Kissimmee Vacation Rentals, Villas, & More

1-50 of 625 Kissimmee Rentals

Sort:
1  2  3  4  5 
Kissimmee Florida Vacation Rentals - Apartment
1 / 29

Kissimmee Apartment
2 Bedrooms / 2 Bathrooms / Sleeps 6

from

$85

/ night

Email Owner
Bedrooms:2
Bathrooms:2
Sleeps:6
Type:Apartment
Per night:$85 - $140
Per week:$595 - $980
Pets allowed:No
Internet:Yes

Specializing in vacation rentals located within Reunion Resort, Windsor Hills Resort and The Retreat at Champions Gate; Magical Vacation Homes offers the finest selection of privately owned, luxury rental properties that are fully furnished and exquisitely designed to provide your...

See more

Close x

Kissimmee Florida Vacation Rentals - Apartment
1 / 7

Kissimmee Apartment
3 Bedrooms / 2 Bathrooms / Sleeps 8

from

$139

/ night

Email Owner
Bedrooms:3
Bathrooms:2
Sleeps:8
Type:Apartment
Per night:$139 - $224
Per week:$973 - $1,568
Pets allowed:No
Internet:Yes

The Mayfair is a beautiful 4- Star vacation townhome located in the popular Terra Verde Resort. This home features nearly 1300 square feet of open vacation living space across two floors. Enjoy access to a private spa on the secluded patio! Impressive community amenities will add...

See more

Close x

Kissimmee Florida Vacation Rentals - Home
1 / 34

Kissimmee Home
4 Bedrooms / 3 Bathrooms / Sleeps 8

“ Excellent ”37 Reviews

from

$125

/ night

Email Owner
Bedrooms:4
Bathrooms:3
Sleeps:8
Type:Home
Per night:$125 - $179
Per week:$983
Pets allowed:No
Internet:Yes

Ideally located just minutes from Disney many great golf courses near by. Why stay in a cramped hotel room when you can stay at Debbie’s Florida Retreat a beautifully decorated, Luxury Pool Home with 4 bedrooms, 3 full bathrooms, a gourmet kitchen and screened- in private...

See more

Close x

Florida Retreat

“ Excellent ”
January 5, 2015
Debbie's Florida Retreat was a great vacation home for our family. The house was very clean and well maintained upon our arrival and the pool and hot tub were a great added amenity. The house is also conveniently located within 20 minutes of all the Orlando attractions. I highly recommend this house if you are staying in the Orlando area for both the amenities and the value for the price.
Robert Fenn, Oak Park, MI

See all reviews

Close x

Kissimmee Florida Vacation Rentals - Home
1 / 18

Kissimmee Home
4 Bedrooms / 3 Bathrooms / Sleeps 10

from

$169

/ night

Email Owner
Bedrooms:4
Bathrooms:3
Sleeps:10
Type:Home
Per night:$169 - $271
Per week:$1,183 - $1,897
Pets allowed:No
Internet:Yes

A holiday home to remember for a lifetime. This could be a good definition for this sunny south facing home away from home, located at Windsor Palms resort, Kissimmee Orlando. Featuring spacious rooms, this house can sleep up to 8 guests. With 4 bedrooms and 3 bathrooms (one suite...

See more

Close x

Kissimmee Florida Vacation Rentals - Condo
1 / 25

Kissimmee Condo
3 Bedrooms / 2 Bathrooms / Sleeps 8

“ Excellent ”67 Reviews

from

$43

/ night

Email Owner
Bedrooms:3
Bathrooms:2
Sleeps:8
Type:Condo
Per night:$43
Per week:$299
Pets allowed:No
Internet:Yes

Best Priced 3 Bedroom Condo For Rent At Windsor Hills. Disney Fireworks View Building - Watch Disney Fireworks, Never Leave Building. Closest To Disney - Be On Property In Two Minutes. - king Master Bed - free Wireless Internet - flat Screen Hdtv And Dvd Players...

See more

Close x

Awesome accomodations

“ Excellent ”
December 4, 2013
I loved this property!!! It was close enough to the parks for a quick drive yet far enough from the hustle and bustle of everything! It felt like a home away from home and would stay there again in a heart beat!
Melissa Marlein, Windsor, Ontario canada

See all reviews

Close x

Kissimmee Florida Vacation Rentals - Villa
1 / 35

Kissimmee Villa
4 Bedrooms / 4 Bathrooms / Sleeps 8

from

$319

/ night

Email Owner
Bedrooms:4
Bathrooms:4
Sleeps:8
Type:Villa
Per night:$319 - $525
Per week:$2,233 - $3,675
Pets allowed:No
Internet:Yes

Specializing in vacation rentals located within Reunion Resort, Windsor Hills Resort and The Retreat at Champions Gate; Magical Vacation Homes offers the finest selection of privately owned, luxury rental properties that are fully furnished and exquisitely designed to provide your...

See more

Close x

Kissimmee Florida Vacation Rentals - Villa
1 / 59

Kissimmee Villa
7 Bedrooms / 4.5 Bathrooms / Sleeps 16

“ Excellent ”4 Reviews

from

$219

/ night

Email Owner
Bedrooms:7
Bathrooms:4.5
Sleeps:16
Type:Villa
Per night:$219 - $439
Per month:$6,570 - $13,170
Pets allowed:No
Internet:Yes

This is an exquisite home which will leave you, your family or guests with warm memories in a home styled, furnished and decorated with no expense spared! This home was purchased in August 2012 and has been completely refurbished with all wood floors throughout the home, ...

See more

Close x

Disney Family Christmas

“ Excellent ”
January 9, 2015
This is a beautiful home that comfortably hosts 16. We enjoyed both the pool and the theater room. The island in the great room was the center of all our activities in the home. There were a few things that we brought to the owners attention, but overall the time spent in the home was very enjoyable. One note, if you are planning on using any of the board games bring your own, unfortunately there are pieces missing from all of the games. I have given information on this rental to two people and would rent again in the future.
Kelly Golden, Houston, texas

See all reviews

Close x

Kissimmee Florida Vacation Rentals - Townhouse
1 / 24

Kissimmee Townhouse
5 Bedrooms / 4 Bathrooms / Sleeps 13

“ Excellent ”1 Review

from

$159

/ night

Email Owner
Bedrooms:5
Bathrooms:4
Sleeps:13
Type:Townhouse
Per night:$159 - $189
Per week:$1,113 - $1,323
Pets allowed:No
Internet:Yes

Fabulous 5 bed/4 bath Town Home with private pool located in Paradise Palms Resort, just 5 minutes from Disney and I4. Room for everyone, so bring the grandparents, in- laws and extended family. Paradise Palms Resort is gated with around the clock 24hr security guards. Splendid...

See more

Close x

Amazing!

“ Excellent ”
August 5, 2014
Absolutely beautiful! The resort was gorgeous the house was clean and well kept. This will be my new place to stay when I vacation to Disney!
Lizame Rozon, New York, ny

See all reviews

Close x

Kissimmee Florida Vacation Rentals - Home
1 / 32

Kissimmee Home
6 Bedrooms / 4 Bathrooms / Sleeps 12

from

$189

/ night

Email Owner
Bedrooms:6
Bathrooms:4
Sleeps:12
Type:Home
Per night:$189 - $305
Per week:$1,323 - $2,135
Pets allowed:No
Internet:Yes

Specializing in vacation rentals located within Reunion Resort, Windsor Hills Resort and The Retreat at Champions Gate; Magical Vacation Homes offers the finest selection of privately owned, luxury rental properties that are fully furnished and exquisitely designed to provide your...

See more

Close x

Kissimmee Florida Vacation Rentals - Home
1 / 42

Kissimmee Home
6 Bedrooms / 5.5 Bathrooms / Sleeps 16

“ Excellent ”6 Reviews

from

$179

/ night

Email Owner
Bedrooms:6
Bathrooms:5.5
Sleeps:16
Type:Home
Per night:$179 - $350
Per month:$5,370 - $10,500
Pets allowed:No
Internet:Yes

Our beautifully furnished 5 star disney vacation villa is situated in the magnificent community of emerald island resort, which is only 3 mile to disney world and close by universal studios, sea world and golf courses etc. You will love this beautiful villa, it has everything you...

See more

Close x

Great vacations

“ Excellent ”
January 13, 2015
Along with my family, had an excellent time during our stay in Kissimmee - Orlando, thanks also to the great house where we stayed. The house is found spacious, clean and well equipped. Also very close to the Disney´s thems parks, restaurants and commerce in general (Wallgreens, Publik, Target, etc.) With security on our next trip to Orlando, we'll be renting your house again. Thanks Lee for his kindness and be aware of all we need.
Mario A Aranguren, Bogotá, Colombia

See all reviews

Close x

Kissimmee Florida Vacation Rentals - Townhouse
1 / 26

Kissimmee Townhouse
3 Bedrooms / 3 Bathrooms / Sleeps 8

from

$68

/ night

Email Owner
Bedrooms:3
Bathrooms:3
Sleeps:8
Type:Townhouse
Per night:$68 - $115
Per week:$480 - $800
Pets allowed:No
Internet:Yes

The Trafalgar Village community is centred around a luxurious club house (a 2 minute stroll from the property) with amenities that include a man made beach and lagoon, lakes (stocked for fishing), a pool and games arcade room, a 48 seat movie theatre, a fitness room, a business...

See more

Close x

Kissimmee Florida Vacation Rentals - Apartment
1 / 8

Kissimmee Apartment
3 Bedrooms / 2 Bathrooms / Sleeps 8

from

$147

/ night

Email Owner
Bedrooms:3
Bathrooms:2
Sleeps:8
Type:Apartment
Per night:$147 - $232
Per week:$1,029 - $1,624
Pets allowed:No
Internet:Yes

The Medway vacation condo is furnished to the highest standards and decorated in bold colors. It is located just west of Walt Disney World in the popular Windsor Palms Resort. This second floor condo, which is easily accessed by an elevator, offers over 1, 200 square feet of vacation...

See more

Close x

The Luxury Villa
1 / 16

Kissimmee Villa
7 Bedrooms / 4.5 Bathrooms / Sleeps 16

“ Excellent ”11 Reviews

from

$143

/ night

Email Owner
Bedrooms:7
Bathrooms:4.5
Sleeps:16
Type:Villa
Per night:$143 - $286
Per week:$999 - $2,000
Pets allowed:No
Internet:Yes

An extremely popular vacation home Located less than three miles from Walt Disney World, 3000+ sq ft spacious living space, 7 bedrooms & 4. 5 bathrooms, fully equipped kitchen & laundry, beautifully decorated living & dining area and a game room, Disney Sunshine is the perfect...

See more

Close x

Family vacation

“ Excellent ”
October 18, 2014
This house was just what we expected/needed! It is comfortable and located close to parks and retail! Nice pool and quiet neighborhood. We plan to stay here again!
Doty Cheezem, Columbia SC

See all reviews

Close x

Kissimmee Florida Vacation Rentals - Villa
1 / 34

Kissimmee Villa
3 Bedrooms / 3 Bathrooms / Sleeps 6

from

$109

/ night

Email Owner
Bedrooms:3
Bathrooms:3
Sleeps:6
Type:Villa
Per night:$109 - $175
Per week:$763 - $1,225
Pets allowed:No
Internet:Yes

Specializing in vacation rentals located within Reunion Resort, Windsor Hills Resort and The Retreat at Champions Gate; Magical Vacation Homes offers the finest selection of privately owned, luxury rental properties that are fully furnished and exquisitely designed to provide your...

See more

Close x

Kissimmee Florida Vacation Rentals - Townhouse
1 / 21

Kissimmee Townhouse
4 Bedrooms / 3 Bathrooms / Sleeps 8

from

$149

/ night

Email Owner
Bedrooms:4
Bathrooms:3
Sleeps:8
Type:Townhouse
Per night:$149 - $239
Per week:$1,043 - $1,673
Pets allowed:No
Internet:Yes

This beautiful Vacation Home Villa at the Bellavida Resort have been designed to appeal to residents of all ages where you can be as private or as social as you want to be. Staying in this spacious 4 bedroom/3 bathroom you'll also have access to the Clubhouse that is over 6700 square...

See more

Close x

Living Room
1 / 16

Kissimmee Home
4 Bedrooms / 3 Bathrooms / Sleeps 10

“ Excellent ”1 Review

from

$100

/ night

Email Owner
Bedrooms:4
Bathrooms:3
Sleeps:10
Type:Home
Per night:$100 - $122
Per week:$700 - $850
Pets allowed:No
Internet:Yes

4 Beds, 3 Full Bath, Private Pool, Gated Community within Lake Berkley Resort Master bedroom with a King size bed 2nd bedroom with a queen size bed 3rd bedroom with two twin size beds 4th bedroom with Two twin size beds 3 full bathrooms A large size private...

See more

Close x

A wonderful house for vacationing.

“ Excellent ”
August 6, 2013
We stayed for two weeks at this amazing house. The property is located at the best spot of Kissimmee. The house is perfect for big groups. The bedrooms, kitchen and living rooms are very large but the master bedroom is the best. We really enjoyed being Mrs. Zang's guests. She is very attentive and friendly. We definitely consider this house for our next trip to Florida.
Felix Briones, NY

See all reviews

Close x

Kissimmee Florida Vacation Rentals - Villa
1 / 31

Kissimmee Villa
5 Bedrooms / 4 Bathrooms / Sleeps 11

from

$315

/ night

Email Owner
Bedrooms:5
Bathrooms:4
Sleeps:11
Type:Villa
Per night:$315 - $475
Per month:$9,450 - $14,250
Pets allowed:No
Internet:Yes

Property Ref: RVH_086 This luxurious vacation rental home is located in the Fairway Ridge South neighborhood, in the desirable west- side of Reunion Resort. This neighborhood is surround by the beautiful landscape of the Tradition golf course designed by Jack Nicklaus. Reunion...

See more

Close x

Kissimmee Florida Vacation Rentals - Condo
1 / 40

Kissimmee Condo
2 Bedrooms / 2 Bathrooms / Sleeps 6

“ Excellent ”2 Reviews

from

$43

/ night

Email Owner
Bedrooms:2
Bathrooms:2
Sleeps:6
Type:Condo
Per night:$43
Per week:$299
Pets allowed:No
Internet:Yes

Watch Walt Disney World Fireworks EVERY NIGHT off of your Screened Balcony. See Magic Kingdom, EPCOT, Hollywood Studios, and Sea World / Universal Studios Fireworks too! This is an AMAZING Windsor Hills 2 Bedroom 2 bath Property with Views of the Fireworks from the Balcony,...

See more

Close x

convenient

“ Excellent ”
December 1, 2014
The condo is conveniently placed minutes from the parks. The condo was nicely decorated and had a nice view off of the balcony. Did not get a chance to use the pool but it looked to be a very nice facility. It was a very good experience over all and would definitely use them again in the future.
earle lavely, frederick Maryland USA

See all reviews

Close x

Kissimmee Florida Vacation Rentals - Home
1 / 16

Kissimmee Home
5 Bedrooms / 4 Bathrooms / Sleeps 12

“ Excellent ”16 Reviews

from

$160

/ night

Email Owner
Bedrooms:5
Bathrooms:4
Sleeps:12
Type:Home
Per night:$160 - $179
Per month:$4,800 - $5,370
Pets allowed:No
Internet:Yes

Dopey's Delight is a Disney vacation rental that is nestled in the popular Indian Creek community, less than 3 miles from Disney's doorstep in Kissimmee, Florida and is perfectly placed for the shops, restaurants, fun and attractions that Orlando has to offer. With 5 bedrooms ...

See more

Close x

Best vacation ever!

“ Excellent ”
December 1, 2014
Wonderful home. Great floor plan . Plenty of room for all 9 of us. Fantastic privacy with 3 split bedroom with their own baths on opposite ends of home and 2 bedrooms that shared a bath. Plenty of dishes and cooking supplies very conducive for home cooked meals. The kitchen was a dream to work in. Easy drive to all Disney attractions and convenient to shops and restaurants. We all had a fantastic time. Home was clean and bright. Would definitely recommend to multi generational families. The space was very easy to share. Would stay again in the future. Only issue was no garbage pickup on Thursday due to thanksgiving holiday which was an issue due to raccoons trying to get into trash. Wish I would have known earlier so I could have talked to owner about an alternative.
Maggie Hendler, Elk Grove Village, Il. USA

See all reviews

Close x

Kissimmee Florida Vacation Rentals - Home
1 / 30

Kissimmee Home
6 Bedrooms / 4 Bathrooms / Sleeps 14

“ Excellent ”1 Review

from

$179

/ night

Email Owner
Bedrooms:6
Bathrooms:4
Sleeps:14
Type:Home
Per night:$179 - $350
Per month:$5,370 - $10,500
Pets allowed:No
Internet:Yes

Our luxury, 5- star Disney vacation villa, 2 Kings, 2 Queens & 4 Twins, is located in the # 1 overall rated Vacation Resort of Windsor Hills. Windsor Hills Resort is considered by many guests and travelers to be the best overall vacation home community in and around the Central...

See more

Close x

Charles Kenny

“ Excellent ”
May 3, 2014
Great location.Spacious house that was very clean and was very comfortable for our family of ten.The pool and jacuzzi were both terrific.We all had a great time and would highly recommend this property.We hope to go back again.
Charles Kenny, Saratoga springs N.Y.

See all reviews

Close x

Kissimmee Florida Vacation Rentals - Home
1 / 25

Kissimmee Home
5 Bedrooms / 5.5 Bathrooms / Sleeps 12

“ Excellent ”1 Review

from

$495

/ night

Email Owner
Bedrooms:5
Bathrooms:5.5
Sleeps:12
Type:Home
Per night:$495 - $695
Per week:$3,465 - $4,865
Pets allowed:No
Internet:Yes

Property Ref: RVH_081 This beautiful home has everything you need to create your dream stay in Reunion Resort. A large pool and spa, luxurious decor that creates a homely ambiance, over 5, 000 sq. ft of spacious living areas and large inviting bedrooms, a cinema and games room...

See more

Close x

Great Stay!

“ Excellent ”
March 17, 2014
Andy was a great host and delivered on everything that was promised. We rented this wonderfully appointed home for a family reunion. It was the perfect venue for both the adults and the four children. The pool/spa was the focal point for everone during the day and the pool table was the venue for most evenings during our nine day visit. We look forward to a return visit. Thanks Andy......!
Dennis Hoskinson, Big Lake, Alaska USA

See all reviews

Close x

Kissimmee Florida Vacation Rentals - Home
1 / 21

Kissimmee Home
4 Bedrooms / 3.5 Bathrooms / Sleeps 10

from

$150

/ night

Email Owner
Bedrooms:4
Bathrooms:3.5
Sleeps:10
Type:Home
Per night:$150 - $180
Per week:$1,100 - $1,300
Pets allowed:No
Internet:Yes

$1100 per week in month of FEBRUARY- JULY 1, 2015 (Cleaning & Taxes included ) OPTIONAL POOL HEAT is $140 per WEEK or $150 a night plus one time $90 cleaning ( Taxes Included ) NO ANIMALS & NO SMOKING NO ANIMALS & NO SMOKING This Luxuriously Huge 2400 Square foot Furnished Italian...

See more

Close x

Kissimmee Florida Vacation Rentals - Home
1 / 28

Kissimmee Home
6 Bedrooms / 5 Bathrooms / Sleeps 14

from

$221

/ night

Email Owner
Bedrooms:6
Bathrooms:5
Sleeps:14
Type:Home
Per night:$221 - $353
Per week:$1,547 - $2,471
Pets allowed:No
Internet:Yes

Looking for a home away from home or just planning a Disney vacation? This spacious rental comfortably accommodates 14 guests. It's just 10 minutes to Disney parks and inside a great resort community: Paradise Palms. It’s a convenient location to access shopping centers, theme ...

See more

Close x

Kissimmee Florida Vacation Rentals - Condo
1 / 22
Bedrooms:3
Bathrooms:2
Sleeps:6
Type:Condo
No rental rates available - please contact the owner
 
Pets allowed:No
Internet:Yes

Our Canadian- owned vacation condo located near Formosa Gardens Boulevard and Silk Road in Kissimmee, FL is available for rent! This lovely 1500 sq. ft condo is spacious enough to house 6 people comfortably with it's 3 bedrooms and 2 bathrooms. It is newly and completely furnished...

See more

Close x

Very nice place!

“ Excellent ”
September 28, 2014
My experience in this place was awesome...,nice and clean 5 points recommend.
Silvia Lobaton, Pennsylvania

See all reviews

Close x

Kissimmee Florida Vacation Rentals - Condo
1 / 9

Kissimmee Condo
1 Bedroom / 1 Bathroom / Sleeps 6

“ Excellent ”1 Review

from

$55

/ night

Email Owner
Bedrooms:1
Bathrooms:1
Sleeps:6
Type:Condo
Per night:$55 - $85
Per week:$385
Pets allowed:No
Internet:Yes

Luxurious Orlando Hotel Condo Suite on Parc Corniche , situated in middle of action at popular International Drive , major Orlando’s vacation destinations. Unit is conveniently located at minutes distance from all destinations and major attractions . Parc Corniche : Rarely...

See more

Close x

Florida I.C.E.d Cake Competition

“ Excellent ”
June 5, 2012
Thanks Rohan L, had the greatest time in Florida and your condo was so clean and well kept will definitely rent again next year...
Maritza Baez, Springfield Ma

See all reviews

Close x

1 / 43

Kissimmee Villa
7 Bedrooms / 5.5 Bathrooms / Sleeps 16

“ Excellent ”19 Reviews

from

$179

/ night

Email Owner
Bedrooms:7
Bathrooms:5.5
Sleeps:16
Type:Villa
Per night:$179 - $339
Per month:$5,370 - $10,170
Pets allowed:No
Internet:Yes

Luxurious and Beautiful Villa is ideally located at exclusive Season Community , about 5 miles short distance from Disney World & about minutes distance from the best restaurants and shops of the Central FL. Close to 24 hrs Wal Mart . Lake Buena Vista Factory Stores, 5 miles away....

See more

Close x

Wonderful house!

“ Excellent ”
March 19, 2015
We enjoyed the house, it was beautiful. Good location, we felt safe in the area. We will definitely go again.
Cindy Westley, Texas, USA

See all reviews

Close x

Kissimmee Florida Vacation Rentals - Home
1 / 35

Kissimmee Home
5 Bedrooms / 4.5 Bathrooms / Sleeps 10

from

$315

/ night

Email Owner
Bedrooms:5
Bathrooms:4.5
Sleeps:10
Type:Home
Per night:$315 - $475
Per month:$9,450 - $14,250
Pets allowed:No
Internet:No

Property Ref: RVH_007 Luxurious comfort, Quality…. This beautiful home with four poster beds, private pool, spa and sun deck enjoys views of the famous Tom Watson Independence course at Reunion Resort. A brand new air conditioned movie and games room has recently been ...

See more

Close x

Kissimmee Florida Vacation Rentals - Condo
1 / 24

Kissimmee Condo
3 Bedrooms / 3 Bathrooms / Sleeps 8

from

$115

/ night

Email Owner
Bedrooms:3
Bathrooms:3
Sleeps:8
Type:Condo
Per night:$115 - $185
Per month:$3,450 - $5,550
Pets allowed:No
Internet:Yes

Property Ref RVH_150 This 1, 630 sq ft top floor condo is located close to the center of Reunion offering convenience and luxury in a peaceful landscaped setting. Located in Whisper Way, within the Villas South neighborhood of Reunion Resort, less than 200 yards from the...

See more

Close x

Kissimmee Florida Vacation Rentals - Home
1 / 9

Kissimmee Home
3 Bedrooms / 2 Bathrooms / Sleeps 6

“ Excellent ”11 Reviews

from

$95

/ night

Email Owner
Bedrooms:3
Bathrooms:2
Sleeps:6
Type:Home
Per night:$95 - $114
Per week:$650 - $795
Pets allowed:Yes
Internet:Yes

Lovely 3 bedroom 2 bathroom villa with private screened in pool, only minutes to Disney and all other major attractions located in Kissimmee, Florida in the most sought out community of Chatham Park. Our Beautiful home comes fully equipped with 2 car garage. Master bedroom has...

See more

Close x

Fun Time

“ Excellent ”
March 28, 2014
We really enjoyed our two week stay. The home was clean and well equiped for a long term stay. The location was great. Easy access to Disney and area attractions. The two maintenance items that came up were addressed quickly. Will stay here again on our next trip.
Craig Smith, Bellevue, NE USA

See all reviews

Close x

Kissimmee Florida Vacation Rentals - Villa
1 / 14

Kissimmee Villa
5 Bedrooms / 5.5 Bathrooms / Sleeps 10

“ Excellent ”9 Reviews

from

$199

/ night

Email Owner
Bedrooms:5
Bathrooms:5.5
Sleeps:10
Type:Villa
Per night:$199 - $299
Per week:$1,393 - $2,093
Pets allowed:No
Internet:Yes

Our exclusive vacation villa offers a private pool and 5 bedrooms that allow up to 10 guests comfortable accommodations. This luxury vacation home is equipped with all the amenities to make you stay relaxing and pleasurable. A fully equipped kitchen, 5 full bathrooms and modern...

See more

Close x

Terra verde resort

“ Excellent ”
December 26, 2014
Its a really nice resort.
Eric Flores, mcallen,Tx USA

See all reviews

Close x

Kissimmee Florida Vacation Rentals - Condo
1 / 24

Kissimmee Condo
3 Bedrooms / 2 Bathrooms / Sleeps 8

“ Excellent ”4 Reviews

from

$70

/ night

Email Owner
Bedrooms:3
Bathrooms:2
Sleeps:8
Type:Condo
Per night:$70 - $105
Per week:$490 - $735
Pets allowed:No
Internet:Yes

Condominium: It is a reasonably priced, professionally decorated and furnished 3- bedroom/2- bathroom condominium offering comfort, space, style, luxury and privacy. It is located at a luxurious and upscale gated Cane Island resort. Discover the endless comfort within this...

See more

Close x

Enjoyed the stay

“ Excellent ”
September 21, 2014
We enjoyed our stay at this condo. We were not there much but it was very clean and spacious. We would stay here again for sure. I guess the only negative is that we could not get the living room tv to work but it didn't matter. Thanks!!
Todd, Woodstock Ga

See all reviews

Close x

Kissimmee Florida Vacation Rentals - Condo
1 / 20

Kissimmee Condo
3 Bedrooms / 2 Bathrooms / Sleeps 8

“ Excellent ”6 Reviews

from

$109

/ night

Email Owner
Bedrooms:3
Bathrooms:2
Sleeps:8
Type:Condo
Per night:$109 - $139
Per month:$3,270 - $4,170
Pets allowed:No
Internet:Yes

MEET THE NEW "SIMBA'S PRIDE! " Disney World area home - the most exciting, vacation home in the Disney World/Orlando area! At less than the cost of many small hotel rooms in the area, and 400%- 500% less than staying "on property" this home is almost a "too good to be true" value....

See more

Close x

Very nice place

“ Excellent ”
February 12, 2015
Clean accommodation's, large rooms & bedrooms. Great place over all!
Heather Kowaleski, Harbor Beach MI

See all reviews

Close x

Kissimmee Florida Vacation Rentals - Home
1 / 49

Kissimmee Home
5 Bedrooms / 5 Bathrooms / Sleeps 12

from

$229

/ night

Email Owner
Bedrooms:5
Bathrooms:5
Sleeps:12
Type:Home
Per night:$229 - $357
Per week:$1,599 - $2,499
Pets allowed:No
Internet:Yes

Welcome to The Windsor Dream - The Ultimate Villa at Windsor Hills – A luxurious south- facing home with private pool and hot- tub, with no rear neighbors. The most important feature of our family retreat is that we offer one of the few south- facing pool homes in Windsor ...

See more

Close x

Kissimmee Florida Vacation Rentals - Townhouse
1 / 13

Kissimmee Townhouse
3 Bedrooms / 3 Bathrooms / Sleeps 8

“ Excellent ”93 Reviews

from

$49

/ night

Email Owner
Bedrooms:3
Bathrooms:3
Sleeps:8
Type:Townhouse
Per night:$49 - $75
Per week:$380 - $525
Pets allowed:No
Internet:Yes

Welcome to 1 of my 2 gorgeous vacation houses located on the same site, couple steps from each other. They are located on the quiet and beautiful Crestwynd Bay in Kissimmee, which has the definition of “convenience”. Whether traveling to the theme parks or heading to play a ...

See more

Close x

Winter home

“ Excellent ”
March 3, 2015
We stayed at One of Sophia Sun's properties for the month of Jan and Feb 2015. My first impression of the townhouse was how immaculate everything was. The special touches the house keepers provided were enjoyable. It was convenient to location of our family and friends. Plus close to many attractions in the area. Sophia was a joy to communicate to if we needed to ask her a question. We would recommend her prosperity to our friends in the North. Of course this was the perfect winter to be in FL seeing that the first snow storm up North dumped 6 feet of snow. Thank you Sophia and Vacationhomerentals for everything.
Alice Setler, Cape Cod MA USA

See all reviews

Close x

Kissimmee Florida Vacation Rentals - Home
1 / 16

Kissimmee Home
3 Bedrooms / 1 Bathroom / Sleeps 8

from

$79

/ night

Email Owner
Bedrooms:3
Bathrooms:1
Sleeps:8
Type:Home
Per night:$79 - $109
Per week:$525 - $699
Pets allowed:No
Internet:Yes

This is a 3 Bedroom 3 Bath Town House Located In Crestwynd Bay And Just A Mile From Disney Gates. The Home Consists Of 1 KING Bed With Attached Bathroom, 1 QUEEN Bed With Bathroom On The Side, 1 Kids Bedroom With 2 Twin Beds Living Room With Sofa. and Love seat. The Home Can ...

See more

Close x

Kissimmee Florida Vacation Rentals - Home
1 / 20

Kissimmee Home
3 Bedrooms / 2 Bathrooms / Sleeps 8

“ Excellent ”1 Review

from

$99

/ night

Email Owner
Bedrooms:3
Bathrooms:2
Sleeps:8
Type:Home
Per night:$99 - $149
Per week:$693 - $1,043
Pets allowed:No
Internet:Yes

Welcome to Indian Ridge Trail South! This well equipped 3 bedroom, 2 bath home is well furnished and has everything you need for a comfortable stay. Come home from a long day at the parks to your vacation home with incredible swimming pool and spa. As you enter the home you...

See more

Close x

Beautiful home!

“ Excellent ”
August 14, 2014
This house was a wonderful place to stay in. Everything you needed and more was at your fingertips. There were many stores in the area, near the house, so it was easy to get what you needed. The pool was great. Everything shown is what you get. It was a great home, and I will defiantly be coming again.
Fatima Makki, New York

See all reviews

Close x

Kissimmee Florida Vacation Rentals - Townhouse
1 / 19

Kissimmee Townhouse
3 Bedrooms / 3 Bathrooms / Sleeps 8

“ Excellent ”19 Reviews

from

$79

/ night

Email Owner
Bedrooms:3
Bathrooms:3
Sleeps:8
Type:Townhouse
Per night:$79 - $93
Per week:$475 - $650
Pets allowed:Yes
Internet:Yes

Our main page at our site My Orlando Stay has more details and pictures. Vacation Home features Sleeps Easily sleep up to 8 people Bedrooms 3 bedrooms, master with King, King/Queen in Guest and 2 twins in Kids room. Bedding and linens provided. Some homes have special features...

See more

Close x

very nice

“ Excellent ”
March 17, 2015
I was very happy with my vacation home. It was clean and well kept and looked like the pictures. It was a quiet and clean complex. All appliances were in working order. The cost was reasonable and the management was very nice.
Denise Clark, West Wyoming PA

See all reviews

Close x

Kissimmee Florida Vacation Rentals - Condo
1 / 17

Kissimmee Condo
3 Bedrooms / 2 Bathrooms / Sleeps 6

“ Excellent ”6 Reviews

from

$50

/ night

Email Owner
Bedrooms:3
Bathrooms:2
Sleeps:6
Type:Condo
Per night:$50 - $150
Per month:$1,500 - $4,500
Pets allowed:No
Internet:No

Windsor Hills is one of the newest and greatest gated community located within the heart of Orlando’s premier tourist attractions. Windsor Hills boasts the closest proximity to Central Florida's theme parks. Windsor Hills has all the amenities of a Five Star Hotel or Resort. Our...

See more

Close x

Perfect

“ Excellent ”
December 14, 2014
Our vacation was absolutely perfect thanks to Tony and his condo at Windsor Hills. Tony, the owner is one of the friendliest and most conscientious people I have ever dealt with. He has everything so well organized that we didn't have any issues during our stay. By having a door code and gate permit, we were able to drive right in and enter our unit. Smooth!! The beautiful condo was definitely an A+++, couldn't have been any cleaner, more comfortable or better furnished and supplied. Everything we needed was there. The grounds were also beautiful, extremely clean and well maintained. The pool too was clean as a whistle and heated to a comfortable temperature. We really enjoyed it. The kids enjoyed the game room and it was handy having a variety store on site. The condo and the entire complex were very quiet. It is an absolutely perfect place to stay; we couldn't have found anything better. We have rented other vacation rentals in the past, but will definitely stay at Windsor Hills in the future. Thank you Tony and the Windsor Hills staff for a great vacation.
Chris Ramsay, London, Ontario, Canada

See all reviews

Close x

Kissimmee Florida Vacation Rentals - Villa
1 / 15

Kissimmee Villa
5 Bedrooms / 4 Bathrooms / Sleeps 12

“ Excellent ”1 Review

from

$170

/ night

Email Owner
Bedrooms:5
Bathrooms:4
Sleeps:12
Type:Villa
Per night:$170 - $190
Per week:$1,185 - $1,325
Pets allowed:No
Internet:Yes

If you're looking for a vacation holiday villa close to Disney World, Orlando, Florida then look no further. Our five bedroom, four bathroom luxury villa is just 5 minutes drive away! This is an absolutely gorgeous villa, with additions each year to make it a real home from...

See more

Close x

Awesome stay

“ Excellent ”
January 9, 2014
We recently rented "tropical View" from December 20th - January 8th 2014 and we had an awesome stay. This house was well maintained, spacious and had everything we needed. The owner even helped us to find a Christmas Tree (Thanks Douglas - everything worked out well!) I cooked a full traditional Christmas Dinner in the lovely well equipped kitchen. I can't say enough about this perfectly located villa. Thanks so much to Douglas and Margaret for sharing your beautiful home with my family. I would definitely stay there again and would highly recommend this property
Sandy Harding, Saint John NB

See all reviews

Close x

1 / 23

Kissimmee Villa
8 Bedrooms / 4.5 Bathrooms / Sleeps 20

“ Excellent ”2 Reviews

from

$219

/ night

Email Owner
Bedrooms:8
Bathrooms:4.5
Sleeps:20
Type:Villa
Per night:$219 - $399
Per month:$6,570 - $11,970
Pets allowed:No
Internet:Yes

(Please also check out my similar 8 bedroom in Emerald Island Resort, property 77602, property 77717 and property 154310) This Executive vacation home near Disney located in Emerald Island Resort is tastefully decorated throughout to make you feel at home. Accent painting, colorful...

See more

Close x

Orlando Holiday

“ Excellent ”
January 2, 2015
The house that we rented in Emerald Island worked out perfectly for our large family! The home was just as described and very convenient to all of the Disney theme parks. Andrew was very quick to respond to one small issue we had with the grill and ther rest of the stay was wonderful!! I would highly recommend this home for anyone planning an Orlando vacation. Fang was wonderful to deal with and the area is close to the parks but located in a tranquil gated community far away from the hustle and bustle. Best of both worlds!!
Deb Dykema, Newburgh, Indiana

See all reviews

Close x

Kissimmee Florida Vacation Rentals - Home
1 / 15

Kissimmee Home
4 Bedrooms / 2 Bathrooms / Sleeps 7

“ Excellent ”2 Reviews

from

$99

/ night

Email Owner
Bedrooms:4
Bathrooms:2
Sleeps:7
Type:Home
Per night:$99
Per week:$693
Pets allowed:No
Internet:Yes

This Luxury Vacation Villa was renovated and newly furnished in Spring 2011. The eclectic designed vacation homes offers accommodations for up to 8 people. The master features a King bed. The second master features a queen bedset. The third bedroom features another queen bed. The ...

See more

Close x

Thanksgiving weekend homebase

“ Excellent ”
December 6, 2014
Great location. Super amenities. Friendly and helpful owner. Awesome. Will stay there again and strongly recommend.
Pablo Gomez III, Miami. fl.

See all reviews

Close x

Kissimmee Florida Vacation Rentals - Villa
1 / 35

Kissimmee Villa
3 Bedrooms / 3 Bathrooms / Sleeps 6

from

$109

/ night

Email Owner
Bedrooms:3
Bathrooms:3
Sleeps:6
Type:Villa
Per night:$109 - $165
Per week:$763 - $1,155
Pets allowed:No
Internet:Yes

Specializing in vacation rentals located within Reunion Resort, Windsor Hills Resort and The Retreat at Champions Gate; Magical Vacation Homes offers the finest selection of privately owned, luxury rental properties that are fully furnished and exquisitely designed to provide your...

See more

Close x

Kissimmee Florida Vacation Rentals - Home
1 / 34

Kissimmee Home
5 Bedrooms / 6 Bathrooms / Sleeps 10

from

$410

/ night

Email Owner
Bedrooms:5
Bathrooms:6
Sleeps:10
Type:Home
Per night:$410 - $645
Per week:$2,870 - $4,515
Pets allowed:No
Internet:Yes

Specializing in vacation rentals located within Reunion Resort, Windsor Hills Resort and The Retreat at Champions Gate; Magical Vacation Homes offers the finest selection of privately owned, luxury rental properties that are fully furnished and exquisitely designed to provide your...

See more

Close x

Kissimmee Florida Vacation Rentals - Home
1 / 8

Kissimmee Home
3 Bedrooms / 2 Bathrooms / Sleeps 6

from

$85

/ night

Email Owner
Bedrooms:3
Bathrooms:2
Sleeps:6
Type:Home
Per night:$85 - $102
Per month:$2,550 - $3,060
Pets allowed:No
Internet:Yes

Suray is our Jewel. A gift from the Orient. A beautiful air conditioned 3 bed 2 bath villa with a west facing screened solar heated pool and deck overlooking a lake. The bedrooms comprise a King bed in the master, Queen bed in the guest and Twin beds in the third Bedroom. The villa...

See more

Close x

Kissimmee Florida Vacation Rentals - Villa
1 / 34

Kissimmee Villa
5 Bedrooms / 6 Bathrooms / Sleeps 10

from

$315

/ night

Email Owner
Bedrooms:5
Bathrooms:6
Sleeps:10
Type:Villa
Per night:$315 - $495
Per week:$2,205 - $3,465
Pets allowed:No
Internet:Yes

Specializing in vacation rentals located within Reunion Resort, Windsor Hills Resort and The Retreat at Champions Gate; Magical Vacation Homes offers the finest selection of privately owned, luxury rental properties that are fully furnished and exquisitely designed to provide your...

See more

Close x

Kissimmee Florida Vacation Rentals - Villa
1 / 8

Kissimmee Villa
5 Bedrooms / 4 Bathrooms / Sleeps 10

from

$170

/ night

Email Owner
Bedrooms:5
Bathrooms:4
Sleeps:10
Type:Villa
Per night:$170 - $220
Per week:$1,190 - $1,540
Pets allowed:No
Internet:Yes

Enjoy a magical style vacation at our none smoking villa Castaway. Set within this very beautiful resort, 24 hour manned security gated community adorned with beautiful dolphin fountains and set amongst protected wetlands. Our villa is situated west just off the 192 on the exclusive...

See more

Close x

1 / 41

Kissimmee Villa
4 Bedrooms / 2 Bathrooms / Sleeps 10

“ Excellent ”18 Reviews

from

$110

/ night

Email Owner
Bedrooms:4
Bathrooms:2
Sleeps:10
Type:Villa
Per night:$110 - $128
Per month:$3,300 - $3,840
Pets allowed:No
Internet:Yes

Welcome to Indian Point Villa, our Villa is fully air- conditioned has four bedrooms two bath rooms a dinning area, kitchen and breakfast area, a double garage/games room its own very large private pool with toddlers pool in a netted area. New to the Pool area is a Hot- Tub/Spa...

See more

Close x

HOME WAS A GREAT STAY

“ Excellent ”
December 29, 2014
This home was a great choice and a quiet stay.All attractions were within minutes.May think twice though about going to Disney world on Christmas day(very busy}. I personally enjoyed the pool area at the house. we paid extra for the heated pool and in December .it was well worth the extra money. the house was set up nice, kitchen was well equipped if you are looking to rent a house in Kissimmee area to just relax this is it!! thanks FRANK
FRANKLIN COPSEY, VIRGINIA

See all reviews

Close x

Kissimmee Florida Vacation Rentals - Home
1 / 18

Kissimmee Home
3 Bedrooms / 3 Bathrooms / Sleeps 8

from

$95

/ night

Email Owner
Bedrooms:3
Bathrooms:3
Sleeps:8
Type:Home
Per night:$95 - $135
Per week:$665 - $945
Pets allowed:No
Internet:No

This wonderful 3 bedroom 2 1/2 bath townhouse is located in the exclusive gated community of Lake Berkley Resort. The townhouse offers a living area on the ground floor and the bedrooms are upstairs for privacy. There is a large community pool, heated Jacuzzi, and clubhouse with...

See more

Close x

Kissimmee Florida Vacation Rentals - Villa
1 / 17

Kissimmee Villa
4 Bedrooms / 4 Bathrooms / Sleeps 10

from

$179

/ night

Email Owner
Bedrooms:4
Bathrooms:4
Sleeps:10
Type:Villa
Per night:$179 - $219
Per week:$1,253 - $1,533
Pets allowed:No
Internet:Yes

Newly Upgraded. Contemporary. Luxurious. Pamper yourself in our spacious 4 bedroom/4 bathroom air conditioned villa with all the amenities you and your family will enjoy. Our comfortable villa sleeps 10 magical guests and features a litany of premium enhancements to make your...

See more

Close x

Kissimmee Florida Vacation Rentals - Townhouse
1 / 28

Kissimmee Townhouse
6 Bedrooms / 5 Bathrooms / Sleeps 14

from

$225

/ night

Email Owner
Bedrooms:6
Bathrooms:5
Sleeps:14
Type:Townhouse
Per night:$225 - $380
Per week:$1,575 - $2,660
Pets allowed:No
Internet:Yes

This beautiful unit is located in Paradise Palms Resort one of Florida's Premier Resorts only 5 minutes from Disney! ! and within a couple miles to restaurants, grocery stores and shopping. Stay in the lap of luxury when you book our professionally decorated unit inParadise....

See more

Close x

1  2  3  4  5 

Kissimmee, Florida Travel Tips

Located only moments from Orlando, the beautiful resort town of Kissimmee offers the best that Florida has to offer. Families looking for vacation rentals in Kissimmee, FL have many accommodations to choose from, but renting a home is the best bang for your buck while on a Kissimmee vacation. Rentals by owner offer much more space and privacy than a hotel room, and renting by owner ensures that homes are very well maintained and updated. Keep reading to learn more tips about how to have a memorable Florida vacation in Kissimmee.
Beaches and Parks
Because it is such a popular tourist destination, there is an abundance of available vacation homes in Kissimmee. Families interested in spending time at the beach can easily find great accommodations, but hurry! Beach houses for rent in Kissimmee, FL are quickly snapped up. Make sure to reserve your spot online well in advance to save time and money.
St. Cloud Lakefront Park and Beach offers a fishing pier, splash pad, family picnic area, volleyball court, and playground. Located along the breathtaking Lake Tohopekaliga, this park is a great place to spend a relaxing afternoon.
Cocoa Beach, located just an hour's drive from Kissimmee, features beautiful weather, whale watching, fine dining, and golf.
Things to Do
A great feature of Kissimmee vacation homes is their central location to a number of popular attractions. Theme parks, outdoor activities, and fun things for the kids can all be found within a short drive. Read on to find out more about the variety of activities waiting for you in the Kissimmee area.
Theme Parks
What probably comes to mind when looking for houses for rent in Kissimmee, FL is the town's close proximity to world-famous theme parks. The magic of Disney World, Universal Orlando, and SeaWorld are only a short drive away while staying at this delightful vacation spot.
Walt Disney World needs no introduction. As the most visited entertainment complex in the world, this beloved attraction boasts four theme parks and two water parks.
Universal Orlando consists of Universal Studios, Islands of Adventure, and Wet N' Wild Orlando. Visitors can enjoy a variety of shows, dining, and events right within the borders of the park.
SeaWorld is another favorite of those visiting the Orlando area. With tons of shows, exhibits, dining, and shopping, there is surely to be something for everyone to enjoy. Kids will adore seeing killer whales, dolphins, manatees, sharks, polar bears, flamingoes, and penguins up close.
Outdoor Adventures
Airboat Tours are available via Aquatic Adventures Airboat Tours . Go bird watching, look out for alligators, or take a combination hiking tour/boat ride and learn all about the wildlife of the Florida wetlands.
Golf is a popular sport in Florida because of its year-round sunny weather. If you're a seasoned pro looking for challenging courses or just want to play mini-golf with the kids, Kissimmee has you covered.
Hot Air Balloon Rides are a great way to top off your Kissimmee vacation. Take a sunrise balloon ride over Central Florida's beautiful landscape and check out the wildlife from high above.
Fun With Kids
The kids will have no shortage of things to do while enjoying their time in Kissimmee vacation homes. Kids and parents will have all the comforts of home while having a blast exploring the nearby attractions. In addition to the great outdoors and amazing theme parks, the Kissimmee area also features lots of relaxing, family-friendly activities.
Medieval Times Dinner & Tournament is guaranteed to always be a fun time. Have dinner while being entertained by a live-action jousting tournament.
Osceola County Pioneer Village and Museum features many exhibits depicting life in the 19th century. Located in northwestern Osceola County, the Pioneer Village has a general store, blacksmith shop, one room schoolhouse, and nature preserve.
Green Meadows Petting Farm , located just minutes from Orlando, teaches kids about a variety of farm animals and even allows them to milk a cow. The farm also has a train ride and offers pony rides.
Loading...
Click for larger map
Loading...
Show Big Map
  • Price

  • Bedrooms

    Guests

  • Amenities

    • More