Holiday houses in Osceola County

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Top-rated holiday rentals in Osceola County

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Guest favourite
The exterior of a townhouse is presented, featuring a warm peach-colored facade with contrasting dark shutters. A garage is visible on the right side, accompanied by neatly trimmed shrubbery and a palm tree in the foreground. A light-gray vehicle is parked in the driveway.
Townhouse in Osceola County
5 out of 5 average rating, 13 reviews

Luna Del Sol, Close To Disney Attractions & Parks

Welcome to the Luna Del Sol Vacation Home-- a spacious 4 bedroom and 2.5 bathroom townhouse-- in the quiet gated Carriage Pointe section of Reunion Resort.This end unit vacation home will meet your needs for either being on the go and taking in all of Orlando's fantastic attractions and parks or wanting a quiet laidback getaway relaxing poolside in the sun. Luna Del Sol is centrally located and in close proximity to numerous stores and restaurants to assist and enhance your stay at Luna Del Sol.

Top Guest favourite
The villa features a single-story design with a spacious front yard and meticulously maintained landscaping. Palm trees and vibrant greenery flank the path to the entrance. Large windows reflect natural light, and a neat driveway leads to a garage, creating an inviting exterior.
Home in Kissimmee
4.98 out of 5 average rating, 51 reviews

3 Miles to Disney! 4 Br/3Ba Pool Villa. Remodeled

3 Miles to Disney. Newly updated 4 br, three full bath pool villa is minutes away from Disney (you can hear the fireworks!), - and Universal,/Sea World/Orlando Airport, are also close. It backs up to a pine forest - so quiet and peaceful. Just a couple miles and you're surrounded by shopping, restaurants - everything you could need. Tastefully decorated with images of Disney artist’s work and Mid-Century touches. You'll want to stay here again and again. We are committed to your satisfaction

Top Guest favourite
Townhouse in Osceola County
4.94 out of 5 average rating, 33 reviews

The Sun-Kissed 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!

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 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

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, 1,100 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 favourite
An inviting outdoor space features a private saltwater pool surrounded by lush greenery. Comfortable seating includes a sectional sofa, an umbrella-covered table, and lounge chairs. A TV is mounted on a wooden wall, offering entertainment options, while decorative plants enhance the tranquil atmosphere.
Home in Kissimmee
4.95 out of 5 average rating, 19 reviews

Luxe Saltwater Pool Home | Golf | 1 Exit to Disney

Plentiful Views | Reunion Resort Luxury Home | Private Saltwater Pool + Golf Views | 1 Exit from Disney A private golf-course retreat inside Reunion Resort — just one exit from Walt Disney World®. Designed for families and groups who want space, privacy, and elevated comfort, this 5-bedroom home blends resort-level amenities with the ease of a fully private residence. Minutes from Disney. Worlds away from ordinary.

Top Guest favourite
Villa in Davenport
4.99 out of 5 average rating, 103 reviews

Amazing Villa near DisneyWorld FREE heated-pool

Have fun with the whole family at this stylish place. Our home has everything you will need for you and your guest to have a great experience. This home is a short drive from Walt Disney World and Orlando Attractions!! Don’t wait book with us now and give you and your family the vacation you all deserve. We can’t wait to welcome you . BBQ ( free to use ) Heated pool (free) Dogs friendly! Extra fee $120 per stay

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, 67 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!

Guest favourite
A large outdoor pool is featured with clear blue water, surrounded by a spacious sun deck. Comfortable lounge chairs are placed along the poolside. A pergola provides shade, while planters with greenery add a touch of nature to the open area. A scenic view of the horizon is visible in the background.
Apartment in Osceola County
4.92 out of 5 average rating, 26 reviews

Reunion Living Near Disney + Luxury Serenity

✨ Discover peace, luxury, and fun in this modern villa at Reunion Resort. Walk to Sunset Walk and Margaritaville for fine dining, live music, and tropical vibes. Only 15 min from Disney parks and surrounded by trees, walking trails, and resort pools. Enjoy a safe, family-friendly area with gym access, bike paths, and a romantic, relaxing atmosphere — perfect for couples or families.

Superhost
Townhouse in Kissimmee
5 out of 5 average rating, 6 reviews

4BR Retreat | Pool | Close to Disney

Home at Bella Vida. If you want a heated pool, you must notify us in advance and we charge $30 per day for pool heating and one time fee of $50 for the bbq. Starter amenities are provided for your arrival, intended for short stays or your first night convenience.

Popular amenities for Osceola County holiday rentals

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