and observe the stars, spaces suitable for unique souvenir photos. Ideal area for cycling and walking. NOTE: if you want an event check our rates first

Top guest favorite

Cottage in Tavares

4.97 out of 5 average rating, 228 reviews

Lakeside Cottage on Lake Dora

A charming 1200 sq ft, two bedroom, two bath cottage located on beautiful Lake Dora with white sand beach. A great place to relax and your home away from home. Just minutes from Tavares (known as the Seaplane City) and Mt. Dora (known as the City of Festivals.) You can bring your boat and tie it up to the dock. Large circular drive with plenty of parking for cars, trailers, etc.