Kissimmee Vacation Rentals

(336 rentals)
LUXURY 6 BED 6 BATH ENCORE RESORT VILLA

$269

per night

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Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • Pool
  • Private Pool

About this property

This 6 bedroom 6 bath home is located at the Encore Resort, less than a 10 minute drive to Walt Disney World and their 4 incredible theme parks! Conveniently located for you and your loved ones to experience and enjoy, Walt Disney World's proximity from this vacation home is an added bonus while staying ...

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Property Type

Kissimmee Villa

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Dory's Magic - Luxury villa with theater room, lake view and south-facing pool

7 BR | 5.5 BA | Sleeps 16 | Quick View

Distance to park: 3 miles to Disney World

$225

per night

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Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • Pool
  • Private Pool

About this property

"Dory's Magic" is our Emerald Island Resort 7 bed/5.5 bath vacation home offering a fully air-conditioned games-room in addition to a south-facing pool/spa and multiple living areas. It offers several complimentary amenities such as BBQ grill, free full-size crib, pack 'n play, stroller, high ...

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Property Type

Kissimmee Villa

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Champions Estate

8 BR | 5 BA | Sleeps 16 | Quick View

$305

per night

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Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Private Pool

About this property

Located in one of the most sought-after resorts in the Orlando area, welcome to Champions Estate. The newly built 8 bedroom, 5 bath pool home is the perfect destination for your family getaway. The home was designed to fit every need that you could have when visiting the area. This villa accommodates ...

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Property Type

Kissimmee Villa

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Brand New, South Facing 7br Pool Home, 8 Miles From Disney. 9020

$199

per night

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Key Amenities

  • Air Conditioning
  • Kid Friendly
  • Pet Friendly
  • Pool
  • Private Pool

About this property

Welcome to the new Solara Resort, the Disney areas newest vacation home retreat community. (5 kings, 4 twins) This brand new 7 bedroom, 6 bath vacation home has just been completed and now ready for rentals. In this spacious home you will find 5 king rooms and two rooms with 2 twin beds in each. Downstairs ...

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Property Type

Kissimmee House

"Lovely"
Reviewed June 11, 2020

Great home!Great home!Great home!Great home!Great home!Great home!Great home!Great home!Great home!Great home!

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Homestead Paradise - Rare Extended Pool Deck

$430

per night

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Key Amenities

  • Air Conditioning
  • Full Kitchen

About this property

This luxury Mediterranean inspired custom home is on an oversized corner lot. Located on the beautiful Tom Watson Independence Reunion Resort golf course and just 6 miles to the gates of Disney.Enjoy Florida sun on the rare extended pool deck that sets this home apart from most in Reunion. Featuring ...

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Property Type

Kissimmee House

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Stunning 4 Bed villa with own pool. Gated 5 Star Resort near Disney

$120

per night

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Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • Pool
  • Private Pool

About this property

We invite you to rent our stunning villa that features 4 bedrooms, 2 bathrooms fully kitchen and a private pool.Our home is very well located in Lake Berkley Resort, a secure gate Resort just minutes from Disney.The living room is spacious with a 3 seats sofa and loveseat to relax and enjoy the ...

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Property Type

Kissimmee Villa

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Resort living while visiting the theme parks and next door to Margaritaville

$150

per night

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Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Private Pool

About this property

Our beautiful FOUR-BEDROOM, THREE-BATHROOM, luxury home is located at the gated community of Emerald Island Resort, surrounded by lush Florida vegetation, is the one of the latest full-facility resort in the Disney area. The winding, palm-lined road that leads to the impressive entry to the resort gives ...

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Property Type

Kissimmee House

"Covit-19"
Reviewed May 31, 2020

Unfortunately due to the current pandemic we were in lockdown in the U.K for the period we should have been in beautiful Florida.The owners of this villa were extremely helpful all through the period ...

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Luxury 7 bed Emerald Island Villa

7 BR | 4.5 BA | Sleeps 16 | Quick View

1

$150

per night

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Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • Pool
  • Private Pool
  • Rentals by Owner

About this property

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

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Property Type

Kissimmee Villa

"2763 Lido Key Dr Emerald Island Resort"
Reviewed July 18, 2019

Enjoyed our stay. Spacious house with room for family of 14 to spread out! All 7 rooms were large. Owner was responsive...we had a problem with the pool fence and someone was out there the next day to fix ...

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Classic Condo | 3 Bed 3 Bath for 6 in Reunion Resort

$110

per night

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Key Amenities

  • Air Conditioning
  • Full Kitchen

About this property

This condo is located in the neighborhood Villas South in Reunion Resort near the many world-class entertainments and theme parks Orlando is notorious for. It has everything you need for an Orlando vacation, including a fully equipped kitchen with stainless steel appliances and a beautiful granite countertop. ...

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Property Type

Kissimmee Condo

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Discover newly refurbished 4 BR Windsor Palms Resort

4 BR | 3 BA | Sleeps 9 | Quick View

Distance to park: 10 miles to Walt Disney World

$159

per night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • Pool
  • Private Pool

About this property

Enjoy Windsor Palms, featuring gated resort style living at its finest! This beautiful, Orlando vacation resort is just 3 miles (4.5 km) from the gates of Walt Disney World. The perfect location for families to enjoy Disney Magical Gatherings. Our totally remodeled and renovated home provides lots of ...

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Property Type

Kissimmee House

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Formosa Gardens Paradise | Fantastic Lake Views

$270

per night

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Key Amenities

  • Air Conditioning
  • Full Kitchen

About this property

This magnificent 7 bedroom estate vacation home is located in Formosa Gardens, a gated community just 3 miles from the magic of Disney!Featuring a breathtaking lake view, this vacation home features 5 king bedroom/bathroom suites, a very large screened private pool and spa, 2 kids’ bedroom, ...

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Property Type

Kissimmee House

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Champions Breeze | 5 Bed Townhome in Champions Gate

$149

per night

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Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Private Pool

About this property

Enjoy these amenities and more at The Retreat, only 12 miles to the gates of Disney World® and 6 miles from Reunion

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Property Type

Kissimmee Townhome

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Cypress Pointe Private Gated Community Features 6 Bedrooms, Pool, Spa, Game Room

$139

per night

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Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Private Pool

About this property

Location, Location, LocationThis luxurious private villa is situated on the private gated community of Cypress Pointe less than 20 minutes drive to the Disney Parks, and about 30 minutes drive to the Universal Studios Theme Parks.Free private parking is available on site, and the driving time ...

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Property Type

Kissimmee House

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3BR 1st Floor Condo Near Disney, Steps from Pool, Loaded with Amenities

$75

per night

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Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • Pool
  • Rentals by Owner

About this property

Built in 2002, Windsor Palms Resort is a gated community approximately five miles from Disney. This luxury complex has a 7500 square foot clubhouse, basket ball courts, volleyball courts, children's play area, olympic-size swimming pool, toddler pool, hot tub, picnic and barbecue area, outdoor bar, convenience ...

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Property Type

Kissimmee Condo

"Disney trip"
Reviewed January 5, 2020

Our stay was wonderful! Clean, close to Disney, beautiful pool! Loved it!! Check-in was easy and quick. Everyone was very polite and helpful.

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3 Miles From Disney - Pet Friendly - Free Wifi - Grill - AC - Baby Equipment

$186

per night

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Key Amenities

  • Air Conditioning
  • Kid Friendly
  • Pet Friendly
  • Pool
  • Private Pool

About this property

Sleeps 8-10. Beachy decor. 2 master suites (one king / one queen) both with private bathrooms. 2 twin bedrooms / 2 twin beds each share the 3rd bathroom. Queen sofa sleeper in the living room. Private pool and free standing hot tub. Extra large fenced rear yard. Great for kids and pets (2-3 pet with paid ...

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Property Type

Kissimmee House

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Sunshine Memories Villa. ☀️❤️ Magical Family Retreat near Disney w/Waterpark

$165

per night

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Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • Pool
  • Private Pool

About this property

Welcome to Sunshine Memories Villa, where you will have an amazing vacation enjoying all that the Orlando area has to offer. Our 5-bedroom 5-bathroom villa is located less than 10 minutes away from Disney in the beautiful gated resort of Windsor Hills. As you step inside the foyer of your vacation home ...

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Property Type

Kissimmee Villa

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The State of Florida has given our vacation rentals the “green light” to reopen

4 BR | 3 BA | Sleeps 8 | Quick View

24

Distance to park: 4 miles to Walt Disney World

$124

per night

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Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • Private Pool
  • Rentals by Owner

About this property

CASA BONITA Near DISNEY! Florida License DWE5916118'Casa Bonita' which means 'Beautiful Home' is a beautifully furnished four bedroom, three bathroom home with a 26ft x 14ft swimming pool and covered lanai and is just a 3.5 mile drive to Walt Disney World Resort.This wonderfully located property ...

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Property Type

Kissimmee House

"Casa Bonita felt like home the moment we walked in."
Reviewed March 21, 2020

I didn't take long for us feel right at home in the house. The exterior appeared to be well maintained and, inside, the house was warmly decorated, visibly comfortable and clean. It had everything we ...

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The perfect Disney vacation home rental property! ATTENTION-ONLY WEEKLY RENTALS

3 BR | 2 BA | Sleeps 8 | Quick View

5

Distance to park: 12 miles to All Disney Theme Park

$89

per night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • Private Pool

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 it ...

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Property Type

Kissimmee Villa

"Perfect Family Vacation Home"
Reviewed March 18, 2019

We rented this home for a week in early February. Everything was perfect. All of the amenities need for our stay were there. The pool was great. All of the restaurants and Theme parks were just a short ...

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3 Miles From Disney - Pet Friendly - Free Wifi - Grill - AC - Baby Equipment

$186

per night

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Key Amenities

  • Air Conditioning
  • Kid Friendly
  • Pet Friendly
  • Pool
  • Private Pool

About this property

The large, fully-equipped kitchen is complete with a microwave and dishwasher! The home’s layout is perfect for watching the fun going on in the pool area from the living room, dining area and kitchen! The fully equipped kitchen offers everything you need to feel at home; both a Kuerig coffee maker ...

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Property Type

Kissimmee House

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EC_1100R Encore Leisure - Movie Room

$329

per night

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Key Amenities

  • Air Conditioning
  • Full Kitchen

About this property

This amazing, one of a kind 4,077sq. ft. home is located inside Encore Resort, just 6 miles from Disney and close to all major theme parks. The home reminds you that you are on vacation. Walking through the doors of this gem will make you feel right at home. The first floor has 3 bedrooms; 2 queen bedrooms ...

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Property Type

Kissimmee House

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Lake View, south facing pool. One straight road to the Mouse House.

3 BR | 2 BA | Sleeps 6 | Quick View

Distance to park: 20 miles to Disney

$86

per night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • Private Pool

About this property

From the hallway you enter the Dining Room & Lounge with patio doors out to the pool deck and breath taking lake view. Off to the right is our Master Bedroom with en-suite shower room, to the left our second & third Bedrooms, with the main bath in-between, giving a private split floor plan. To ...

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Property Type

Kissimmee Villa

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Kissimmee, Florida, 4 Bedrooms

4 BR | 2 BA | Sleeps 8 | Quick View

1

$171

per night

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Key Amenities

  • Kid Friendly

About this property

Come and enjoy this exquisite four bedroom home which is beautifully furnished. The ground floor consists of a grand entrance leading onto the private lounge and dining room, which then lead on to a large diner kitchen and on to a large family TV lounge. There are 2 full bathrooms and 4 toilets.From ...

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Property Type

Kissimmee House

"Best stay ever"
Reviewed January 14, 2019

My family and I loved the house and would book with you and recommend you to out family and friends

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Lakeside pool villa, kissimmee 3 miles disney

$171

per night

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Key Amenities

  • Air Conditioning
  • Private Pool

About this property

Location, Location, Location, situated just 3 miles from Disneys Animal Kingdom and less than a mile from the Formosa gardens shopping area and restaurants on the US192 you are perfectly placed to hit the parks before the rush, come home to cool down by the pool for dinner and hit the parks again for ...

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Property Type

Kissimmee Villa

"Lovely Villa, Great Location"
Reviewed June 14, 2019

Really nice villa. Plenty of living space. Sleeps up to 12 but there were 7 of us so it was really roomy.Pool area is so nice, with a view over a lake with lots of wildlife to see. Pool also has a colour ...

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Affordable Disney Villa - just 5 minutes to Disney

$109

per night

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Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Private Pool

About this property

Our property maintains a gap of 3 days between each booking for health safety measures during this crisis and we also follow stated mandated cleaning procedures and guidelines after each guest checks out.This Disney Villa is a fully furnished home and is one of the best kept turnkey properties you ...

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Property Type

Kissimmee Villa

"Perfection vacation getaway"
Reviewed March 24, 2020

I rented this house for my 1 week vacation to Disney and Universal Studios and was truly impressed by all it offered. To start the location was perfect, as it was close to both theme parks (being minutes ...

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Marvelous Emerald Is. Villa Water view

$204

per night

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Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • Pool
  • Private Pool

About this property

Enjoy our 8 bedrooms 12 beds villa around Disney World & other theme parks, or if you are winter bird just get away from the cold freezing weather.Prestigious Emerald Island Resort, a 24/7 gated community with security guards to ensure your safety during your stay. Unique large open back yard ...

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Property Type

Kissimmee Villa

"The Spring Games"
Reviewed March 17, 2020

House was great but the need for more bathrooms is needed for a large group. Great location for the parks.

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Beautiful Villa with South Facing Pool

6 BR | 4 BA | Sleeps 13 | Quick View

2

Distance to park: 3 miles to Disney World

$195

per night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • Pool
  • Private Pool

About this property

This 6 bedroom, 4 bathroom villa is located on the 5 star premier gated and guarded resort community of Windsor Hills which only minutes away from the Disney theme parks. Windsor Hills is consistently voted the number one vacation home rental community in the Walt Disney World area. The villa has a ...

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Property Type

Kissimmee Villa

"Fab place to stay"
Reviewed September 4, 2019

Having been to Orlando many times Windsor Hills is my favourite place to stay. It is a gated community and very close to everything. The communal pool and facilities are brilliant. This villa is spotless ...

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Clean Luxurious Vacation home close to Disney World

$280

per night

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Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • Pool
  • Private Pool

About this property

This Luxurious Vacation home in Orlando is at the Encore Club by Reunion. Many visitors come to stay at our conveniently located house to enjoy many of the activities in the Orlando area.Surrounded by many attractions, you will never get bored. It is close to to numerous golf courses. It is a great ...

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Property Type

Kissimmee House

"Stunning property"
Reviewed September 11, 2019

This house was stunning and made our stay one to remember. The facilities and service on the property are great and you don’t have the leave. You can spend all day at the water park and the meals at ...

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Modern Serenity Vacation Home | Private and Screened Pool | Home Theater |

$310

per night

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Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Private Pool

About this property

THIS HOME IS LOCATED IN THE RETREAT AT CHAMPIONS GATE, WHICH IS 6 MILES FROM REUNION RESORTThis home has everything you need for your next vacation. This brand new home with 8 beds and 5 baths can accommodate up to 16 guests with a spacious living area, fully equipped kitchen, private and screened ...

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Property Type

Kissimmee House

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Florida Family Vacation Rental Home In Disney Area!!!

$120

per night

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Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • Pool
  • Private Pool

About this property

We really appreciate your interest in our property, and we are working to re-open it for rental according to guidelines given by the state of Florida and the county of Osceola. We support the precaution of leaving one full day between the departure day of one guest and the arrival day of the next. We ...

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Property Type

Kissimmee Bungalow

"Perfect Disney Vacation House"
Reviewed October 25, 2019

The house was well equipped and stocked with plenty of towels and blankets. Seemed to be updated . LVT flooring throughout. Very clean and comfortable. Pool was a little cold..I recommend adding pool heat ...

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Solara Luxury Resort Holiday Home. 1525

$229

per night

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Key Amenities

  • Air Conditioning
  • Pet Friendly
  • Pool
  • Private Pool

About this property

Welcome to our newest Solara bedroom resort home. This home is currently being completed and will be ready for rentals soon. The home will feature 5 spacious king bedrooms and 2 bedrooms with 2 twins in each room.There will be a movie room loft area with huge 100 inch screen with projector and a sectional ...

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Property Type

Kissimmee House

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Currently Not Accepting Bookings - due to Covid.

$120

per night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • Pool
  • Private Pool
  • Rentals by Owner

About this property

Enjoy a magical vacation just 3 miles from all the Disney parks at the Pineapple Vacation Villa situated in the elegant Windsor Palms Resort. -Our holiday home offers all of the latest features in vacation rentals. With four bedrooms including two master-en-suites with private bathrooms plus two twin ...

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Property Type

Kissimmee Villa

"Lovely place"
Reviewed February 16, 2020

My family just stayed here with family friends this past week. We couldnt have asked for such a wonderful place to stay. It had everything we needed to be more than comfortable for the week. The neighborhood ...

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Any Closer to Disney and You'll Need a Park Pass! Southfacing Pool

$175

per night

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Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly

About this property

Less than 2 miles and only 5 minutes to Disney! Located in the new and most upscale location, the Emerald Island Resort, just 3 traffic signals from Disney off of Hwy 192 in Kissimmee. We feature concierge & shuttle service, so you are never "on your own" unless you want to be! Tennis and ...

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Property Type

Kissimmee Villa

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Stunning 5 Bed 4 Bath Villa with own private pool. Gated Resort close to Disney.

$130

per night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • Pool
  • Private Pool

About this property

Welcome to our stunning, larger than average, 5 Bed 4 Bathroom villa with a beautiful view of the conservation area at the rear as background of our private pool. All rooms in the villa are spacious. The villa is furnished and maintained to a very high standard.The villa is located just off US 192 ...

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Property Type

Kissimmee Villa

"A family favorite"
Reviewed January 26, 2020

We loved it here. In our 15+ years of renting villas for our family vacations, this one tops the list. It has plenty of room for everyone to have their own space, yet the kitchen and living room are very ...

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Fabulous Oakwater Resort in Kissimmee near Mystic Dunes Golf

3 BR | 2 BA | Sleeps 6 | Quick View

Distance to park: 2 miles to Walt Disney World

$99

per night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • Pool
  • Private Pool

About this property

Welcome to this gorgous condo with your own balcony overlooking the conservation and pond. With 3 bedrooms and affordable rates this will be the best place in Oakwater Resort, Kissimme, for your family to unwind after hopping around Orlando parks. This resort is just 1.5 miles to Walt Disney World!!Sleeps ...

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Property Type

Kissimmee Condo

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Mad Men Magic Kingdom House *Pool&Spa* 6mi to Disney*Dog and Family Friendly*

$250

per night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • Pet Friendly
  • Pool
  • Private Pool
  • Rentals by Owner

About this property

As you step through the front door of this 2800-square-foot home, you are immediately drawn to the unique geometric wall design and mid-century modern decor throughout the house. The lighting is spectacular as you enter the great room and look through the two sliding glass doors onto the patio where the ...

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Property Type

Kissimmee Villa

"Great Stay!"
Reviewed June 30, 2020

Our family loved the house! Our kids enjoyed every moment of swimming in the pool and Rebecca was a great host! Very accommodating with quick responses, we couldn’t have asked for a better stay. We will ...

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Beautiful 3 Bedroom 2 Bathroom Townhouse. Amazing Resort. Minutes to Disney.

3 BR | 2 BA | Sleeps 6 | Quick View

4

Distance to park: 5 miles to Walt Disney World

$115

per night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • Pool
  • Rentals by Owner

About this property

Beautiful 3 Bedroom 2 Bathroom Townhouse just off of 192 in Kissimmee, Fl. Minutes to Walt Disney World, Universal Studios, Sea World, Outlet shopping. You can walk to great restaurants and shopping. One of the best locations in the community. Only one building back from the Clubhouse and Pool, and ...

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Property Type

Kissimmee Condo

"Amazing!"
Reviewed January 2, 2020

We booked this online, had never done anything like this before. The owner was very responsive to my emails and questions. When we arrived at the gate we were greeted by security who reviewed our info ...

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7 Bed 4.5 Bath 2746LK Enchanted Emerald Oasis South Facing Pool Emerald Island!

$200

per night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • Private Pool

About this property

Enchanted Emerald Oasis Enchanted Emerald Oasis is an amazing luxury vacation villa that is well appointed! This 2,880 square foot 2 story home Just outside the gates of Disney World Resort, minutes to Universal Studios, Seaworld, Gatorland, and all other theme parks! Also, a great location for golfers ...

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Property Type

Kissimmee Villa

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Fairway Comfort | 6 Bedroom 6.5 Bath Pool Villa with Movie Room!

$335

per night

View Details

About this property

Welcome to Fairway Comfort. Located on the Westside of the incredible Reunion Resort within the Fairway Ridge community, and situated on the Jack Nicklaus-designed Tradition Golf Course. Fairway Elegance will fulfill all your vacation wants and needs. The home is located close to all the attractions of ...

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Property Type

Kissimmee House

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HUGE POOL AND SPA

4 BR | 2 BA | Sleeps 7 | Quick View

1

$90

per night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Private Pool
  • Rentals by Owner

About this property

4/15/20 ----PLEASE CALL FOR SPECIAL DEALS DURING THIS TIME. SPECIALS FOR 2 ADULTS. $70/night . 80/night max 4. personal check.WELL CARED FOR HOME IN LOVELY COMMUNITY. HOME BACKS TO CONSERVATION SO YOU ARE NOT OVERLOOKED AND IS A FEW STEPS FROM RETENTION POND WITH POND VIEWS FROM THE POOL DECK. ...

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Property Type

Kissimmee House

"Amazing time"
Reviewed June 14, 2020

This is one of the most beautiful homes I've ever stayed in. Plenty of space with private pool cant get any better. Very good location and neighborhood. Will be going back very soon.

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Perfect 9 Bed Resort Vacation Home. 8899

$189

per night

View Details

Key Amenities

  • Air Conditioning
  • Kid Friendly
  • Pool
  • Private Pool

About this property

Introducing our newest 9 bedroom luxury Resort home in the fantastic Windsor at Westside Resort. (6 kings, 2 full, 2 twin, 1 bunk with trundle)No expense has been spared to furnish this 9 bedroom home with 2 bedrooms on the main floor and an additional 7 bedrooms on the second floor.You will ...

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Property Type

Kissimmee House

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Four Bedroom Family Vacation Home Close to Disney!

4 BR | 2.5 BA | Sleeps 8 | Quick View

3

Distance to park: 4 miles to Disney World

$130

per night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • Private Pool

About this property

Great vacation home just three miles from the gates of Disney! Flat screen TV's in living room and all 4 bedrooms. Free wireless hi-speed internet and cable TV. HD TV in living room and all bedrooms. King bedroom has a flat screen 50" TV and 2 additional bedrooms have a built in DVD player in the ...

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Property Type

Kissimmee House

"Excellent Stay"
Reviewed August 15, 2019

Kay’s Retreat was the perfect destination for our recent vacation! Everything was perfect. She thought of everything we might need during our stay. The house was clean and comfortable. Will absolutely ...

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Bella Vida Resort - Welcome To Cozy 4 Beds 3 Baths Villa - Close To Disney

About this property

** THIS PROPERTY FOLLOWS CDC CLEANING GUIDELINES ** We welcome you to our beautiful & cozy house with 4 bed / 3 bath with Private Pool + Spa. This home has all the amenities necessary for your family and friends to spend a precious and memorable vacation in Orlando. Located in Kissimmee, only 9 ...

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Property Type

Kissimmee House

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My Disney Townhouse

4 BR | 3.5 BA | Sleeps 10 | Quick View

3

Distance to park: 5 miles to Animal Kingdom

$100

per night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • Pool
  • Rentals by Owner

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

"Excellent place to stay."
Reviewed December 3, 2019

The location is amazing-everything was close every one was friendly pool was great hot tub was amazing. I love it so much that I will like to buy a property there.Can some one tell me how I can buy ...

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Luxury Legacy Dunes condo close to Disney, Golf and Orlando Fun!

4 BR | 2 BA | Sleeps 10 | Quick View

1

Distance to park: 5 miles to Disney World

$69

per night

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Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • Pool
  • Rentals by Owner

About this property

Superb Remodeled 4 bedroom condo at 2 bedroom price! Legacy Dunes Resort. 4 bedroom/2 bathroom 1400 sq ft condo with screened balcony and children's playground & lake view. Easily accessible for the entire family so you can bring Grandma and Granddad. Or two couples each with two children, or groups ...

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Property Type

Kissimmee Condo

"Recently renovated 4 bedroom condo in a great complex, close to everything."
Reviewed January 29, 2019

This is our third extended stay in this unit. We enjoy the closeness to Disny as well as the closeness to grocery shopping and most of the chain restaurants. This gated complex is set back from Route 192 ...

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Beautiful, fully air conditioned 3 bedroom townhouse

$80

per night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • Pool

About this property

This beautiful, fully air conditioned, elegant townhouse sleeps 6. There is a large living and dining area. The luxury fitted kitchen with breakfast bar is fully equipped with all appliances and everything else you would expect making it a real home from home. This townhouse features a master suite with ...

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Property Type

Kissimmee Townhome

"spacious comfortable townhouse"
Reviewed May 17, 2020

Beautifully situated townhome with very well equipped kitchen, wonderful walks around immaculate compound, lots of attractions, shops food etc. nearby.

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Homestead Vista - Arcade Room, Amazing Custom Bunk Beds & Golf Course Views

$399

per night

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Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Pool
  • Private Pool

About this property

This luxury custom home is located right on the stunning Reunion Resort golf course and just 6 miles to the gates of Disney.Enjoy one of the best outlooks in Reunion from the southeast facing pool deck, unobstructed views of holes #7 and #8 of the beautiful Tom Watson golf course. The private pool ...

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Property Type

Kissimmee House

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♥Disney Area♥☆24hrs gated☆CornerTownHouse PrvtPool

4 BR | 3 BA | Sleeps 8 | Quick View

1

Distance to park: 18 miles to Magic Kingdom

$119

per night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • Private Pool
  • Rentals by Owner

About this property

☆ Bella Vida Resort ☆ Walmart Walk-in distance ☆ All Lines/Towels Provided ☆ 24hrs Gated Community ☆ Private Pool ☆ Cable TV ☆ Free UNLIMITED Wireless Internet ☆ Easy Self Checkin-Personalized door coded ☆ Smart NEST Thermostat ☆ Complete Kitchen ☆ In Unit Washer&Dryer ☆ ...

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Property Type

Kissimmee Townhome

"Excellent location, amazing pool!"
Reviewed February 24, 2019

Everything was perfect!!! Righlights: reception, furniture, cleaning, accommodations, location, pool.. I´m definitively coming back!

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West Reunion Estate | Games Room, Theater and South Facing Pool!

$349

per night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Pool
  • Private Pool

About this property

Situated within the West-side of the exclusive Reunion Resort and Just 6 miles from the gates of Disney World!Pull up to your home away from home, and prepare to indulge in luxury. This home has been furnished with no expense spared. This beautiful home boasts a rare combination of characteristics ...

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Property Type

Kissimmee House

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Renovated Home with Private West Facing Pool and close to Amenities

$232

per night

View Details

Key Amenities

  • Air Conditioning
  • Pool
  • Private Pool

About this property

Are you looking for a vacation home that has been beautifully renovated with a west facing private heated pool/spa, in Windsor Hills Resort with its NEW water park, and is very close to Disney World? This is it . . .Name Of Home: Blue Bridge Villa At Windsor Hills Location: Windsor Hills Resort ...

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Property Type

Kissimmee House

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Popular Luxury Resort Home, Private Pool, 10 Minutes From Disney!☀️

$192

per night

View Details

Key Amenities

  • Air Conditioning
  • Kid Friendly
  • Pool
  • Private Pool

About this property

6 Bed-4.5 Bath, 2 Masters, Disney Themed Kid's Rooms, Game Room, Private Pool Welcome to Fab Five Villa! We are offering wholesale daily rates. These are our lowest rates ever! These sale rates apply to any open dates on our calendar. Book now.We are looking forward to sharing our dream home with ...

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Property Type

Kissimmee House

"Beautiful home great location"
Reviewed March 18, 2020

We were a family of 12 visiting from Michigan. We did not know what to expect as this was my first ever Airbnb booking. The reviews were hit and miss. This home did NOT disappoint. It was beautiful, clean, ...

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Kissimmee Vacation Rentals

Kissimmee Weather

 | 

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

Find your ideal Kissimmee vacation rental today
 
Aiming to take an incredible vacation to this year? Ditch the traditional hotel and opt for one of our Kissimmee vacation rentals instead. We have plenty of condos available in Kissimmee on FloridaRentals.com. Whether you’re looking for luxury Kissimmee villa rentals or kid-friendly mansions with an arcade, you can find it on our site.
 
Kissimmee, Florida travel advice
 
A short drive south of Orlando finds you in sunny, friendly Kissimmee. Here you’ll be near all the theme parks, but you’ll be away from the bustling crowds. Rentals will cost less than a stay in Orlando, so you’ll have extra cash to spend on park tickets and meals. This area also offers activities for those who love outdoor exploration, with exotic plants and animals in the local nature preserves.
 
Top attractions
 
The Florida theme parks are the major draw for visitors to the area. Walt Disney World, Universal Studios, SeaWorld, and the Wizarding World of Harry Potter draw millions of families every year. 
 
The fun doesn’t stop as kids and adults alike can mingle with their favorite characters, feel the chills and thrills of amusement rides, and cool off in the area’s water parks. If the theme parks don’t meet your need for speed, spend an afternoon at Fun Spot America. With two unique go-kart tracks and 18 rides you’ll be dizzy with delight. 
 
The Museum of Military History offers exhibits that highlight the bravery and humanity of the men and women who have served in the armed forces. Genuine artifacts, military relics, photographs and memorable accounts by former soldiers are on display here.
 
For some Florida history, stop in to Osceola County Pioneer Village and Museum. This museum features many exhibits depicting life in the 19th century. The Pioneer Village has a general store, blacksmith shop, one room schoolhouse, and nature preserve.
 
Family-friendly activities
 
Strap on your hiking boots and take off on the Shingle Creek Regional Trail. The trail offers a beautiful, natural environment for cyclists, pedestrians, canoeists/kayakers, bird watchers and other nature lovers.  A wide variety of habitats on the trail include Lake Tohopekaliga waterfront and islands, a pristine cypress swamp, an orange grove and wild grasslands.
 
For a more cuddly experience, Green Meadows Petting Farm has over 50 acres of animals to greet and family rides. If you’re visiting during spring training, stop in to see the Houston Astros practice as Osceola County Stadium. 
 
Of course, the options for fun aren’t limited to the parks. For golfers, Central Florida is a veritable paradise. With dozens of award-winning courses within a few square miles, you should definitely pack your clubs when visiting. If your family prefers mini-golf you have plenty of options, too. 
 
Kissimmee Lakefront Park features a playground and splash park for kids, BBQ grills for a cookout, and fishing piers. For more along these lines, nearby St. Cloud Lakefront Park and Beach offers a family picnic area and volleyball court. Located along the breathtaking Lake Tohopekaliga, these parks are great options to spend a relaxing afternoon.
 
Spend your evenings in Old Town Kissimmee, where every Saturday night there is a classic car cruise through the city streets, accompanied by a live band. In Old Town you’ll also find everything from high end retailers to souvenir shops. There is live music playing almost every night, and restaurants offering pizza, Tex-Mex, or anything in between. 
 
Annual events
 
Osceola Heritage Park has a variety of world-class shows and sporting events. You'll find the Silver Spurs Rodeo here, too. It's a real crowd pleaser, offering a taste of the Wild West and reflective of the area's ranching heritage. You can watch bull riding, bronco bucking, barrel racing, steer wrestling, team roping, and even those funny rodeo clowns.
 
Kissimmee vacation home rentals on FloridaRentals.com
 
Booking one of our vacation homes in Kissimmee on FloridaRentals.com can save you 20% over our competitors. Plus, we have a wide array of inventory appealing to any group size or traveler tastes. Book today!