Vacation rentals in Howey-in-the-Hills

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

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Top guest favorite

An inviting living area showcases large arched windows allowing natural light to fill the space. A cozy seating arrangement is complemented by a small dining table and chairs. Decorative elements are present on window sills, adding charm to the atmosphere.

Farm stay in Howey-in-the-Hills

4.96 out of 5 average rating, 112 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 sun-drenched pool area features a sparkling blue pool surrounded by comfortable seating. A table with an umbrella and colorful chairs offer space for relaxation. The sunroom with large windows provides views of the inviting outdoor space, enhancing the overall tranquil setting.

Home in Lady Lake

4.96 out of 5 average rating, 319 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

The inviting exterior features a two-story home framed by lush green grass and mature trees. Arched windows and a symmetrical design enhance the charm, while a driveway leads to the front entrance, providing easy access to the peaceful surroundings.

Guesthouse in Leesburg

4.98 out of 5 average rating, 397 reviews

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

Guest favorite

A tiny home is showcased with a grey exterior and a metal roof. Two wooden chairs are positioned on a grassy area in front, and flower pots add color near the entrance. Steps lead up to the front porch, providing access to the inviting interior.

Tiny home in Howey-in-the-Hills

4.96 out of 5 average rating, 147 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, 125 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 well-appointed sleeping area features a white bed frame with plush bedding in navy and white tones. Two bedside tables with navy blue lamps flank the bed. Decorative pillows, including a map-themed cushion, add interest, while framed botanical prints hang above the headboard.

Cottage in Mount Dora

4.98 out of 5 average rating, 166 reviews

Newly Renovated Cottage, Easy Walk to Downtown!

Walking distance to all Downtown Mount Dora has to offer! Our lovely 2 bedroom, 1 bath 1940s cottage has been recently renovated. Features fully outfitted kitchen, deck with gas grill and outdoor firepit. Comfortable and elegant living space with 65 inch smart TV. Primary bedroom features King bed and smart tv. Second bedroom has two cozy twin beds. Bikes available for use. Whether you’re coming to relax, boat, shop or partake in one of Mount Dora's many festivities, consider staying here!

Guest favorite

A bright and inviting living area showcases a light-colored sofa with neutral-toned throw blankets. A wall-mounted television is positioned above a contemporary media console, while natural light filters through two windows covered with sheer curtains.

Guesthouse in Clermont

4.97 out of 5 average rating, 132 reviews

Coastal Cottage in Clermont

Welcome to our newly renovated coastal cottage! Located in the heart of Clermont, only 1 mile from downtown, the south lake trail, & only minutes from all of the best restaurants, shopping, & coffee shops in Clermont! This is the perfect location for triathletes in training or families visiting Disney World (or any of the theme parks) – Orlando’s best attractions are less than 30 miles away! This sweet & sunny lakeside studio has everything you’ll need for a comfortable visit!

Guest favorite

A comfortable living area features a spacious couch with reclining sections and soft cushions. A Smart TV is placed on a black media console next to a stylish clock, while light filters through striped curtains. A small table holds a notepad, providing additional convenience.

Apartment in Minneola

4.96 out of 5 average rating, 119 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.

Superhost

Aerial view of The Faith Estate, showcasing the historic Victorian-style house surrounded by lush greenery and expansive lawns. The blue exterior contrasts with the vibrant landscape, while serene lake waters reflect the soft colors of the sunset sky, enhancing the natural beauty of the setting.

Home in Leesburg

4.88 out of 5 average rating, 134 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.

Top guest favorite

A modern living area features a vibrant red sofa and two gray armchairs, offering ample seating. A stylish coffee table sits centrally, complemented by a small plant centerpiece. A large television is positioned opposite the seating, with soft lighting from table lamps creating a welcoming ambiance.

Apartment in Clermont

4.98 out of 5 average rating, 109 reviews

Modern Suite in the Heart of Downtown Clermont 101

Attention Triathletes! Brand-new, Modern Suite, "Heart" of Downtown Clermont. Steps to quaint downtown restaurants, shops, and local Breweries. Conveniently close to the Clermont/Minneola Trail, Host of the Prestigious Triathlons and the Waterfront Park. Unique location for athletes! See all Clermont has to offer including the National Training Center and enjoy close proximity to Walt Disney World, Sea World and International Drive. Only 30 Min. to Downtown Orlando.

Guest favorite

A circular fire pit area is surrounded by six blue adirondack chairs, set on a stone patio. Lush greenery and colorful plants frame the space, with a view of the house and pool area in the background. Sunlight brightens the inviting outdoor gathering spot.

Home in Clermont

4.92 out of 5 average rating, 118 reviews

Spacious Bungalow with Private Pool and Courtyard

Whether you seek relaxation or adventure, this house offers the best of both worlds! Relax in this spacious bungalow with a private courtyard, pool, hot tub, and fire pit! Take a short walk to downtown Clermont and discover the charming shops, restaurants, and breweries! Explore the sights and attractions that Central Florida has to offer! Whether you crave the vibrancy of downtown or the tranquility of your own oasis, this property offers the best of both worlds!

Top guest favorite

A swing adorned with vibrant flowers hangs from a large tree beside a modern, light-colored house. Sunny skies illuminate the patio area, where potted plants are arranged neatly. The lawn is well-maintained, featuring a mix of grass and decorative stone pathways.

Cottage in Clermont

4.91 out of 5 average rating, 117 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