Kissimmee Vacation Rentals

(360 rentals)
Private South Facing Pool w/ Jacuzzi & Kiddy pool - 4 bed, 3 bath

$164

per night

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Key Amenities

  • Air Conditioning
  • Private Pool

About this property

RECENTLY REFURBISHEDLuxurious 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

"Superb Villa"
Reviewed October 18, 2019

The villa is located in a gated community in a quiet area - very safe and secure. Villa facilities are excellent with pool, hot tub and games room. Well maintained by local staff. Pool is south facing ...

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Large spacious home/Private pool/Close 2 Disney

$165

per night

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Key Amenities

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

About this property

Spacious, Clean family sized home with a fantastic open concept setting. Located within a gated resort community only 7 miles to Disney, and minutes to shops/restaurants makes the location ideal. The home has been freshly painted, decorated with brand new living room furniture. Perfect for social settings, ...

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Property Type

Kissimmee House

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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

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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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Modern 5BD 5BA Windsor at Westside Sleeps 14 Pool/Spa Games Room TV Loft

$189

per night

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Key Amenities

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

About this property

5 Bedrooms 5 Bathrooms SLEEPS UP TO 14 Family Room with large HD Cable TV Upstairs TV Loft/Den is a great kids hang out space All bedrooms with Flat Screen TVs Fully Equipped Chefs Gourmet Kitchen with Granite Counters and Stainless Steel Appliances Formal Dining Room seating 8 plus breakfast bar ...

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Property Type

Kissimmee House

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Bella Vida 6 Bedrooms Private Pool *Disney Area*

$180

per night

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Key Amenities

  • Air Conditioning
  • Pool
  • Private Pool

About this property

Extraordinary 6 bedroom, 5.5 bathroom Villa with private pool located in a gated resort community of Bella Vida. Located in Kissimmee just a few minutes from Disney theme parks.· 6 Bedrooms · 5.5 Baths · Modern kitchen is fully equipped and includes refrigerator, stove, mircowave ...

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Property Type

Kissimmee Villa

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The Princess Villa in Emerald Island Close to Disney World

$200

per night

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Key Amenities

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

About this property

Welcome to our beautiful villa close to Disney World . Our home fully is fully furnished and all the amenities to make your stay very enjoyable and comfortable. We have 2 kids theme rooms that little kids will enjoy sleeping in. We have 3 bunk beds in each of the theme rooms. In the garage has been ...

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Property Type

Kissimmee Villa

"Met expectations"
Reviewed October 16, 2019

Pros: It was an easy process and easy check in. Home was in a nice convenient area and met my group needs. Home was equipped with needed items. Had excess to resort amenities.Cons; There was extra ...

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Gigantic Pool 6 BR 4 BA, Two Themed Bedrooms, XBox/Games room

6 BR | 4 BA | Sleeps 13 | Quick View

Distance to park: 3 miles to Disney World Animal Kingdom

$249

per night

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Key Amenities

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

About this property

Welcome to BigPoolVilla!Our 6 bed (3 en-suite masters) 4.2 bath villa (with a spectacular pool) is where you want to be - as close to Disney as it gets, only at 2 miles from Disney in the prestigious Rolling Hills at Formosa Gardens Estate on a QUIET street.The Pool is Gigantic it's in the top ...

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Property Type

Kissimmee Villa

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❤️ Make Your Memories Magical ❤️ Family Friendly ❤️ 4 Miles to Disney

5 BR | 4 BA | Sleeps 12 | Quick View

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

$360

per night

View Details

Key Amenities

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

About this property

Imagine coming home at the end of an exhilarating day at the theme parks...You grab a refreshing drink from the fridge, flake out on the sofa in the outdoor living area right by the pool and reminisce about all the amazing things you did that day.The kids are splashing around in the pool, you ...

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Property Type

Kissimmee House

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Heritage Charm - 3 Bedroom Luxury Condo | Top Floor with Amazing Views

$89

per night

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Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Pet Friendly

About this property

This spectacular third floor 3 bed, 2 bath 1,352 sq ft. condo in Heritage Crossing has amazing views over 5 different holes on the Reunion Palmer golf course. Enjoy beautiful sunsets from your own private balcony with the magnificent heritage crossing pool and hot tub just a few steps away. The living ...

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Property Type

Kissimmee Condo

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"The Waters Edge" This Really is The Classiest of Them All - Award Winning Home.

7 BR | 6 BA | Sleeps 22 | Quick View

Distance to park: 2 miles to Disney

$450

per night

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Key Amenities

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

About this property

WOW!!! Even the other villa owners say this about our home, If you are looking for the best, go no further. This is strictly for you sun seekers, as apart from visiting the Mouse; the sun after all is another great reason to visit Florida. This home has a elegantly-shaped, 36-foot by 20-foot, heated, ...

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Property Type

Kissimmee Villa

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Designer 7BD 5BA Windsor at Westside Private Pool Spa TV Den/Loft Games Room

$315

per night

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Key Amenities

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

About this property

7 Bedrooms 5 Bathrooms Family Room with large HD Cable TV Upstairs TV Loft/Den with HD Cable TV All bedrooms with Flat Screen TVs Fully Equipped Chefs Gourmet Kitchen with Granite Counters and Stainless Steel Appliances Formal Dining Room seating 8 plus breakfast bar and outdoor dining Private ...

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Property Type

Kissimmee Villa

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Encantada 3116

4 BR | 3 BA | Sleeps 10 | Quick View

$105

per night

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Key Amenities

  • Kid Friendly
  • Pool
  • Private Pool

About this property

Townhome - ENCANTADA RESORT Lovely 4 bedroom, 3 bathroom townhome with private pool located in a gated resort community of Encatada. Located in Kissimmee just a few minutes from Disney theme parks.Cable and high speed internet Our spacious townhome has a lounge area which seats 8-10 guests. Dining ...

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Property Type

Kissimmee Townhome

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4 Bed 8541LI Emerald Island Resort

$130

per night

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Key Amenities

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

About this property

Cedar Key is a very spacious executive home overlooking the woodland conservation area in the high quality, resort community Emerald Island which is only a few minutes drive from Disney World. It has 4 bedrooms, 3 bathrooms and a brilliant games room.Emerald Island is a unique resort style gated community ...

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Property Type

Kissimmee House

"Amazing house and outstanding hosts"
Reviewed August 27, 2018

Had an amazing time at this beautiful villa, could not have wished for better. Hosts were extremely helpful and responded so speedily I couldn’t believe it! We will be back!

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Luxury 4 Bed Villa on gated Resort. Private pool/jacussi. Close to Disney.

$120

per night

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Key Amenities

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

About this property

Our luxury 4 bedroom home is located within the top rated community of Lake Berkley.The villa is furnished to a very high standard and is fully Air-conditioned throughout keeping the villa cool in the warm Florida weather.The tastefully furnished lounge has two large comfortable sofas and is equipped ...

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Property Type

Kissimmee Villa

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Solara Luxury | Amazing Pirate Ship & Surf Van Custom Bunk Beds,

$330

per night

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Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Pool
  • Private Pool

About this property

If You're Looking For One Of The Best 5 Bedroom Vacation Homes In Solara Resort, Or Central Florida, Look No Further!Located just minutes from Orlando’s theme parks, shopping, dining and other area attractions, this luxury villa is located in Solara Resort. Solara Resort is jusStay close to ...

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Property Type

Kissimmee House

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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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Up-to-date calendar-Quick response-Easy to reserve-Near Disney-Clean-Low cost!

4 BR | 3 BA | Sleeps 8 | Quick View

22

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.No pets.This wonderfully located ...

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Property Type

Kissimmee House

"House as advertised in the perfect location for a Disney Vacation"
Reviewed January 9, 2020

Disney was 10 minutes away and with the traffic in that area this was a supper bonus. We way more than just Disney and still central location (many toll roads so take small bills and many quarters). House ...

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South facing heated pool and spa

6 BR | 4 BA | Sleeps 12 | Quick View

4

Distance to park: 3 miles to Disney World

$175

per night

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Key Amenities

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

About this property

Situated in the Window Hills resort community about 2 miles from Disney, this 6-bedroom, 4-bath vacation rental home specializes in providing fantastic Florida vacations! With 2,812 square feet and accommodations for 14, guests can enjoy not only the private pool and spa in the enclosed lanai but also ...

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Property Type

Kissimmee House

"Very, nice and closed to Disney"
Reviewed January 8, 2020

Es muy céntrico y muy callado y seguro el lugar además limpio y la recepción muy amables en todo momento

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Fantastic 5BD 4BA Private pool/spa PLUS Windsor at Westside Resort Facilities!

$193

per night

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Key Amenities

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

About this property

5 Bedrooms 4 Bathrooms Family Room with large HD Cable TV All bedrooms with Flat Screen TVs Fully Equipped Chefs Gourmet Kitchen with Granite Counters and Stainless Steel Appliances Formal Dining Room seating 6 plus breakfast bar and outdoor dining Very Private screened Pool and Spa with Lanai with ...

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Property Type

Kissimmee House

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Fantastic 9BD 6BA Sleeps 20 Home Cinema, Game Room, Pool Spa Free use of Resort

$290

per night

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Key Amenities

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

About this property

9 Bedrooms 6 Bathrooms Sleeps 20 Family Room with large HD Cable TV Upstairs Movie Loft with Projection Cinema Screen All bedrooms with Flat Screen TVs Fully Equipped Chefs Gourmet Kitchen with Granite Counters and Stainless Steel Appliances Formal Dining Room seating 18 plus breakfast bar and ...

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Property Type

Kissimmee House

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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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5 Star Villa with private pool and lake view. Gated Resort near Disney.

$115

per night

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Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Pool
  • Private Pool

About this property

This stunning 4 Bed 2 Bath Villa enjoys one of the premier positions on Lake Berkley Resort with an unspoilt beautiful view over the lake. Enjoy breakfast, lunch or dinner on the pool patio whilst watching the wildlife on the lake. If you enjoy fishing then you only need to walk a few yards to fish in ...

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Property Type

Kissimmee Villa

"My stay at 1042 Berkley resort"
Reviewed July 10, 2019

The Villa was excellent location we were very impressed by the immaculate condition of the said Villa and had Wonderful stay would recommend your villa to anyone also got great service from Management ...

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3 Miles to Disney! Pool, Games Room, WiFi, BBQ, *FREE Spa Heat from May-Sept*

$145

per night

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Key Amenities

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

About this property

SPECIAL PROMOTION! FREE spa heat for all stays from May - September!Well kept spacious 4 bedroom 3 bath pool home located in the Emerald Island Resort only 3 miles from Walt Disney World! Excellent one floor layout perfect for families of all ages.Clean & comfortable! With 2 MASTER BEDROOMS ...

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Property Type

Kissimmee House

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Southwest Facing Pool with a Lake View 6 Bed 5.5 Bath Lady Bug Villa

$225

per night

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Key Amenities

  • Full Kitchen
  • Private Pool

About this property

Home Description:Home Name: Ladybug VillaSpacious Executive Lakeview with Southwest facing pool home in the 24 hour guard gated community of Emerald Island. All the amenities for you to enjoy including Wi-Fi, Large Pool/Spa & Game Room. This 2 storey home has a Master Bedroom with ensuite ...

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Property Type

Kissimmee House

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Beautiful Reunion. 5 BD 4.5BA. Balcony Views. Private Pool. Tiki Bar Game Room.

$242

per night

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Key Amenities

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

About this property

This beautiful 5 bedroom golf view pool home has been constructed by one of Reunion's leading builders and boasts many upgrades throughout. Located on the west side of the resort which is becoming the most prestigious location for rental homes in Central Orlando. No other resort can compare to Reunion ...

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Property Type

Kissimmee House

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9 Bedroom Home in Gated Community With Pool- Windsor at Westside

9 BR | 6 BA | Sleeps 18 | Quick View

Distance to park: 9 miles to Disney Magic Kingdom

$280

per night

View Details

Key Amenities

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

About this property

This 9 bed/6 bath home features a spacious king bedroom with ensuite downstairs. Enjoy the open concept main floor living area with a large family room looking out to the covered lanai, patio and pool. Additionally, there is a second king bedroom on the floor with access to a full guest bathroom. Upstairs ...

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Property Type

Kissimmee House

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

$349

per night

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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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Gorgeous Modern Luxurious W/ pool, hot tub, fitness centre mins away from Disney

$143

per night

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Key Amenities

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

About this property

Welcome to 7558 Sunville Avenue, your home away from home. This luxurious townhome at Summerville Resort features 3-bedroom, (plus a bonus room) and 3.5 bathrooms easily accommodating up to 8 guests comfortably. This brand new luxury townhome is perfect for a family or a big group who are coming to enjoy ...

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Property Type

Kissimmee Townhome

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Golden Villa | 6 Bed 4 Bath Pool Home with Golf Course Views in Reunion Resort

$235

per night

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Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Pool
  • Private Pool

About this property

Enjoy comfort during your next vacation in this gorgeous 6 bedroom 4.5 bath, the perfect home for you and your family to stay in. Located in the Reunion Resort allows for you to easily access world-famous theme parks and attractions.As soon as you pull into the driveway of your new vacation home you’ll ...

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Property Type

Kissimmee Villa

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Beautiful 3 Bed villa with own South facing private pool. Close to Disney.

$110

per night

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Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Private Pool

About this property

We welcome you to our beautiful 3 Bed 2 Bathroom villa with your own private south facing pool.The villa benefits from 2 large sitting rooms, ideal when the kids and adults want their own space. Both sitting rooms have comfortable leather sofas.Large screen TV and games console.Full air conditioning ...

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Property Type

Kissimmee Villa

"clean, functional and affordable base for our holiday"
Reviewed October 23, 2019

great location for Disney theme parks and shopping, restaurants, quick responses from owner and property management company, enjoyed the clean pool.

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7 BR pool home located in Terra Verde Resort

7 BR | 4.5 BA | Sleeps 14 | Quick View

Distance to park: 10 miles to Walt Disney World

$210

per night

View Details

Key Amenities

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

About this property

Enjoy plenty of room for your family and friends in this Orlando vacation home in one of the best locations in the area, Terra Verde Resort in Kissimmee. This 7-bedroom with 4.5 baths sleeps up to 14. Your fun begins the minute you open the door!  All ...

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Property Type

Kissimmee House

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Fun Filled Florida Holidays 5

1 BR | 1 BA | Sleeps 5 | Quick View

$75

per night

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Key Amenities

  • Air Conditioning
  • Kid Friendly
  • Pet Friendly
  • Pool
  • Rentals by Owner

About this property

High End with light and airy decor and 1.5 miles away from Disney. Our beautiful home is minutes to Disney with shopping and restaurants right around the corner. We put allot of time and money into our unit and most importantly try our best to make the whole experience memorable Staying in our home is ...

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Property Type

Kissimmee Condo

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Affordable Comfortable 3BD 3BA Encantada Resort with Hot Tub

$108

per night

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Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • Pool

About this property

The superb 3 bedroom townhouse newly furnished has all the comfort of a private home. It has a fully equipped kitchen, all linens including towels, a large living and dining areal, alarm clock with radio and television in all bedrooms, free wireless Internet (Wifi), free local and long distance calls ...

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Property Type

Kissimmee Townhome

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5 Bedroom 3 Bathroom - South facing vacation rental Villa near Disney

$135

per night

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Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Private Pool

About this property

Planning to visit Disney during 2020How would you like to rent our 5 bed 3 bath rental villa that has its own south facing screened private swimming pool that is located on the exclusive Lake Berkley gated Resort in Kissimmee Orlando Florida.We are just minutes from the theme parks like Disney ...

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Property Type

Kissimmee Villa

"Great visit"
Reviewed November 19, 2019

We had a lovely home and very relaxing holiday. Everyone was very helpful and a beautiful well kept grounds and area. Will be coming back.

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Waldo's in Windsor Hills, 5 bedroom, All EnSuite, Pool/Spa Villa

$200

per night

View Details

Key Amenities

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

About this property

Waldo's Windsor Hideout is a Spacious Luxury Villa fully furnished modern open plan style, finished in a warm florida colour scheme. Find Waldo, he is hiding in every room!We offer all the faciities that you could want in this comprehensively equipped villa. We include Fully Air Conditioned rooms, ...

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Property Type

Kissimmee Villa

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HUGE POOL AND SPA

4 BR | 2 BA | Sleeps 7 | Quick View

$85

per night

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Key Amenities

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

About this property

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. SHADED PATIO WITH TABLE AND CHAIRS AND BBQ GRILL.KING, KING AND 4 TWIN BEDS WITH THEMED TWIN BEDROOMS - LITTLE MERMAID AND DORY. ...

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Property Type

Kissimmee House

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Family Friendly Golf View Home, South Facing Pool & Tiki Bar

$169

per night

View Details

Key Amenities

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

About this property

Our beautiful 5 Bed, 4 Bathroom home is located on a generous corner plot. With a south facing Pool and stunning views over the second tee of the Arnold Palmer Golf Course on Reunion ResortIncluded within the rental is a one bedroom Guest Suite, ideally used for extended family.4 Bedrooms are ...

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Property Type

Kissimmee House

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Reunion Manor | Luxury 8 Bed Home, Custom Kids Bedrooms, Balcony w/ great views

$740

per night

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Key Amenities

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

About this property

Truly one of a kind custom, luxury home situated inside of the world famous Reunion Resort. The home is located within the well established Homestead community boasting spectacular views of the Independence golf course.Stepping into the grand entrance of the exquisitely designed home, you will be ...

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Property Type

Kissimmee House

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

3 BR | 2 BA | Sleeps 6 | Quick View

4
Owner special: BOOK NOW FOR SPRING & SUMMER. STAY 6 NIGHTS GET THE 7th NIGHT FREE ON ALL NON HOLIDAY WEEKS.

Distance to park: 5 miles to Walt Disney World

$99

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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Florida Hills Luxury Pool Home with Hot Tub, Kid's Pool, Pool, Games Area & W-Fi

4 BR | 3 BA | Sleeps 9 | Quick View

Distance to park: 11 miles to Hollywood Studios

$142

per night

View Details

Key Amenities

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

About this property

4 Bedrooms, 3 Bathroom Pool Home, Sleeps 9, Close to Theme Parks"Florida Hills" our family owned 4 Bedroom 3 Bathroom Luxury Family Vacation Home has High Speed Wireless Internet Access, Hot Tub, heated swimming pool, separate children's pool and Games Area.Our pool home is only a 10 ...

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Property Type

Kissimmee House

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The Formosa Grand Mansion! Lakefront! Infinity Pool & Spa! Cinema! Pure Luxury!

$571

per night

View Details

Key Amenities

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

About this property

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

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Property Type

Kissimmee Villa

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Disney by, Celabration, Kissimmee, family condo, gated, Free WI-FI

$85

per night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen

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 Kissimmee/Cerebration area Florida. Walking ...

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Property Type

Kissimmee Condo

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Windsor at Westside -RHS8989 Unit

$264

per night

View Details

Key Amenities

  • Air Conditioning
  • Kid Friendly
  • Pool
  • Private Pool

About this property

This home is simply luxurious and waiting for you to come and enjoy all that it has to offer! Boasting 6 bedrooms and 4.5 baths, this home is not shy when it comes to space. To begin, each living space this home provides is absolutely stunning. As a part of the Grand Collection, this home is expertly ...

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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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Disney Retreat

3 BR | 2 BA | Sleeps 7 | Quick View

$110

per night

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Key Amenities

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

About this property

No booking fees and a great deal if you stay at least two weeks in February - ASK THE OWNER! Welcome to this beautifully furnished gorgeous 3 - bedroom and 2-bathroom Villa. This stunning home features a very private and heated ($) glistening swimming pool with plenty of seating, LED TV’s And ...

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Property Type

Kissimmee Villa

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Disney! Brand New 4 bed Private Pool IHR1041

$120

per night

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Key Amenities

  • Air Conditioning
  • Pool
  • Private Pool

About this property

At the center of our state-of-the-art, 18-acre amenity complex is the 13,000 square foot Grand Clubhouse that brings together a unique combination of amenities and activities for guests enjoying all that the community has to offer.From the huge Resort-style, heated pool to the FlowRider® Surf ...

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Property Type

Kissimmee Townhome

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MAGIC PLAYHOUSE

6 BR | 3 BA | Sleeps 12 | Quick View

$175

per night

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Key Amenities

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

About this property

This Villa was Newly Renovated and has a Modern and Luxurious updated look. The Spacious, 3200 square-foot property boost six bedroom , 3 Full Baths 6 miles from the Disney World entrance. This single villa comes complete with spectacular furnishings and major appliances and all the cooking accessories ...

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Property Type

Kissimmee House

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Disney Vacation Rental/heated pool - call for Nov/Dec. Specials now

4 BR | 3 BA | Sleeps 8 | Quick View

Distance to park: 3 miles to Mgm

$119

per night

View Details

Key Amenities

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

About this property

Beautiful 4 bedroom /3 bath private villa only 3 miles to Disney and other parks. Including heated pool/jacuzzi and game room. Free wifi and phone use in USA and Canada and PR. Fully furnished with all kitchen needs . Greatest location to shopping , all major restaurants and stores including supermarkets ...

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Property Type

Kissimmee Villa

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Refinished/Painted S. Facing Pool/Spa, Updated Decor, Near Disney, Sleeps 8

4 BR | 3 BA | Sleeps 8 | Quick View

6

Distance to park: 4 miles to Disney

$115

per night

View Details

Key Amenities

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

About this property

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

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Property Type

Kissimmee House

"Amazing Disney home!!!!!!"
Reviewed December 4, 2019

We just came home from vacation and my children are already talking about going back to the vacation home!! It had everything we needed and more!! My children loved the pool and game room! It was very ...

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☀️❤️ Sunshine Memories near Disney: ❤️ by Families

$200

per night

View Details

Key Amenities

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

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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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

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!