Kissimmee Vacation Rentals

(222 rentals)
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Kissimmee House
5 BR | 4 BA | Sleeps 10 | Quick View
Sleeps 10, 5 bedrooms, 4 bathrooms
10 reviews

$165

avg/night

$165
avg per night
View Details

Key Amenities

  • Air conditioning
  • Hot tub
  • Private pool
  • WiFi

About this property

Welcome to our stunning spacious 5 bedroom, 4 bath home located in the much sought after community of Tuscan Hills near DisneyThis beautiful home offers 2 masters en-suite bedrooms and 3 sitting rooms.Full air con and hi-speed WiFi throughout.The villa uniquely has 3 sitting rooms, two of ...

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Property Type

Kissimmee House

Featured review

"Beautiful house for our family of 7"

This house was supplied with everything to make us comfortable and even had games and toys to enjoy. There was a pool table, pacman machine and foosball machine in the garage which everyone enjoyed playing. ...

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Kissimmee House
8 BR | 5 BA | Sleeps 16 | Quick View
Sleeps 16, 8 bedrooms, 5 bathrooms
7 reviews

Distance to park: 6 miles to Disney world

$286

avg/night

$286
avg per night
View Details

Key Amenities

  • Air conditioning
  • Hot tub
  • Pet friendly
  • Private pool
  • Rentals by owner
  • WiFi

About this property

Welcome to our luxury finished 3600 Sq ft pool home at beautiful Crystal Cove Resort. It is conveniently located close to shopping and dining (less than 1 mile away). Disney is only 6 miles away. Just minutes from major attractions like Sea World, Universal Studios, Aquatica and the Convention Center ...

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Property Type

Kissimmee House

Featured review

"Pleasant Stay in Crystal Cove"

Large and spacious home in Kissimmee. Close to many attractions and restaurants. Bedrooms, kitchen and bathrooms. Pleasant and easy to maintain for extended stay. Washer and Dryer on site make vacation ...

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Kissimmee Townhome
4 BR | 3 BA | Sleeps 8 | Quick View
Sleeps 8, 4 bedrooms, 3 bathrooms
3 reviews

Distance to park: 6 miles to Disney,Seworld

$128

avg/night

$128
avg per night
View Details

Key Amenities

  • Air conditioning
  • Hot tub
  • Pet friendly
  • Pool
  • Rentals by owner
  • WiFi

About this property

Welcome to the beautiful Coral Cay Resort. It is one of the most popular resort destinations in the Kissimmee/Orlando area for its proximity to theme parks and other major attractions. Situated 6 miles from Disney,1 mile to Walmart and target, 8 miles to Seaworld and Convention Center.This 1500 ...

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Property Type

Kissimmee Townhome

Featured review

"Wonderful location"

Very nice home, close to Disney and shopping places. Very quiet friendly neighborhood. Def will be booking again in the future

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Kissimmee Condo
4 BR | 3 BA | Sleeps 8 | Quick View
Sleeps 8, 4 bedrooms, 3 bathrooms
8 reviews

Distance to park: 2 miles to Disney’s Animal Kingdom Park

$125

avg/night

$125
avg per night
View Details

Key Amenities

  • Air conditioning
  • Hot tub
  • Pool
  • WiFi

About this property

Welcome to the Sun Lake Resort. We have 4 identical 1650 sqft units with 4 bedrooms and 3 bathrooms. The beautiful condo faces to sun lake and it has a spacious screened patio. It only takes 1 minute walk to a plaza for shopping and restaurants which is very convenient! More importantly, you are only ...

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Property Type

Kissimmee Condo

Featured review

"Awesome stay"

Beautiful resort and room was great. Great location and staff was very helpful. Would highly recommend this property.

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Kissimmee House
5 BR | 5.5 BA | Sleeps 13 | Quick View
Sleeps 13, 5 bedrooms, 5.5 bathrooms
4 reviews

Distance to park: 12 miles to Disney's Magic Kingdom Park

$359

avg/night

$359
avg per night
View Details

Key Amenities

  • Air conditioning
  • Private pool
  • Rentals by owner
  • WiFi

About this property

Welcome to Westside Villa! -20 minute drive to all Disney Parks -Private, heated pool; gas grill; EV charger on-site -Modern arcade: racing simulators, virtual reality, vintage games -3 king size suites with smart TVs -2 uniquely themed bunk rooms (Star Wars and Fairy Tale) -All bedrooms have ensuite ...

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Property Type

Kissimmee House

Featured review

"Amazing"

The house was simply amazing. The family could not believe what I had rented when we arrived, so spacious. So many things games/entertainment in the house. The house was very clean, the beds were really ...

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Kissimmee Villa
5 BR | 3 BA | Sleeps 10 | Quick View
Sleeps 10, 5 bedrooms, 3 bathrooms
8 reviews

$160

avg/night

$160
avg per night
View Details

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

Your villa is located on the gated 5 Star Lake Berkley Resort in Kissimmee. 5 Beds, 3 Bath home that is beautifully furnished throughout (Big TV/Games Room/Heated Pool/Free Internet). Our villa is furnished to a very high standard and being all one level is ideal for one or two families. The villa ...

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Property Type

Kissimmee Villa

Featured review

"Lake Berkley Villa"

We have rented from this agent multiple times and are always beyond pleased. Each home we have rented were great and the location is perfect. Any communications before, during and after have always been ...

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Kissimmee Condo
3 BR | 2 BA | Sleeps 8 | Quick View
Sleeps 8, 3 bedrooms, 2 bathrooms

Distance to park: 3 miles to Disney World

$129

avg/night

$129
avg per night
View Details

Key Amenities

  • Air conditioning
  • Hot tub
  • Pool
  • WiFi

About this property

Welcome to Surrounded in Magic! Please check your spam for any quotes.For current 2025 availability, see calendar in photos: Email us for a quote.Kids of all ages will love this magical, bright and spacious Disney & Universal Studios themed (1400 sq ft), 3-bedroom, 2-bath, 1st floor condo. ...

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Property Type

Kissimmee Condo

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Kissimmee Villa
3 BR | 2 BA | Sleeps 6 | Quick View
Sleeps 6, 3 bedrooms, 2 bathrooms
5 reviews

$150

avg/night

$150
avg per night
View Details

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

Luxury Screened-In, Lake Front, Private Pool Home! This amazing 3 bedroom, 2 bathroom, Disney Area Vacation Rental Home is located in the family-friendly residential community of Eagle Pointe. Just a few short miles from Orlando's World-Renowned Theme Parks including the Walt Disney World Resort, ...

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Property Type

Kissimmee Villa

Featured review

"soaring eagle lane"

tidy villa nice views our small lake ducks will come up to be fed nice size pool overall good villa games room in garage

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Kissimmee Villa
7 BR | 4.5 BA | Sleeps 14 | Quick View
Sleeps 14, 7 bedrooms, 4.5 bathrooms
16 reviews

$161

avg/night

$161
avg per night
View Details

Key Amenities

  • Air conditioning
  • Pet friendly
  • Private pool
  • Rentals by owner
  • WiFi

About this property

This luxury villa is perfectly located on the exclusive Emerald Island Resort community less than 3 miles from Walt Disney World, Florida. The property has 7 bedrooms two of which are master bedrooms with en suite bathrooms and a further two and a half bathrooms.This stunning elegant and spacious ...

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Property Type

Kissimmee Villa

Featured review

"Great stay"

Great stay at this villa in Emerald Island, location is perfect for all the parks as well as going to the beaches. Katrina was very responsive12 in our party, 4 of which were children, the property ...

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Kissimmee Villa
4 BR | 3 BA | Sleeps 8 | Quick View
Sleeps 8, 4 bedrooms, 3 bathrooms

$120

avg/night

$120
avg per night
View Details

Key Amenities

  • Air conditioning
  • Hot tub
  • Private pool
  • WiFi

About this property

his unique 4-bedroom, 3-bathroom luxury Town home is situated on the new community of Tuscan Hills. Tuscan Hills is a new secure gated community, with extensive oak landscaping, located in Davenport on highway 27, close to highway 192, and only minutes from interstate 4.The town house is on over two ...

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Property Type

Kissimmee Villa

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Kissimmee House
7 BR | 4 BA | Sleeps 14 | Quick View
Sleeps 14, 7 bedrooms, 4 bathrooms

Key Amenities

  • Air conditioning
  • Pool
  • WiFi

About this property

This 7 bedroom/4½ bathroom private house features a huge 10' x 40' covered lanai, with ceiling fans, extra patio furniture and a large flatscreen TV (accessed only by Netflix/Hulu, etc). Nice pool area in general. Interior furnishings are nice (certainly not spectacular). This is ...

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Kissimmee House

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Kissimmee Villa
4 BR | 4 BA | Sleeps 8 | Quick View
Sleeps 8, 4 bedrooms, 4 bathrooms
3 reviews

$155

avg/night

$155
avg per night
View Details

Key Amenities

  • Air conditioning
  • Hot tub
  • Private pool
  • WiFi

About this property

4 Bedroom villa with 4 ensuite bathrooms.This exquisite villa is an ideal destination for a family holiday, offering a prime location.Situated within walking distance of the resort clubhouse and pool.Hi speed WiFi and air con throughout the villa.Set against a backdrop of serene ...

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Property Type

Kissimmee Villa

Featured review

"Great villa"

Recently had a family vacation it was an amazing villa. Clean and great location close to everything. Will definitely rent again.

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Kissimmee House
6 BR | 5 BA | Sleeps 13 | Quick View
Sleeps 13, 6 bedrooms, 5 bathrooms
3 reviews

$286

avg/night

$286
avg per night
View Details

About this property

Spacious 6 bed, 5 bath, sleeps thirteen Fully screened South facing pool with relaxing spa Formal, informal and outside dining options Upstairs TV lounge with a further two living areas downstairs Pool table in the games room Located on gated resort of Solterra with excellent amenities

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Property Type

Kissimmee House

Featured review

"Loved it.."

We had a wonderful time can't wait to visit again. I believe the kids favorite part was the pool. They did not want to leave..

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Kissimmee Villa
4 BR | 2 BA | Sleeps 8 | Quick View
Sleeps 8, 4 bedrooms, 2 bathrooms
1 review

$155

avg/night

$155
avg per night
View Details

Key Amenities

  • Air conditioning
  • Pet friendly
  • Private pool
  • WiFi

About this property

Luxury villa right on lake edge. South facing poolNestled in the heart of Kissimmee, this large 4 bedroom lake front Villa is the perfect blend of relaxation, adventure, and convenience for an unforgettable getaway. Upon entering, guests are greeted with stunning views of the tranquil lake, setting ...

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Property Type

Kissimmee Villa

Featured review

"Very nice villa"

We had a lovely vacation at this very nice villa. It has everything you would need. Clean and modern, We will book again. David and family

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Kissimmee House
5 BR | 4 BA | Sleeps 10 | Quick View
Sleeps 10, 5 bedrooms, 4 bathrooms

Distance to park: 6 miles to Disney World

$236

avg/night

$236
avg per night
View Details

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

This beautiful 5 bedroom house is located in Crystal cove gated community. Perfect vacation home for families with small children or large groups. This vacation villa offers a sunny private pool, relaxing spa overlooking the lake. There are 2 master suites, private pool, community pool / gym. Pool ...

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Property Type

Kissimmee House

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Kissimmee House
8 BR | 5 BA | Sleeps 16 | Quick View
Sleeps 16, 8 bedrooms, 5 bathrooms
5 reviews

Distance to park: 6 miles to Disney world

$254

avg/night

$254
avg per night
View Details

Key Amenities

  • Air conditioning
  • Hot tub
  • Pet friendly
  • Private pool
  • Rentals by owner
  • WiFi

About this property

Welcome to our brand new luxury finished 3600 Sqft pool home at beautiful Crystal Cove Resort. It is conveniently located close to shopping and dining (less than 1 mile away). Disney is only 6 miles away. Just minutes from major attractions like Sea World, Universal Studios, Aquatica and the Convention ...

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Property Type

Kissimmee House

Featured review

"Very good! Great Location!"

Really enjoyed our stay. Convenient location, spacious house, very clean. Close to Disney parks, grocery stores, restaurants, etc. We'd like to stay again for our next trip.

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Kissimmee Villa
4 BR | 2 BA | Sleeps 8 | Quick View
Sleeps 8, 4 bedrooms, 2 bathrooms
6 reviews

$155

avg/night

$155
avg per night
View Details

Key Amenities

  • Air conditioning
  • Hot tub
  • Private pool
  • WiFi

About this property

Lake front property with stunning sunsets.Newly renovated this spacious home has been completely refurbished as the perfect rental getaway for families seeking a modern villa.Nestled alongside a picturesque lake, this property features a generous pool surrounded by ample deck space, offering the ...

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Property Type

Kissimmee Villa

Featured review

"Very nice house"

We had an amazing stay at this very nice house. Everything was perfect. We enjoyed the pool very much. House is in great loaction. Hope we can stay again in couple of years. Pam

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Kissimmee House
3 BR | 2 BA | Sleeps 8 | Quick View
Sleeps 8, 3 bedrooms, 2 bathrooms
3 reviews

$130

avg/night

$130
avg per night
View Details

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

This beautiful home is a 3-bedroom, 2-bathroom with its own private screened pool. The home is located in Lindfields; a peaceful subdivision situated approximately 10 minutes from the Walt Disney World entrance and is conveniently located for the other attractions. It is an ideal location with easy access ...

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Property Type

Kissimmee House

Featured review

"Perfect location"

This well maintained villa was in the perfect location, close enough to the parks that it didn’t take long to get there but far enough away for it to be tranquil. We had a great view from our pool & the ...

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Kissimmee Villa
4 BR | 3 BA | Sleeps 8 | Quick View
Sleeps 8, 4 bedrooms, 3 bathrooms
17 reviews

$130

avg/night

$130
avg per night
View Details

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

A stunning, larger than average 4 Bed 3 Bathroom villa.There are 2 sitting rooms both with lots of comfortable seating. Both rooms have large screen TVs, ideal for when the adults want to watch the latest sports programme whilst the kids enjoy the latest Disney film. Netflix subscription is also included ...

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Property Type

Kissimmee Villa

Featured review

"Highly recommend this villa"

We have just returned home after spending two great weeks at this amazing villa.It was spacious,spotlessly clean, with very comfortable beds and all the amenities you need for a relaxing, enjoyable holiday. The ...

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Kissimmee House
10 BR | 7 BA | Sleeps 20 | Quick View
Sleeps 20, 10 bedrooms, 7 bathrooms

Key Amenities

  • Air conditioning
  • Hot tub
  • Private pool
  • WiFi

About this property

Exciting NEW 10 bedroom family vacation home Offering privacy and space for everyone 4300 square feet of awesomeness 2 separate large living areas Relaxing pool with spa Covered outdoor dining and seating Games loft with pool table and foosball Windsor Island Resort offers a wide variety of world ...

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Property Type

Kissimmee House

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Kissimmee House
8 BR | 6 BA | Sleeps 18 | Quick View
Sleeps 18, 8 bedrooms, 6 bathrooms

Key Amenities

  • Air conditioning
  • Rentals by owner
  • WiFi

About this property

Windsor at Westside Resort features a large 10,000 sq.ft. clubhouse which includes a resort-style pool, lazy river, water slide, & hot tub. Other amenities include a gym, beach volleyball, cabana rentals, basketball court, game room, tiki bar and concierge desk.Location is great with a Kissimmee ...

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Kissimmee House

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Kissimmee Villa
5 BR | 3 BA | Sleeps 10 | Quick View
Sleeps 10, 5 bedrooms, 3 bathrooms

$187

avg/night

$187
avg per night
View Details

Key Amenities

  • Air conditioning
  • Private pool
  • Rentals by owner
  • WiFi

About this property

Spacious open plan 5 bedroom, 3 bathroom, 2 seating areas, fully air conditioned villa with own private enclosed oversize 30 foot heated pool which over looks one of the tranquil lake within the scenic and safe family environment of the gated community of Lake Berkley Resort Kissimmee, Florida.This ...

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Property Type

Kissimmee Villa

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Kissimmee Vacation Rentals

Kissimmee Weather

F° | C°

7222°  489°
JANUARY
7323°  499°
FEBRUARY
7725°  5312°
MARCH
8228°  5814°
APRIL
8731°  6418°
MAY
9032°  7021°
JUNE
9233°  7222°
JULY
9233°  7222°
AUGUST
9032°  7122°
SEPTEMBER
8429°  6518°
OCTOBER
7926°  5714°
NOVEMBER
7323°  5010°
DECEMBER

Soak up the Sun on Your Next Trip to Kissimmee Vacation Rentals


There’s nothing quite like a vacation to sunny Florida, a unique and inviting state with a huge variety of distinctive cities and natural areas to explore. One popular vacation destination in Florida is Kissimmee, a charming city with plenty to see and do just south of the Orlando metropolitan area. 

Kissimmee has a lot more to offer visitors than just excellent weather year-round. With a huge variety of scenic nature, shopping opportunities, and outdoor activities, Kissimmee itself has lots to offer every member of the family, not to mention its extremely close proximity to some of Orlando’s biggest amusement parks. 

You could stay in a busy hotel during your trip to Kissimmee, but then you wouldn’t be able to get a truly immersive experience of local city life. Kissimmee vacation rentals allow you to enjoy Kissimmee from inside its authentic residential neighborhoods. Additionally, having your own home to live in rather than a jam-packed hotel will provide some much-needed peace and quiet during your vacation. It will also offer plenty of space for the whole family to spread out.  

Top Tips for Traveling to Kissimmee Rentals


Like most other Florida cities, Kissimmee enjoys sunshine and clear skies throughout the majority of the year. However, the tropical climate of the state means that bouts of rain can occur throughout the seasons, particularly during the summer months, peaking in August. 

In addition to a higher likelihood of rain, the summer season in Kissimmee tends to be the most humid time of year. That’s why most vacationers choose mid to late spring or early autumn to make their trip to the city. At those times of the year, vacationers can enjoy great weather and lots of outdoor activities. 

Though the Kissimmee Gateway Airport is located centrally within the city, most vacationers taking commercial flights will fly into Orlando International Airport. It is located roughly 17 miles northeast of the city center, about halfway between Kissimmee and Orlando. Vacationers coming in from elsewhere in Florida can access Kissimmee by road using U.S. Route 192 and U.S. Route 441.

Things to Do Nearby Kissimmee House Rentals


Some of the most popular natural areas around Kissimmee are the swamps, which are located in major local bodies of water like Lake Tohopekaliga (known around town as Lake Toho). At Boggy Creek Airboat Adventures, you can experience the swamps from the water and get the thrill of a lifetime on an airboat driven by a local wetlands expert. Get up-close views of gator ponds, discover precious gemstones, and then grab a delicious lunch with the family at Boggy Bottom BBQ! 

Looking to explore a piece of history during your trip to Kissimmee? Medieval Times Dinner & Tournament allows visitors to step into the 11th century for an evening of authentic feasting, jousting, and sword fighting in true medieval style! Enjoy a delicious four-course meal, incredible performances, and a truly unforgettable experience for the entire family.
 
Any vacation to Kissimmee isn’t complete without a trip or two to Old Town, a popular outdoor attraction with opportunities for shopping, dining, and family fun. Old Town is made up of an 18-acre stretch of classic city attractions, including the Old Town Ferris Wheel, the Great Magic Hall, and Mortem Manor, a year-round haunted house that is open for visitors to explore.

Kissimmee Annual Events


Kissimmee is a vibrant area with lots of annual festivals and events to enjoy in and around the city throughout the year. Kissimmee locals and visitors alike flock to the Ford Cuban Sandwich Festival each May near downtown Kissimmee, which celebrates the colorful history of Cuban cuisine in the area. Watch as local dining professionals attempt to build the world’s biggest Cuban sandwich during the event!
 
The Ford Taste of Latino Festival is another local opportunity to celebrate and experience the best in authentic Latin cuisines in Kissimmee. The event features a contest to find the Top Latino Chef as well as plenty of live music and dance performances to enjoy as you taste a variety of Latin dishes. 

Not sure if you’ll be in town for any of Kissimmee’s larger annual events? You can enjoy Show Car Saturday Nights every Saturday night in the city on Margaritaville Boulevard. Check out the city’s best classic cars from a variety of eras and enjoy the plethora of delicious eateries and exciting shops located along the boulevard.

Wining and Dining in Kissimmee  


Between your outdoor activities and trips to local amusement parks while in Kissimmee, you’re sure to need some satisfying food and refreshing drinks to complete your perfect day. Luckily, Kissimmee is home to some of the best restaurants that Florida has to offer, combining authentic local flavors with worldly cuisine. 

To start your day off right with a delicious and hearty breakfast, look no further than Woodsby’s Countryside Café. This spot has authentic, cozy diner vibes to spare, not to mention a stacked menu of classic breakfast favorites, coffee bar items, and unique dishes you won’t want to miss out on. 

Tarantino’s Italian Restaurant is a great choice for a vacation date night or simply a nice dinner out with the family. A hearty Italian meal is a great way to finish a fun day of activities, and you’re sure to get that and more at Tarantino’s. If you bring the family along, you can take advantage of the takeout dinner special, which feeds four and includes a massive entrée, salad, and garlic bread.


FAQ

How many vacation rentals are there in/around Kissimmee?

There are 222 Kissimmee vacation rentals available on FloridaRentals.com. From villa rentals to house rentals and beyond, find a unique vacation rental for you to enjoy a memorable vacation in Florida.

How much does it cost to rent a vacation rental in Kissimmee?

There are vacation rentals available in Kissimmee for as low as $57 per night with an average price per night of $173.

Can I rent a house in Kissimmee?

Yes, you can find house rentals in Kissimmee close to Lakefront Park, Monument of States, and Old Town. Don't forget to stop in to Shingle Creek Park or the nearby theme parks!

Do any vacation rentals in Kissimmee have a pool?

Yes, there are 173 vacation rentals in Kissimmee with a pool on FloridaRentals.com. Search using our filters and book one for your next vacation!