Holiday houses in Webster

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Top-rated holiday rentals in Webster

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Guest favourite
A serene river scene is depicted, featuring a lone kayaker maneuvering through calm waters reflecting the sky and surrounding trees. Vibrant autumn foliage borders the riverbanks, creating a peaceful ambience in a natural setting.
Holiday home in Bushnell
4.94 out of 5 average rating, 142 reviews

Withlacoochee River House w/ Kayaks, Bikes, Canoes

Located on the main channel of the Withlacoochee River across from the State Forest, this home offers relaxation and recreation. The home is equipped with canoes & kayaks to launch from the backyard, and bikes to enjoy the 40+ miles of paved and mountain bike trails. Come home to relax by the fireplace and enjoy the river view, hang out and fish from the river bank, lie out back in a couple hammocks, or fire up the grill. This home is a great vacation getaway for couples, families, & friends!

Top Guest favourite
Aerial view captures a rustic two-story home surrounded by expansive green lawns and mature oak trees draped in Spanish moss. The roof is metal, and a wraparound porch enhances the outdoor space, suggesting a serene retreat in a peaceful country setting.
Home in Webster
4.98 out of 5 average rating, 63 reviews

Unique Country home in Sumter County, Florida.

Take it easy at this unique and tranquil getaway. You will be close to lakes, beaches, and major cities like Orlando, Tampa, Ocala and communities like the Villages. Close to Bushnell, Inverness, Tavares, Lake Dora, Crystal River, Homosassa, the I-75 corridor and Florida's West Coast. Florida Country at it's very best! The original orange groves, local farmer markets and wildlife. Take a airboat ride and see alligators in their natural habitat. Attend an event at the Sumter county fairground.

Top Guest favourite
The exterior of the waterfront residence is illuminated with colorful string lights, creating a festive ambiance. A spacious patio area is visible, featuring a dining table and seating. Large glass windows allow for views of the living space inside, enhancing the open-air feel.
Place to stay in Mount Dora
4.98 out of 5 average rating, 265 reviews

The Boat House on Lake Dora - Downtown Waterfront

WATERFRONT! The Boat House is an 800sf private residence built directly over Lake Dora offering panoramic lakefront views. Located on Mount Dora's Famous Boat House Row, right in the heart of downtown Mount Dora, where you can roll out of bed and walk a few steps to one of the quaint coffee shops. The Boat House was once a tin boat shed with floors open to the water and housed two boats. Today, you will find warm, cozy furnishings, comfortable beds, a quiet location and sunsets every evening!

Top Guest favourite
A close-up of a smiling fox is captured, showcasing its bright eyes and soft, fluffy fur. The animal's ears are perked up, indicating curiosity, while its mouth is open in a playful expression against a blurred background.
Farm stay in Dade City
4.94 out of 5 average rating, 370 reviews

Florida Breeze -Wildlife Sanctuary- 5 miles to I75

Have you ever wanted the opportunity to feed an egg to a fox? Or feed a grape to a lemur? Hand feed a deer or sheep? Dance with a cockatoo? If so you’ll get to have these and many more experiences here during your stay. Our Airbnb is different, and our main focus is on offering rememberal experiences to our guests. We have a small family run 501C-3 wildlife rescue here on our 18 acre facility that you will be staying at. We do live on the property, but in a detached house across the driveway.

Guest favourite
Home in The Villages
4.83 out of 5 average rating, 64 reviews

Golf and Water Just South of Sumter Landing

This vacation, really treat yourselves! That's what we are here for :). When we saw the view, it took our breath away! The white picket fence, expansive golf and water view is perfect! The location in Largo just south of Sumter Landing (1.5 ml) and a stone's throw from the pool and rec center clinched it for us. Inside we offer reclining furniture, fully stocked kitchen a king adjustable bed in the master and 3 tv's. Outside offers fabulous swivel rockers to enjoy coffee and the sunrise!

Guest favourite
Home in The Villages
5 out of 5 average rating, 5 reviews

Waters Edge, ¼ mile to Eastport, 3 BR, 2 bath

Welcome to this brand-new 3BR/2BA home, perfectly located 1/4 mile from Eastport Town Square in The Villages! Enjoy a modern, comfortable stay w/ a king bed in the primary suite, two queen bedrooms, & smart TVs throughout. The new kitchen features stainless appliances, quartz counters, & all your cooking essentials. Fast Wi-Fi and an in-unit washer/dryer. Relax outside on the furnished huge lanai, or explore amazing nearby amenities: Waters Edge Pool & Rec Center Bellaire Executive Golf

Guest favourite
The exterior of the home showcases a spacious front porch with a charming swing surrounded by greenery. The light-colored walls and dark roof contrast with the extensive lawn, while large windows provide views into the inviting interior. A decorative star and hanging plants enhance the porch's welcoming appearance.
Farm stay in Webster
4.88 out of 5 average rating, 94 reviews

Quiet Farmhouse close to major theme parks

Come enjoy a peaceful stay in the woods at "Quet’s place" a serene gravel road through historic Richloam will lead you right up to your getaway. Relax and take a swing on the front porch and watch the wild turkeys pass by or bring the whole family for a thrilling vacation. "Quet’s place" is only one hour from all major Florida theme parks. Whether you are looking to get away from it all and relax in the country or have the thrill of a lifetime with your family, this is the place to be!

Guest favourite
A shaded gazebo with wooden seating is positioned on a concrete slab, surrounded by lush green grass. The cabin features a brown exterior and a welcoming porch, framed by trees and Spanish moss, offering a serene and natural setting.
Cabin in Leesburg
4.83 out of 5 average rating, 24 reviews

Lakefront Magic Wilderness Cabin

Make some forever memories at this unique and family-friendly place! Nestled on an acre of oak and cypress forest, The Magic Wilderness Cabin evokes the timeless beauty of early Florida lake life with a whimsical nod to it's original beginnings at a world famous theme park. The Magic Wilderness Cabin welcomes you to delight in the quiet nature of beautiful Lake Harris and the Harris chain while watching the sunset over the the scenic shores of the lake from our private dock

Top Guest favourite
A relaxing outdoor space features a circular seating area with bright green chairs surrounding a fire pit. A stack of firewood is placed nearby, with twinkling string lights overhead. In the background, a dining area and a hot tub can be seen within a spacious yard.
Farm stay in Webster
4.98 out of 5 average rating, 40 reviews

Welcome happy Campers, have fun!

Enjoy peaceful surroundings & have fun with our little furry friends @theranchsite 5 minutes away from the chase wildlife sanctuary and the 29 Mile Van Fleet Trail . Just 25 minutes to the Clermont Downtown and 1 hour to Tampa , Orlando ,Ocala and the theme parks . In the heart of Florida and closer to the most stunning springs in the state . Bushnell Motorsport park offers an incredible high speed rental kart experience ,no reservation required and only 25 minutes away .

Top Guest favourite
Cottage in Coleman
4.97 out of 5 average rating, 191 reviews

Peaceful Farm Cottage Near Villages | Garden, Pets

Escape to this cozy tiny cottage with king-size bed, full bath, kitchenette, and pet-friendly comfort. Relax under starry skies, enjoy farm views, and pick fresh vegetables or fruit from the garden and trees when in season. Just 15 min to The Villages, 20 min to Wildwood, 35 min to Ocala, 1 hr to Orlando, minutes from Brownwood live music, and quick access to the Turnpike & I-75. Perfect for a romantic, stylish getaway close to springs, trails, and local attractions.

Guest favourite
The charming cabin is framed by a wooden pergola adorned with hanging flower pots. Lush greenery surrounds the entrance, with large plants in decorative containers positioned at the front. A clear sky above adds brightness to the inviting exterior.
Cabin in Inverness
4.95 out of 5 average rating, 124 reviews

Tin Roof Cabin at The Cove

Are you craving a break? This quaint, comfortable cabin is perfect for solo travelers and couples with "Wanna get away vibes". Inside enjoy the charm of stained ceilings, live wood oak, a kitchenette, queen bed, and a beautiful bathroom with a walk in shower. With designated parking and steps away from the restaurant you can enjoy the convenience and comfort. Just 30 minutes to major Florida Springs. Enjoy the real Florida at day and The Cove at night!

Superhost
An inviting A-Frame log home is displayed, featuring natural wood paneling and a spacious sleeping area with a neatly made bed. A cozy living space is visible, showcasing a smart TV and comfortable seating. A serene bathroom is equipped with modern fixtures and light blue walls.
Home in Clermont
4.82 out of 5 average rating, 104 reviews

Pumba's Place - FUN, Lake, Pool- NO Cleaning fees!

Pumba’s Place is a renovated A-Frame log cabin in the family-friendly gated community of Vacation Village. Perfect for families and adventurers, it features fast WiFi, smart TVs, a fully stocked kitchen & laundry. Enjoy private Lake Louisa access, a heated Olympic pool, tennis, basketball, biking trails & more. Just 25 mins to Disney and 5 mins to Downtown Clermont & the National Training Center

Popular amenities for Webster holiday rentals

  1. Airbnb
  2. United States
  3. Florida
  4. Sumter County
  5. Webster