Kissimmee Vacation Rentals

(348 rentals)
Stunning home with private South facing pool. gated Resort close to Disney,

$114

per night

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Key Amenities

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

About this property

A stunning, larger than average, 4 Bed 3 Bathroom townhouse with a beautiful view of the conservation area at the rear as backdrop to our private pool. Unlike many other properties our pool is totally private and NOT overlooked by any neighbours. Situated on safe secure Bella Vida Resort. Close to shops ...

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Property Type

Kissimmee House

"Great owners"
Reviewed April 14, 2020

Unfortunately. My wife and i had planned our honeymoon for a 7 day stay. but because of the illness covid-19 they call it left us no other choice bit to halt and stay in pa. The owner was sympathetic ...

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Solara Sunshine | 7 Bed Home with Pool and Gameroom in Solara Resort

$245

per night

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Key Amenities

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

About this property

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 just a 5 minute (2.7 mile drive) from a Publix supermarket and restaurants. Enjoy unlimited access to all the 8 acre resort has plenty to ...

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Property Type

Kissimmee House

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Private Pool/6TVs/GasBBQ/Wifi, Man-guarded resort, 3 miles to Disney

$119

per night

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Key Amenities

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

About this property

One of the closest possible communities to Walt Disney World (less than 3 miles away), Emerald Island is a quiet oasis in which to spend your vacation. Emerald Island is an exclusive gated community less than a mile from the world famous US Highway 192 where you will find shops, restaurants, and entertainment. ...

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Property Type

Kissimmee Villa

"Perfect!"
Reviewed April 1, 2020

This home is absolutely beautiful! Very convenient and great neighborhood! Ann and Gary are awesome hosts:). We will be back!

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Modern 5BD 4BA Windsor at Westside Private Pool & Spa Games Room

$189

per night

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Key Amenities

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

About this property

5 Bedrooms 4 Bathrooms Family Room with large HD Cable TV Upstairs Loft 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 screened Pool ...

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Property Type

Kissimmee Villa

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Gino's Vacation Home

5 BR | 5 BA | Sleeps 10 | Quick View

2

$143

per night

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Key Amenities

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

About this property

Vacation Home 5.6 miles from Disney.This beautiful fully furnished with open floor plan, mediterranean style 5 bedroom 5.5 bathroom house is located just 5 miles from Walt Disney World and is only a 30 minute drive from Orlando International Airport. Not only is this home open and spacious, but private ...

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Property Type

Kissimmee Villa

"Unable to go due to pablum"
Reviewed April 20, 2020

We were unable to use this property, but dealing with the owner was a very positive experience. He answered promptly and had no issues cancelling and was extremely helpfully I would not hesitate to deal ...

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Windsor Hills resort Private Pool Home (FREE WATER PARK USE DURING STAY!)

6 BR | 3.5 BA | Sleeps 14 | Quick View

Owner special: Available Cancel For ANY Reason Travel Protection!

Distance to park: 2 miles to Disney World

$226

per night

View Details

Key Amenities

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

About this property

COVID 19 INFO UPDATED ON OUR WEBSITE, INCLUDES PAYMENT PLANS, CANCEL FOR ANY REASON COVERAGE, FLEXIBLE CHANGE DATE TERMS, DISCOUNTS FOR STAYS DURING PARK CLOSURES AS WELL AS DISCOUNTS FOR ADVANCE BOOKINGS.PLEASE SEE RATE NOTES FOR RATES FOR VARIOUS SEASONS AND SIZE HOMES 4-6BR Private pool homes ...

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Property Type

Kissimmee House

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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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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

$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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Solterra Paradise Villa | Extended Pool Deck, Movie Room, Amazing Kids Bedrooms

$599

per night

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Key Amenities

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

About this property

Located just minutes from Orlando's theme parks, shopping, dining and other area attractions, this luxury villa is located in Solterra Resort. Solterra resort is just a 5 minute (2.5-mile) drive from a Publix supermarket and other stores. There is also an IMAX movie theater and many other stores such ...

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Property Type

Kissimmee Villa

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Fairway Family Getaway - Amazing Games Room and Kids Bedrooms!

$299

per night

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Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Private Pool

About this property

Welcome to your Family Getaway! This beautiful 6 bedrooms 5.5 Bath is located in the Fairway Ridge community inside of the prestigious Reunion Resort with expansive, and breathtaking views of the sunset over the signature Jack Nicklaus course.Walk into your home away from home, and set your worries ...

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Property Type

Kissimmee House

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Luxury 4Bed/3Bath villa -private pool with spa on Gated Resort just off 192 road

$120

per night

View Details

Key Amenities

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

About this property

Single story villa on popular gated resort Terra Verde which has excellent Clubhouse facilities. Large open plan living area with fully fitted Kitchen (large American fridge with ice/water, microwave, oven, dishwasher, plenty of pans and cutlery and crockery). Breakfast nook and Dinning area plus ...

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Property Type

Kissimmee Villa

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Beautiful & Spacious Family Villa in Rolling Hills, Kissimmee 4BR / 2BA

$98

per night

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Key Amenities

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

About this property

***NO PETS***4 Bedroom / 2 Bathroom (1,822 sqft) Single Story South Facing Private Pool Electric Pool Heat is an additional cost.Living Room: TV / DVD Dining Area - Seats 6 Breakfast Table - Seats 4Master Bedroom 1: Queen/ TV / Garden Tub Bedroom 2: Double Bedroom 3: Twins Bedroom ...

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Property Type

Kissimmee Villa

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Solana Retreat - Rare Large Corner Lot, Walk to the Clubhouse

$169

per night

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Key Amenities

  • Air Conditioning
  • Full Kitchen

About this property

This beautiful 6-bed villa has lots of privacy with a screened-in pool & spillover spa surrounded by hedges and tropical plants. The back of the home also faces a large retention pond instead of neighboring lots and here you can get plenty of Florida sunshine. There are six sun loungers to share around ...

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Property Type

Kissimmee Villa

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One mile from Disney, Celabration, family condo, gated, Free WI-FI

3 BR | 2 BA | Sleeps 6 | Quick View

Distance to park: 1 miles to Disney Animal Kingdom

$85

per night

View Details

Key Amenities

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

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 distance ...

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Property Type

Kissimmee Condo

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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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LUXURIOUS 14B 13BA PRIVATE POOL/PATIO Sonoma Resort-2613CYA - Property 4831

$515

per night

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Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Private Pool

About this property

Be sure to visit our website to check availability on all our homes!Visit us at lostinthemagic . comSonoma Resort - Kissimmee, Florida is only 15 minutes to the area's main attraction... Walt Disney World. This brand new resort community sits nestled just outside of Orlando, between W. Osceola ...

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Property Type

Kissimmee House

"Vacation Home"
Reviewed September 25, 2019

For starters this home was absolutely beautiful!! The pictures shown here do not do it any justice. The neighborhood was really quiet, the tv’s were already set up to watch Netflix, Hulu, and Amazon Prime. ...

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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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Highest Ranked Home Newly Renovated Lowest Weekly Rate Price includes all Fees

$85

per night

View Details

Key Amenities

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

About this property

New Flooring New Air Conditioning ,New Mattresses, Gel Toppers , Keurig ,Our prices include everything! No hidden maid service fee or security fee or taxesOUR PRICES INCLUDE ALL TAXES AND FEESOur resort, is a Gated community  it is a 5 star resort only 5 minutes from the Disney Parks ...

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Property Type

Kissimmee Condo

"honest owner"
Reviewed March 7, 2019

unfortunately had to cancel last minute because of health to both my wife and I. owner was more than reasonable about problem. not everyone would have been more helpful as he was.

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Clean Luxurious Vacation home close to Disney World

6 BR | 6 BA | Sleeps 12 | Quick View

1
Owner special: Book your stay from now to August and get free use of the bbq.

$280

per night

View Details

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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Amazing 7BD 5BA Windsor at Westside. Game Room. Cinema Room. Pool & Spa

$315

per night

View Details

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 Loft with Cinema Screen All bedrooms with Flat Screen TVs Fully Equipped Chefs Gourmet Kitchen with Granite Counters and Stainless Steel Appliances Formal Dining Room seating 10 plus breakfast bar and outdoor dining Private screened ...

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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

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

4 BR | 3 BA | Sleeps 8 | Quick View

2

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

"Florida Vacation"
Reviewed May 30, 2020

Sadly we werent able to make this trip from Scotland due to virus. We were only partially refunded which was a bit disappointing. Lost £600 which is a lot to lose under the circumstances.

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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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Gated Resort, Spacious Town-home with pool and fancy club Paradise Palms Resort

$89

per night

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Key Amenities

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

About this property

Welcome to this beautiful vacation townhouse located in most desired Paradise Palms Gated Resort community, built in 2012. It is internationally known for its close to Walt Disney World (5 miles) and its paradise fancy clubhouse. It is also close to plenty of restaurants, shopping, and other recreational ...

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Property Type

Kissimmee Townhome

"Beautiful home"
Reviewed September 13, 2019

My family & I stayed in this amazing house & the service was good. We had no issues and everything was set up nicely to make payments convenient & easy. The hood vent stopped working & they came out to ...

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Windsor Palms Resort-2334CISPDITHP

$115

per night

View Details

Key Amenities

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

About this property

Windsor Palms Resort- Kissimmee, Florida is an upscale gated community located just 2 miles from Walt Disney World. This luxury resort sits nestled just off Hwy 192 in Kissimmee, Florida and is one of the most desired resorts in the Orlando area. During your stay, you will enjoy this well-appointed home ...

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Property Type

Kissimmee Townhome

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

5 BR | 4 BA | Sleeps 11 | Quick View

12

Distance to park: 4 miles to Disney World

$134

per night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly

About this property

Florida State License DWE5910390 (Near Disney) COME SWIM WITH MICKEY! This beautiful 5-Bed 4-Bath home located in the very popular community of Indian Creek is one of only three homes in the development with a Mickey Pool. Featuring two en-suites with private baths and three other bedrooms and two ...

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Property Type

Kissimmee House

"A great vacation destination."
Reviewed April 26, 2020

There were five adults in our group and each one of us had a great time at Mickey's Villa. When we needed extra lounge chairs for the pool area, Bob came right away with the extra chairs. The house is ...

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

4 BR | 3 BA | Sleeps 8 | Quick View

7

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

"Nice place, quiet street,"
Reviewed January 23, 2020

House was clean, beds comfortable, pool was too cool to use even with the heater. Close to Disney, walmart and restaurants.

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ULTRA LUXURY 6 BR VILLA MARGAUX W POOL NEAR DISNEY

6 BR | 5.5 BA | Sleeps 12 | Quick View

1

Distance to park: 10 miles to Disney

$235

per night

View Details

Key Amenities

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

About this property

Look no further for your family vacation getaway, introducing Villa Margaux! This gorgeous Spanish style villa located in the well known gated community of Bella Vida is truly one of a kind, boasting luxurious coastal interiors. This gem of a villa boasts 6 spacious bedrooms complete with en suite bathrooms, ...

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Property Type

Kissimmee Villa

"Amazing house, fully equipped"
Reviewed February 6, 2020

Everything was perfect. The house is very well equipped and very comfortable. The pool heater worked OK and we could really use it during the whole month we stayed. Game room is amazing. The lake view ...

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Beautiful Family Home Close to Everything.

$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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South facing heated pool and spa

6 BR | 4 BA | Sleeps 12 | Quick View

5

Distance to park: 3 miles to Disney World

$175

per night

View Details

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

"Family vacation"
Reviewed February 23, 2020

The house was perfect for us. The two masters were a big plus. Kids rooms were great and the addition of a crib helped a lot. We appreciatedhigh chair but had brought our own booster. The house was clean ...

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Champions Estate

8 BR | 5 BA | Sleeps 16 | Quick View

$305

per night

View Details

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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Westside Charm | 7 Bed Private Pool Home

$205

per night

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Key Amenities

  • Air Conditioning
  • Full Kitchen

About this property

Windsor at Westside is a gated vacation rental community close to Disney featuring an 8,000 sq.ft. clubhouse with the Tu Casa Bar & lounge, market & deli, video arcade, sundries shop & fitness center. Other fantastic amenities such as a playground, volleyball court & multi-purpose sports ...

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Property Type

Kissimmee House

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Toy Story Tower

6 BR | 4 BA | Sleeps 14 | Quick View

Distance to park: 5 miles to Disney World

$243

per night

View Details

Key Amenities

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

About this property

Toy Story Tower is an imposing, six bedroom vacation home located within the prestigious gated community of Windsor Hills Resort. Here, you can enjoy the very best in luxurious accommodation all while being located just minutes from Walt Disney World Resort as well as many other great attractions. As ...

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Property Type

Kissimmee House

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Your private oasis a step away from Disney is awaiting for your arrival !!!

$209

per night

View Details

Key Amenities

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

About this property

Disney on your Doorstep is just a charming, relaxing, and feel at home, kind of home... you know when you're sitting by the pool and the kids are having a ball, that you've picked the right spot.... our, wonderful 5 bedroom, 4 bathroom vacation home with private pool, spa & Game room in the exclusive ...

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Property Type

Kissimmee House

"Home away from Home"
Reviewed March 25, 2020

This was our second year staying at this home. The owner and management - Karen - are fantastic to work with. Lots of linens and pool towels, exceptionally clean, a an immediate feeling of home!!! ...

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Fairway Joy | 5 Bedroom Pool Home with Extended Pool Deck and Conservation Views

$209

per night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Pool
  • Private Pool

About this property

This luxurious and comfortable home is located in Reunion Resort and has 3,203 square feet of living space, complete with a pool and balcony. The location of this property allows you to enjoy the resort’s many amenities and attractions that central Florida has to offer.This vacation home is ...

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Property Type

Kissimmee Villa

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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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Paradise Breeze - Brand New 5 Bed Pool Villa

$190

per night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Pet Friendly

About this property

Paradise Breeze - Brand New 5 Bed VillaThis large 3,045 sq.ft pool home is located within the Patriots Landing neighborhood of the exclusive Reunion Resort.Patriot's Landing offers Key West-style luxury homes with pastel color schemes. This very distinctive neighborhood is surrounded on three ...

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Property Type

Kissimmee House

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Newly Decorated Beautiful Themed Villa -3 Miles to Disney-South Facing Pool

$136

per night

View Details

Key Amenities

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

About this property

Newly decorated villa in November 2019 contains new laminate floor in all bed rooms and family room and two theme rooms for the kids: Minions for the boys and Princesses for the girls. Your Vacation Villa is nestled on the exclusive Emerald Island Resort, one of the nearest top resorts to Walt Disney ...

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Property Type

Kissimmee Villa

"Princess and Minnions Rooms"
Reviewed February 17, 2020

The location of this home was very convenient. It was a very quiet neighbourhood. It was close to restaurants, grocery store, shopping malls, gas stations, souvenir shops, Disney, Seaworld, Universal ...

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EC_1100R Encore Leisure - Movie Room

$329

per night

View Details

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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Wyndham Reunion, Orlando 3 Bedrooms Minutes From Disney(Sleeps 8-10)

$159

per night

View Details

Key Amenities

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

About this property

3 Bedroom Villa, 3 Bath Deluxe Villa (Sleeps 8-10 Max) Reunion 3BD/2BA - At Reunion Resort you will experience a comfortable yet sophisticated vacation experience. Whether you are coming to Orlando to visit Theme Parks, Golf or looking for 'Me-Time' and relaxation, this Resort is suited for creating ...

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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

View Details

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

"Luxury"
Reviewed May 13, 2019

Very nice home lovely pool area for the kids beautiful neighborhood that we rent againThe kids wanted to stay in the pool the whole time in the house has so much room for our entire family spacious plenty ...

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Champions Escape | 2 Kids Bedrooms and Games Room with Pool Table, Screened Pool

$240

per night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Pool
  • Private Pool

About this property

airs you will find the master suite featuring a king bed with large en-suite bathroom with walk in showers and large counter space. There is a second bedroom downstairs with king bed and attached shared bathroom.Upstairs you will find the additional 6 bedrooms, 2 of which are kids themed rooms, a ...

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Property Type

Kissimmee House

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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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Lake Front Luxury Villa Closest to Resort Club House! Wood/tile floors.

9 BR | 6 BA | Sleeps 20 | Quick View

Distance to park: 5 miles to Disney

$288

per night

View Details

Key Amenities

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

About this property

This luxury vacation home is located in the Windsor at Westside upscale resort community - A perfect destination for DISNEY WORLD (10 minutes away), golf, and relaxing and celebrating with family and friends. It features 4369 sq. ft. living space and is luxuriously furnished with top line furniture,large ...

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Property Type

Kissimmee Villa

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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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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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Orlando condo with Pool View

3 BR | 2 BA | Sleeps 5 | Quick View

2

Distance to park: 20 miles to Disney World

$1

per night

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Key Amenities

  • Air Conditioning
  • Rentals by Owner

About this property

Preferred Jupiter Equestrian family community is a way of life that isn’t available anywhere else. It is common to see residence riding horses or driving a golf cart alongside the road. The community offers space and tranquility, Sidewalks, Nature Trails, Wildlife, Hiking, Biking, Playground, Country ...

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Property Type

Kissimmee Condo

"The location is amazing - the beach is on the doorstep! This is a great family-fri"
Reviewed April 5, 2019

The location is amazing - the beach is on the doorstep! This is a great family-friThe location is amazing - the beach is on the doorstep! This is a great family-friThe location is amazing - the beach is ...

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Beautiful lakeside villa with private pool.

$74

per night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Private Pool

About this property

Beautiful south facing lakeside villa with solar and electric heated pool. Great location for all the theme parks, Disney 20 mins, Seaworld 15mins, Universal 30 mins and Cocoa Beach/Kennedy Space Centre 45 mins. Local English management contact and fully inspected/licensed by the Florida Hotels Board. ...

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Property Type

Kissimmee Villa

"Really lovely rental"
Reviewed May 5, 2020

We were really surprised at how spacious the house was. The screened in pool area was pure heaven. Very close to lots of shopping and wonderful parks. Even the neighbors on both sides were great. We enjoyed ...

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Amazing 7BD 5BA Solara Resort. Private Pool/Spa. Cinema Room. Games Room.

$220

per night

View Details

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 Loft with Cinema Screen All bedrooms with Flat Screen TVs Fully Equipped Chefs Gourmet Kitchen with Granite Counters and Stainless Steel Appliances Formal Dining Room seating 10 plus breakfast bar and outdoor dining Private screened ...

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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!