Kissimmee Vacation Rentals

(229 rentals)
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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 Villa
3 BR | 3.5 BA | Sleeps 6 | Quick View
Sleeps 6, 3 bedrooms, 3.5 bathrooms

Distance to park: 4 miles to Disney

$216

avg/night

$216
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 Villa
7 BR | 6 BA | Sleeps 14 | Quick View
Sleeps 14, 7 bedrooms, 6 bathrooms
4 reviews

$346

avg/night

$346
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 9 | Quick View
Sleeps 9, 4 bedrooms, 3 bathrooms

$185

avg/night

$185
avg per night
View Details

Key Amenities

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

About this property

Immerse yourself in luxury at our Kissimmee villa, perfectly located minutes from Disney and Universal. Nestled in a secure gated community, our home boasts a private pool and spa, a fully-equipped modern kitchen, and comfortable bedrooms including a master suite with a king bed. Exclusive amenities include ...

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Property Type

Kissimmee Villa

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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

$158

avg/night

$158
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 Townhome
3 BR | 3 BA | Sleeps 8 | Quick View
Sleeps 8, 3 bedrooms, 3 bathrooms
4 reviews

$231

avg/night

$231
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
4 BR | 2.5 BA | Sleeps 9 | Quick View
Sleeps 9, 4 bedrooms, 2.5 bathrooms
10 reviews

Distance to park: 6 miles to Disneyworld

$133

avg/night

$133
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 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

$239

avg/night

$239
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
4 BR | 3 BA | Sleeps 8 | Quick View
Sleeps 8, 4 bedrooms, 3 bathrooms
9 reviews

Distance to park: 4 miles to Disney World

$150

avg/night

$150
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
4 BR | 3 BA | Sleeps 8 | Quick View
Sleeps 8, 4 bedrooms, 3 bathrooms

$193

avg/night

$193
avg per night
View Details

Key Amenities

  • Air conditioning
  • WiFi

About this property

Are you looking for a private home in Kissimmee for your next Florida vacation? Rolling Hills 7965 is just the place! This home is suited for up to 8 guests and features 4 bedrooms and 3 bathrooms. When you step inside, you’ll notice that the décor is upscale and tasteful to suit the style ...

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Property Type

Kissimmee House

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

Distance to park: 3 miles to Disney

$175

avg/night

$175
avg per night
View Details

Key Amenities

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

About this property

The Magic Emerald Island Villa invites you to experience an elegant escape near Disney World and Universal Studios. Our 4-bedroom, 3-bathroom villa accommodates up to 9 guests in comfort and style: • The main master bedroom features a king-size bed, a private en suite bathroom with a garden tub, ...

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Property Type

Kissimmee House

Featured review

"5*+ Magic Emerald Island Villa"

Excellent villa wonderful host. From the very first enquiry about renting Yelena’s Magic Emerald Island villa she was fantastic, guiding me through the booking and rental period until we left. Yelena ...

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

$253

avg/night

$253
avg per night
View Details

Key Amenities

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

About this property

Enjoy a whimsical getaway when you book a stay at this sleek, refreshing, 8-bedroom, 6-bathroom vacation rental home. Take a dip in the private pool, fix up something tasty in the fully equipped kitchen, play a game of pool in the game room, or head to the community fitness center for a quick workout. ...

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Property Type

Kissimmee House

Featured review

"Kissimmee Home/Windsor"

My family & I enjoyed our stay at this lovely home during the summer time. This house gave us an enjoyable experience that we will all remember. We didnt have any problems with the house and we hope to ...

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

$139

avg/night

$139
avg per night
View Details

Key Amenities

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

About this property

Indian Creek Disney Retreat is a beautiful 1800SF, well maintained home in the Indian Creek subdivision which is literally on Disney's doorstep and your home away from home. Indian Creek is not a gated community but has a lot of community amenities. In the 1st section of Indian Creek you will ...

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Property Type

Kissimmee Villa

Featured review

"Florida Vacation! ️"

My family and I retuned back to Lisa’s beautiful home the week of Thanksgiving for a week long trip. This is our 2nd time staying in her house and we absolutely loved it! The house was so clean from top ...

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

$129

avg/night

$129
avg per night
View Details

Key Amenities

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

About this property

Close to the Attractions but away from the crowds. 4 bedroom/3 bath single story home on "lake". Ducks, Sandhill Cranes, sometimes a falcon, turtles. King, king, and 4 twin beds, TV in all bedrooms, WiFi, FREE US, Canada and US Territory phone calls. Fully furnished. Not suitable for ...

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Property Type

Kissimmee House

Featured review

"Great Location for your stay."

The home was very comfortable and dealing with the owner was a breeze. Check in was very easy and the location is ideal for Disney and Universal visitors. Nice lake view and several chairs for outdoor seating. ...

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

$214

avg/night

$214
avg per night
View Details

Key Amenities

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

About this property

RECENTLY REFURBISHED Luxurious Windsor Palms with an extra wide cul de sac lot and with a pool that is not overlooked. Our guests enjoy terrific privacy in one of the premier resorts in the Disney vicinity. We have a south facing pool with kiddy pool and stand alone hot tub. Numerous child friendly ...

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Property Type

Kissimmee Villa

Featured review

"Awesome vacation"

Everything was perfect from start to finish. House was better than we expected, owner was great to deal with and will for sure book this house again and have already referred friends to book this property ...

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

$174

avg/night

$174
avg per night
View Details

Key Amenities

  • Air conditioning
  • WiFi

About this property

If you’re searching for Orlando vacation rentals that will have plenty of room for your entire family, look no further than Windsor Palms with private pool. This incredible home can fit up to 10 guests between its 4 bedrooms and 3 bathrooms. You’ll find another incredible amenity around every ...

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Property Type

Kissimmee House

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Kissimmee Villa
4 BR | 2.5 BA | Sleeps 8 | Quick View
Sleeps 8, 4 bedrooms, 2.5 bathrooms
1 review

Distance to park: 3 miles to Disneys Animal Kingdom

$202

avg/night

$202
avg per night
View Details

Key Amenities

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

About this property

Our Home Features are 4 bedrooms consisting of 1 Master suit with en-suite bathroom located on the main level. 1 Queen and 2 twin rooms,1 twin room is themed Winnie the Poo,on the upper level, these bedrooms share the upper bathroom all bedrooms are equipped with TV and DVD player. There is a further ...

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Property Type

Kissimmee Villa

Featured review

"Tolles Haus"

Hallo, Wir haben hier mit der Familie Urlaub gemacht. Das Haus ist groß genug für acht Personen. Es ist super ausgestattet mit tollem Blick und schönem Pool. Der Vermieter ist sehr um eine tolle Atmosphäre ...

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

$140

avg/night

$140
avg per night
View Details

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

Luxury villa right on lake edge. Free fishing on 3 lakes. Gated 5 Star Resort. FREE Gas BBQ. Hi speed WiFi and air con throughout the villa. Our 4 Bed, 2 Bath villa is furnished to a very high standard and benefits from a perfect lake view position. Free fishing on 3 well stocked lakes. The ...

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Property Type

Kissimmee Villa

Featured review

"Great Stay"

My family and I chose to do Disney for the holiday. We stayed at one of your florida rentals. I must say that we had a pleasant stay. Very nice and quiet community. I would definitely return as a frequent ...

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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

$205

avg/night

$205
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 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

$97

avg/night

$97
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 House
5 BR | 5 BA | Sleeps 12 | Quick View
Sleeps 12, 5 bedrooms, 5 bathrooms
2 reviews

$316

avg/night

$316
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 House
3 BR | 2 BA | Sleeps 10 | Quick View
Sleeps 10, 3 bedrooms, 2 bathrooms
20 reviews

$180

avg/night

$180
avg per night
View Details

Key Amenities

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

About this property

Sunset Lakes is ideally situated, just 4 miles from Disney World and a short drive from other popular attractions like Universal Studios, Sea World, and more. The proximity to Orlando and other destinations makes it a prime choice for travelers. The gated community offers various amenities such as a community ...

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Property Type

Kissimmee House

Featured review

"Vacation retreat/$15 Uber to Disney/ HGTV looking retreat"

We are completing our stay in the morning at this beautiful vacation retreat! We brought the family all seven of us ranging from age in two years old to 60 years old. The pool and patio is incredibly maintained, ...

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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
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 Villa
6 BR | 5 BA | Sleeps 12 | Quick View
Sleeps 12, 6 bedrooms, 5 bathrooms

Distance to park: 5 miles to Disney’s Animal Kingdom

$275

avg/night

$275
avg per night
View Details

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

Christmas Week Deal: Early Check-In or Late Check-Out Included at 1pm! Welcome to your elegant vacation retreat in Emerald Island Resort, Orlando, FL! This spacious 6-bedroom, 5-bathroom home has been recently upgraded and is located just 3 miles from Walt Disney World and only minutes from top attractions ...

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Property Type

Kissimmee Villa

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

Distance to park: 3 miles to Disney World

$143

avg/night

$143
avg per night
View Details

Key Amenities

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

About this property

4 Bedroom (2 master suites) 3 full baths, separate living and family rooms, will sleep up to 10 people. Decor in this house is Timeless!! Pool is newly resurfaced! The game room includes an 8 foot pool table and foosball table,. The private pool deck provides a distant view of the nightly DisneyWorld ...

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Property Type

Kissimmee House

Featured review

"Wonderful home!"

My family and I stayed here for a week and would definitely return. The home was spacious and clean. because it sat high, the back was private and did not look into another yard. The owner was very responsive ...

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

Distance to park: 3 miles to Disney Parks

$129

avg/night

$129
avg per night
View Details

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

This home is thoughtfully furnished. Recently upgraded with a Tempur-Pedic contour supreme king size mattress, LED TV in every bedroom, Frozen themed and Mickey themed twin rooms. This four bedroom luxury home is specifically set up for vacationing guests. The house, just three miles from Disney, is located ...

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Property Type

Kissimmee House

Featured review

"Great vacation home"

We had the opportunity of spending 12 days at this beautiful palm breeze villa. This home came with everything we needed. Very close to all attractions and short distance to shopping. Our host made all ...

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

$201

avg/night

$201
avg per night
View Details

Key Amenities

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

About this property

ASK ABOUT SPECIAL REDUCED NIGHTLY RATE REMAINING WINTER AND SUMMER 2025 DATES! Luxury 4 BR / 3 Bath Villa with Private Pool and Spa in Guarded Gated Resort Close to Disney Welcome to the Disney Getaway Villa, located in the beautiful and luxurious Emerald Island Resort. This villa is “the ...

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Property Type

Kissimmee House

Featured review

"Lovely and clean"

We have rented many homes in the Orlando area and this was one of our favourites. Great home, with lots of space. Clean. The pool area was lovely and pool was nice and warm. The home owners were so kind ...

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

Distance to park: 6 miles to Disney

$368

avg/night

$368
avg per night
View Details

Key Amenities

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

About this property

AMAZING Pool Deck Extension cira 2023! Its the BIGGEST pool deck at the resort! Plus JAW DROPPING, Fancy, Fun, Fountain Jets w/ LED lighting, high-end glass tile & a Mickey Mosaic giving you an ULTIMATE luxury pool experience. This SALT WATER POOL/SPA will leave your skin feeling soft w/ no eye-sting ...

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Property Type

Kissimmee Villa

Featured review

"Amazing house"

We had an amazing time and the house had everything we needed and wanted for our vacation in Florida. If you are going to Florida we recommend this house. It's has a great pool and patio and can accommodate ...

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Kissimmee House
4 BR | 2 BA | Sleeps 6 | Quick View
Sleeps 6, 4 bedrooms, 2 bathrooms
11 reviews

$131

avg/night

$131
avg per night
View Details

Key Amenities

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

About this property

CHEERY AND BRIGHT. Just what a vacation home should be. 4 bedrooms, 2 bathrooms, great views and just minutes from all the fun. Fully furnished , just bring personal items or things you cannot live without. Located in Eagle Pointe, a well sought-after vacation home community. Just minutes from what ...

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Property Type

Kissimmee House

Featured review

"Great Villa"

This is a lovely villa in a beautiful setting overlooking the lake. Great range of shops and restaurants within a short drive. 15 minutes drive to Disney parks. We loved it so much we have booked again ...

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Kissimmee Villa
8 BR | 6 BA | Sleeps 17 | Quick View
Sleeps 17, 8 bedrooms, 6 bathrooms
1 review
owner special
Owner special: 20% off in January, February and March.

$280

avg/night

$280
avg per night
Owner special:
20% off in January, February and March.

View Details

Key Amenities

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

About this property

Disney Wood Wonderland*** 7 miles from Disney popular attractions Disney's Animal Kingdom Theme Park and Epcot. Walt Disney World and Magic Kingdom Park.

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Property Type

Kissimmee Villa

Featured review

"Couples retreat"

The house was well accommodated for the amount of guests. It was very specious, well maintained. We were satisfied with our stay.

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Kissimmee House
8 BR | 4.5 BA | Sleeps 16 | Quick View
Sleeps 16, 8 bedrooms, 4.5 bathrooms
24 reviews

Distance to park: 3 miles to Disney's Animal Kingdom

$289

avg/night

$289
avg per night
View Details

Key Amenities

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

About this property

Thank you for considering Mickey's Mansion for your vacation rental. Our 8 bedroom, 4.5 bath home is situated in a prime location in the Four Corners of Kissimmee (just minutes to Disney), and offers both a bustling atmosphere and a peaceful retreat. There's no better way to unwind and escape ...

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Property Type

Kissimmee House

Featured review

"Beautiful, Well Furnished & Well Equipped Home - will definitely book again"

LOCATION: This house is located within the gated community of Emerald Island Resort. The community comprises of other single-family homes, a central club house with its own swimming pool, games room, ...

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

$403

avg/night

$403
avg per night
View Details

Key Amenities

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

About this property

Escape to a magical 8-bed 6-bath retreat for up to 16 guests at the Windsor at the Westside resort community. This is an entire home rental. Super Mario game room, Beauty and the Beast dining, Paris-themed kitchen, Guardians of the Galaxy primary bedroom. Upstairs: Hollywood, Pirates, Mickey Mouse, Princesses, ...

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Property Type

Kissimmee Villa

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

Distance to park: 5 miles to Disney World/Animal Kingdom

$298

avg/night

$298
avg per night
View Details

Key Amenities

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

About this property

Our Disney vacation villa is furnished to the highest standard and offers your family the luxury of a Five star hotel combined with the relaxed atmosphere of a family vacation home. Soak up the Florida sun on our extended deck where you can relax in the pool and spa, or simply enjoy the shade of the lanai ...

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Property Type

Kissimmee Villa

Featured review

"Fantastic Stay"

We loved staying at this house it was truly amazing. There were 9 of us altogether, 6 adults and 3 children aged 10,8 & 4. The kids loved the games room and the pool, everything you could wish for in ...

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Kissimmee House
4 BR | 3 BA | Sleeps 8 | Quick View
Sleeps 8, 4 bedrooms, 3 bathrooms
1 review

Distance to park: 2 miles to Disney's Animal Kingdom

$200

avg/night

$200
avg per night
View Details

Key Amenities

  • Air conditioning
  • Hot tub
  • Private pool
  • WiFi

About this property

4 Bedroom /3 Bath / Pool & Spa Vacation Home CONTACT US AND REQUEST A DETAILED QUOTE !! No Booking Fees - Book Direct with the Homeowner Check our Reviews on VRBO - Property #284051

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Property Type

Kissimmee House

Featured review

"Awesome"

Thank you Awesome Would do again Very close to everything Great pool sand hot tub Felt safe Thank you again

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

Distance to park: 5 miles to Walt Disney World

$200

avg/night

$200
avg per night
View Details

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

Located in the 5 star gated (guarded) resort of Windsor Palms, this 4 bedroom home is minutes away from Disney World, Universal Studios, and other major attractions. Keyless entry for easy access. You'll find all the comforts of home including a private pool, flat screen HDTVs, XBOX 360 and N64, ...

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Property Type

Kissimmee Villa

Featured review

"Great Family Holiday"

We recently rented over the holidays. Amazing location and accommodated our family of 7 perfectly. The house had many new renovations. The kitchen was extremely well stocked and roomy. Our 5 adult children ...

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

Distance to park: 4 miles to Disney's Animal Kingdom

$160

avg/night

$160
avg per night
View Details

Key Amenities

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

About this property

This home sleeps 8 with two master king suites and two twin rooms with two twin beds in each. All bedding is quality, clean, and comfortable with European duvets and covers. Mattress and pillow protectors on all beds. A private swimming pool and a stand-alone hot tub are yours to enjoy throughout your ...

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Property Type

Kissimmee Villa

Featured review

"Great and affordable"

Rented this place to go to Halloween horror nights. The place was clean and actually had all the equipment and everything for the game room which I’ve rented more luxurious homes to have pool sticks with ...

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Kissimmee House
5 BR | 2 BA | Sleeps 11 | Quick View
Sleeps 11, 5 bedrooms, 2 bathrooms

$137

avg/night

$137
avg per night
View Details

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

The 5 Bedrooms-2 Bathrooms non-smoking house offers free private parking, free Wifi, 5 smart TVs, game room, fence gated private pool, a full equipped kitchen & Washer & Dryer. THIS HOUSE IS SELF-CATERING. Please stop by your nearest supermarket to purchase personal toiletries and desired meals. ...

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Property Type

Kissimmee House

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

Distance to park: 3 miles to Walt Disney World

$180

avg/night

$180
avg per night
View Details

Key Amenities

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

About this property

4 Bedrooms| 2 Baths| Sleeps 8|Private Pool|Games Room|Disney-Themed Kids Rooms| Updated Decor| If you’re looking for the perfect home away from home for your family’s perfect Disney vacation, look no further. Our bright, airy house in the desirable 5-star Emerald Island Resort means that ...

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Property Type

Kissimmee House

Featured review

"Fantastic Villa"

We have recently returned from a fantastic stay at Joanna’s villa and couldn’t recommend highly enough. After a long day of travel the immediate comfort we felt opening the door of what would be our ...

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Kissimmee Townhome
3 BR | 2.5 BA | Sleeps 6 | Quick View
Sleeps 6, 3 bedrooms, 2.5 bathrooms
4 reviews

$115

avg/night

$115
avg per night
View Details

Key Amenities

  • Air conditioning
  • Hot tub
  • Pool
  • WiFi

About this property

Welcome to our beautiful townhome villa located at the luxurious 24-Hour Guard-Gated Emerald Island Resort in Kissimmee, Florida. Just 3 miles from Disney World's main gate. No cramped pool deck! No Shade from nearby houses blocking that fabulous Florida Sun! No shortage of pool chairs, tables ...

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Property Type

Kissimmee Townhome

Featured review

"Outstanding rental!"

We spent three weeks in this rental and had a wonderful stay. Location is terrific. Very close to the pool, yet very quiet. Owner was great to work with and fast with communication. Home is clean and well ...

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

Distance to park: 3 miles to Disney World

$164

avg/night

$164
avg per night
View Details

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

Sample the Florida lifestyle in our four-bedroom, three-bathroom spacious air-conditioned villa with 26ft x 13ft privately screened, heated, south-facing swimming pool and spa. Located on the peaceful Indian Creek community, our holiday home is comfortably furnished throughout, only 3 miles away from ...

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Property Type

Kissimmee Villa

Featured review

"Great location and a lovely accommodation"

Perfect location for the Disney theme parks as well as SeaWorld and Universal Studios. Very modern interior decor, and fresh and vibrant linens and accessories. Would highly recommend and will visit again.

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

Distance to park: 8 miles to Walt Disney World

$145

avg/night

$145
avg per night
View Details

Key Amenities

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

About this property

**Please email me directly for the most current availability** Private Villa on property at Margaritaville Resort, Kissimmee, Fla. - Complimentary Wi-Fi - In-unit washer/dryer - Unassigned parking in the lot in front of the home (motorcycles allowed) Orlando & Airport - Less than 30 minutes ...

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Property Type

Kissimmee Townhome

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

$207

avg/night

$207
avg per night
View Details

Key Amenities

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

About this property

Great Game Room,4/3,Pool,Spa,100mgbps wifi,2 Masters,65' 4KTV, 4 miles to Disney Going on a magical vacation? Why not stay in a magical place! We combine the magic of DisneyWorld with high-end comfort and conveniences to ensure every guest has the best vacation experience. Often referred to as ...

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Property Type

Kissimmee House

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

Distance to park: 6 miles to Walt Disney World

$180

avg/night

$180
avg per night
View Details

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

Name Of Home: Ohana Mouse House Location: Windsor Hills Resort (24/7 guard gated community - Disney World only mins away!) Home Highlights: Recently Renovated Home - Private Pool - Bunk Bedroom with PS4 Property Type: Townhouse, Two Stories (1,437 SF) Bedrooms: 3 Total - 1 Master w/ King Bed, ...

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Property Type

Kissimmee Townhome

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

$258

avg/night

$258
avg per night
View Details

Key Amenities

  • Air conditioning
  • Hot tub
  • Private pool
  • WiFi

About this property

Welcome to Minnie's Mansion! A 5 bd/ 5 bth pool home located in the closest community to Disney World-Windsor Hills Resort! This resort features, $2.1 mil Lagoon Style pool with Zero Depth Entry and Water Slides. Also, with a Water Park for the littles! Clubhouse has Sundry Shop /Deli, Games Room, ...

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Property Type

Kissimmee Villa

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

Distance to park: 3 miles to Disney Animal Kingdom

$140

avg/night

$140
avg per night
View Details

Key Amenities

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

About this property

Great location - fabulous pool area South West Facing - Fully Fenced Area

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Property Type

Kissimmee Villa

Featured review

"honeypot villa"

This house was perfect for our family vacation. This was my kids first time in Florida - and the house was a much better idea than a hotel. We had 6 people staying with us, and we all fit perfectly. Will ...

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Kissimmee Villa
5 BR | 4 BA | Sleeps 15 | Quick View
Sleeps 15, 5 bedrooms, 4 bathrooms
5 reviews

$337

avg/night

$337
avg per night
View Details

Key Amenities

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

About this property

Villa Overview No extra charges! 5 bedrooms, 4 full bathrooms Sleeps 15 guests ~440 square foot Star Wars theme room upstairs with two full over full bunk beds between a 3D TIE Fighter and swirly slide Twin bunk bed with a trundle in the Lego-themed room, complete with multi-color ...

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Property Type

Kissimmee Villa

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

$150

avg/night

$150
avg per night
View Details

Key Amenities

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

About this property

Beautiful 4 bedroom/3 bathroom house in the luxurious Emerald Island Resort - Only ~ 4 miles from Disney & close to other major attractions! This home is equipped with a heated private pool, spa & game room. There is a large SMART TV in the living room & in each bedroom. There are queen beds ...

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Property Type

Kissimmee House

Featured review

"Fantastic gem"

Just spent two weeks in this beautiful villa. Definitely a home from home and everything you need for a holiday near to all the parks . Plenty of shops and restaurants nearby and we definitely sampled ...

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Kissimmee Villa
7 BR | 5 BA | Sleeps 14 | Quick View
Sleeps 14, 7 bedrooms, 5 bathrooms
5 reviews

Distance to park: 7 miles to Disney Magic Kingdom

$261

avg/night

$261
avg per night
View Details

Key Amenities

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

About this property

* Gated and Guarded Resort 7 -10 minutes to Disney * Stunning Lake Views from Pool Deck * Pool with 24 Hour Spa on Over ride - Handrails * Lots of Baby Equipment - Free to Use * 2 Lounges - Leather sofas * Game Room Disney Themed -Air conditioned - Slate Bed Pool Table *New Gaming Station PS4, ...

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Property Type

Kissimmee Villa

Featured review

"Fabulous home and perfect location"

The home is absolutely beautiful, very clean and has everything you could possibly need or want in a rental home. The only thing we had to add was our own food and toiletries. The location was perfect, ...

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Kissimmee Apartment
1 BR | 1 BA | Sleeps 4 | Quick View
Sleeps 4, 1 bedroom, 1 bathroom

Distance to park: 7 miles to Disney World

$81

avg/night

$81
avg per night
View Details

Key Amenities

  • Air conditioning
  • Rentals by owner
  • WiFi

About this property

1/1 Condo. Queen sofabed in living room. Queen bed in master with desk and chair. Full kitchen. Just 7 miles from Disney, centrally located. Gated community , Complex has 2 pools, gym, tennis courts. Laundry room with full size washer/dryer in unit. Free wifi and streaming. Second floor unit.No elevators. No ...

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Property Type

Kissimmee Apartment

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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 229 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 $180.

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