Holiday houses in Osceola County

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Top-rated holiday rentals in Osceola County

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Guest favourite

A serene view of a dock extending into a calm lake at sunrise. The sun rises above the horizon, casting warm hues across the sky and reflecting on the water's surface. Reeds frame the scene, enhancing the natural surroundings.

Home in Lake Wales

4.88 out of 5 average rating, 32 reviews

Lakefront 2br w/pier & dock 4,500-ac Lake Rosalie

Peaceful getaway on Lake Rosalie w/ 4,530 ac of beautiful water w/ bass, catfish and crappie fishing. Birds routinely viewed from the dock include eagles, osprey, sandhill cranes, herons and more! Often making an appearance are a pair of otters and the Florida alligator! Morning sunrise over the lake from the sunroom or the dock is one of our favorite times! Add a cup of coffee is the best! Rowboat, golf cart, large patio w/grill and pier & dock to view the wildlife and enjoy time at the lake!

Top Guest favourite

An inviting living area features a comfortable tufted chaise lounge and a cozy recliner. A flat-screen TV is mounted above a classic fireplace, surrounded by soft curtains that frame bright windows. The floor showcases warm wooden tones, contributing to a homely ambiance.

Cottage in Lake Wales

4.97 out of 5 average rating, 151 reviews

Charming, renovated 1917 Cottage

Charming, renovated 1917 cottage in beautiful neighborhood. One block from large lake with walking/running trail, 3.5 miles to Bok Tower, 12 miles to Legoland, 38 miles to Disney World, 47 miles to Universal Studios, and 63 miles to Busch Gardens. Pet friendly! King size bed in bedroom, double sofa bed in living area. Newly renovated kitchen has full size refrigerator, sink, microwave, stove top and large toaster oven. Big backyard with beautiful landscaping. Separate driveway. Lots of privacy!

Top Guest favourite

A serene lakeside scene featuring colorful Adirondack chairs arranged on a grassy area. A calm lake reflects soft evening light, with a palm tree visible in the distance. The sky is adorned with clouds, hinting at a gentle sunset.

Home in Babson Park

5 out of 5 average rating, 10 reviews

Midcentury Lakefront Home on Crooked Lake

Located in Babson Park on Crooked Lake in Central Florida, our 3/2, 1500 sq feet midcentury modern home, sits at the end of a private drive on a family-owned peninsula, surrounded by water, with 100 feet of private beachfront. Minutes from several theme parks and family restaurants. Secure your boat in the canal in the back of the a house. There 2 kayaks, outdoor seating, a 2-car carport, gas BBQ grill, with views from every room. Your family can enjoy fishing and water sports all day long!

Guest favourite

Home in Osceola County

5 out of 5 average rating, 28 reviews

The Magical Retreat near Disney

Welcome to your Orlando retreat! This spacious 5-bedroom, 4.5-bathroom townhome at the exclusive Azur Resort offers everything you need for an unforgettable vacation. Designed with comfort and style in mind, this home is ideal for families, groups, and anyone looking to explore the magic of Orlando. Located just mins from Orlando's top attractions- Disney World, Universal, and world-class shopping and dining. You’re at the center of it all! Book now and start making memories at the Azur Resort!

Guest favourite

A bright and airy living space features a comfortable sofa and a coffee table atop a decorative rug. A ceiling fan and large glass doors lead to an outdoor area, while a sleek television adorns the wall opposite. Natural light enhances the neutral color palette.

Home in Lake Wales

5 out of 5 average rating, 26 reviews

Premium Lake Wales Getaway!

Beautiful townhouse, conveniently located in growing Lake Wales! Hotel-like feel with home-like comfort. Whether you're visiting for one night or planning an extended stay, this updated and stylish space lacks for nothing. We have you covered! Conveniently located near the infamous Bok Tower Gardens, Legoland, Peppa Pig Theme Park, with Disney World and world-famous, FL beaches within a couple hours away your options are endless. We hope you choose to stay with us for your special getaway!

Guest favourite

Home in Lake Wales

4.94 out of 5 average rating, 119 reviews

Fishing Lakefront Paradise w/ Boat Slip & Parking!

Welcome to Florida Lakefront Paradise! ⭐️ Breathtaking Sunsets ⭐️ Bass Fishing ⭐️ Reserved Boat Slip ⭐️ Fish Cleaning Station ⭐️ Boat Wash Station ⭐️ Marina with Ice/Gas ⭐️ Large Fire Pit Area ⭐️ Located on Kissimmee Chain of Lakes ⭐️ Smart TV's ⭐️ Screened Lakefront Back Patio ⭐️ High Speed Internet ⭐️ Spacious ⭐️ Balcony Facing the Lake ⭐️ 30 minutes to Lego Land ⭐️ 20 minutes to Bok Tower Gardens ⭐️ 1 hour to Disney World ⭐️ 18 minutes to Spook Hill ⭐️ 18 minutes to Kissimmee State Park

Guest favourite

A modern two-story house is showcased, featuring a bright exterior and a spacious driveway. Lush green grass surrounds the property, while palm trees add a tropical touch. Large windows on the upper level allow for ample natural light, highlighting the clean lines of the architecture.

Home in Kissimmee

4.96 out of 5 average rating, 119 reviews

Villa Resort Club

VILLA LUJOSA - BARRIO SÚPER HERMOSO POOL HEATER HOUSE - Diviértete con toda la familia en este alojamiento con estilo moderno , te encantará el área de picnic frente de la casa , el área de juegos y piscina con calentador , un espacioso lugar de hierba artificial para jugar tus niños y en una zona muy trankila cerca de los parques de Disney y del aereopuerto MCO . TE ENCANTARÁ LA CASA Local utility or county personnel may access exterior areas for maintenance without prior notice.

Guest favourite

An aerial view showcases a large pool surrounded by lounge chairs and palm trees. The pool area is defined by well-maintained landscaping, with a hot tub and a nearby shaded structure visible in the background, creating an inviting atmosphere.

Condo in Osceola County

4.89 out of 5 average rating, 120 reviews

Stunning Orlando Condo 3 BR/2 bath, pets OK

This resort community is amazing to drive around in, let alone stay in. Just 20 to 25 minutes away from Disney World and Universal Studios and everything Orlando has to offer. Convenience stores (7-11), Dunkin' Donuts, CVS pharmacy, restaurants and grocery stores within walking distance. Three gorgeous pools and hot tub Jacuzzis, and world-class gym in the resort in this gated community with security. 5 minute drive to Champions Gate and I-4 highway. Up to 2 dogs/cats ($25/day/animal)

Top Guest favourite

The exterior of a large, two-story home is displayed, featuring a light-colored facade and a covered front porch. Lush landscaping surrounds the driveway, which is paved with stone. A garage door is positioned on the right side, complemented by decorative lanterns and palm trees.

Home in Osceola County

4.98 out of 5 average rating, 81 reviews

Large Private Home on Golf course by Disney

Bring the whole family to this great place with lots of room for fun. With fantastic views of the 4th hole on the Tom Watson golf course and your own private pool and hot tub everyone will enjoy this stylish and modern vacation home. Located in premier Reunion Resort and only 10 minutes to Disney you can have it all! This home boats over 4000sq feet, two very large masters suites, 2 additional bedrooms and plenty of space throughout the home. There are 6 tvs! Pets are welcome too!

Top Guest favourite

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

4.97 out of 5 average rating, 1,104 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.

Guest favourite

A wooden barrel sauna is situated in a serene garden space surrounded by bamboo. The sauna features two benches and a wooden door, with soft lighting highlighting its natural texture and the tranquil atmosphere of the area.

Campervan/RV in Lake Wales

4.84 out of 5 average rating, 130 reviews

Bamboo Bus -Sauna/ Pool/Fire pit/Grill

Take it easy at this unique, romantic and tranquil spa like getaway. Come and enjoy a piece of heaven with friends and family. Take a soak on the pool, Relax at the barrel sauna, fire up the grill, make some smores on the fire, sit back and relax. Close to lakes and state parks. Bring your kayaks to have a great day at Lake Pierce less than a mile away. Drive 45Mins to Disney and 20mins to Legoland. We'll see you soon!

Top Guest favourite

A serene landscape captures two shipping container structures amidst lush greenery. Soft colors of the sunset blend with a gentle rainbow, enhancing the natural surroundings. The garden features various plants and mulch, creating a peaceful retreat atmosphere.

Shipping container in Osceola County

4.97 out of 5 average rating, 68 reviews

Beautiful off-grid tiny home cottage #3

Retreat to the food covered grounds of this off-grid oasis in Central Florida, reconnect to the beauty and vibrancy of nature, and experience the magnitude of freedom and abundance it has to offer on your sustainable getaway. Your shipping container has a full kitchen, mini-split cooler and spacious shower with an on-demand water heater fed by pristine well water... you would never know you're off-grid!