Kissimmee Vacation Rentals

(360 rentals)
booking message booking message

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pool
  • Private pool

About this property

"The renovations on this home took an entire year due to the amount of incredible detail. The entire home is a highlight. Star Wars is the theme. The highlights of the highlights are the movie theater, game room, the themed bedrooms and the pool area with the beautiful view of the water behind. The ...

View all property information

Property Type

Kissimmee House

Show less

8 BR | 6 BA | Sleeps 16 | Quick View

4.9 rating on other travel sites

$687

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pool
  • Private pool

About this property

"This was our first time renting a home for a vacation. This vacation rental has changed our future vacation options forever. Everything about the home and community was A+. The kids didn't want to leave and the grown ups enjoyed the amenities more than the kids. I would recommend this home for rental ...

View all property information

Property Type

Kissimmee House

Show less

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pool
  • Private pool

About this property

"When you walk through the front door, you immediately walk into fun with the adult area's pool table and large TV. And that's just the beginning. There's an awesome game room, 3 themed bedrooms, and in the pool area are a poolside theater and bar counter with TV. You will be totally entertained ...

View all property information

Property Type

Kissimmee House

Show less

6 BR | 4 BA | Sleeps 14 | Quick View

5.0 rating on other travel sites

$471

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pool
  • Private pool

About this property

"We have stayed in many Windsor hills homes and this is THE one to stay in! Beautifully decorated, fun and so comfortable!" Beth MARE YOU LOOKING for a very special vacation home? This is it . . . Totally renovated by a professional decorator and includes an incredible game room, a private ...

View all property information

Property Type

Kissimmee House

Show less

4 BR | 2.5 BA | Sleeps 8 | Quick View

6
LAST MINUTE DEAL 3/20 - 4/30: Book now and $125 cleaning fee is waived!

Distance to park: 4 miles to Disney World

$180

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • 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 ...

View all property information

Property Type

Kissimmee House

"Fantastic!"

The description of the home is everything it says it is. There are no exaggerations or stretching of the truth. If I were to go to Disney again, I would first look to see if Kay was renting her home. ...

See all reviews

Show less

DEAL

5 BR | 3.5 BA | Sleeps 12 | Quick View

$321

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pool
  • Private pool

About this property

This newly remodeled 5bd/3.5bath gated community home is waiting for you to visit! Saltwater pool, game room IN the house, all new flooring, granite countertops in kitchen, new pool furniture, new decorations, community playground and SO much more! This home is located only 5 miles from Disney World and ...

View all property information

Property Type

Kissimmee Villa

Show less

7 BR | 4.5 BA | Sleeps 16 | Quick View

4.9 rating on other travel sites

$498

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pet friendly
  • Pool
  • Private pool

About this property

KEY FEATURES 7 Spacious, themed bedrooms; 4 kings, 2 queens, 2 doubles + 2 sofa beds 4.5 Large bathrooms; 3 full ensuites, 1 shared full, 1 half Modern kitchen; dining area and kitchen island seating Two separate lounge areas; each with a Smart TV and comfortable seating High-speed WiFi throughout ...

View all property information

Property Type

Kissimmee House

Show less

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pool
  • Private pool
  • Rentals by owner

About this property

PLEASE EMAIL AND ASK FOR RATES. DIFFERENT TIMES OF THE YEAR HAVE DIFFERENT RATES AN MINIMUM STAYS - THANKS.Free WiFi, 3 miles to Disney, Huge pool and spa, Game room (pool table, air hockey, big screen tv, leather sectional, Wii), Internet access (wireless), Completely, private back yard, BBQ Grill, ...

View all property information

Property Type

Kissimmee House

Show less

8 BR | 6 BA | Sleeps 16 | Quick View

4.8 rating on other travel sites

$621

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pool
  • Private pool

About this property

"One word - FUN!! Incredible movie theater inside. Awesome movie theater poolside. And, a really cool Star Wars themed game room with LED lighting. The home is professionally decorated. It's beautiful, yet very comfortable." Cindy C.LOOKING for an incredibly fun vacation home to rent? This ...

View all property information

Property Type

Kissimmee House

Show less

8 BR | 6 BA | Sleeps 16 | Quick View

4.9 rating on other travel sites

$657

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pool
  • Private pool

About this property

"Private, peaceful, comfortable, and FUN!! Incredible movie theater inside. Awesome movie theater poolside. And, a really cool Star Wars themed game room. The pool and spa are very private. The home is beautiful, and it is a very short walk to the clubhouse and water park." Keith C.LOOKING ...

View all property information

Property Type

Kissimmee House

Show less

Key Amenities

  • Air conditioning
  • Kitchen
  • Pool

About this property

A beautiful vacation condo located in a prestigious gated and guarded community, for you to relax and spend time with your family and friends. With the prime location in Kissimmee near Disney World, major parks and restaurants, shops and so much more, this 3BD/2BA condo unit is designed for your best ...

View all property information

Property Type

Kissimmee Condo

Show less

5 BR | 4 BA | Sleeps 12 | Quick View

2
LAST MINUTE DEAL 3/18 - 4/28: Free pool heat on remaining March & April dates.

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

$408

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • 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

"Family Birthday Vacation"

Everything was great! The house was very spacious. The back area a bit small but still great! We had a blast!

See all reviews

Show less

DEAL

7 BR | 7 BA | Sleeps 14 | Quick View

Owner special: Save 10-35% off of Last-Minute Bookings!  *Price listed includes already discounted rates

$448

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kitchen
  • Private pool

About this property

Reunion Resort -Kissimmee, Florida is only 15 minutes to the area's main attraction... Walt Disney World. This gated luxury resort sits nestled just outside of Orlando, Florida and has quickly become one of the most desired resorts in the Orlando area. This home will provide you and your family with an ...

View all property information

Property Type

Kissimmee House

Show less

4 BR | 2.5 BA | Sleeps 11 | Quick View

Distance to park: 14 miles to Disney

$266

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kitchen
  • Private pool

About this property

Enjoy Orlando, Florida, home to Disney World, Sea World, Universal Studios, and Islands of Adventure, in style. Conveniently located on Crescent Lakes. The house is spacious where family can enjoy being together and also have some alone time. Our home is within 11 miles approximately of all the Orlando ...

View all property information

Property Type

Kissimmee House

Show less

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pool
  • Private pool
  • Rentals by owner

About this property

GroovyMouseHouse, 8-bedroom luxury villa with private pool and spa, located at The Encore Resort in Reunion, is perfect for families wanting an unforgettable stay in Orlando.Conveniently located close to Disney theme parks, restaurants, supermarkets and golf courses, it benefits from all the amazing ...

View all property information

Property Type

Kissimmee Villa

"Absolutely Perfect!"

Walking in the house was breathtaking. We loved every minute of the stay. The rooms were all so spacious and cozy. Disney world was right around the corner and the pool was perfect for evening swims. We ...

See all reviews

Show less

$129

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • 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. Not suitable for ...

View all property information

Property Type

Kissimmee House

"Relaxing stay"

It was the perfect neighborhood that was quiet and relaxing. It definitely wasn’t far from the attractions. We enjoyed our stay!!

See all reviews

Show less

4 BR | 3 BA | Sleeps 8 | Quick View

8
Owner special: Save 10-35% off of Last-Minute Bookings!  *Price listed includes already discounted rates

$258

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kitchen
  • Private pool

About this property

Storey Lake - Kissimmee is a brand new vacation community located just 4 miles from the magical world of Disney and just minutes to Universal, Sea World and the many water parks in the area. Central Florida is also home to some of the nation's top-rated golf courses and many are within a 10-minute drive ...

View all property information

Property Type

Kissimmee Townhome

"Relaxing"

The home was as expected. overall it was a nice experience. The kitchen could use new cookware and silverware.Kathy

See all reviews

Show less

5 BR | 5 BA | Sleeps 12 | Quick View

5.0 rating on other travel sites

$511

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pool
  • Private pool

About this property

"We just got home from our 1 week stay and are already wishing we were back! The home was beautiful and looked just as pictured in the listing. We were very close to the parks and shopping but yet felt like we were secluded. The neighborhood is wonderful and was great for walks. The pool and game ...

View all property information

Property Type

Kissimmee House

Show less

4 BR | 3 BA | Sleeps 8 | Quick View

3
Owner special: Save 10-35% off of Last-Minute Bookings!  *Price listed includes already discounted rates

$202

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kitchen
  • Private pool

About this property

The Retreat at Champions Gate - Kissimmee, Florida is a new upscale gated resort community located just 12 miles from Walt Disney World. This luxury home sits nestled just outside of Orlando, Florida and will quickly become one of the most desired locations in the Orlando area. During your stay, you will ...

View all property information

Property Type

Kissimmee Villa

"Nice getaway spot"

Wanted to getaway for a few days and visit Epcot. This Townhouse is beautifully decorated,spacious,clean and the splash pool just topped it off. This community is ideally located within 10 minutes drive ...

See all reviews

Show less

8 BR | 6 BA | Sleeps 16 | Quick View

4.8 rating on other travel sites

$610

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pool
  • Private pool

About this property

"This home is so much fun and is the best we have ever stayed in! The 2 theaters were a hit, and my kids could not get enough of the game room. So much to do in there- play pool, foosball, air hockey, shuffleboard, arcade style video games and PS4 games. We also spent so much time enjoying the private ...

View all property information

Property Type

Kissimmee House

Show less

3 BR | 2 BA | Sleeps 6 | Quick View

Owner special: Save 10-35% off of Last-Minute Bookings!  *Price listed includes already discounted rates

$159

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kitchen

About this property

Reunion Resort -Kissimmee, Florida is only 15 minutes to the area's main attraction... Walt Disney World. This gated luxury resort sits nestled just outside of Orlando, Florida and has quickly become one of the most desired resorts in the Orlando area. This home will provide you and your family with an ...

View all property information

Property Type

Kissimmee Condo

Show less

8 BR | 5 BA | Sleeps 20 | Quick View

2

$453

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pool
  • Private pool

About this property

Welcome To The Emerald Island Resort, Orlando's Premier Gated Community *** ***Fantasmic Location***closest Resort To Disney*** ***free Wireless Internet Just Bring Your Laptop*** Our 7/bedroom 5.5/bath villa (with 4 Master Bedrooms, all King bed with full private bath!) 3 bedroom each have 2 single ...

View all property information

Property Type

Kissimmee House

"Emerald Island Resort"

My family and I highly recommend this home for your vacation rental. It contained everything we needed and much more. Its space, cleanliness, and comfort was exactly what we were looking for. Its location ...

See all reviews

Show less

6 BR | 4 BA | Sleeps 16 | Quick View

3

Distance to park: 2 miles to Disney

$412

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pet friendly
  • Private pool
  • Rentals by owner

About this property

Clean NEWLY Renovated. NEW Air Conditioned Game Room!! Close .3 mile to the FREE Water Park & across from the big playground!! We have 2 homes side-by-side for larger groups and a 3rd home just a few doors down.* just 2 miles to Disney * Private Heated Pool & Spa * FREE Water park * Foosball, ...

View all property information

Property Type

Kissimmee House

"Lovely large house"

Stayed here with our kids and grandkids. Enjoyed the large space and pool. The property was clean and fully equipped with comfortable beds. Would highly recommend!

See all reviews

Show less

3 BR | 2 BA | Sleeps 8 | Quick View

8

Distance to park: 12 miles to All Disney Theme Park

$109

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Private pool

About this property

If you will be visiting Orlando Florida for all of the great attractions including Walt Disney World, Universal Studios, Sea World theme parks, and all of the other major attractions? You can stay in our beautifully decorated 3 bedroom private villa, which boasts it's own private pool for less than it ...

View all property information

Property Type

Kissimmee Villa

"Vacation"

our stay her was nice. It had all our basic needs and a nice private pool. We plan to return to this home on our next trip. The only thing we haven't received our deposit yet. But I'm sure it will be soon.

See all reviews

Show less

6 BR | 4 BA | Sleeps 12 | Quick View

8

Distance to park: 3 miles to Disney World

$344

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • 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

"Perfect for our family"

Located a couple miles from Animal Kingdom and close to other Disney World attractions, the home was perfect for 3 generations of our family. It is spacious and well appointed. The kids loved the private ...

See all reviews

Show less

7 BR | 4.5 BA | Sleeps 14 | Quick View

3

Distance to park: 4 miles to Animal Kingdom

$250

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pool
  • Private pool
  • Rentals by owner

About this property

Conveniently located on the Exclusive Emerald Island Resort. With 7 Bedrooms and 4.5 bathrooms, Berni’s Home from Home can easily accommodate two families travelling together or will give one family plenty of space.Enjoy relaxing by your very own private extended south facing pool or spend some ...

View all property information

Property Type

Kissimmee Villa

"Very well maintained home"

This home was lovely and very well kept. Would rent again if the occasion arose that we needed a home this big again.

See all reviews

Show less

3 BR | 2 BA | Sleeps 8 | Quick View

1
LAST MINUTE DEAL 3/27 - 3/29: Discount for the 2 nights available.. price for night 135 instead of $150...

Distance to park: 10 miles to 9

$144

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Private pool

About this property

Vous serez accueilli et logé dans cette maison de vacances ayant 03 chambres et 02 salles de bains située seulement à 15 minutes en voiture de Walt Disney World ,dans un reel cul de sac vous procurant à coup sûr paix et tranquillité dans cette Communauté ...

View all property information

Property Type

Kissimmee Villa

"Great place!"

We had a family of 6 ( 3 adults and 3 children) and it was PERFECT for our size family. Sadly it rained most of our visit so we weren’t able to use the pool but everything else was just like home. I really ...

See all reviews

Show less

DEAL

Key Amenities

  • Air conditioning
  • Kitchen
  • Private pool

About this property

This Disney Villa is a fully furnished home and is one of the best kept turnkey properties you will find in Indian Creek ! Has an airy open floor plan, lots of light. Enjoy the crystal clear South facing pool and the covered lanai on your sunny and warm Florida holidays.This luxurious private home ...

View all property information

Property Type

Kissimmee Villa

"Close to Disney and Sea World!"

We stayed here for 6 nights. The pool was nice with the heat on. It was in the upper 80’s while we were there. I love the floor plan with the cathedral ceiling. We were only a few minutes from the theme ...

See all reviews

Show less

3 BR | 2.5 BA | Sleeps 6 | Quick View

Distance to park: 2 miles to Disney Animal Kingdom

$160

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pet friendly
  • Pool
  • Rentals by owner

About this property

Touches of Disney around every corner make this town home a fun spot to stay during your Florida adventure! Enjoy Orlando, Florida, home to Disney World and a lot of other AMAZING attractions! This property is located on the Exclusive Emerald Island Resort and is inviting and convenient for any planned ...

View all property information

Property Type

Kissimmee Townhome

Show less

7 BR | 6 BA | Sleeps 14 | Quick View

1
Owner special: Save 10-35% off of Last-Minute Bookings!  *Price listed includes already discounted rates

$546

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kitchen
  • Private pool

About this property

The Retreat at Champions Gate - Kissimmee, Florida is a new upscale gated resort community located just 12 miles from Walt Disney World. This luxury home sits nestled just outside of Orlando, Florida, and will quickly become one of the most desired locations in the Orlando area. During your stay, you ...

View all property information

Property Type

Kissimmee House

"Very nice"

Very nice place. Great location close to Disney with nice resort feel with pool, kids splash zone, and lazy river. Highly recommend this place.

See all reviews

Show less

5 BR | 5 BA | Sleeps 10 | Quick View

4.8 rating on other travel sites

$450

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pool
  • Private pool

About this property

"We loved staying at this house, it is in a convenient location to the parks, and groceries are nearby. The house was clean and well-equipped. Our grandkids really enjoyed the themed rooms, the game room, and of course the pool! The gated resort community is awesome, and the water park/big pool were ...

View all property information

Property Type

Kissimmee House

Show less

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pool
  • Private pool

About this property

Sunset Lakes is an upscale sought after gated community four miles from Disney World and only a short drive to Universal Studios, Sea World, I Drive, Reunion Championship Golf and many more local attractions. Orlando is 24 miles north, Bush Gardens, Cocoa Beach, Daytona Beach and Kennedy Space Center ...

View all property information

Property Type

Kissimmee House

"Home away from home!"

We are regular Airbnb travelers and would rate this stay one of the nicest, best located, and real value of all the places we have stayed. The place was very clean, modern, had everything we needed to feel ...

See all reviews

Show less

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Private pool
  • Rentals by owner

About this property

This is a beautiful 7 bedrooms / 5 full and 2 half bathrooms. The home is perfectly located in the quiet gated community of Cumbrian Lakes. The home has a fabulous view of one of the lakes in the community which is south facing. This house has just been upgraded with all new furniture and has plenty ...

View all property information

Property Type

Kissimmee Villa

"Fabulous house"

Great home, great comfort, great owner. Everything ever expected and more. Clean home, quiet neighborhood, close to shopping and Disney. The pool area was excellent with heater on. it was truly a very enjoyable ...

See all reviews

Show less

5 BR | 5 BA | Sleeps 12 | Quick View

2

Distance to park: 2 miles to Walt Disney World

$301

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pool
  • Private pool

About this property

Terrific 5-bedroom/5-bathroom rental home owned by firefighters and located in Windsor Hills Resort. This beautiful villa includes upstairs and downstairs King Bedroom suites with new mattresses. It also has a Queen Bedroom, Twin Bedroom and sleeper sofa on the first floor. And there is an another Twin ...

View all property information

Property Type

Kissimmee House

"Disney get away"

Had a great time at this property love location definitely recommend.The clubhouse at this resort was really well-maintained and we had a great time

See all reviews

Show less

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pool
  • Private pool

About this property

Located in popular Sonoma Resort, our home is the perfect place to stay for a care and stress-free holiday away. Whether you are looking to spend long days lounging by the pool, exploring the parks or stretching your legs on one of the surrounding golf courses, this is the perfect location. Guests benefit ...

View all property information

Property Type

Kissimmee Villa

Show less

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pool
  • Private pool

About this property

7 bedroom 4.5 bath waterfront home located in the highly desired Emerald Island resort close to Disney and Universal Studios. The ground floor of this villa is an open concept with a living area featuring a 65" Smart 4k tv. The granite countertop kitchen boasts all new 2022 stainless appliances. ...

View all property information

Property Type

Kissimmee Villa

Show less

Key Amenities

  • Air conditioning
  • Kitchen
  • Pool
  • Private pool

About this property

If cozy decor, epic themed bedrooms, and multiple entertainment quarters are at the top of your vacation checklist, look no further than this adorable villa—located just minutes from Disney World in the amazing new Solara Resort! The kids will marvel at the wizard-themed bedroom, featuring life-sized ...

View all property information

Property Type

Kissimmee House

Show less

7 BR | 5.5 BA | Sleeps 16 | Quick View

$350

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pet friendly
  • Pool
  • Private pool

About this property

Spacious & Bright Luxury House. Two story home at the Amazing Champions Gate Community. The house ncludes 7 Bedrooms, 6 Bathrooms, large Game room, Private Pool, Patio, outdoor furniture, themed bedrooms. The ideal vacation spot for families and groups. Privacy pool screens - No neighbors view from ...

View all property information

Property Type

Kissimmee House

Show less

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pool
  • Private pool
  • Rentals by owner

About this property

Booking is available from the website in Owner info.Modern architecture, state-of-the-art furnishings, and hip-to-the-minute décor make this 5 bedroom, 5 bath getaway in Storey Lake a bonafide safe haven for luxury and comfort. This home is brimming with amenities, from an action-packed game ...

View all property information

Property Type

Kissimmee House

"Great place, nice price!"

The themed kids' rooms and game room are topping on this rental a club house with so much going on for everyone, including pickup/drop off service to and from the club house. Heated pool and gas grill. ...

See all reviews

Show less

8 BR | 5 BA | Sleeps 16 | Quick View

Owner special: Save 10-35% off of Last-Minute Bookings!  *Price listed includes already discounted rates

$759

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kitchen
  • Private pool

About this property

The Retreat at Champions Gate - Kissimmee, Florida is a new upscale gated resort community located just 12 miles from Walt Disney World. This luxury home sits nestled just outside of Orlando, Florida and will quickly become one of the most desired locations in the Orlando area. During your stay, you will ...

View all property information

Property Type

Kissimmee House

Show less

6 BR | 5.5 BA | Sleeps 18 | Quick View

1

Distance to park: 4 miles to Animal Kingdom

$470

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pool
  • Private pool

About this property

Pack your bags for an unforgettable trip to the happiest place on Earth at 'Minnie's Maingate Manor'! Minnie’s Maingate Manor is a 6-bedroom, 5.5-bathroom vacation rental home with themed bedrooms, sleeping accommodations for 16, and a private screened-in pool and spa. This Florida escape is perfect ...

View all property information

Property Type

Kissimmee House

"Amazing"

Such an amazing home! You want for nothing. My grandkids were in awe of the dress up clothes.They loved the games room. It was very clean. The pool was warm and they had so many beach towels and pool toys. ...

See all reviews

Show less

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pet friendly
  • Private pool
  • Rentals by owner

About this property

Immerse yourself in this much-beloved world and find the hidden easter eggs in the room as you open the door to Potter's Place. This charming open-concept themed home is ready to make you feel revitalized. From a cleaned, well-maintained space to a fully equipped kitchen to cozy beds and pillows, your ...

View all property information

Property Type

Kissimmee Townhome

Show less

Key Amenities

  • Air conditioning
  • Kitchen
  • Pool
  • Private pool

About this property

After. *** Location Location Location*** It’s all about. ‘The View’The uninterrupted view of the 14 acre lake and bird island, takes unwinding by the pool to a new level! Relax on a sun bed, or perhaps get wrinkly in the spa whilst ...

View all property information

Property Type

Kissimmee Villa

"Beautiful Home and View"

This Beautiful Home with a Lake View! This Home is very well maintained, the kitchen is supplied with everything you need. Game room is a fun room with pool table, video games, TV, books, ect. Little ...

See all reviews

Show less

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pool
  • Private pool

About this property

"Kids and adults love the game room. Really cool. Movie theater in the converted garage is incredible - better than being at a regular movie theater. And, maybe your biggest treat will be the poolside theater. Very pretty and comfortable home and full of fun." Keith C.LOOKING for an incredibly ...

View all property information

Property Type

Kissimmee House

"Great spot! Exactly as described!"

Terrific house. Has everything you need. All the electronics were working as they should. The theatre room and the outdoor pool/tub were the highlights. When I had question about the place while I was there, ...

See all reviews

Show less

4 BR | 2 BA | Sleeps 7 | Quick View

2

$133

avg/night

View Details

Key Amenities

  • Air conditioning
  • 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 .KING, KING AND 4 TWIN BEDS WITH THEMED TWIN BEDROOMS - LITTLE MERMAID AND DORY. TV IN ALL ...

View all property information

Property Type

Kissimmee House

"Excellent villa in great location."

Very good villa for our two week holiday. The villa was equiped with everything we needed for our holiday. Host was very friendly and helpful. Happy to return for a future visit.

See all reviews

Show less

6 BR | 4 BA | Sleeps 14 | Quick View

4.9 rating on other travel sites

$506

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pool
  • Private pool

About this property

ARE YOU LOOKING for a just renovated beautiful vacation home that is full of fun? This is it . . . Avenger theme game room - South facing (plenty of sun) private saltwater pool and spa - Poolside movie theater - Themed kids bedrooms - And much more. Also, it's located in Windsor Hills Resort - the closest ...

View all property information

Property Type

Kissimmee House

Show less

9 BR | 6.5 BA | Sleeps 22 | Quick View

4.8 rating on other travel sites

$465

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pet friendly
  • Pool
  • Private pool

About this property

Get ready to experience the vacation of a lifetime at Big Top Family Vacation Villa, situated in the heart of Solara Resort. This stunning villa boasts 9 spacious bedrooms and 6.5 luxurious bathrooms, providing ample space for up to 22 guests. Perfectly located just 8 miles away from Walt Disney World ...

View all property information

Property Type

Kissimmee Villa

Show less

7 BR | 4.5 BA | Sleeps 16 | Quick View

3

Inquire for rates

View Details

Key Amenities

  • Air conditioning
  • Kitchen
  • Pool
  • Private pool

About this property

Relax and Enjoy this 7 Bedroom Pool Vacation Home Set in a Beautiful Gated Community. A large beautiful 7 bedroom & 4 1/2 bathroom vacation home within minutes of Disney . All the comforts of home & just minutes from the magical world of Disney. This quality vacation home is extremely spacious ...

View all property information

Property Type

Kissimmee House

"Nice and Clean!"

This home is very nice and clean. We enjoyed our stay. The only issue is the pool. We paid extra for 2 weeks pool & spa heating but we only enjoyed the spa 3 days out of the 14 days. The pool will shot ...

See all reviews

Show less

3 BR | 2 BA | Sleeps 8 | Quick View

3

Distance to park: 12 miles to All Disney Theme Park

$112

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Private pool

About this property

If you will be visiting Orlando Florida for all of the great attractions including Walt Disney World, Universal Studios, Sea World theme parks, and all of the other major attractions? You can stay in our beautifully decorated 3 bedroom private villa, which boasts it's own private pool for less than it ...

View all property information

Property Type

Kissimmee Villa

"2021 vacation"

A well kept nice home. Everything as shown in the pictures. Excellent communication from owner and the property manager.

See all reviews

Show less

5 BR | 4 BA | Sleeps 12 | Quick View

5

Distance to park: 6 miles to Disney Animal Kingdom

$232

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kitchen
  • Pool
  • Private pool

About this property

***FREE WIRELESS INTERNET JUST BRING YOUR MOBILE DEVICES**. (Please note - there is no landline in the home)Sleeps a maximum 12 guests, with a maximum of 8 guests over the age of 14 years old.As you enter our lovely home, you will be impressed with the soaring 17ft high ceilings in the spacious ...

View all property information

Property Type

Kissimmee House

"Lovely home"

Lovely home will definitely recommend to others wish the pool and jacuzzi was heated though. Bring tissue and your own dish liquid and own laundry detergent if staying full week

See all reviews

Show less

Map
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

Soak up the Sun on Your Next Trip to Kissimmee Vacation Rentals

There’s nothing quite like a vacation to sunny Florida, a unique and inviting state with a huge variety of distinctive cities and natural areas to explore. One popular vacation destination in Florida is Kissimmee, a charming city with plenty to see and do just south of the Orlando metropolitan area. 

Kissimmee has a lot more to offer visitors than just excellent weather year-round. With a huge variety of scenic nature, shopping opportunities, and outdoor activities, Kissimmee itself has lots to offer every member of the family, not to mention its extremely close proximity to some of Orlando’s biggest amusement parks. 

You could stay in a busy hotel during your trip to Kissimmee, but then you wouldn’t be able to get a truly immersive experience of local city life. Kissimmee vacation rentals allow you to enjoy Kissimmee from inside its authentic residential neighborhoods. Additionally, having your own home to live in rather than a jam-packed hotel will provide some much-needed peace and quiet during your vacation. It will also offer plenty of space for the whole family to spread out.  

Top Tips for Traveling to Kissimmee Rentals

Like most other Florida cities, Kissimmee enjoys sunshine and clear skies throughout the majority of the year. However, the tropical climate of the state means that bouts of rain can occur throughout the seasons, particularly during the summer months, peaking in August. 

In addition to a higher likelihood of rain, the summer season in Kissimmee tends to be the most humid time of year. That’s why most vacationers choose mid to late spring or early autumn to make their trip to the city. At those times of the year, vacationers can enjoy great weather and lots of outdoor activities. 

Though the Kissimmee Gateway Airport is located centrally within the city, most vacationers taking commercial flights will fly into Orlando International Airport. It is located roughly 17 miles northeast of the city center, about halfway between Kissimmee and Orlando. Vacationers coming in from elsewhere in Florida can access Kissimmee by road using U.S. Route 192 and U.S. Route 441.

Things to Do Nearby Kissimmee House Rentals

Some of the most popular natural areas around Kissimmee are the swamps, which are located in major local bodies of water like Lake Tohopekaliga (known around town as Lake Toho). At Boggy Creek Airboat Adventures, you can experience the swamps from the water and get the thrill of a lifetime on an airboat driven by a local wetlands expert. Get up-close views of gator ponds, discover precious gemstones, and then grab a delicious lunch with the family at Boggy Bottom BBQ! 
Looking to explore a piece of history during your trip to Kissimmee? Medieval Times Dinner & Tournament allows visitors to step into the 11th century for an evening of authentic feasting, jousting, and sword fighting in true medieval style! Enjoy a delicious four-course meal, incredible performances, and a truly unforgettable experience for the entire family. 
Any vacation to Kissimmee isn’t complete without a trip or two to Old Town, a popular outdoor attraction with opportunities for shopping, dining, and family fun. Old Town is made up of an 18-acre stretch of classic city attractions, including the Old Town Ferris Wheel, the Great Magic Hall, and Mortem Manor, a year-round haunted house that is open for visitors to explore.
Kissimmee Annual Events

Kissimmee is a vibrant area with lots of annual festivals and events to enjoy in and around the city throughout the year. Kissimmee locals and visitors alike flock to the Ford Cuban Sandwich Festival each May near downtown Kissimmee, which celebrates the colorful history of Cuban cuisine in the area. Watch as local dining professionals attempt to build the world’s biggest Cuban sandwich during the event! 
The Ford Taste of Latino Festival is another local opportunity to celebrate and experience the best in authentic Latin cuisines in Kissimmee. The event features a contest to find the Top Latino Chef as well as plenty of live music and dance performances to enjoy as you taste a variety of Latin dishes. 
Not sure if you’ll be in town for any of Kissimmee’s larger annual events? You can enjoy Show Car Saturday Nights every Saturday night in the city on Margaritaville Boulevard. Check out the city’s best classic cars from a variety of eras and enjoy the plethora of delicious eateries and exciting shops located along the boulevard.

Wining and Dining in Kissimmee  

Between your outdoor activities and trips to local amusement parks while in Kissimmee, you’re sure to need some satisfying food and refreshing drinks to complete your perfect day. Luckily, Kissimmee is home to some of the best restaurants that Florida has to offer, combining authentic local flavors with worldly cuisine. 

To start your day off right with a delicious and hearty breakfast, look no further than Woodsby’s Countryside Café. This spot has authentic, cozy diner vibes to spare, not to mention a stacked menu of classic breakfast favorites, coffee bar items, and unique dishes you won’t want to miss out on. 

Tarantino’s Italian Restaurant is a great choice for a vacation date night or simply a nice dinner out with the family. A hearty Italian meal is a great way to finish a fun day of activities, and you’re sure to get that and more at Tarantino’s. If you bring the family along, you can take advantage of the takeout dinner special, which feeds four and includes a massive entrée, salad, and garlic bread.


FAQ

How many vacation rentals are there in/around Kissimmee?

There are 360 Kissimmee vacation rentals available on FloridaRentals.com. From house rentals to villa rentals and beyond, find a unique vacation rental for you to enjoy a memorable vacation in Florida.

How much does it cost to rent a vacation rental in Kissimmee?

There are vacation rentals available in Kissimmee for as low as $64 per night with an average price per night of $259.

Can I rent a house in Kissimmee?

Yes, you can find house rentals in Kissimmee close to Lakefront Park, Monument of States, and Old Town. Don't forget to stop in to Shingle Creek Park or the nearby theme parks!

Do any vacation rentals in Kissimmee have a pool?

Yes, there are 292 vacation rentals in Kissimmee with a pool on FloridaRentals.com. Search using our filters and book one for your next vacation!