Kissimmee Vacation Rentals

(349 rentals)
Disney Vacation Rental/heated pool - call for Sept/Oct. specials start at $89.99

$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 ...

View all property information

Property Type

Kissimmee Villa

Show less

Encantada Resort Townhouse with pool 3 bedrooms

Inquire for rates

View Details

Key Amenities

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

About this property

This amazing townhouse located at Encantada Resort has been recently upgraded. The fully equipped kitchen has new granite countertops and everything you need to eat at home or prepare some snacks for the parks. There is a dining set for 6 that shares the open plan with the living room where there is a ...

View all property information

Property Type

Kissimmee Townhome

Show less

Treat Yourself w/ Private South Facing Pool in Montego Bay, Kissimmee 3BR / 2BA

$83

per night

View Details

About this property

***NO PETS***3 Bedroom / 2 Bathroom (1,565 sqft) Single Story Electric Pool Heat is an additional cost. South Facing PoolLiving Room (Front) Living Room (Back): TV / DVD Dining Area - Seats 6 Breakfast Table - Seats 4Master Bedroom 1: QUEEN / TV / POOL ACCESS Bedroom 2: FULL / TV / ...

View all property information

Property Type

Kissimmee House

Show less

South facing heated pool and spa

6 BR | 4 BA | Sleeps 12 | Quick View

2

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 ...

View all property information

Property Type

Kissimmee House

"Ramsey condo"
Reviewed August 1, 2019

Reddington beach is amazing. Felt safe and family oriented. Right on the beach and close to many restaurants. Amazing sunsets, will come back again.

See all reviews

Show less

Stunning Villa Starlake | 6-Bedroom Pool Home with Lake View | Sleeps 12

6 BR | 3 BA | Sleeps 12 | Quick View

Distance to park: 5 miles to Walt Disney World

$139

per night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Private Pool

About this property

A warm inviting welcome awaits you and your family at our Vacation Pool Home - Closest to Disney! Our fully loaded pool home is equipped with everything to help ensure that you enjoy the best vacation ever and it's sure to 'TICK ALL THE BOXES' on your wish list! An spacious house has a beautiful swimming ...

View all property information

Property Type

Kissimmee House

Show less

Minutes From Mickey - 3Bed 3Bath Townhome with South Facing Pool

3 BR | 3 BA | Sleeps 6 | Quick View

7

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

$110

per night

View Details

Key Amenities

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

About this property

“Minutes-From-Mickey” is our beautiful townhome, situated in the 5-Star Windsor Palms Resort community less than 4 miles from Walt Disney World in sunny Central Florida, giving quick and easy access to the area’s many theme and water parks, golf courses, restaurants, shopping and other ...

View all property information

Property Type

Kissimmee Townhome

"We loved the townhome"
Reviewed May 17, 2019

We arrived on May 5, 2019 and for the next 10 days we totally felt at home in Jane's lovely, clean townhome. All the amenities were there for us - a fully ready-to live in environment (we just had to add ...

See all reviews

Show less

HUGE POOL AND SPA

4 BR | 2 BA | Sleeps 7 | Quick View

$85

per night

View Details

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. ...

View all property information

Property Type

Kissimmee House

Show less

Kissimmee, Florida Family Vacation Rental Home In Disney Area

$100

per night

View Details

Key Amenities

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

About this property

Welcome to family comfort and convenience minutes from Disney & other area attractions!Close to shopping, dining, golf and other recreational activities, this 4 bedroom, 2 bathroom, air conditioned, pool home is single storey, with fenced & locked rear yard for extra privacy & security ...

View all property information

Property Type

Kissimmee Bungalow

Show less

*Fabulous South Facing Lake View 6 Bed Villa*

$228

per night

View Details

Key Amenities

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

About this property

Sunset Villa, located in the ideally situated community of Sunset Lakes, offers you and your party the unique opportunity to spend your Florida vacation in a quiet rural setting, yet only a short drive away from the theme parks, restaurants, shopping malls and all the many attractions Orlando has to offer.Sunset ...

View all property information

Property Type

Kissimmee Villa

Show less

NEW - Disney Themed Rooms, Exclusive Resort w/ Waterpark, 2 miles to Disney!

6 BR | 4 BA | Sleeps 14 | Quick View

Owner special: Special Offer - Last minute deals available for November and December!! Rates starting at $179 USD

$225

per night

View Details

Key Amenities

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

About this property

DISNEY THEMED ROOMS! Spacious villa w/PRIVATE POOL and RESORT AMENITIES. This villa is located in the upscale, family friendly, 5 star Windsor Hills Resort and located at the doorsteps of Walt Disney World!!!We are newly listed (August 2019) and looking to get the word out. For the months of ...

View all property information

Property Type

Kissimmee Villa

Show less

Large villa on secure and safe gated Resort, with private pool. Close to Disney.

$120

per night

View Details

Key Amenities

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

About this property

We invite you to stay at our villa which is a 4 Bedroom 3 Bathroom luxury vacation home, however there is a sofa bed in the sitting room so the villa can sleep 10 guests.The villa is fully equipped with everything you will need including air con throughout, private pool, WiFi, fully equipped kitchen, ...

View all property information

Property Type

Kissimmee Villa

"It was a great vacation home"
Reviewed August 4, 2019

Vacation home was very clean, everything as promised, check in process was smooth. We had a great time.

See all reviews

Show less

Gino's Vacation Home

5 BR | 5 BA | Sleeps 10 | Quick View

1

$143

per night

View Details

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 ...

View all property information

Property Type

Kissimmee Villa

"Excellent Orlando Villa"
Reviewed April 15, 2018

Hi Gino & Eva Just wanted you to know we had a fantastic time in your fabulous Villa/Home We all enjoyed every part of it Ideally positioned Large double bedrooms with comfy beds Excellent pool ...

See all reviews

Show less

NEW! Encore Reunion Home w/Pool - 20 Min to Disney.

$223

per night

View Details

Key Amenities

  • Air Conditioning

About this property

Experience a unique hybrid of family-fun and high-end luxury at Orchid in Encore Reunion, an 8-bedroom, 7-bathroom vacation rental home in Kissimmee. Located at Encore Club, this 3,412-square-foot house for 18 guests sits within 20 minutes of the Disney parks and offers easy access to a pool, clubhouse, ...

View all property information

Property Type

Kissimmee House

Show less

4 Bed 8541LI Emerald Island Resort

$130

per night

View Details

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 ...

View all property information

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!

See all reviews

Show less

Executive Condo in Stunning Windsor Palms Resort !!! 3BR / 2BA Heated Pool

$70

per night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly

About this property

3 Bed / 2 Bath CONDO (3rd Floor) Community Pool (Heated) Small Movie Theatre Gym Living Room : TV Dining Area - Seats 4 Breakfast Bar - Seats 2 Master Bedroom 1 : Queen / TV Bedroom 2 : Full Bedroom 3 : Twins Free Wi-FI access

View all property information

Property Type

Kissimmee Condo

Show less

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 ...

View all property information

Property Type

Kissimmee House

Show less

SPECIAL FOR SEPTEMBER - CLEAN HOUSE 7 MINUTES FROM DISNEY FOR FAMILIES BBQ

$375

per night

View Details

Key Amenities

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

About this property

This Luxurious home is only 7 minutes from Disney It is close to to a few golf courses. It is a great for families and groups. If you are coming with basket ball teams, volley ball teams, dance competions, soccer, tennis or any other sports event in Orlando this home is perfect for a group of 12 guests.This ...

View all property information

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 ...

See all reviews

Show less

Holiday Rest

3 BR | 2 BA | Sleeps 7 | Quick View

1

$98

per night

View Details

Key Amenities

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

About this property

Thinking about taking a Florida Vacation? Why not stay at our wonderful 1950 Sq ft property with three spacious bedrooms two bathrooms. Feature a fantastic floor plan with ceramic Tiles throughout. Master bedroom has a King sized bed, TV, Jacuzzi, stand up shower, his /her sink and a walk in closet. ...

View all property information

Property Type

Kissimmee House

"Our vacation house"
Reviewed February 19, 2018

Found the property very nice, close to all our vacation needs, owner and property manager attentive and friendly, on a personal note the pool did not get warm enough for my taste, good experience

See all reviews

Show less

End of the year special--New Waterpark-Windsor Hill Luxury 6B/4B/Pool house

$185

per night

View Details

Key Amenities

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

About this property

Large 6 Bedroom Executive Vacation Home With 2 Themed Kids Rooms, Sleeps 14 Disney Dream Vacation Villa is located in the #1 rated upscale five-stars Windsor Hills Resort at the doorstep of Disney world.This property was newly thoroughly renovated. Web photos here won't be able to show all the beautiful ...

View all property information

Property Type

Kissimmee House

Show less

Nice 7 BR/5 BA Luxury Villa with POOL/SPA,Wi-Fi,LCD TVs, BBQ,3 miles to Disney

7 BR | 4.5 BA | Sleeps 16 | Quick View

2

Distance to park: 3 miles to Disney world

$149

per night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Pet Friendly
  • Pool

About this property

Newly furnished luxurious 2-story Villa home opens its door to welcome you! This villa is furnished with two master suite and one large bedroom with upscale King-size beds; two bedrooms with queen-size beds; and two bedrooms with two twin-beds each. All bedding and mattresses are Brand New with top quality ...

View all property information

Property Type

Kissimmee Villa

"Family Vacation"
Reviewed July 27, 2019

I must say this was a very nice house. It was very clean and easy to access. The owners Amy and Gary are very nice and they even remembered that we had rented from them a couple of years ago. The house ...

See all reviews

Show less

Fairway Ridge Paradise

5 BR | 4 BA | Sleeps 10 | Quick View

1

$240

per night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Pool
  • Private Pool

About this property

This beautiful home is located in the Fairway Ridge South neighborhood in the Westside of Reunion Resort and overlooks the Tradition golf course designed by Jack Nicklaus. Reunion Resort is only 6 miles to the gates of Disney!The large deck, pool, and spa of this luxurious vacation rental home are ...

View all property information

Property Type

Kissimmee House

"Family Vacation"
Reviewed September 30, 2018

Beautiful community and homes in peaceful surroundings.

See all reviews

Show less

Snow White Villa Close to Disney World

6 BR | 4 BA | Sleeps 14 | Quick View

Distance to park: 2 miles to Disney World Resort

$200

per night

View Details

Key Amenities

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

About this property

We offer a luxurious decorated home close to Disney World Resort. Kid friendly house, with plenty of things to do in the house. The house is very close to Orlando Disney World Resort. It has 6 bedrooms and 4 bath. There is plenty of space to accommodate a large family gathering for 2 or even 3 families. ...

View all property information

Property Type

Kissimmee Villa

Show less

HUGE 6- Bed Disney/Orlando Resort Vacation Home

6 BR | 5 BA | Sleeps 12 | Quick View

1

Distance to park: 6 miles to Walt Disney World Resort

$229

per night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Pool
  • Private Pool

About this property

Storey Lake Resort is one of the newest Disney/Orlando area Florida vacation rental communities offering a world-class family-friendly resort experience.Ideally located at the corner of State Road (SR535) and Osceola Parkway Kissimmee, Storey Lake Resort grants easy access to nearby major attractions ...

View all property information

Property Type

Kissimmee House

"Christmas Vacation Rental"
Reviewed January 3, 2019

We totally enjoyed our family Christmas vacation in Florida. The rental was close to everything we needed but we did find that the kitchen lacked a few of the essentials. We ended up having to purchase ...

See all reviews

Show less

Tripoli Court at Windsor Westside

9 BR | 6 BA | Sleeps 24 | Quick View

2

Distance to park: 2 miles to Sunday's Grill

$288

per night

View Details

Key Amenities

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

About this property

For last minute rentals or longer extended rentals, please inquiry about our discounted rates.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. ...

View all property information

Property Type

Kissimmee Villa

"Family Vacation"
Reviewed July 21, 2019

We had 19 family members for this reunion. The size of the house was perfect. The kids enjoyed the pool very much.Having four master suites was perfect.The upstairs loft area was a great hangout ...

See all reviews

Show less

***At Disney's Door*** Just 5 minutes to Animal Kingdom!

4 BR | 3 BA | Sleeps 10 | Quick View

1

Distance to park: 3 miles to Animal Kingdom, DIsney World

$193

per night

View Details

Key Amenities

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

About this property

Enjoy a magical Disney-style vacation at this luxurious Emerald Island Resort house. This luxurious private home includes a custom-built over-sized south-facing pool with Jacuzzi/spa. Constructed in the elegant Emerald Island Resort, this house offers all the latest features in vacation rentals. With ...

View all property information

Property Type

Kissimmee House

"Excellent Experience"
Reviewed February 27, 2018

This was a last minute booking so we were very pleased that Nancy could accommodate us.Having stayed here before we knew the villa and the service that Nancy would provide and once again we were not disappointed. ...

See all reviews

Show less

Florida Lake VILLA #5

7 BR | 4 BA | Sleeps 16 | Quick View

1

$246

per night

View Details

Key Amenities

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

About this property

7 Bedroom homes in a quiet location with Lake view. Villa 5 is one of 5 homes we own in the same street on Crescent Lakes and is ideal for large groups, family reunions, church groups or sports teams. It has an over-sized deck and is south facing. Like all our other homes in Crescent Lakes the home offers ...

View all property information

Property Type

Kissimmee Villa

"Great place to stay!"
Reviewed February 11, 2019

We loved staying at this house! It had everything we needed and my boys loved the game room and pool/hot tub! I would definitely rent here again! They were also very accommodating during our stay!

See all reviews

Show less

5 Bedrooms Reunion Resort 106

5 BR | 5 BA | Sleeps 12 | Quick View

$425

per night

View Details

Key Amenities

  • Air Conditioning
  • Oceanfront
  • Pool
  • Private Pool

About this property

Located just 5 miles from Disney World, this expansive home offers more than 3,617 sq ft of luxury living space and can sleep up to 12 guests. Inside offers a stylish open-plan living and dining area, a fully-equipped kitchen and immaculate en-suite bedrooms, one of which features access to a private ...

View all property information

Property Type

Kissimmee House

Show less

86468 6-Bedroom Pool Home, Resort Amenities.

6 BR | 5 BA | Sleeps 12 | Quick View

Distance to park: 5 miles to Walt Disney World Resort

$249

per night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • Pool

About this property

May Madness Special! $25 OFF PER NIGHT! Offer code: MAYMAD *New bookings only-restrictions applyJust 5 minutes to Disney and all of the amenities of a 5 star hotel! This 3,014 sq feet vacation rental pool home offers 6-bedrooms, 5-baths, a Private Pool, Upgraded Granite Counter Tops and has plenty ...

View all property information

Property Type

Kissimmee House

Show less

Great value Cane Island Condo

3 BR | 2 BA | Sleeps 6 | Quick View

Distance to park: 3 miles to Disney World

$99

per night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • Pool

About this property

***SPECIAL OFFER: BOOK ANY DATES AND STAY BEFORE NOVEMBER 20TH AND I WILL DISCOUNT THE RATE. CONTACT ME TO GET THIS SPECIAL OFFER**** Welcome home to Cane Island Apartments! Located on the north side of Kissimmee, residents of our wonderful apartment community enjoy many amenities including an extensive ...

View all property information

Property Type

Kissimmee Villa

Show less

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. ...

View all property information

Property Type

Kissimmee Villa

"We wish we could keep this a secret"
Reviewed September 14, 2019

What a wonderful house. The pool, the space, the location was just perfect. We visited Universal Parks and Disney within minutes and had time to swim each evening in the beautiful refreshing private pool. ...

See all reviews

Show less

DISNEY Family Vacation / Lakefront Townhome / New Bedding / 4 Miles To Disney!

4 BR | 3 BA | Sleeps 8 | Quick View

Distance to park: 4 miles to Disney Parks

$99

per night

View Details

Key Amenities

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

About this property

Your Dream Family Vacation....Close to Every Major Attraction...Disney's Magic Kingdom, Universal Studios, Epcot. Sea World, Animal Kingdom, etc. Secure ...Gated Resort.....Very SAFE! Our Totally Re Modeled....4 Bedroom Town-home Looks Brand NEW! Our View from the Balcony, is the BEST in The Club ...

View all property information

Property Type

Kissimmee Townhome

Show less

❤️ 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 ...

View all property information

Property Type

Kissimmee House

Show less

Streaming Palms Villa - 5 mile to Animal Kingdom

$130

per night

View Details

Key Amenities

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

About this property

This spacious vacation rental has 5 bedrooms, 4 full bathrooms, offers accommodations for 10 travelers and a perfect location, just minutes from all of the Walt Disney World Resort theme parks. You and your family will spend magical days at the happiest place on earth and your evenings soaking your tired ...

View all property information

Property Type

Kissimmee House

Show less

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

$164

per night

View Details

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 ...

View all property information

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 ...

See all reviews

Show less

HOME AWAY FROM HOME- ENJOY THE VIEW

$85

per night

View Details

Key Amenities

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

About this property

Close to the Attractions but away from the crowds. 4 bedroom/3 bath single story home on "lake". Ducks, Sandhill Cranes, sometimes a falcon, turtles. King, king, and 4 twin beds, TV in all bedrooms, WiFi, FREE US, Canada and US Territory phone calls. Fully furnished.Times are approximate: ...

View all property information

Property Type

Kissimmee House

"Clean and relaxing!"
Reviewed October 13, 2019

We loved our stay! The house was clean and the neighborhood was quiet but still close to everything! Diane & Bob were easy to get a hold of and very kind! This is by far our favorite vacation rental! ...

See all reviews

Show less

The Lake House at Sunset Lakes - Upscale Lakeside Villa Near Disney

4 BR | 2 BA | Sleeps 8 | Quick View

Distance to park: 7 miles to Walt Disney World

$150

per night

View Details

Key Amenities

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

About this property

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

View all property information

Property Type

Kissimmee Villa

Show less

Heavenly Retreat-3BR-Pool, WiFi, BBQ, TVs in all Rooms, Disney/Orlando

3 BR | 2 BA | Sleeps 7 | Quick View

Distance to park: 12 miles to Disney

$100

per night

View Details

Key Amenities

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

About this property

Heavenly Retreat, a designated rental vacation home, was just remodeled in a casual and comfortable style. It is a complete turn key ready vacation home with a full equipped kitchen, three bedrooms, and two bathrooms for up to 6 guests. The pool offers lots of privacy and relaxing atmosphere.This ...

View all property information

Property Type

Kissimmee House

Show less

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 ...

View all property information

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 ...

See all reviews

Show less

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 ...

View all property information

Property Type

Kissimmee House

Show less

Fabulous condo with beautiful view

$75

per night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Pool
  • Private Pool

About this property

This comfortable and tastefully decorated 4BR condo has all of the amenities of your own home. This condo has a large master bedroom with ensuite bathroom with a king sized bed, flat screen LCD TV The second bedroom has a king size bed with cable TV. The third bedroom has two twins with cable TV and the ...

View all property information

Property Type

Kissimmee Condo

Show less

Palm Tree Villa Florida, 5 Star Review Rating with Pool Lift & Wheel in Shower

$125

per night

View Details

Key Amenities

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

About this property

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

View all property information

Property Type

Kissimmee Villa

Show less

Lovely 4 BR 2.5 bath townhouse with lakeview in a gated community near Disney

$120

per night

View Details

Key Amenities

  • Air Conditioning
  • Pool

About this property

Fully furnished townhouse condo with 2 master suites. Sleeps 8. Located in a gated community called Coral Cay Resort. Parking for 3 vehicles. Wonderful heated pool and spa, 2 playgrounds, barbecue pits. Pets allowed to 30 lbs. There is a pet fee. Clubhouse has a gym, theater, reading area. Quiet community. ...

View all property information

Property Type

Kissimmee Townhome

Show less

CLOSE TO DISNEY BUT NOT EXPENSIVE

$70

per night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Pool

About this property

Nice 3/2 condo. Granite counters, new cupboards, tile floors except for bedrooms. patio with table & chairs. Pool, hot tub, workout area, playground, grills, Close to the Attractions, and less than 10 minutes from 24 hour Walmart, fast food, fine dining, shopping. You can be at Disney Springs or ...

View all property information

Property Type

Kissimmee Condo

"Response time to inquiry"
Reviewed August 6, 2019

I did not rent the home, I inquired about staying there the same day and the owner got back to me in a matter of hours. I was surprised it was even within the same day as I contacted last minute. Great ...

See all reviews

Show less

The Five Star Villa (Near Disney)

5 BR | 4 BA | Sleeps 10 | Quick View

29

$139

per night

View Details

Key Amenities

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

About this property

FIVE STAR VILLA Near DISNEY! Florida License DWE5918319Welcome to a piece of paradise in the heart of Florida just minutes from the Walt Disney World theme parks !This comfortable and spacious five bedroom vacation home can accommodate a family or group of ten! Two master suites with adjoining ...

View all property information

Property Type

Kissimmee Villa

"My Family Loved The Villa"
Reviewed September 19, 2019

My family and I stayed at Mickey's Villa and we were so pleased. We started brainstorming on when to return to the Villa 2 days into the trip. The house wss very neat and clean and the Mickey decor was ...

See all reviews

Show less

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

View Details

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 ...

View all property information

Property Type

Kissimmee Villa

Show less

Kissimmee, Florida, 4 Bedrooms

4 BR | 2 BA | Sleeps 8 | Quick View

1

$171

per night

View Details

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 ...

View all property information

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

See all reviews

Show less

Luxury 10 Suite villa, man-guarded, amazing clubhouse at Reunion Encore Club

$443

per night

View Details

Key Amenities

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

About this property

** Please kindly send us an inquiry before you book. ** The Encore Club at Reunion offers an excellent choice of luxury vacation rental homes for guests to relax and enjoy a dream visit to Kissimmee! With Walt Disney World, just 6 minutes drive away from your own front door, this new, luxury gated community ...

View all property information

Property Type

Kissimmee Villa

"Fantastic location and perfect for a large family vacation"
Reviewed March 18, 2019

This place was amazing! We travelled with 19 people (15 adults/4 kids) there was more than enough space for all of us. The home was in excellent condition and super clean throughout. Booking was easy and ...

See all reviews

Show less

The Floridian : Ultra Luxuary 5BR Pool Home, 2 Master Suites, Sleeps 12!

$239

per night

View Details

Key Amenities

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

About this property

Enjoy our three-thousand square foot, custom luxury pool home, less than four miles from Disney World. We offer two master suites with king-size beds (one with Jacuzzi), two queen-bedrooms, one twin-bedroom, and queen size pullout-couch, all on one floor. This is not your typical Rolling Hills house. ...

View all property information

Property Type

Kissimmee House

"Our Dream Vacation"
Reviewed July 30, 2018

This home was PERFECT for my family! It was very spacious and had everything we needed to make us comfortable. Very close to Disney and close to a lot of nice eating places we could not have chosen a ...

See all reviews

Show less

Affordable Home Near Disney World

$100

per night

View Details

Key Amenities

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

About this property

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

View all property information

Property Type

Kissimmee Villa

"BEAUTIFUL"
Reviewed October 3, 2019

My husband and I went here on our honeymoon and we loved everything about this home! Not only was it extremely close to all of the Disney parks but it was very beautiful, calming and spacey! The pool and ...

See all reviews

Show less

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, ...

View all property information

Property Type

Kissimmee Villa

Show less

Expand map | Close map
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!