Some info has been automatically translated. Show original language

Holiday houses in Osceola County

Find and book unique accommodation on Airbnb

Top-rated holiday rentals in Osceola County

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

%{current} / %{total}1 / 1
Guest favourite
Home in Kissimmee
4.88 out of 5 average rating, 17 reviews

Comfort Home with BBQ, Private Pool & Hot tub

Step into our inviting single home where coziness eagerly awaits you! This beautiful Villa is nestled in the prestigious, award-winning Terra Verde Resort, a guard-gated community in Kissimmee, just 30 feet from the clubhouse and a mere 10 minutes from Disney. BBQ grill & Pool Heating are optional and must be requested at least one day before arrival. Terra Verde Resort HOA requirement: Upon check-in, guests must purchase a $25 non-refundable gate card for each vehicle entering the community.

Guest favourite
A private pool is framed by a screened enclosure, featuring a gentle waterfall and bordered by comfortable lounge chairs. The serene lake view is visible beyond the pool, complemented by lush greenery lining the shore.
Villa in Kissimmee
4.86 out of 5 average rating, 198 reviews

Near Disney Gated LakeView Pvt Heated Pool

LIMITED PROMOTION! FREE CLEANING FOR BOOKING 2 WKS OR MORE! LOWEST CLEANING FEE! Military dscnts. New Pool Heatr, Dolby ATMOS, 65" LED TV w/ Airplay. Remote office setup. Sunset Lakes a secure gated comnty ~12 min from Disney & other parks. Villa offers Lake View pvt pool, gorgeous sunset, Playroom, Fishing dock. Fully furnished, sparkling clean w/ 5 bds - 1 King, 2 Qns, 2 Twin beds w/ 3 baths, kitchen & lndry. Come & enjoy your next trip to Disney & leave everything to a fantastic experience!

Guest favourite
A spacious living room is displayed with a large modular couch and a coffee table. Light-colored curtains frame the glass doors leading to the outdoor patio, which is surrounded by greenery. A vibrant area rug adds color to the tiled floor.
Townhouse in Kissimmee
4.85 out of 5 average rating, 48 reviews

Themed home - Private Spa - 10 mins to Disney

Thematic beautiful 3 bedroom, 2.5 bath townhouse, with a private back patio with spa, in the beautiful Regal Oaks Resort (right next to Old Town). New townhouse, with over 1400 sqft. Plenty of room to enjoy your family and friends. Tired of the parks? You can still have fun at the home or at the Regal Oaks clubhouse (just a block away), which offers a cafe/restaurant, bar, a big pool overlooking a lake with 2 water slides, a spa, a gym and a convenience store. (NO RESORT FEES) Snowbirds Welcome

Guest favourite
Home in Osceola County
4.86 out of 5 average rating, 22 reviews

The Villa Retreat / near Disney

Welcome to a newly built 5bedroom/4bath, 2 Story townhouse dream vacation. Located in a prime area, just 20 mins away from Disney World,Disney springs,SeaWorld, Orlando Outlets, restaurants, shops & more. Just 5 mins off of I-4. (Resort is still under construction during the weekdays but nearing the end phase . Come enjoy a peaceful , family oriented stay at the Azur Resort before things get into full effect. Each unit is fully furnished and equipped for your family stay. Must be 21 to rent.

Top Guest favourite
An inviting outdoor area showcases a private pool and spa, surrounded by lounge chairs and colorful beach balls. A dining table and large gas grill offer options for outdoor meals. Lush greenery lines the fence, providing privacy and a vibrant backdrop against a sunny sky.
Home in Four Corners
5 out of 5 average rating, 59 reviews

Gorgeous 5BR @ Encore Next to Disney - 305

Modern 3,000sf luxury home, with 5 bedrooms, at world's renowned Encore Resort at Reunion. Featuring 5 bedrooms, 5 1/2 bathrooms, a game room, a beautiful backyard, a private pool and spa. 6 Minutes away from Super Walmart and Publix supermarket 15 Minutes away from Disney Parks 15 minutes away from Disney Springs 15 Minutes away from Premium Outlets 20 Minutes away from Universal Studios 20 Minutes away from International Drive attractions *PLEASE MAKE SURE TO READ THE HOUSE RULES*

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!

Guest favourite
Townhouse in Kissimmee
4.93 out of 5 average rating, 15 reviews

Regal Oaks/3 Miles to Disney/Waterslides/Old Town

This fresh, clean home is located on a quiet court with large windows and beautiful views. It features THREE full bathrooms. The primary bedroom offers a king bed, walk-in closet, ensuite, and private balcony. Two bedrooms have wall-mounted TVs. The open kitchen includes a breakfast bar for quick meals. The living room leads to a private lanai with lounge chairs and dining space. Enjoy resort amenities, waterslides, and a short walk to Old Town, Fun Spot, shops, and restaurants.

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, 1,097 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
Home in Kissimmee
4.85 out of 5 average rating, 13 reviews

Amazing Retreat at Lake Berkley

5-Bed Lake Berkley Villa with Private Pool - Near Disney! Stunning 5-bed, 3-bath home in gated Lake Berkley Resort, minutes from Disney. Sleeps 10 with king master, 1 king, 1 queen, 2 twins. Enjoy a private pool, game room, full kitchen, Wi-Fi, TVs, and laundry. Resort offers clubhouse, tennis, and lake views. Perfect for families, just 10 min from theme parks, dining, and shopping. No smoking/pets. Pool heat extra. Book your magical Orlando escape!

Guest favourite
A themed bedroom displays four house banners from a popular series above two double beds. Each bed is neatly arranged with fresh linens and towels. A nightstand is positioned between the beds, featuring decorative items and a lamp. Natural light enters through a window covered by sheer curtains.
Townhouse in Kissimmee
4.83 out of 5 average rating, 156 reviews

❤️THE❤️ ADVENTURE❤️ HOUSE❤️ (3BD/2BA/4 SmartTV/Lakefront)

⚠️ BOOKING REQUIREMENTS: (please do not book if you dont meet or do not agree with the requirements) ✔️Minimum age of 25 yo is required to book this unit and be ready to present photo ID when requested. Must attend the trip. ✔️Be one single family living outside Orlando area and visiting parks. ✔️Be kind, clean, and well-organized. ✔️Must carefully read and agree with (1) listing description, (2) house rules and (3) checkout instructions.

Top Guest favourite
A dining area with a rectangular table set for six features simple decor and a centerpiece. A cozy living space is visible with a sofa, chairs, and a TV. Light streams in through large windows, accentuating the open layout and inviting atmosphere.
Townhouse in Osceola County
4.99 out of 5 average rating, 96 reviews

Amazing townhouse near Orlando theme parks

Welcome! This is your place to gather, relax and enjoy, near everything! Orlando theme parks are only between 6 to 20 miles away, and other attractions for all ages and preferences are also nearby. This spacious 4 beds and 2.5 baths home is fully equipped. It is also family friendly, so you will have the basic items for your children's stay. We are sure that you will experience a cozy ambience and that you will enjoy your stay here!

Guest favourite
Townhouse in Kissimmee
4.86 out of 5 average rating, 101 reviews

Disney Area| Private Pool| Resort Waterpark 2956

Minutes from Disney, this spacious 4-bedroom townhome is located in the sought-after Storey Lake Resort. Relax in your private screened pool after a day at the parks and enjoy access to amazing resort amenities including water slides, lazy river, clubhouse, fitness center and kayak rentals. Comfortably sleeps up to 12 guests with a full kitchen, fast WiFi and free parking. Perfect for families visiting Disney and Orlando attractions.

Popular amenities for Osceola County holiday rentals

Destinations to explore

  1. Airbnb
  2. United States
  3. Florida
  4. Osceola County