Kissimmee Vacation Rentals

(370 rentals)
booking message booking message

4 BR | 3 BA | Sleeps 8 | Quick View

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

$210

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 townhome 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 Townhome

Show less

5 BR | 5 BA | Sleeps 10 | Quick View

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

$321

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

Key Amenities

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

About this property

Make unforgettable family memories that will last a lifetime on your next stay at our massive and luxurious home, Tranquility Retreat! Located near the attractions, shopping and theme parks, you'll have access to 2 themed game rooms and all the bells & whistles - think gourmet kitchen, huge living ...

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

$492

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

8 BR | 5 BA | Sleeps 16 | Quick View

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

$556

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

4 BR | 3 BA | Sleeps 9 | Quick View

1
Owner special: Stay for 2 weeks and get 10% off listed price! For Periods from May 25 to June 30, 2023 only

$136

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Private pool

About this property

Luxury Villa near Universal Studios and 12 Minutes from Disney with Large Private Pool, Game Room and Free Wifi. LCD TVs and Game Room in the villa complement the upscale furnishings and large pool included in the villa. There is plenty of space to spread out with 4 bedrooms and 3 bathrooms.Welcome ...

View all property information

Property Type

Kissimmee Bungalow

"GREAT HOLIDAY"

We have just had a great holiday staying in Royal Palms Villa. Lovely villa in great location for all parks etc. very clean and safe area to stay, Owners very friendly ,efficient and pleasant to deal ...

See all reviews

Show less

8 BR | 4.5 BA | Sleeps 16 | Quick View

Distance to park: 4 miles to Disney

$236

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Private pool

About this property

Property Description With a sunny pool and spa, games room, access to the amazing resort facilities and plenty of space for everybody, this is a perfect home for your family Orlando vacation. Situated in Kissimmee, on the popular Emerald Island gated resort, close to Disney theme parks, shops and restaurants. ...

View all property information

Property Type

Kissimmee Villa

Show less

Key Amenities

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

About this property

Nestled within the exclusive Veranda Palms Resort and surrounded by Shingle Creek Preserve is this spacious, family-friendly home that sleeps up to 26 guests over its 12 themed bedrooms. Perfect for large groups the home offers a chef's kitchen, a stunning resort style yard with a heated pool & hot ...

View all property information

Property Type

Kissimmee Villa

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
  • Pet friendly
  • Private pool

About this property

Beautiful Lake View Luxury Villa with great entertainment options, purpose-built Airbnb fully equipped with all the latest amenities.We aim to provide our guests with a safe, clean, and convenient place to come home to; wherever you go to the local attractions, shop, or are here on business, we keep ...

View all property information

Property Type

Kissimmee Villa

Show less

3 BR | 2 BA | Sleeps 8 | Quick View

10

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

"Love the place!"

Love the place. Easy access to everything!!! One level I loved. It was great to have a washer and dryer.

See all reviews

Show less

$132

avg/night

View Details

Key Amenities

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

About this property

CHEERY AND BRIGHT. Just what a vacation home should be. 4 bedrooms, 2 bathrooms, great views and just minutes from all the fun. Fully furnished , just bring personal items or things you cannot live without. Located in Eagle Pointe, a well sought-after vacation home community. Just minutes from what ...

View all property information

Property Type

Kissimmee House

"Home away from home"

This home has all the needs for your vacation home. Great location and host was very attentive. This vacation home is situated in a neighborhood close to shopping areas and nearby to major attractions.

See all reviews

Show less

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • 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

"Lovely Villa with a lot of extras !"

Beautiful place for a relaxing holiday or just 15 minutes away from the Disney and Resorts area . The home was perfect and the welcome package was great. Andy was great and checked in on us during our stay. ...

See all reviews

Show less

5 BR | 4 BA | Sleeps 12 | Quick View

5

Distance to park: 6 miles to Disney Animal Kingdom

$244

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

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

9 BR | 5 BA | Sleeps 18 | Quick View

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

$575

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 House

Show less

6 BR | 4 BA | Sleeps 12 | Quick View

8

Distance to park: 3 miles to Disney World

$342

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

$126

avg/night

View Details

Key Amenities

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

About this property

Come relax in this 4 bedroom, 3 bathroom home. Sit on the screened in pool deck and just watch the wildlife , eat meals, have a cup of coffee and just relax. You are on vacation. Two king beds, queen and 2 twin beds .

View all property information

Property Type

Kissimmee House

"Disney Bound 2021"

The location was perfect with easy access. The house was very nice with a great view overlooking the pond. Had everything we needed. About 15 to 20 minutes away from Disney. Ms. Diane is a great host. Will ...

See all reviews

Show less

9 BR | 6.5 BA | Sleeps 22 | Quick View

4.9 rating on other travel sites

$439

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

8 BR | 5 BA | Sleeps 16 | Quick View

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

$551

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

"Perfect!"

My family and I loved it so much ! Definitely would go back again ! Everything was so clean ‘ so much to do and my kids did not want to leave!

See all reviews

Show less

8 BR | 6 BA | Sleeps 16 | Quick View

4.8 rating on other travel sites

$433

avg/night

View Details

Key Amenities

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

About this property

"Great house, even better than the listing indicated. Great pool and hot tub, huge living area and plenty of space for a group of 14. The movie room was great, with a highlight of watching Space X launch a rocket on the big screen, then walking to back yard to watch it in the sky. The upstairs is ...

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

$500

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

4 BR | 3 BA | Sleeps 9 | Quick View

1

Distance to park: 3 miles to Disney

$175

avg/night

View Details

Key Amenities

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

About this property

The Magic Emerald Island Villa has 4 bedrooms and 3 bathrooms with a maximum occupancy of 9. Professionally decorated, fully stocked kitchen. There are 6 flat screen TVs with cable. Private pool/spa for your enjoyment. Beds are super comfy for a good night's sleep after a full day at Disney or Universal. ...

View all property information

Property Type

Kissimmee House

"Everything our family needed"

Everything was just as it was described online, and meet all of our needs as a family of 5 plus a grandparent. The home was in a beautiful community and only a short drive to shopping, restaurants and Disney.

See all reviews

Show less

6 BR | 5 BA | Sleeps 13 | Quick View

3

$293

avg/night

View Details

About this property

Spacious 6 bed, 5 bath, sleeps thirteen Fully screened South facing pool with relaxing spa Formal, informal and outside dining options Upstairs TV lounge with a further two living areas downstairs Pool table in the games room Located on gated resort of Solterra with excellent amenities

View all property information

Property Type

Kissimmee House

"Loved it.."

We had a wonderful time can't wait to visit again. I believe the kids favorite part was the pool. They did not want to leave..

See all reviews

Show less

4 BR | 3 BA | Sleeps 8 | Quick View

16

Distance to park: 4 miles to Disney

$143

avg/night

View Details

Key Amenities

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

View all property information

Property Type

Kissimmee House

"Perfect rental for all of our needs!"

This was a Christmas vacation never to be forgotten! We had the time of our lives! My children, grandchildren and I enjoyed the comforts and privacy of a home where we could take in all the theme parks ...

See all reviews

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

Key Amenities

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

About this property

Our Emerald Island Townhouse has a prime location within the resort, right in front of one of the heated pool and spa's, with plenty of chairs and sun loungers to relax on after a busy day in the parks. Also close by are the tennis courts and a children's play area.The house consists of approximately ...

View all property information

Property Type

Kissimmee Townhome

Show less

Key Amenities

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

About this property

Looking for a dream vacation home near Walt Disney World? Look no further than this stunning 7 bedroom, 4 and half bath private home with two master suites; screened pool with covered lanai, themed bedrooms and a game room. This spacious and elegant property can accommodate up to 15 guests and is located ...

View all property information

Property Type

Kissimmee Estate

Show less

8 BR | 6 BA | Sleeps 16 | Quick View

4.9 rating on other travel sites

$467

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

7 BR | 7 BA | Sleeps 14 | Quick View

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

$438

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

6 BR | 5 BA | Sleeps 12 | Quick View

2

$283

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kitchen
  • Private pool

About this property

Modern Elegance best describes Our Beautiful, Completely Renovated from top to bottom in 2019. Executive Home with 4 MASTER EN-SUITES situated in the exclusive “Emerald Island Resort” only a 5-minute drive from Disney and only ¾ mile from HWY 192 Shops and restaurants!This home ...

View all property information

Property Type

Kissimmee House

"Magic villa at emerald"

Great trip house had alot of flies but other then that we had a lovely time it was nice in clean but the mop and broom was for a toddler

See all reviews

Show less

Key Amenities

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

About this property

Our luxury Kissimmee vacation villa will comfortably sleep 10 people. It is fully air-conditioned for your comfort, and has a very roomy and spacious floor plan. It has 2 lounge areas (one with 2 full sofas, and a ceiling fan, the other with a love seat and a sofa bed), both have cable T.V. The kitchen ...

View all property information

Property Type

Kissimmee Villa

"Family vacation"

Our family truly enjoyed our stay in the Florida rental, we didn't want to leave. Had all the comfort of home, our grandchildren loved swimming everyday ️, and the best thing about this place was everything ...

See all reviews

Show less

6 BR | 4 BA | Sleeps 14 | Quick View

4.8 rating on other travel sites

$419

avg/night

View Details

Key Amenities

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

About this property

"What a delightful home! It exceeded all of our expectations...There was a television in almost every room, two living rooms with comfortable seating, coffee bar, game room, fun children's bedrooms with a "secret room", pool with large movie screen, and plenty of outdoor loungers and seating...I ...

View all property information

Property Type

Kissimmee House

Show less

Key Amenities

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

About this property

"Have lots of fun and relax in this beautifully renovated vacation home in Windsor Hills Resort! The air conditioned Star Wars themed game room (with a life-size Storm Trooper) and the poolside movie theater and bar make this home a one-of-a-kind." Cindy CARE YOU LOOKING for lots of fun ...

View all property information

Property Type

Kissimmee House

"Endless FUN"

From the pool with a movie projector to the games room this house was amazing!!! Would highly recommend and will definitely be using again.Close to Disney and Universal is a bonus.

See all reviews

Show less

10 BR | 8 BA | Sleeps 20 | Quick View

4
Owner special: Save 10-35% off of Last-Minute Bookings!  *Price listed includes already discounted rates

$619

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Private pool

About this property

Sonoma 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 and W. Irlo Bronson Memorial Hwy and conveniently located next to "The Loop", a premier shopping ...

View all property information

Property Type

Kissimmee House

"Awesome house!"

We held our annual Married Couples Retreat. It was above and beyond all of my expectations. More than enough room for everyone that no one was on top of each other. Definitely will yes again!

See all reviews

Show less

3 BR | 2 BA | Sleeps 8 | Quick View

1

Distance to park: 10 miles to 9

$139

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

Key Amenities

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

About this property

Beautiful 4 bedroom/3 bathroom house in the luxurious Emerald Island Resort - Only ~ 4 miles from Disney & close to other major attractions! This home is equipped with a heated private pool, spa & game room. There is a large SMART TV in the living room & in each bedroom. There are queen beds ...

View all property information

Property Type

Kissimmee House

"Clean, comfortable and aesthetically pleasing"

We stayed for about 2 weeks. Home is extremely comfortable with enough of everything we needed. The owners are easy to work with and the property management very responsive. The location is superb for all ...

See all reviews

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

$210

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

"Condo"

This condo was very clean and well stocked. It had extra kitchen items like an indoor grill. The pool was also very clean. The owners were very accommodating when we had some travel changes due to a ...

See all reviews

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

$452

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

Key Amenities

  • Air conditioning
  • Kitchen
  • Pool
  • Private pool

About this property

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

View all property information

Property Type

Kissimmee Villa

"Nice villa"

We had a good time at this villa overlooking lake with a very nice gated community we enjoyed our vacation

See all reviews

Show less

3 BR | 2 BA | Sleeps 8 | Quick View

3

Distance to park: 12 miles to All Disney Theme Park

$114

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

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

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

5 BR | 5 BA | Sleeps 12 | Quick View

5.0 rating on other travel sites

$330

avg/night

View Details

Key Amenities

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

About this property

"Spacious, well-equipped, clean and a quick drive to the Disney parks. Great game room. You couldn't ask for anything more!" Melissa MARE YOU LOOKING for a vacation home with an incredible game room, a private south facing pool and SPA, totally renovated home, in Windsor Hills Resort with ...

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

$334

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

8 BR | 5 BA | Sleeps 16 | Quick View

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

$556

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

4 BR | 3 BA | Sleeps 10 | Quick View

9

Distance to park: 3 miles to Walt Disney Animal Kingdom

$170

avg/night

View Details

Key Amenities

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

About this property

Star Lake Villa has 4 Bedrooms & 3 Bathrooms (2 master suites) – a beautiful pool – on a Lake with a games room.  This is a beautiful lakeside home is in the peaceful exclusive community of Rolling Hills Estates in Kissimmee off of Formosa Gardens Dr. It is close to everything, ...

View all property information

Property Type

Kissimmee Villa

"Great stay!!"

We have rented quite a few houses in this area over the years and this one is by far the nicest. It was very clean and in a great location. We would definitely stay again!!

See all reviews

Show less

8 BR | 7 BA | Sleeps 16 | Quick View

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

$389

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kitchen

About this property

PLEASE NOTE: Encore Resort amenities are not included in the rental of this homeEncore Club at Reunion-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 ...

View all property information

Property Type

Kissimmee House

"Excited!!"

I didn't go yet but I'm going next summer with my best friend and our families. More excited to go now that I have heard great new about it!!

See all reviews

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

$156

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

Key Amenities

  • Air conditioning
  • Kitchen
  • Pool
  • Private pool

About this property

A Truly Luxurious Executive Retreat, Main Level Features: Quality Ceramic Tile Flooring throughout. Spacious Family Room with Vaulted Ceiling and Corner Leather Sofa.70″ TV with 5.1 surround sound with blue tooth capabilities. Formal Dining Room/ Sitting Area with table for six, Fabulous Kitchen ...

View all property information

Property Type

Kissimmee House

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 370 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 $90 per night with an average price per night of $244.

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 314 vacation rentals in Kissimmee with a pool on FloridaRentals.com. Search using our filters and book one for your next vacation!