Top 9 Vacation Rentals In Osceola County, Florida - Updated 2024

| 5 min read

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 May 21, 2024.

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.

Stayed at this property?
Saint Cloud, Florida, United States
803 reviews   Superhost Wifi Available
Treehouse 1 Bed 2 Guests 1 Bedroom 1 Bathroom

Accommodates: 2

Top guest reviews
Amenities & Room:
the hurricane fan that's up in the corner was perfect for white noise and air movement while sleeping
simple breakfast tea coffee and sweet treats were provided and wonderful touches throughout the tree house
the bed is comfortable the view is gorgeous and the peace is invaluable
the treehouse has amazing & adorable amenities from the shower to the kitchen
with two shower heads and very plush towels the bathroom amenities were quite lovely
all new and clean and comfy
it was incredibly clean
the smell was so fresh when we walked in everything was so clean
it was extremely beautiful and clean
the building is special and also very clean with everything we needed for our stay
rick was an amazing host
rick was so kind and helpful
when you arrive expect outstanding hospitality from the hosts
karen and rick were fantastic hosts to my fiance and i
they are great hosts beautiful scene from the treehouse
there is also publix close by and other great local restaurants
karen and rick's place is so unique and beautifully built it made for a wonderful get away
the treehouse is definitely a unique place
we will definitely be back and i recommend this place 1000%
i will definitely recommend this place
Read more reviews

2. Homey Private room in guest suite (from USD 54)

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.

Stayed at this property?
Kissimmee, Florida, United States
487 reviews   Superhost Wifi Available
Private room in guest suite 1 Bed 2 Guests 1 Bedroom 1 Bathroom

Accommodates: 2

Top guest reviews
Amenities & Room:
the amenities and extras in the room are amazing
immaculate space with thoughtful touches like usb port outlets hair dryer fluffy towels and extra blankets
a/c worked excellent and we loved the pool
wonderful accommodations and amenities (pool and private entrance)
a remote for the ac/heat was provided as was complimentary wifi
very clean and comfortable
good communication and clean
everything was clean and organized
clean quiet & convenient
clean and easy private access
sherry was an amazing host
fantastic space and friendly host
sweeties host you will even meet
great place and great host
they are great hosts with a wonderful place
in a great location
very comfortable and close to stores and restaurants
wow such a cute place perfect for our quick trip to universal
i get the best rest here and close to everything without being in the middle of everything
such a cute and comfortable place to stay
Read more reviews

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.

Stayed at this property?
Kissimmee, Florida, United States
383 reviews   Superhost Wifi Available
Treehouse 1 Bed 2 Guests 1 Bathroom

Accommodates: 2

Top guest reviews
Amenities & Room:
amazing view and very cozy
photos don't due it justice it's even more beautiful in person super cozy and quiet
the fan kept the bugs away
shower/bathroom was nice and roomy
very clean everything is as advertised
very clean and very unique
everything was super clean and was very accommodating
super clean quaint and very unique experience
very clean and nice touches throughout
host was kind and quick to respond to any questions
we loved the treehouse and wish we had longer to enjoy it hosts were very timely with communication
close to restaurants and entertainment
amazing and very cute place
close to parks restaurants and adventures
great place to get away for a few days
we really enjoyed this calm and unique place
Read more reviews

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.

Stayed at this property?
St. Cloud, Florida, United States
392 reviews   Superhost Wifi Available
ENTIRE RENTAL UNIT 1 Bed 2 Guests 1 Bedroom 1 Bathroom

Accommodates: 2

Top guest reviews
Amenities & Room:
we took home many great photos of kayaking at sunset and breakfast at sunrise
the bed was soothingly comfortable all in all this place was amazing so beautiful and cozy
very beautiful and a true cozy and homey feel
super clean and very cute
the place was super clean with very thoughtful touches
everything is clean beautiful and modern we will definitely be coming again
the place is private clean stylish and its nice and quiet
the place was so cozy and clean
the hosts are super sweet
the best hosts you can ask for
cheryl is an outstanding host she even kept me company out by the lake to watch the sunset
they were gracious hosts and there if we needed anything
value and wonderful hosts thank you
awesome location convenient to the airport
what a cute newly newly renovated place
tucked back in a quiet lane along a lake is this cute quaint stylish little get away
a perfect place to "unplug" but still feel right at home
the location was perfect for a quit get away to unplug and unwind
Read more reviews

5. Bright and cozy Disney condo (from USD 65)

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.

Stayed at this property?
Kissimmee, Florida, United States
180 reviews   Superhost Wifi Available
ENTIRE CONDO 2 Beds 6 Guests 2 Bedrooms 2 Bathrooms

Accommodates: 6

Top guest reviews
Amenities & Room:
nice pools and many shops nearby
appreciated the fast wi-fi
the beds were good and she also had some streaming apps included on the tv which was awesome
functional is a better word then cozy
the house is cozy with good common space
everything was very clean and organized
large spacious and clean property
nice place clean and quiet
pool area clean and kid friendly condo was clean and beds were large
accommodations were spacious and everything was very clean
lily was a perfect host and on top of things with communication
they were kind to let us do a late check out
lily was a great host with fast responses the apartment was spacious and a great location for me
lily and her father are very friendly and they reply fast
the people in the complex were friendly and the pool was nice
excellent located for the parks
we love its excellent location very close to shopping stores and easy access to everywhere
everything very organized great location quiet neighborhood
very good location and easy to access the property
awesome place and so close to the parks
Read more reviews

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.

Stayed at this property?
147 reviews   Wifi Available
condo 6 Guests 2 Bedrooms 2 Bathrooms

Accommodates: 6
Minimum Nights: 6
Refund Policy : 100% refund if you cancel at least 14 days before check-in.

Top guest reviews
Amenities & Room:
we had a wonderful 7 nights stay in this apartment
clean and well maintained property
nicely decorated and exceptionally clean
this condo is always clean & well stocked with towels bedding dishes & cooking pots & pans
it was safe clean comfortable well-stocked and beautifully decorated
pool area was very nice to and very clean
the owners are great to work with
the location is excellent
good 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 perfect
perfect location if you're going to disney world
great location for local restaurants and the disney parks
Read more reviews
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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.

Stayed at this property?
Kissimmee , FL, US
40 reviews  
villa 10 Guests 5 Bedrooms 3 Bathrooms
Top guest reviews
Amenities & Room:
the pool was perfect - nicely heated for the little ones
easy wifi access comfortable rooms and eat instruction manual that answered all other questions
my families stay was so much more comfortable and enjoyable because of it
this property was awesome we were 5 adults and 5 kids it was spaciuos with enough room for everyone
everything was clean and very nice
the property was clean and comfortable
it had plenty of space and the house was clean and well maintained
upon arrival at this villa the overall appearance was neat and clean
the home was clean and well maintained and we did not expereience a single issue during our stay
betina and annette were very helpful in the many questions i had
i had a chance to meet the owners and they ere very friendly
the owner was 100% correct and very gentle
friendly gate people
even the guard at the gate was very helpful in giving directions to the many different attractions
the location was great - so close to shopping and eating
very good location close to restaurants and dinner shows
all very accessible and easy to get to from the location
perfect for big family great location would recommend to everyone vacationing with 6 or more people
also we visited several attractions in the area all very close to the villa -- easy
Read more reviews
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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.

Stayed at this property?
Kissimmee, FL, US
villa 8 Guests 3 Bedrooms 2 Bathrooms
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9. Charming four-bedroom villa with private pool (from USD 147)

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.

Stayed at this property?
143 reviews   Wifi Available
villa 8 Guests 4 Bedrooms 3 Bathrooms

Accommodates: 8
Minimum Nights: 4
Refund Policy : 100% refund if you cancel at least 60 days before check-in.

Top guest reviews
Amenities & Room:
turtles and even 2 deer on the other side of the lake
Luckily just 6 of us so didnt need to use that room
The landscaping round the villa and the view across the lake to the trees
they loved having a bedroom and a bathroom
2 tables one was for 6 people the other for 4 2 sofas would seat 5 adults
It was clean and very well
We found it very clean and tidy
It is clean and well maintained with everything catered for The pool area
The house was clean and has everything you need
(we paid for pool heat)
quiet cool Maintained company said it was maximum temp that the owner allowed
each They were very happy with the WiFi
Denise was very prompt in replying to any questions I had
We saw lots of wildlife - birds squirrels
The owners were so easy to work with and quickly answered any questions we had
The location is great for shopping theme parks and restaurants
It is only a few minutes drive from the 192 but so peaceful
New en suite shower area is great addition
Lake Berkeley is a very quiet gated community
Very nice house and a good location
Read more reviews
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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.

Any must-sees we missed? Tell us about them in the comments section or write a post here to help out fellow travelers!
Disclosure: Trip101 selects the listings in our articles independently. Some of the listings in this article contain affiliate links.


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Klariza is a freelance writer driven by wanderlust and a passion for food. She also spends her spare time reading books to explore the unknown, seeking refreshments, and gaining a more stable life...Read more

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