Holiday rentals in Webster

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Top-rated holiday rentals in Webster

Guests agree: these stays are highly rated for location, cleanliness and more.

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Top guest favourite
Cottage in Coleman
4.97 out of 5 average rating, 205 reviews

Romantic Escape on Peaceful Mini Farm

Escape to a peaceful private farm cottage just minutes from Villages. Enjoy a romantic, cozy retreat with a private fenced courtyard, mini farm charm, and thoughtful comforts throughout. Pets are welcome with no surprise fees. Easy self check-in and simple checkout make your stay stress-free. Close to Brownwood, dining, shopping, and I-75. Extra parking may be available for boats, trailers, or larger vehicles with advance notice. Traveling with family or friends? Ask about nearby sister rentals.

Top guest favourite
A spacious living area features a dark leather sofa and a coffee table on a textured area rug. Modern decor, including pendant lights and a fan, complements the rich green walls. Large windows provide natural light, while a dining area is visible in the background.
Home in Brooksville
4.98 out of 5 average rating, 102 reviews

South Brooksville Ave. Bungalow

Welcome to our historic home in Downtown Brooksville! This peaceful unit is located on one of the most historic streets in Brooksville, Florida! We are walking distance to local restaurants, shops, museums, concerts and trails! Sit, relax and enjoy the outdoors from one of the three decks or around the fire pit! Come and visit Florida's Nature Coast! We are near to Weeki Wachee River! Crystal River to visit the manatees and many other springs! Bike from here right to Withlacoochee State Trail!

Top guest favourite
Farm stay in Dade City
4.94 out of 5 average rating, 392 reviews

Florida Breeze - 18 Acre Wildlife Sanctuary

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.

Top guest favourite
The exterior of a converted Chinook helicopter is showcased, featuring a fenced area and a welcoming entryway. The surrounding landscape includes greenery and sky, with details of the helicopter's design visible, blending seamlessly into the natural setting.
Plane in Brooksville
4.98 out of 5 average rating, 170 reviews

Get to the Choppa! One-of-a-kind 2/1 Helicopter!

Experience a truly UNIQUE Stay! “Chinook” is situated on a serene 5-acre compound inside the breathtaking Withlacoochee State Forest and the thrilling Croom Motorcycle Area, outside of Brooksville, FL. This unforgettable vacation experience is sure to take your adventure to new heights! Our one-of-a-kind accommodation, a REAL repurposed Chinook CH-47D helicopter, promises a stay like no other. This iconic “choppa” with the modern amenities of home, can not be found anywhere else in the world!

Top guest favourite
A welcoming exterior features a red-trimmed entryway and wooden ramp leading to the door. Two chairs are placed on a grassy patch, while a round clock is mounted on the wall, surrounded by trees that provide shade.
Guest house in Webster
4.94 out of 5 average rating, 35 reviews

Withlacoochee Oasis

If you are coming to enjoy the Withlacoochee area, this is a great place to be close to all She has to offer. Bicycle- Located 8 miles from the Withlacoochee bicycle trailhead, 10 miles from Lake Townsend Preserve Trailhead on the Withlacoochee bicycle trail. 19 miles to the Van Fleet trail Mable trailhead.. Kayaking the River- We are 2 miles to River Junction State Park. launch to Silver Lake Hiking- A 6.8 mile trail from River Junction to Iron Bridge to Hog Island all which are State Parks.

Top guest favourite
The cabin is surrounded by lush greenery, positioned on a private peninsula. A spacious deck with seating faces the water, offering a serene view of the canal. Natural light filters through the trees, illuminating the inviting structure.
Cabin in Floral City
4.97 out of 5 average rating, 183 reviews

Private Waterfront Cabin Retreat with Kayaking

Your private retreat on an acre nestled on a canal to the Withlacoochee River, wrapping around 2 sides of the property. Relax on your porch overlooking the water as you watch the birds and deer play. Kids will love the tire swing, toys such as Lego, Lincoln logs, pool table and ski ball. Kayaks available to our guests awaiting adventure. Bond around the fire pit, walk the trails, lounge in the hammocks, and fish on the dock. Setup the big screen to watch a movie. Welcome to your get-a-way!

Top guest favourite
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.
Guest house in Leesburg
4.98 out of 5 average rating, 436 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 food 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 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
4.99 out of 5 average rating, 73 reviews

Top 1% Guest Favorite • The Webster House

Entire private home on 1 acre Three queen bedrooms • Sleeps up to 6 * Known for exceptional cleanliness * Fully equipped kitchen * Dog friendly — No pet fees * Minutes from many of the area's most popular wedding venues and ideal for bridal party staging * Perfect for family visits, business travel, local events, and extended stays * Just a minute from the Webster Public Library, offering ,printing, scanning, and meeting rooms—perfect for business travelers, remote workers * Ample parking

Top guest favourite
A charming green cottage is set among tall pine trees, featuring a wooden porch and a welcoming entrance. A small window is visible on one side, complemented by outdoor lighting. Bright flowers line the base of the cottage, enhancing its rural setting.
Tiny home in Groveland
4.97 out of 5 average rating, 180 reviews

Lovely Meadow Farm Cottage

This lovely farm cottage can be found in a secluded meadowland under various oaks and pines along a natural cypress dome. Spectacular star lit night skies accompanied by hooting owls, whippoorwills, and fire flies make for an unforgettable camp fire atmosphere. Amenities include an outdoor shower, washer, dryer, barbecue, fire pit, fishing and outdoor wrap around patio. Ponds, canals, and Florida wetland host a variety of birds, mammals, fish and reptiles including the Florida gator.

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.
Home in Webster
4.89 out of 5 average rating, 102 reviews

Quet’s Place | 10-Acre Retreat in Richloam

Escape to the peace and quiet of Old Florida at Quet’s Place, a private 10-acre retreat tucked down a scenic gravel road in historic Richloam. Relax on the front porch with your morning coffee, watch wild turkeys and deer pass by, and unwind in a setting that feels a world away from the noise. Whether you're looking to slow down and enjoy the country or explore nearby attractions, this is the perfect place to relax and recharge.Just about an hour from Florida’s major theme parks.

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, 54 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
A welcoming outdoor dining area is featured on a wooden deck, accompanied by three wooden stools and a small table. A decorative plant is positioned on the table. An American flag is displayed, and string lights are hung overhead, creating a cozy atmosphere.
Home in Webster
5.0 out of 5 average rating, 30 reviews

Peaceful Country Retreat

Escape the city noise and relax at your country getaway. Listen to the birds and cows while enjoying your morning coffee on the front porch swing. Hike or cycle the 30 mile long Van Fleet State Trail which runs through the state forest , located just a 4 minute bike ride from the home. Property borders the Withlacoochee State Forest for all the hikers and nature lovers. Enjoy views of the large oaks, wildlife and neighboring cow fields.

Popular amenities for Webster holiday rentals