Kissimmee Vacation Rentals

(236 rentals)
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Kissimmee House
7 BR | 4.5 BA | Sleeps 14 | Quick View
Sleeps 14, 7 bedrooms, 4.5 bathrooms

$454

avg/night

$454
avg per night
View Details

Key Amenities

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

About this property

Perfect Family Destination Best lania/pool Minutes to Disney/Attractions/Conveniences Fun/Clean/Comfortable This is a fantastic house for family getaways! Enjoy the Food and Wine Festivals. Mickey's Not So Scary Halloween Party, Unforgettable Disney Christmas celebration, and everything else ...

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Property Type

Kissimmee House

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

$156

avg/night

$156
avg per night
View Details

Key Amenities

  • Air conditioning
  • Hot tub
  • Private pool
  • WiFi

About this property

MAGIC HOUSE, is a beautifully furnished 4 bedrooms, 3 bathrooms home with a 26ft x 14ft swimming pool and Spa,. covered lanai. It is only a 3 mile drive to Walt Disney World Resort. It's in easy reach of all other major attractions. MAGIC HOUSE is a luxury villa located in the quiet friendly neighborhood ...

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Property Type

Kissimmee House

Featured review

"Fun Time with Family"

Home was nice and neat when we arrived. Roomy and close to grocery stores and other shopping areas. Will visit again and recommend to others.

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Kissimmee House
9 BR | 5 BA | Sleeps 22 | Quick View
Sleeps 22, 9 bedrooms, 5 bathrooms
1 review

$266

avg/night

$266
avg per night
View Details

Key Amenities

  • Air conditioning
  • Hot tub
  • Private pool
  • WiFi

About this property

Brand new, very spacious, modern 9-Bed 5-Bath pool home in an exclusive, private gated golf resort. You'll love the feeling of luxury and space throughout the house, the 2 King en-suite master bedrooms, 4 kids themed bedrooms, 3 additional King bedrooms, the games room, the private pool and spa, ...

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Property Type

Kissimmee House

Featured review

"Florida Holiday"

Hi there! We enjoyed our stay quite a bit. However, there were a few things that could have improved our stay. The one lounger was damaged and the one chair was damaged. There was not a bottle opener ...

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Kissimmee Villa
3 BR | 3.5 BA | Sleeps 6 | Quick View
Sleeps 6, 3 bedrooms, 3.5 bathrooms

Distance to park: 4 miles to Disney

$236

avg/night

$236
avg per night
View Details

Key Amenities

  • Air conditioning
  • Hot tub
  • Private pool
  • WiFi

About this property

Welcome to Magic Village Views, part of Trademark Collection by Wyndham. "Boutique style 3BDR very spacious Town house, ideally located in Magic Village community……right next to Disney’s parks like Magic Kingdom. All Units have unique furnishings, complete kitchens with gas range, ...

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Property Type

Kissimmee Villa

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Kissimmee House
4 BR | 2 BA | Sleeps 8 | Quick View
Sleeps 8, 4 bedrooms, 2 bathrooms

$119

avg/night

$119
avg per night
View Details

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

Whether you are looking for a place to relax and unwind, or a place to call home while you are making memories and enjoying fun-filled days at Orlando's many attractions, you will want to bring your entire family to Indiana J's Attraction! This spacious, newly refurbished and decorated home ...

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Property Type

Kissimmee House

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

Distance to park: 4 miles to Disney World

$155

avg/night

$155
avg per night
View Details

Key Amenities

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

About this property

Welcome to La Casita on the Island (The Little House on the Island) "Our house, our casita" If you want a place to relax and enjoy the beautiful weather of Florida, I invite you to see the "encanto" (charm) that you can experience during your stay at La Casita on the Island. Enjoy ...

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Property Type

Kissimmee House

Featured review

"Great Villa"

Had a fantastic stay in the villa. Would definitely stay again and highly recommend. It was extremely clean and in a great location near shops, resturaunts and 192 and Disney. Would highly recommend and ...

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Kissimmee House
15 BR | 16 BA | Sleeps 33 | Quick View
Sleeps 33, 15 bedrooms, 16 bathrooms

$330

avg/night

$330
avg per night
View Details

Key Amenities

  • Air conditioning
  • Hot tub
  • Private pool
  • WiFi

About this property

The whole crew will love the swimming pool. It has a spill-over jacuzzi hot tub and a spacious sundeck with lounge chairs. After a swim, why not enjoy a poolside BBQ meal? There's space for 12 guest to dine al fresco. Bring out your inner Gordon Ramsey while cooking on your private grill! Had ...

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Property Type

Kissimmee House

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

Distance to park: 4 miles to Disney

$215

avg/night

$215
avg per night
View Details

Key Amenities

  • Air conditioning
  • Hot tub
  • Private pool
  • WiFi

About this property

You will love it here in our Boutique styled Condos featuring contemporary interiors, located in Magic Village gated community only 5 minutes away from Disney’s Animal Kingdom. Step into your private villa and discover a chic and contemporary yet invitingly cozy sanctuary. All three bedrooms are ...

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Property Type

Kissimmee House

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Kissimmee Bungalow
4 BR | 3 BA | Sleeps 9 | Quick View
Sleeps 9, 4 bedrooms, 3 bathrooms
6 reviews

$137

avg/night

$137
avg per night
View Details

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

Luxury Villa near Universal Studios and 12 Minutes from Disney with Large Private Pool, Game Room and Free Wifi. LCD TVs and Game Room in the villa complement the upscale furnishings and large pool included in the villa. There is plenty of space to spread out with 4 bedrooms and 3 bathrooms. Welcome ...

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Property Type

Kissimmee Bungalow

Featured review

"The house was fantastic and a great location."

The house was very easy to find, quiet neighborhood and Walmart was 2 minutes away. The was neat and tidy with all kitchen amenities needed to prepare a home cook meal. The Air conditioner was the best, ...

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

$170

avg/night

$170
avg per night
View Details

Key Amenities

  • Air conditioning
  • Hot tub
  • Private pool
  • WiFi

About this property

Water View and Outdoor Spa! Stay close to just about everything and enjoy easy access to our world-renowned theme parks, exciting golf, mega shopping and exceptional dining. Ideal for your next family vacation, this attractive 4 bedroom, 3 bath Disney area vacation home is conveniently located just ...

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Property Type

Kissimmee Villa

Featured review

"Our Walt Disney World vacation"

The villa was absolutely wonderful as well as the pool and exactly as shown on the site picture. We were in Florida for 10 nights. The company which takes care of the site was also great, they responded ...

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Kissimmee Villa
9 BR | 10 BA | Sleeps 26 | Quick View
Sleeps 26, 9 bedrooms, 10 bathrooms
16 reviews

$965

avg/night

$965
avg per night
View Details

Key Amenities

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

About this property

Imagine a vacation like no other spent in a 9 bedroom, 10 bath custom luxury lakefront pool villa. The Formosa Grand is located in the exclusive gated community of Formosa Gardens Estates and one of the closest communities to Disney (less than 10 minutes!!) No expense was spared in the gorgeous estate ...

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Property Type

Kissimmee Villa

Featured review

"50th birthday celebration"

We booked this for my husbands 50th birthday getaway and it was all we imagined! The place was very spacious and the owner was easy to communicate with. The pool and the outdoor living areas are spectacular. ...

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

Distance to park: 7 miles to Walt Disney World

$208

avg/night

$208
avg per night
View Details

Key Amenities

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

About this property

Welcome to our Florida villa, the Lake House at Sunset Lakes. The Lake House at Sunset Lakes is an upscale rental villa in the greater Orlando Florida area, minutes away from Disney’s Magic Kingdom and theme parks, your choice of fine golf courses and many other attractions. This four bedroom house ...

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Property Type

Kissimmee Villa

Featured review

"Lake house villa"

Lovely villa,spotlessly clean & well equipped,management company are very helpful & quick to respond,Jane the owner was also very helpful & quick to respond to any enquiries we had,great location & the ...

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Kissimmee House
5 BR | 4.5 BA | Sleeps 15 | Quick View
Sleeps 15, 5 bedrooms, 4.5 bathrooms

$238

avg/night

$238
avg per night
View Details

Key Amenities

  • Air conditioning
  • Hot tub
  • Pet friendly
  • Private pool
  • WiFi

About this property

Welcome to our luxurious and spacious vacation home situated in the stunning gated community of Windsor at Westside. This magnificent 5-bedroom, 4.5-bathroom villa boasts everything you need for an unforgettable vacation with your family and friends, Close to theme parks, shopping mall outlets, restaurants ...

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Property Type

Kissimmee House

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Kissimmee Villa
Studio | 4.5 BA | Sleeps 14 | Quick View
Sleeps 14, 0 bedrooms, 4.5 bathrooms

$340

avg/night

$340
avg per night
View Details

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

7 bedroom 4.5 bath waterfront home located in the highly desired Emerald Island resort close to Disney and Universal Studios. The ground floor of this villa is an open concept with a living area featuring a 65" Smart 4k tv. The granite countertop kitchen boasts all new 2022 stainless appliances. ...

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Property Type

Kissimmee Villa

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Kissimmee House
6 BR | 3 BA | Sleeps 14 | Quick View
Sleeps 14, 6 bedrooms, 3 bathrooms
1 review

Distance to park: 5 miles to Disney World

$180

avg/night

$180
avg per night
View Details

Key Amenities

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

About this property

Experience a relaxing & unforgettable vacation in this stunning Tiffany Blue-colored villa, nestled in a peaceful & safe residential neighborhood. Enjoy easy access to theme parks, golf, restaurants, and supermarkets, all just a short drive away. Don't miss out - contact me with any questions! ...

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Property Type

Kissimmee House

Featured review

"Amazing family-friendly home w/ a stunning pool"

Excellent location very close to Disney World. Beautiful and clean home. Host is very welcoming and helpful. The pool is stunning. The pictures do not do it justice. Wish we would have stayed longer!

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Kissimmee Villa
5 BR | 3 BA | Sleeps 12 | Quick View
Sleeps 12, 5 bedrooms, 3 bathrooms
10 reviews

Distance to park: 3 miles to Disney

$185

avg/night

$185
avg per night
View Details

Key Amenities

  • Air conditioning
  • Hot tub
  • Private pool
  • WiFi

About this property

5 bedrooms, 3 bathrooms, sleeps 10 - 12. Spacious, 5 bed, 3 bath, luxury villa with Private Pool, Spa +Games Room (pool, air hockey and football tables) Guests have full use of all facilities of the Prestigious Emerald Island Resort, including Club House with pool, spa & licensed Tiki Hut Bar, ...

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Property Type

Kissimmee Villa

Featured review

"Very Comfortable"

Very comfortable stay! We had a group of 4 adults and 3 kiddos, and each of us enjoyed our stay. House was very clean and well appointed. Owner was a pleasure to deal with, and VERY responsive to our needs. ...

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Kissimmee House
7 BR | 4.5 BA | Sleeps 14 | Quick View
Sleeps 14, 7 bedrooms, 4.5 bathrooms
15 reviews

Distance to park: 3 miles to Disney World Parks

$253

avg/night

$253
avg per night
View Details

Key Amenities

  • Air conditioning
  • Hot tub
  • Private pool
  • WiFi

About this property

This spacious vacation rental home in Orlando is ideal for large families, accommodating up to 14 guests. The property features 7 bedrooms and 4.5 bathrooms, including two King Master Suites—one located on each floor. The first-floor suite includes a walk-in shower and a separate garden tub for ...

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Property Type

Kissimmee House

Featured review

"Were Dreams really come true- AMAZING"

Marisela made our booking experience exceptional. She was very responsive and outstanding hosts. The home is absolutely beautiful and meticulously maintained! It is located in a secure gated community and ...

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Kissimmee House
15 BR | 15 BA | Sleeps 36 | Quick View
Sleeps 36, 15 bedrooms, 15 bathrooms

$1085

avg/night

$1,085
avg per night
View Details

Key Amenities

  • Air conditioning
  • Hot tub
  • Pet friendly
  • Private pool
  • WiFi

About this property

This vacation home isn't just a place to stay; it's your own personal wonderland. Step outside, and you'll be greeted by a backyard oasis that dreams are made of – a sparkling swimming pool with a spillover jacuzzi hot tub and a sun-soaked sundeck, complete with lounging chairs that ...

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Property Type

Kissimmee House

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Kissimmee Townhome
3 BR | 2.5 BA | Sleeps 8 | Quick View
Sleeps 8, 3 bedrooms, 2.5 bathrooms
1 review

$118

avg/night

$118
avg per night
View Details

Key Amenities

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

About this property

You have arrived in the "Vacation Capital of the World" and you're going to love staying in our luxury, 3 bedroom, 2.5 bath, fully equipped vacation townhouse rental situated near DisneyWorld and all other theme park attractions. The property rental is located within the resort community ...

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Property Type

Kissimmee Townhome

Featured review

"Beautiful Condo! Exactly as shown!"

We are a retired couple who stayed for 3 months from Jan to March. Beautiful Condo, exactly as pictured. Furniture is very comfy. Close to all attractions. We felt very safe. Publix and Walmart are ...

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Kissimmee Townhome
4 BR | 3.5 BA | Sleeps 10 | Quick View
Sleeps 10, 4 bedrooms, 3.5 bathrooms
12 reviews

Distance to park: 5 miles to Animal Kingdom

$108

avg/night

$108
avg per night
View Details

Key Amenities

  • Air conditioning
  • Pool
  • Rentals by owner
  • WiFi

About this property

Enjoy Orlando, Florida, home to Disney World, Sea World, Universal Studios, and Islands of Adventure, in style. Our home is within minutes of all the Orlando attractions, golf courses, shopping, and exciting night life. Our richly appointed vacation Townhouse will give you luxurious living and a vacation ...

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Property Type

Kissimmee Townhome

Featured review

"Cozy stay at townhouse"

My wife, son and I stayed for the month of April. The resort property is well maintained. Garbage is picked up daily and each home has a bin right in front of the home. The condo was very clean upon ...

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

Distance to park: 4 miles to Disney

$152

avg/night

$152
avg per night
View Details

Key Amenities

  • Air conditioning
  • Hot tub
  • Private pool
  • WiFi

About this property

Magical Dreams come true in our elegant private 4 bedroom villa, 3 bathroom, all located on one floor, Quiet upgraded comforts of home and luxuries of an exceptionally rated vacation resort/hotel. Newly resurfaced and freshly painted pool and spa is sure to impress. There will be no waiting in line ...

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Property Type

Kissimmee House

Featured review

"Perfect rental for all of our needs!"

This was a Christmas vacation never to be forgotten! We had the time of our lives! My children, grandchildren and I enjoyed the comforts and privacy of a home where we could take in all the theme parks ...

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

Distance to park: 5 miles to Disneyworld and Disney Springs

$98

avg/night

$98
avg per night
View Details

Key Amenities

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

About this property

You have arrived in the "Vacation Capital of the World" and you're going to love staying in our luxury, three bedroom, two bath, fully equipped vacation condo rental situated near DisneyWorld and all other theme park attractions. The property rental is located within the resort community ...

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Property Type

Kissimmee Condo

Featured review

"Holiday season in Kisimmee"

Excellent vacation in Florida Sunsations. Condo is close to main attractions , restaurants and airport. Excellent communication with owner Barry Paulus. Will return next year.

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Kissimmee Villa
4 BR | 3 BA | Sleeps 10 | Quick View
Sleeps 10, 4 bedrooms, 3 bathrooms
2 reviews

$189

avg/night

$189
avg per night
View Details

Key Amenities

  • Air conditioning
  • Hot tub
  • Private pool
  • WiFi

About this property

Our villa is beautifully furnished and airconditioned and has a heated swimming pool and spa for that morning swim and for you family’s personal enjoyment there is a security fence to protect the young ones. A covered lanai on an extended pool deck includes a large table with seating for four plus ...

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Property Type

Kissimmee Villa

Featured review

"Excellent Villa"

Well equiped, excellent location, friendly and helpful estate. The villa was one of the best we have hired over the past 20 years. The gated estate was first class, helpful and friendly clubhouse. Close ...

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

$141

avg/night

$141
avg per night
View Details

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

This Disney Villa is a fully furnished home and is one of the best kept turnkey properties you will find in Indian Creek ! Has an airy open floor plan, lots of light. Enjoy the crystal clear South facing pool and the covered lanai on your sunny and warm Florida holidays. This luxurious private home ...

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Property Type

Kissimmee Villa

Featured review

"Excellent villa"

We have been so pleased with this villa. Very clean, has everything we need and more. Very close to Disney and easy to get to Univerdal Studios and SeaWorld as well as easy commute from the airport. Would ...

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Kissimmee House
3 BR | 3.5 BA | Sleeps 6 | Quick View
Sleeps 6, 3 bedrooms, 3.5 bathrooms

$212

avg/night

$212
avg per night
View Details

Key Amenities

  • Air conditioning
  • Hot tub
  • Pool
  • WiFi

About this property

Luxury vacation homes accommodations feature contemporary interiors, located in Magic Village gated community only 5 minutes away from Disney’s Animal Kingdom. Step into your private villa at Magic Village Yards and discover a chic and contemporary yet invitingly cozy sanctuary. All Bedrooms are ...

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Property Type

Kissimmee House

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Kissimmee House
6 BR | 5.5 BA | Sleeps 18 | Quick View
Sleeps 18, 6 bedrooms, 5.5 bathrooms
58 reviews

Distance to park: 4 miles to Animal Kingdom

$171

avg/night

$171
avg per night
View Details

Key Amenities

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

About this property

Some of the best features of this house from Guest Reviews • Beautiful Vinyl Plank Flooring in all bedrooms, halls and on the steps • Less than a 4-mile drive to Disney World’s Animal Kingdom Theme Park • Two leather couches and a recliner with a total of 5 power reclining seats • ...

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Property Type

Kissimmee House

Featured review

"Spacious, well-appointed house in a great location close to the Disney Parks."

The owner provided very detailed and helpful information regarding the house, the Orlando area and the Disney parks before we arrived. The house was very clean and tidy and all the rooms were as described. ...

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

Distance to park: 12 miles to All Disney Theme Park

$109

avg/night

$109
avg per night
View Details

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

If you will be visiting Orlando Florida for all of the great attractions including Walt Disney World, Universal Studios, Sea World theme parks, and all of the other major attractions? You can stay in our beautifully decorated 3 bedroom private villa, which boasts it's own private pool for less than ...

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Property Type

Kissimmee Villa

Featured review

"New Years Getaway"

Stayed month of January..Villa was very well equipped and very comfortable.Location was fantastic being so close to all attractions. Would highly recommend for anybody to stay..

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Kissimmee House
7 BR | 4.5 BA | Sleeps 14 | Quick View
Sleeps 14, 7 bedrooms, 4.5 bathrooms
1 review

$454

avg/night

$454
avg per night
View Details

Key Amenities

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

About this property

5 star property! Reviews say it all! You will be delighted by the great combination of lux comfort and Disney theming for the whole family! Located in the upscale Emerald Island Resort gated community, our newly remodeled home is a welcome oasis to return to after a long day enjoying the parks. Relax ...

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Property Type

Kissimmee House

Featured review

"Where to even start!!!"

Whenever we travel, I read reviews. Some reviews you wonder about because no two people seem to see it the same way. However with this house everyone seemed to love it and after staying there I can see ...

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Kissimmee House
4 BR | 3 BA | Sleeps 10 | Quick View
Sleeps 10, 4 bedrooms, 3 bathrooms
4 reviews

$164

avg/night

$164
avg per night
View Details

Key Amenities

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

About this property

POOL SAFETY FENCE!!!! - Florida law requires that doors leading out to the pool have an alarm. THAT IS NOT ENOUGH!. If you are traveling with children please make sure the house you are renting has a pool safety fence. WE HAVE A NO PET POLICY FOR ALERGY REASONS This Beautiful home is well situated, ...

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Property Type

Kissimmee House

Featured review

"Florida 2024"

This was a nice peaceful place just didn't like the holes outside screen for the pool n no baking dishes..we like to bake

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Kissimmee Villa
6 BR | 4 BA | Sleeps 12 | Quick View
Sleeps 12, 6 bedrooms, 4 bathrooms
2 reviews

$200

avg/night

$200
avg per night
View Details

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

Beautiful two-story home with 6 bedrooms and 4 bathrooms. This home is situated on a quiet street within the Solterra Resort. It boasts modern open plan living. It has an additional outdoor balcony space along with a large private pool and spa, loungers, outdoor table and chairs with an optional BBQ ...

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Property Type

Kissimmee Villa

Featured review

"Amazing villa"

Totally overwhelmed, villa is amazing, very spacious. Highly recommended. We will book this villa again next family gathering. jim

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

Distance to park: 1 miles to Disney Animal Kingdom

$97

avg/night

$97
avg per night
View Details

Key Amenities

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

About this property

Come and enjoy your vacation in this comfortable condo, right by Disney. Yes Enjoy Three large screen TV's, DVD and free Wi-FI. Yes Beautiful/alluring condo, 1 mile from Disney world and minutes from other attractions, Such as sea world and Universal studio. In Celebration area Florida. Walking ...

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Property Type

Kissimmee Condo

Featured review

"Great location, clean and comfortable."

We had everything we needed. Excellent communication. Perfect location. Close to the parks as well as restaurants, etc! We will be back.Thanks

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Kissimmee House
6 BR | 5.5 BA | Sleeps 13 | Quick View
Sleeps 13, 6 bedrooms, 5.5 bathrooms

$364

avg/night

$364
avg per night
View Details

Key Amenities

  • Air conditioning
  • Hot tub
  • Private pool
  • WiFi

About this property

Newly renovated and professionally decorated with upscale furnishings, this luxury family vacation home is an ideal get-away to relax with family and friends following visits to busy theme parks and area attractions. As a large private manor, located on a quiet cul-de-sac, Emerald Escape is a modern ...

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Property Type

Kissimmee House

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Kissimmee House
12 BR | 11 BA | Sleeps 26 | Quick View
Sleeps 26, 12 bedrooms, 11 bathrooms

$390

avg/night

$390
avg per night
View Details

Key Amenities

  • Air conditioning
  • Hot tub
  • Pet friendly
  • Private pool
  • WiFi

About this property

From the minute you pull through the gated entry you will be lost in your dream vacation. Located at the beautiful Veranda Palms Resort, this 26 guest capacity vacation home has everything you could possibly need for a fantastic stay. Let's start with the gorgeous sundeck patio at the back of ...

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Property Type

Kissimmee House

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Kissimmee House
12 BR | 11.5 BA | Sleeps 24 | Quick View
Sleeps 24, 12 bedrooms, 11.5 bathrooms

$530

avg/night

$530
avg per night
View Details

Key Amenities

  • Air conditioning
  • Hot tub
  • Pet friendly
  • Private pool
  • WiFi

About this property

Nestled over at the Bella Vida Resort, just a measly 5 miles away from the magical kingdom of Walt Disney World (yeah, we're basically neighbors!), this 12 bedroom mansion is big enough to host 24 of your favourite people. Let's kick things off with the amazing back deck. Picture this: a ...

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Property Type

Kissimmee House

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Kissimmee House
4 BR | 3 BA | Sleeps 10 | Quick View
Sleeps 10, 4 bedrooms, 3 bathrooms

$197

avg/night

$197
avg per night
View Details

Key Amenities

  • Air conditioning
  • Pet friendly
  • Private pool
  • WiFi

About this property

Charming brand new 4 br, 3 bath townhouse with pool. Located in the desirable Storey Lake Resort, in the new quiet Preserve Area, It has capacity for 12 guests. Storey Lake has a resort-style clubhouse full of amenities and fun for families, including a business center, basketball court, ping pong table, ...

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Property Type

Kissimmee House

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Kissimmee House
5 BR | 5 BA | Sleeps 12 | Quick View
Sleeps 12, 5 bedrooms, 5 bathrooms
2 reviews

$394

avg/night

$394
avg per night
View Details

Key Amenities

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

About this property

Booking is available from the website in Owner info. Modern architecture, state-of-the-art furnishings, and hip-to-the-minute décor make this 5 bedroom, 5 bath getaway in Storey Lake a bonafide safe haven for luxury and comfort. This home is brimming with amenities, from an action-packed game ...

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Property Type

Kissimmee House

Featured review

"Great place, nice price!"

The themed kids' rooms and game room are topping on this rental a club house with so much going on for everyone, including pickup/drop off service to and from the club house. Heated pool and gas grill. ...

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Kissimmee Apartment
1 BR | 1 BA | Sleeps 3 | Quick View
Sleeps 3, 1 bedroom, 1 bathroom

$91

avg/night

$91
avg per night
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Key Amenities

  • Air conditioning
  • Pool
  • Rentals by owner
  • WiFi

About this property

A newly constructed one-bedroom, one-bathroom luxury apartment situated in the charming area of Kissimmee, conveniently located from theme parks, attractions, restaurants, and shopping. This upscale apartment is equipped with all the amenities to ensure comfort, security, and an exceptional experience ...

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Property Type

Kissimmee Apartment

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Kissimmee House
6 BR | 4 BA | Sleeps 14 | Quick View
Sleeps 14, 6 bedrooms, 4 bathrooms
3 reviews

$352

avg/night

$352
avg per night
View Details

Key Amenities

  • Private pool
  • Rentals by owner
  • WiFi

About this property

Welcome to your ultimate themed vacation experience in the heart of Kissimmee, Florida! Prepare to embark on an extraordinary journey as you step into this spectacular 6-bedroom, 4-bathroom house in the prestigious Windsor Hills community. This newly listed paradise has been meticulously designed to immerse ...

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Property Type

Kissimmee House

Featured review

"Two week stay"

We stayed for two weeks in August/September. Great house and location to the parks. Kids enjoyed the pool table and game systems. Would book again.

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Kissimmee House
4 BR | 2.5 BA | Sleeps 9 | Quick View
Sleeps 9, 4 bedrooms, 2.5 bathrooms
10 reviews

Distance to park: 10 miles to Disneyworld

$138

avg/night

$138
avg per night
View Details

Key Amenities

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

About this property

Our villa is modern style furnished, has everything you would expect in a holiday home, 4 bedrooms, 2 with king-size beds, 1 with single bed´s, 1 with triple bunk bed all with private TV. 2 bathrooms, 1 guest toilet, fully equipped kitchen, etc. with ceran stove, fridge, oven, microwave, coffee ...

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Property Type

Kissimmee House

Featured review

"Looking for a great vacation rental for the kids? This is it!!"

What a nice house! It has everything you could want in a vacation home. A very nice pool, patio and attached BBQ area with gas grill, literally a ton of DVD's to keep everyone entertained in the evening, ...

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Kissimmee Villa
7 BR | 6 BA | Sleeps 14 | Quick View
Sleeps 14, 7 bedrooms, 6 bathrooms
4 reviews

$347

avg/night

$347
avg per night
View Details

Key Amenities

  • Air conditioning
  • Hot tub
  • Private pool
  • WiFi

About this property

Introducing 101 Happy Memories Florida Villa, your gateway to unforgettable vacations in the heart of Formosa Gardens, just minutes from the enchantment of Disney World! Step into luxury with our private heated pool and spa, perfect for unwinding after a day of adventure. Thrill-seekers will love our ...

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Property Type

Kissimmee Villa

Featured review

"2nd time still a charm"

We enjoyed a stay here 3 years ago and we lucky enough to find it available again in 2024. We can't say enough except that the property was somehow even an improvement over the 1st time. This is a great ...

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

$190

avg/night

$190
avg per night
View Details

Key Amenities

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

About this property

Palm Tree Villa Florida, is tucked away in the much sought after location of Doral Woods. This large 4 Bedroom, 3 Bathroom villa, is ideal for making the perfect vacation. This is our own holiday home, so the furnishings are to a high standard, as you can see from the pictures and video. Fully Air ...

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Property Type

Kissimmee Villa

Featured review

"Lovely Villa with a lot of extras !"

Beautiful place for a relaxing holiday or just 15 minutes away from the Disney and Resorts area . The home was perfect and the welcome package was great. Andy was great and checked in on us during our stay. ...

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Kissimmee House
8 BR | 6 BA | Sleeps 16 | Quick View
Sleeps 16, 8 bedrooms, 6 bathrooms
8 reviews

$376

avg/night

$376
avg per night
View Details

Key Amenities

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

About this property

5 star Property! Welcome to Sunset Magic Villa! Delightful Windsor at Westside Resort home villa 8 bedrooms (2 Downstairs/6 Upstairs) and 6 full bathrooms. Space for up to 16 guests, (stretch out and relax with all the comforts of home) WEST facing private pool ensuring stunning sunset ...

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Property Type

Kissimmee House

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Kissimmee Townhome
3 BR | 3 BA | Sleeps 9 | Quick View
Sleeps 9, 3 bedrooms, 3 bathrooms
11 reviews

Distance to park: 5 miles to Animal Kingdom Lodge

$174

avg/night

$174
avg per night
View Details

Key Amenities

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

About this property

**The private pool is not heated unless requested by the guest. Pool heating is available for an additional fee of $10.00 per day. Pool heating must be arranged and paid for prior to arrival.** *No long-term rentals - 14 nights maximum *Minimum rental age is 25 years old (exception for married couples ...

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Property Type

Kissimmee Townhome

Featured review

"FANTASTIC property!"

This is the place to stay! This rental truly felt like a home away from home. It was a short drive to countless restaurants and shopping...location is perfect! If you're going to Disney, you'll only ...

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Kissimmee Villa
4 BR | 2 BA | Sleeps 10 | Quick View
Sleeps 10, 4 bedrooms, 2 bathrooms

$165

avg/night

$165
avg per night
View Details

Key Amenities

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

About this property

The heart and soul of any Disney vacation is the centerpiece in this Mickey Mouse themed villa. Leading from the living/dining room is the upgraded and fully-equipped kitchen, which includes a ceramic top range, side by side refrigerator/freezer, dishwasher, garbage disposal, and microwave. Along with ...

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Property Type

Kissimmee Villa

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Kissimmee House
7 BR | 5.5 BA | Sleeps 14 | Quick View
Sleeps 14, 7 bedrooms, 5.5 bathrooms
2 reviews

Distance to park: 5 miles to Disney World

$244

avg/night

$244
avg per night
View Details

Key Amenities

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

About this property

Excellent Private Detached Family Vacation home/Villa located in the Prestigious Man Gated Vacation Resort of EMERALD ISLAND RESORTS. SPECIAL DISCOUNTS FOR LONGER STAYS !!! . Monthly bookings during January to April at special rates. _________________________________________________________________ This ...

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Property Type

Kissimmee House

Featured review

"Amazing 7 Bed rooms Villa Near Disney"

Our stay with Family and friens were superb. Cost is just a fraction of what otherwise with any Hotels. VEry large House with 7 Bedrooms and 6 Wash rooms. Own private pool and lanai . Bbq grill was provided ...

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Kissimmee Villa
6 BR | 4 BA | Sleeps 14 | Quick View
Sleeps 14, 6 bedrooms, 4 bathrooms
2 reviews

$613

avg/night

$613
avg per night
View Details

Key Amenities

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

About this property

Just 2 miles to Disney, in Orlando's favorite resort community, Windsor Hills. When only the best will do, our luxurious 6 bed/4 bath sleeps up to 14 and covers more than 3500 sq ft with every comfort that you would expect from a 5* resort. Check out our south-facing private pool with spillover ...

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Property Type

Kissimmee Villa

Featured review

"Clean and Spacious Family Home"

The property was clean and spacious! The location offered privacy and comfort. King, 2 queen, 4 twin beds offered plenty of comfort. Well kept with attentive management.

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

Distance to park: 7 miles to Disney Hollywood Studio

$144

avg/night

$144
avg per night
View Details

Key Amenities

  • Air conditioning
  • Hot tub
  • Private pool
  • WiFi

About this property

Beautiful, clean and spacious 5 bedroom and 4 bath house in the most sought after community near Disney! 10 minutes drive to Disney and you can hear the Disney fireworks at night. Close to stores, restaurants and tons of shops. The house was renovated and professionally designed recently. The house has ...

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Property Type

Kissimmee House

Featured review

"Great Location!"

We had a great stay. The house is located in a close proximity to many places we visited. Would stay again.

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

$255

avg/night

$255
avg per night
View Details

Key Amenities

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

About this property

A fabulous home-base for your trip to Orlando! Just Minutes to Theme Parks. Home Features: * 3 Bedrooms * 1 King, 1 Queen, 2 Full, 1 Twin (Sleeps 7-8) * All New Mattresses * TV's in every bedroom * USBs & Outlets convenient for charging * 3 Bathrooms * All En-Suite * ...

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Property Type

Kissimmee Townhome

Featured review

"Loved it."

Beautiful House, and a wonderful experience from start to finish! Cant wait to go back! The home was spacious and beautifully decorated and Lisa was a Pleasure to work with, and very helpful.

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Kissimmee House
9 BR | 8 BA | Sleeps 18 | Quick View
Sleeps 18, 9 bedrooms, 8 bathrooms
11 reviews

Distance to park: 3 miles to Disney Animal Kingdom

$698

avg/night

$698
avg per night
View Details

Key Amenities

  • Air conditioning
  • Hot tub
  • Private pool
  • WiFi

About this property

Mickey's Oyster is a luxurious oasis designed to make your Disney World vacation unforgettable. Nestled in a prestigious, gated community just minutes away from the magic, this freshly remodeled and renovated home offers an enchanting escape with all the comforts of a five-star resort. Luxurious ...

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Property Type

Kissimmee House

Featured review

"Hartley House family gathering"

We have just returned from a great family holiday in Florida we took all our family away for our fiftieth wedding anniversary ,three years late .We stayed at Hartley House ,we have never stayed in a american ...

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Kissimmee House
10 BR | 8 BA | Sleeps 20 | Quick View
Sleeps 20, 10 bedrooms, 8 bathrooms

$180

avg/night

$180
avg per night
View Details

Key Amenities

  • Air conditioning
  • Hot tub
  • Pet friendly
  • Private pool
  • WiFi

About this property

Home Features: · 10 bedrooms, 8 bathrooms · Smart TVs in every bedroom and both the living room and upstairs lounge · Modern, fully equipped chef's kitchen with new stainless steel appliances · Granite countertop island with bar-stool seating · In-home Washer ...

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Property Type

Kissimmee House

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Kissimmee Vacation Rentals

Kissimmee Weather

 | 

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 236 Kissimmee vacation rentals available on FloridaRentals.com. From house rentals to villa 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 $65 per night with an average price per night of $181.

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 183 vacation rentals in Kissimmee with a pool on FloridaRentals.com. Search using our filters and book one for your next vacation!