Osceola County, located in the central portion of Florida, is a place where you can experience nature and life through wonderful Florida activities. The county seat of Osceola, Kissimmee is a family-oriented area where you can enjoy playgrounds and explore walking paths. Some of the most popular attractions in the area are Walt Disney World Resort, Universal Orlando Resort, and SeaWorld Orlando, which you can enjoy once you visit Osceola. Also, activities like biking and golfing are possible because of the trails and golf courses located here. Shopping might also interest you as you can visit The Loop, a large outdoor shopping mall. If you plan on booking a vacation at Osceola County, you’re thinking right. Check out top vacation rentals in Osceola County, Florida, here.
We handpicked these listings carefully, considering (wherever possible) Superhost status, recent guest reviews, location, accommodation type, prices, availability of dates, decor, and amenities. The image galleries get refreshed with the latest updates regularly. They were last updated on October 25, 2024.
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1. Comfortable treehouse in Saint Cloud (from USD 165)
Looking for a perfect getaway from your busy everyday life? Karen and Rick’s Treehouse is one at the top of the list. Located in Saint Cloud, Florida, it is equipped with a bedroom, a full bathroom, a kitchenette, and a wrap-around deck. The kitchenette here is fitted with an air cook as well as an electric frying pan that you can use to make meals here during your stay. This accommodation can sleep up to six people. Moreover, amazing bird-watching and horseback riding opportunities are found here.
Top guest reviews
Host:
rick was an amazing hostrick was so kind and helpfulwhen you arrive expect outstanding hospitality from the hostskaren and rick were fantastic hosts to my fiance and ithey are great hosts beautiful scene from the treehouseLocation:
there is also publix close by and other great local restaurantskaren and rick's place is so unique and beautifully built it made for a wonderful get awaythe treehouse is definitely a unique placewe will definitely be back and i recommend this place 1000%i will definitely recommend this placeCleanliness:
all new and clean and comfyit was incredibly cleanthe smell was so fresh when we walked in everything was so cleanit was extremely beautiful and cleanthe building is special and also very clean with everything we needed for our stayRead more reviewsAmenities & Room:
the hurricane fan that's up in the corner was perfect for white noise and air movement while sleepingsimple breakfast tea coffee and sweet treats were provided and wonderful touches throughout the tree housethe bed is comfortable the view is gorgeous and the peace is invaluablethe treehouse has amazing & adorable amenities from the shower to the kitchenwith two shower heads and very plush towels the bathroom amenities were quite lovely
Superhost
2. Homey Private room in guest suite (from USD 63)
Situated at Kissimmee, Florida you will find this cozy private room rental, your home away from home. It offers a queen-sized bed, TV with Netflix, a 24/7 Pool, security cameras at the front door and driveway, free parking spaces, and other essential amenities. It is also a home for three sweet Shih Tzus and two sweet cats that are eager to meet you. Additionally, romance packages done by event planners are available here as well. It is also 40 minutes away from Walt Disney World and other popular attractions in Orlando. The rental is conveniently located, so it’s perfect for those who want to experience the sights and sounds in Central Florida.
Top guest reviews
Host:
sherry was an amazing hostfantastic space and friendly hostsweeties host you will even meetgreat place and great hostthey are great hosts with a wonderful placeLocation:
in a great locationvery comfortable and close to stores and restaurantswow such a cute place perfect for our quick trip to universali get the best rest here and close to everything without being in the middle of everythingsuch a cute and comfortable place to stayCleanliness:
very clean and comfortablegood communication and cleaneverything was clean and organizedclean quiet & convenientclean and easy private accessRead more reviewsAmenities & Room:
the amenities and extras in the room are amazingimmaculate space with thoughtful touches like usb port outlets hair dryer fluffy towels and extra blanketsa/c worked excellent and we loved the poolwonderful accommodations and amenities (pool and private entrance)a remote for the ac/heat was provided as was complimentary wifi
3. Charming treehouse in the woods (from USD 143)
This treehouse is made for people who want some much-needed time to relax. It’s a great place to escape to if you want to get away from the hustle and bustle of the city. A great feature of this place is that all amenities are comparable to those of a first-class hotel. It includes a double bed, TV, air conditioning and heating system, Wi-Fi and a kitchenette. Equipped with a barbecue grill and a balcony, and with a remarkable view of the woods, this treehouse is impressive both inside and out.
Top guest reviews
Host:
host was kind and quick to respond to any questionswe loved the treehouse and wish we had longer to enjoy it hosts were very timely with communicationLocation:
close to restaurants and entertainmentamazing and very cute placeclose to parks restaurants and adventuresgreat place to get away for a few dayswe really enjoyed this calm and unique placeCleanliness:
very clean everything is as advertisedvery clean and very uniqueeverything was super clean and was very accommodatingsuper clean quaint and very unique experiencevery clean and nice touches throughoutRead more reviewsAmenities & Room:
amazing view and very cozyphotos don't due it justice it's even more beautiful in person super cozy and quietthe fan kept the bugs awayshower/bathroom was nice and roomy
4. Gorgeous lakefront apartment (from USD 75)
This cozy, secluded lakefront apartment is located on a quiet private road within walking distance of a public park, boat dock, and well-kept beach. At this newly renovated property, guests have access to one bedroom, a kitchenette, bathroom, and private lanai. A grill, Wi-Fi, cable TV, and a workstation are also made available for use. Furthermore, guests have free access to kayaks and canoes which can be launched directly from the property’s private canal. From the shore of a 12,000-acre lake, guests can enjoy breathtaking sunsets and incredible views of wildlife in their natural habitat.
Top guest reviews
Host:
the hosts are super sweetthe best hosts you can ask forcheryl is an outstanding host she even kept me company out by the lake to watch the sunsetthey were gracious hosts and there if we needed anythingvalue and wonderful hosts thank youLocation:
awesome location convenient to the airportwhat a cute newly newly renovated placetucked back in a quiet lane along a lake is this cute quaint stylish little get awaya perfect place to "unplug" but still feel right at homethe location was perfect for a quit get away to unplug and unwindCleanliness:
super clean and very cutethe place was super clean with very thoughtful toucheseverything is clean beautiful and modern we will definitely be coming againthe place is private clean stylish and its nice and quietthe place was so cozy and cleanRead more reviewsAmenities & Room:
we took home many great photos of kayaking at sunset and breakfast at sunrisethe bed was soothingly comfortable all in all this place was amazing so beautiful and cozyvery beautiful and a true cozy and homey feel
5. Bright and cozy Disney condo (from USD 73)
This spacious two-bedroom condo, located just fifteen minutes from Disney, is ideal for both family vacations and long-term rentals. Providing first-rate amenities which particularly include a comfortable queen-sized bed, Wi-Fi, gym access, and hot tub and pool access, this 1,000-square-foot (92-square-meter) gated community is undoubtedly a must-visit. It is also remarked with very comfortable, clean room and highly accommodating owner. Aside from that, with Shingle Creek Regional Park right next door, guests can enjoy the beauty of nature right in their own backyard.
Top guest reviews
Host:
lily was a perfect host and on top of things with communicationthey were kind to let us do a late check outlily was a great host with fast responses the apartment was spacious and a great location for melily and her father are very friendly and they reply fastthe people in the complex were friendly and the pool was niceLocation:
excellent located for the parkswe love its excellent location very close to shopping stores and easy access to everywhereeverything very organized great location quiet neighborhoodvery good location and easy to access the propertyawesome place and so close to the parksCleanliness:
everything was very clean and organizedlarge spacious and clean propertynice place clean and quietpool area clean and kid friendly condo was clean and beds were largeaccommodations were spacious and everything was very cleanRead more reviewsAmenities & Room:
nice pools and many shops nearbyappreciated the fast wi-fithe beds were good and she also had some streaming apps included on the tv which was awesomefunctional is a better word then cozythe house is cozy with good common space
6. Luxury condo in Cane Island resort (from USD 87)
Cane Island Resort is a well-designed place for vacations. Guests are welcomed here with a beautiful view of palm trees and flowers. The place has a clubhouse where a pool table, foosball, video games, and a kitchen with a 3,200-square-foot (297-square-meter) lounge with a large plasma TV are freely accessible for use. It also has a high-definition television located in the main living room, granite countertops in the kitchen and bathrooms, as well as double sinks in both bathrooms. All of the furniture, linens, artwork, and accessories were combined to create a beautiful visual experience. The master bedroom has a king-sized bed with a bronze canopy and a wide walk-in closet. Plus, it provides toys for the kids to play with. Lastly, there is a lovely balcony with a table and four chairs where you can lounge.
Top guest reviews
Host:
the owners are great to work withLocation:
the location is excellentgood location for visiting disney (about 15 minutes away depending on traffic and which park)it was close to the places we wanted to go and the price was perfectperfect location if you're going to disney worldgreat location for local restaurants and the disney parksCleanliness:
clean and well maintained propertynicely decorated and exceptionally cleanthis condo is always clean & well stocked with towels bedding dishes & cooking pots & pansit was safe clean comfortable well-stocked and beautifully decoratedpool area was very nice to and very cleanRead more reviewsAmenities & Room:
we had a wonderful 7 nights stay in this apartment
7. Five-bedroom apartment with pool (from USD 130)
This place is ideal for those who want to spend their vacation in the sun. It is a five-bedroom unit that can accommodate up to 10 persons. Guests here also have access to a pool and a games room. Remarkably, the resort is situated near 3 lakes and features a nature trail that circles a 14-acre natural lake with plenty of baby ducks to feed, a private beach with a barbecue area, and a picturesque gazebo that is perfect for weddings.
Top guest reviews
Host:
betina and annette were very helpful in the many questions i hadi had a chance to meet the owners and they ere very friendlythe owner was 100% correct and very gentlefriendly gate peopleeven the guard at the gate was very helpful in giving directions to the many different attractionsLocation:
the location was great - so close to shopping and eatingvery good location close to restaurants and dinner showsall very accessible and easy to get to from the locationperfect for big family great location would recommend to everyone vacationing with 6 or more peoplealso we visited several attractions in the area all very close to the villa -- easyCleanliness:
everything was clean and very nicethe property was clean and comfortableit had plenty of space and the house was clean and well maintainedupon arrival at this villa the overall appearance was neat and cleanthe home was clean and well maintained and we did not expereience a single issue during our stayRead more reviewsAmenities & Room:
the pool was perfect - nicely heated for the little oneseasy wifi access comfortable rooms and eat instruction manual that answered all other questionsmy families stay was so much more comfortable and enjoyable because of itthis property was awesome we were 5 adults and 5 kids it was spaciuos with enough room for everyone
8. Lake view villa with private pool (from USD 88)
The villa can comfortably accommodate up to eight people as it is large and spacious. It has three bedrooms, two bathrooms (one of which is master-en-suite), and its own Grecian-style, screened and heated pool, which is available for an additional fee depending on the season. Moreover, it is well-positioned as it is close to various great locations. It is only about 10 minutes away from Orlando International Airport and 25 minutes away from Disneyworld.
9. Charming four-bedroom villa with private pool (from USD 202)
This villa is a single-story building with four bedrooms and three bathrooms, and it can house up to eight persons. It also has its own private pool and spa. Guests are provided with plenty of amenities including a tennis court, a pool heating service, a formal dining area, a breakfast bar, a fully equipped kitchen, and an HD TV to name some. Moreover, it is furnished with first-class furniture, adding to the luxurious feel and comforts that will make your stay in Florida a memorable one.
Top guest reviews
Host:
quiet cool Maintained company said it was maximum temp that the owner allowedeach They were very happy with the WiFiDenise was very prompt in replying to any questions I hadWe saw lots of wildlife - birds squirrelsThe owners were so easy to work with and quickly answered any questions we hadLocation:
The location is great for shopping theme parks and restaurantsIt is only a few minutes drive from the 192 but so peacefulNew en suite shower area is great additionLake Berkeley is a very quiet gated communityVery nice house and a good locationCleanliness:
It was clean and very wellWe found it very clean and tidyIt is clean and well maintained with everything catered for The pool areaThe house was clean and has everything you need(we paid for pool heat)Read more reviewsAmenities & Room:
turtles and even 2 deer on the other side of the lakeLuckily just 6 of us so didnt need to use that roomThe landscaping round the villa and the view across the lake to the treesthey loved having a bedroom and a bathroom2 tables one was for 6 people the other for 4 2 sofas would seat 5 adults
10. Cozy unit, complete with amenities (from USD 100)
This is a three-bedroom unit that can accommodate six people is well-situated near Disney. It has a 6,000-square-foot (557-square-meter) clubhouse with a gym, video arcade space, and pool tables. The property also provides access to a community pool and spa, a beach area with hammocks, a children’s playground with a mini rock wall, and a fully stocked fishing lake. Inside the unit, a fully equipped kitchen is provided on the ground floor. The first floor houses the master bedroom with a queen bed, while another queen bedroom is located on the second floor. On the third floor, there is a bedroom fitted with two twin beds. All of the necessities for a perfect vacation are offered in this place.
Top guest reviews
Host:
the security gate and front desk staff are super friendly and helpfulstaff at the property was forthcoming and helpfulgreat host greal location great valueLocation:
from the house we reached all parks we visited within 20-30 minutes so the location is perfectCleanliness:
condo looked and smelled clean upon arrivalit was clean and comfortablegreat property in a nice and clean resortit was clean and stocked with mostly everything you needclean and carefully furnished houseRead more reviewsAmenities & Room:
the other issue was the ceiling fan in the master bedroombesides these few issues we had a very comfortable stay
Enjoy and experience nature in Osceola County
There are a lot of things you can enjoy in Osceola for free. Here, you can visit attractions like Kissimmee Lakefront Park, the Main Gate Flea Market, Old Town, and many more. Get this chance to relax and enjoy life at the same time. Make your trip more memorable by choosing a great accommodation for your stay.
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