Top 10 Luxury Airbnbs In Kissimmee, Florida - Updated 2024

Contributing Writer
| 8 min read

Located in Florida’s Osceola County, Kissimmee is just around a 30-minute drive from Orlando. The family-friendly city is favored by travelers because it is near several amusement parks. Tourists can stay in Kissimmee and drive down to Walt Disney World Resort in less than half an hour. You can also explore plenty of scenic spots in Kissimmee. Go fishing at Kissimmee Lakefront Park or plan a family trip to Lake Tohopekaliga. Other must-visit spots include Shingle Creek Regional Park and the city’s entertainment district. During your vacation here, stay in top-notch accommodations in upscale neighborhoods for an overall comfortable experience. Read on below to get acquainted with the top luxury Airbnbs in Kissimmee, Florida.

Great places for a drink in Kissimmee

  • Formosa Winery Tasting House: Offering over 50 international wines on tap, draft beers, and seasonal delicacies, Formosa Winery Tasting House is a great place to spend an afternoon. I’d love to try out one of their bottomless mimosas!

  • Vintage Vino Wine Bar: The Tuscan-themed wine/beer/cheese bar will be a great spot to relax with friends.

We handpicked these listings carefully, considering (wherever possible) Superhost status, recent guest reviews, location, accommodation type, prices, availability of dates, decor, and access to luxury services and amenities. The image galleries get refreshed with the latest updates regularly. They were last updated on July 07, 2024.

More information about booking an Airbnb in Kissimmee

Kissimmee is a popular destination due to its proximity to various theme parks in the area, and the average rate for a single home in the area is about 174 USD, according to reports on Awning.

Take note that the State of Florida is currently moving regulations against short-term rentals. So keep yourself updated on the regulations in order to have a hassle-free vacation.

Our top picks for luxury Airbnbs in Kissimmee

1. Elegant Airbnb with themed rooms (from USD 265)

Best for: Families with little children

Located in the beautiful Terra Verde Resort, this seven-bedroom home is undoubtedly one of the top Airbnbs in Kissimmee. The accommodation is a great choice for a group of friends on a vacation or families visiting with children. It has a Marvel-themed games room with an air hockey table, a pool table, and a TV that will keep you entertained for hours. I might not even leave the home at all with these many recreational amenities available! Other rooms have a Minion theme, a Mickey Mouse theme, and a Star Wars theme.

You can relax in the covered pool or on the patio, both of which offer views of the lake.

Luxury amenities to indulge in: Heated private pool, game room, themed bedrooms, private hot tub, luxurious decor

More information from the hosts, Luis & Tati:

  • Beaches: Cocoa Beach; Playalinda Beach
  • Theme Parks: Busch Gardens; LEGOLAND Florida Resort

What guests loved about this luxury Airbnb:

“Perfect place to stay with a larger group. The kids loved the theme rooms and really enjoyed the pool. The location was perfect for Disney and our competition at wide world sports. The owners were great and responded to us within minutes. Would highly recommend!!!” - by Kim (Sugar Grove, Illinois)

“We went as a family trip to celebrate my son’s 6th birthday. Everyone fell in love with the house especially the “Game Room” and theme bedrooms.” - by Carolina (New Jersey, United States)

Stayed at this property?
Kissimmee, Florida, United States
4.0 km (2.5 mi) from Congo River Golf
151 reviews   Wifi Available
ENTIRE HOME 9 Beds 16 Guests 7 Bedrooms 4 Bathrooms

Accommodates: 16

Top guest reviews
Amenities & Room:
the beds were very comfortable and the view was perfect
good rental with a great view from the pool
the heated pool and full game room kept the children constantly entertained
the view from the pool was awesome
kids absolutely enjoyed sleeping in all the themed rooms
very clean quiet & comfortable environment
very clean welcoming and beautifully decorated
the place was clean
our stay was awesome the house is gorgeous clean and the community was extremely peaceful
looks just like the pictures and it was very clean
the owners did a wonderful job including everything we could use
the owners were prompt in their responses to any inquiries and their assistance was greatly appreciated
the owners were prompt in their responses to any inquiries and their assistance was greatly appreciated
it was all very easy and the hosts were easy to get ahold of and very responsive
the house is beautiful location is perfect
beautiful kitchen and great location
fantastic place and a fantastic location
i love the walk in closets
omgggg i love love love you guys (website hidden by airbnb) beautiful and fairly close to everything
Read more reviews

2. Harry Potter-themed mansion (from USD 153)

Best for: Harry Potter fans

This holiday home is located within a short distance from The Wizarding World of Harry Potter. It’s the perfect accommodation for fans of the series. With an enchanted Hogwarts theme, this Airbnb with a pool features a living room with a number of books that will make you feel like you’re in the magical dormitory. A number of board games and a wooden chess board await you at this Airbnb vacation home, too.

Each of its rooms has been designed to mimic the colors of the four Hogwarts Houses, so it’s up to you to decide where you belong. I feel like it will be a great place to bring the kids.

Luxury amenities to indulge in: Swimming pool, Nintendo Switch, covered patio, hot tub

More information from the Superhosts, Alex and Sofi:

  • Food Scene: El Tenampa Mexican Restaurant (authentic Mexican food at great prices); Lakeside Bar + Grill (excellent waffles and Eggs Benedict)
  • Sightseeing: Shingle Creek Regional Park (offers kayak/canoe/paddle board rentals)

What guests loved about this luxury Airbnb:

“This Air B&B was perfect for out family. My kids loved the decorations and had a blast with the Harry Potter robes and wands. The pool was perfect.” - by Cassi

“Amazing home for any Harry Potter fan! My family thoroughly enjoyed the home and the pool/hot tub is a big bonus and a great way to relax after a long day at the parks.” - by Nick (Magnolia, Texas)

Stayed at this property?
Kissimmee, Florida, United States
4.43 km (2.8 mi) from Congo River Golf
443 reviews   Superhost Wifi Available
Entire villa 8 Beds 12 Guests 5 Bedrooms 3 Bathrooms

Accommodates: 12

Top guest reviews
Amenities & Room:
we do wish there would have been a closet or space for a ‘cupboard under the stairs’ room
if you are a potter fan
as a big harry potter fan i loved staying here
the house slept six of us with room to spare so sleeping 10 would be easy
nicely decorated and decent communication until the a/c wasn't working
however i recommend buying your own cleaning supplies to clean up common area places
the place was clean
house was very clean
when we arrived the house was clean and stocked with all the necessities
very clean and spacious plenty of room for a big family to be comfortable
the host was amazing and always responded to our questions
everything was awesome the hosts were great with communicating
hosts are extremely gracious and responsive
we had a fantastic stay here the hosts were very attentive and super easy to reach
they were very communicative before and throughout our stay to ensure everything was smooth
what a great place to get away
otherwise this place is very cool and convenient for a large family
a great place for potter heads
Read more reviews

3. Spacious home close to major attractions (from USD 247)

Best for: Big families

Staying at this property allows you to be close to Florida’s world-famous attractions. Major points of interest, such as Disney World, SeaWorld Orlando, Universal Studios, ESPN Wide World of Sports Complex, and various shops and restaurants, are within easy reach from here.

This six-bedroom rental is ideal for a big family visiting Kissimmee. A dedicated workspace and Wi-Fi are available here, making this suitable for travelers who want to catch up with work during their vacation. To relax, take a dip in the pool or unwind in the spacious living room. I might just prefer to soak in the pool all day. In the backyard, you can find a spa pool, as well. You will also have access to a communal fitness center, pool, and sports facilities.

Luxury amenities to indulge in: Private pool with optional heating, free starter kit, free high-speed Wi-Fi, access to clubhouse with lazy river, splash pad, water slides, fitness center, basketball and sand volleyball court, tiki bar, ice cream shop, kayaking, and mini golf

What guests loved about this luxury Airbnb:

“We stay here for a multi-family Disney trip and couldn’t have been happier. We comfortably fit 4 couples and 2 kids and the house didn’t feel crowded or uncomfortable. The kids absolutely loved the pool, which was super warm/comfortable after we paid for pool heat in February.” - by Brittany

“We used the clubhouse and had a lot of fun there with the mini golf and community pool and just hanging out alongside the kayak area. The only downside was the bar line was always very very long.” - by Alex (Sioux Falls, South Dakota)

Stayed at this property?
Kissimmee, Florida, United States
847 meters (0.6 ft) from Congo River Golf
58 reviews   Superhost Wifi Available
ENTIRE HOME 6 Beds 12 Guests 6 Bedrooms 6 Bathrooms

Accommodates: 12

Top guest reviews
very nice clean modern house
everything was clean and sparkling
everything is clean and communication is very good
what more can you ask for from a host??thank you glasstone
i would recommend this place for sure just to keep in mind all aspects of consideration
Read more reviews

4. Private abode with cinema (from USD 600)

Best for: Group getaways

This luxury home is located near The Loop, which means you are never too far away from shopping, dining, and entertainment options. This Airbnb vacation home features 9 bedrooms, majority of which have a queen-sized bed, ideal for up to 20 guests. Enjoy mesmerizing views of the sunset from many parts of this holiday home, including the swimming pool with a hot tub. The accommodation also has its own cinema and games room. I’m already planning a movie night here!

Private entrance to the property ensures the safety of guests at all times. For added convenience, the driveway can fit up to seven cars.

Luxury amenities to indulge in: Private heated pool, pool toys, access to clubhouse with gym and pool, hot tub, game room, theater room

What guests loved about this luxury Airbnb:

“Amazing home with tons of space. We had a group of 8 people and everyone had their own room. Location within the community was right next to the clubhouse with a huge side yard of grass to use. Pool and outdoor area was great to hangout at as well. And WOW the movie theater was better than expected! Great picture and even better sound. House had everything you need and more. ” - by Zander (Fort Lauderdale, Florida)

“The theater room was better than going to the movies! The sound system in there was top of the line. The game room was a nice touch and was a lot of fun. The pool and hot tub were very refreshing and used all the time.” - by Thomas (Evesham Township, New Jersey)

Stayed at this property?
Kissimmee, Florida, United States
2.57 km (1.6 mi) from Congo River Golf
103 reviews   Superhost Wifi Available
ENTIRE HOME 12 Beds 16 Guests 9 Bedrooms 9 Bathrooms

Accommodates: 16

Top guest reviews
Amenities & Room:
* kids and adults loved watching movies in the theater room
* was a treat to watch the super bowl on the massive tv in the family area
this house is perfect clean and the privacy for all rooms
very clean and layout of the house was very open and functional
* sparkling clean when we checked in made us feel immediately comfortable and safe
great house clean and great for our large group we would definitely stay again
we had a wonderful time with our family and the place was sparkling clean
amazing home amazing hosts
elaine & jorge were great hosts
they were quick responders very kind and over all amazing
elaine & jorge are amazing hosts the house was beautiful and just as expected
great full patio the host was very responsive and the house was fully loaded coming back again
highlights:* location within the estate is fabulous so private with the amazing wetlands outlook
this place was a wonderful place to stay at
Read more reviews

5. Cozy home for 16 (from USD 326)

Best for: Friends’ getaways

Surrounded by greenery and a tranquil atmosphere, this rental is a great holiday home for up to 16 people. The availability of a travel cot, children’s books and toys, a high chair, window guards, and board games make this property a great choice for those traveling with kids. Aside from six bedrooms, it has a full kitchen with a big island, a spacious living room, and a pool table.

Additionally, staying in this home meal you will have full access to the community clubhouse, gym, swimming pool, and hot tub. Take a leisurely stroll within Sonoma Resort at Tapestry, which has several artificial lakes, as well.

Luxury amenities to indulge in: Private pool, hot tub, 24-hour gatekeeper, access to a clubhouse with shared pool, hot tub, and waterfalls, themed children’s room, home theater room, gourmet kitchen

More information from the Superhost, Bruna:

  • Drinks and Nightlife: Bahama Breeze (good music and family dining spot); Disney Springs (great food and drinks and even a show by Cirque Du Soleil)
  • Parks & Nature: Moss Park (boating and jet skiing spot)

What guests loved about this luxury Airbnb:

“Beautiful home. Enjoyed the space for large family gathering. Pool and game room were especially nice for our grandkids. Peaceful neighborhood. Bruna was very responsive to any of our needs.” - by JoAnn

Stayed at this property?
Kissimmee, Florida, United States
2.83 km (1.8 mi) from Congo River Golf
91 reviews   Wifi Available
ENTIRE HOME 10 Beds 16 Guests 6 Bedrooms 6 Bathrooms

Accommodates: 16

Top guest reviews
Amenities & Room:
house is very comfortable with lots of space for guest
nice theater room on the second floor instead of an open loft area
the game room is a bonus to keep everyone entertained
if you want a beautiful home with a lot of space and a beautiful pool
very clean and plenty of space
house was super clean nice and big
great house well kept and clean
the house was sparkling clean and very well equipped for our stay
the house was more beautiful than expected and really clean
she is an excellent host
host is very responsive and helpful
bruna was a great host and was quick with communicating
bruna the host was very nice and responded quickly to any concerns
bruna is a great host very responsive and helpful
the location is great and close to all shopping and parks
the house and location are fantastic only 20 min from airport shopping malls everywhere (just 5 min drive)
it was perfect for our family trip to disney about 20 mins away from park
this was a great place to stay new house with all features like the pool and jacuzzi
our stay at bruna’s place was excellent beautiful house and so nicely decorated
Read more reviews

6. Tastefully decorated abode

Best for: Staycations

Located in the charming Sonoma Resort, this vacation rental is a short drive from Disney Park and other points of interest in Orlando. The games room in this accommodation features a foosball table, a large wall-mounted TV, playing cards, and arcade basketball, making it a great spot for hanging out with friends.

Another spot guests can unwind in is the patio, which features comfortable sofas, sun loungers, and a heated swimming pool.

Luxury amenities to indulge in: Games room, heated swimming pool, stunning designs, chic decor, stylish furnishings

Stayed at this property?
Kissimmee, Florida, United States
3.09 km (2.0 mi) from Congo River Golf
65 reviews   Wifi Available
ENTIRE HOME 12 Beds 16 Guests 7 Bedrooms 6 Bathrooms

Accommodates: 16

Top guest reviews
Amenities & Room:
3 families (13 in total) had the most comfortable luxurious experience in this villa
there was tons of room and so many useful amenities
it has great amenities and a fantastic kitchen for family meal times and big tvs for cinema nights
the property is clean with great amenities such the pool grill and gym in the community
we enjoyed the large open space and the outdoor area including the pool
otherwise very clean inside
it was clean and updated
the house was really clean
great place very comfortable and spacious and clean
it’s decorated beautifully and very clean
maintenance staff were kind and responsive
check-in was easy and the host was responsive when contacted
great location as well
beautiful spacious villa in an ideal location
this is a beautiful house close to the disney theme parks
Read more reviews

7. Gorgeous 13-bedroom sanctuary by the lake

Best for: Get-togethers and pool vacations

This luxury Airbnb in Kissimmee ensures a memorable vacation in Florida. Featuring 13 bedrooms and 10 bathrooms, this holiday home is spacious enough to accommodate up to 16 guests very comfortably. Go for a stroll by the lakeside or just read a book by the pool. Surrounding the pool are lots of sun loungers.

A well-equipped kitchen, a hot tub, and a gym are some other amenities here that will ensure that you have a comfortable and pampered holiday.

Luxury amenities to indulge in: Large pool, gym, hot tub, lakefront location

Stayed at this property?

2.99 km (1.9 mi) from Congo River Golf
34 reviews   Wifi Available
Entire villa 15 Beds 16 Guests 13 Bedrooms 10 Bathrooms

Accommodates: 16

Top guest reviews
Amenities & Room:
the huge island in the kitchen was amazing for entertaining
the rooms are beautiful and huge
so nice and clean love every second
the unit was clean and organized
the place is beautiful everything was clean and tidy just as promised
this place is so spacious clean and beautiful it was such a pain free experience checking in and out
romelia was a great host and responded quickly to any questions or concerns
very friendly host and very reasonable and responsive
romelia was a great host and the house is able to accommodate a very large group
Read more reviews

8. Large property with private pool

Best for: Families with children

This property is located just minutes from Walt Disney World Resort and various attractions. However, just staying inside this house already guarantees a memorable vacation. This 12-bedroom mansion can comfortably sleep up to 16 individuals. They can relax in the private pool, bond in the games room, which comes with a gaming console and a pool table, or share stories in the spacious living room.

The home also features indoor and outdoor dining tables. Barbecue facilities are available on site should you wish to have a cook-out.

Luxury amenities to indulge in: Games room, pool table, private pool, spa whirlpool, chic furnishings, themed bedrooms

Stayed at this property?
Kissimmee, Florida, United States
4.13 km (2.6 mi) from Congo River Golf
43 reviews   Wifi Available
Entire house 18 Beds 16 Guests 12 Bedrooms 11 Bathrooms

Accommodates: 16

9. Stylish vacation home for families

Best for: Family getaways

Luxury defines this stylish property. This rental is located within Storey Lake Resort, and you’ll have full access to the large swimming pool, a nine-hole mini-golf course, a kids’ splash park, a lazy river, and waterslides.

The home itself is perfect for families. One of the six bedrooms has a Toy Story theme, while another room has a Frozen theme, making this property a great choice for travelers with kids. Another highlight of this holiday home is the Star Wars-themed games room. When it’s time for movie night, head to the Mickey Mouse-themed cinema.

Luxury amenities to indulge in: Resort amenities including a swimming pool, nine-hole mini-golf course, splash park, splash park, and waterslides, themed bedrooms, movie room

Stayed at this property?

599 meters (0.4 ft) from Congo River Golf
36 reviews   Wifi Available
ENTIRE HOME 9 Beds 13 Guests 6 Bedrooms 6 Bathrooms

Accommodates: 13

Top guest reviews
Amenities & Room:
the theater room was amazing and our grandkids enjoyed the game room
Read more reviews

10. Contemporary getaway with patio

Best for: Large families

This five-bedroom vacation rental with state-of-the-art furnishings and upscale interiors will make your holiday in Kissimmee unforgettable. Make a meal for yourself and your family in the fully equipped kitchen with modern appliances. There, you’ll find a refrigerator, a microwave, dishes and silverware, a dishwasher, a stove, an oven, a coffee maker and deluxe stainless-steel appliances.

The large living room, which has a flat-screen TV, leads to the patio and pool area. A game room with an arcade is also available for guests’ enjoyment.

Luxury amenities to indulge in: Pool, game room with arcades, themed bedrooms

Stayed at this property?

800 meters (0.5 ft) from Congo River Golf
47 reviews   Wifi Available
ENTIRE HOME 7 Beds 12 Guests 5 Bedrooms 5 Bathrooms

Accommodates: 12

Top guest reviews
Amenities & Room:
excellent place with amazing amenities the pool is beautiful and the grill was outstanding
everything was great except the wifi was not good at all
lovely decor lots of space screened and heated pool and jacuzzi
great communication very clean and great location
the house was beautiful and clean
very clean and had everything we needed during our stay
the place was really nice & modern looking and very clean
the house was beautiful and clean
dennis was an awesome host
dennis was very responsive and answered any questions i had
the host would respond quickly so that’s always good
the location was perfect
location is excellent and neighborhood is nice
this house is in a great location
it’s a great place for your next vacation
Read more reviews

Spend a memorable vacation in Kissimmee

The close proximity of Kissimmee to Orlando makes the city a perfect starting point for those who want to explore the area. Plus, it also has upscale communities with luxurious homes. For the best of both worlds, book one of the top luxury Airbnbs in Kissimmee, Florida, now.

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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