Kissimmee Vacation Rental Getaways


Refine Your Search
Check-In 
calendar

Check-Out
calendar
  • Property Options
  • Amenities
  • Location Type
  • Bed
  • Bath
  • Sleeps
Max Price Per Week $
  • Special Offers
  • Online Booking
  • Home/Villa
  • Cottage/Cabin
  • Condo/Townhome
  • Bed & Breakfast
  • Apt/Room/Suite
  • Air Conditioning
  • Washer/Dryer
  • Full Kitchen
  • Satellite/Cable TV
  • Handicap Access
  • High Speed Internet
  • Elevator
  • Maid Service
  • Garage Parking
  • Pets Allowed
  • Private Pool
  • Pool Access
  • Hot Tub
  • Fireplace
  • Smoking allowed
  • Beach Access
  • Beach Front
  • Golf on site
  • Golf nearby
  • Ocean Front
  • Ocean View
  • Lake Front
  • Lake View
  • Ski in/out
  • Walk to Slopes
  • Skiing nearby
 
Sort by: Type BR/BA/Sleeps Price

8132 Sun Palm

Kissimmee
Welcome to Windsor Palms Resort and this stunning 4 bedroom, 3 bathroom rental home located near the...
Home 4 / 3 / 10

*
Online booking available

$260 - $330
Per Night

$1820 - $2310
Per Week

2104 Rome

Kissimmee
Located in the heart of the premier resort community of Windsor at Westside, this magnificent Spanis...
Home 6 / 4.5 / 12

*
Online booking available

$405 - $545
Per Night

$2835 - $3815
Per Week

Reunion Madison, 8 Bedrooms, Encore Club, Private Pool, S...

Kissimmee
Madison at Encore Club in Reunion is an 8-bedroom air-conditioned luxury home that sleeps 15 people ...
Home 8 / 7 / 15

*
Online booking available

$450 - $950
Per Night

$2520 - $4975
Per Week

Reunion Fremont Ii, 10 Bedrooms, Encore Club, Private Poo...

Kissimmee
Fremont II at Encore Club at Reunion Resort is a 10-bedroom / 10-bathroom luxury home that sleeps 20...
Home 10 / 10 / 20

*
Online booking available

$550 - $1200
Per Night

$3300 - $6225
Per Week

Elegant Townhome with Private Pool in Windsor Hills!

Kissimmee
Great location, 3 bed 3 bath town home with private pool in Windsor Hills. Walk to club house and ma...
Cabin 3 / 3 / 8

*
Online booking available

$145 - $225
Per Night

$1015 - $1575
Per Week

2831 Oakwater Drive

Kissimmee
This lovely condo consists of one king bed, one queen bed and two twin beds, all bedrooms equipped w...
Condo 3 / 2 / 6

*
Online booking available

$145 - $200
Per Night

$1015 - $1400
Per Week

4 BRs 3 BAs townhome at The Villas at Seven Dwarfs (mzl)

Kissimmee
The Villas at Seven Dwarfs Lane is the #1 and newest premier resort and vacation rentals in the Orla...
Condo 4 / 3 / 8

*
Online booking available

$105 - $200
Per Night

$735 - $1400
Per Week

7795 Basnett Circle

Kissimmee
Enjoy an amazing vacation in Florida at this lovely home in Kissimmee. With five bedrooms and five b...
Home 5 / 5 / 10

*
Online booking available

$315 - $420
Per Night

$2205 - $2940
Per Week

7737 Comrow Street

Kissimmee
Welcome to this newly decorated 5 bedroom pool home located in Windsor Hills. There are also 5 bathr...
Home 5 / 5 / 10

*
Online booking available

$315 - $420
Per Night

$2205 - $2940
Per Week

Reunion Madison, 8 Bedrooms, Encore Club, Private Pool, S...

Kissimmee
Madison at Encore Club in Reunion is an 8-bedroom air-conditioned luxury home that sleeps 15 people ...
Home 8 / 7 / 16

*
Online booking available

$450 - $950
Per Night

$2520 - $4975
Per Week

Beautiful 4 bedroom 3 bathroom Townhome with Splash Pool

Kissimmee
This lovely 4 bedroom (1 king master, 1 queen on the first floor and 2 with 2 twins), 3 bathroom tow...
Home 4 / 3 / 8

*
Online booking available

$185 - $255
Per Night

$1295 - $1785
Per Week

7660 Comrow Street Unit 203

Kissimmee
Luxury condo with an idyllic setting – this is one of the few residences in Windsor Hills with a dir...
Condo 3 / 2 / 8

*
Online booking available

$155 - $225
Per Night

$1085 - $1575
Per Week

8024 King Palm Circle

Kissimmee
Brighton floor plan 1816 sqft.4 bedroom 3 bath home (1 story) South facing pool Welcome to this ele...
Home 4 / 3 / 8

*
Online booking available

$260 - $330
Per Night

$1820 - $2310
Per Week

2809 Almaton Loop Unit 104

Kissimmee
Beautifully decorated new 3 bedroom 2 bath condo in sought after Windsor Hills resort community. Ne...
Condo 3 / 2 / 6

*
Online booking available

$155 - $225
Per Night

$1085 - $1575
Per Week

Luxury 5 bedroom 4.5 bath Home Close to Theme Parks

Kissimmee
Come stay with us in this beautiful 5 bedroom 4.5 bath Reunion Vacation home only 10 minutes from Di...
Home 5 / 4.5 / 14

*
Online booking available

$230 - $349
Per Night

$1610 - $3283
Per Week

Reunion Kingston, 6 Bedrooms, Encore Club, Private Pool, ...

Kissimmee
Reunion Kingston Home at Encore Club is a 6-bedroom, 5.5 bathroom air-conditioned home that sleeps u...
Home 6 / 5.5 / 12

*
Online booking available

$350 - $725
Per Night

$2016 - $3775
Per Week

2120 Rome Drive

Kissimmee
This new luxury vacation home is located in the man-gated Windsor at Westside upscale resort communi...
Home 6 / 4.5 / 12

*
Online booking available

$405 - $545
Per Night

$2835 - $3815
Per Week

Stunning 5 BR 5 BA with west facing pool...close to Disney

Kissimmee
This 5 bedroom, 5 bath home has a west facing pool/spa and has open views from the back of the house...
Home 5 / 5 / 12

*
Online booking available

$300 - $430
Per Night

$2100 - $3010
Per Week

2438 Sweetwater Club Circle Unit 50

Kissimmee
Why stay in a hotel room when you can rent this 3 bedroom 2 baths condominium located in Sweetwater ...
Villa 3 / 2 / 8

*
Online booking available

$105 - $105
Per Night

$735 - $735
Per Week

7659 Sir Kaufman Court

Kissimmee
Lovely, 3 bedroom /3bath two-story townhome can sleep 6 comfortably. Bedding includes one King-size...
Home 3 / 3 / 6

*
Online booking available

$180 - $265
Per Night

$1260 - $1855
Per Week

7758 Tosteth Street

Kissimmee
Floor Plan (The Spencer) 2,966 sq. ft. 2 story home with pool and spa. (South facing pool) We invit...
Home 5 / 5 / 12

*
Online booking available

$315 - $420
Per Night

$2205 - $2940
Per Week

7769 Teascone Blvd

Kissimmee
Sevillle floor plan 2236sqft 5 bedroom 5 barth (2 story) Pool home We invite you to enjoy your next ...
Home 5 / 5 / 12

*
Online booking available

$360 - $485
Per Night

$2520 - $3395
Per Week

8952 Majesty Palm Road

Kissimmee
Welcome to this beautiful 4 bedroom, 3 bathroom townhome in the stunning community of Paradise Palms...
Home 4 / 3 / 8

*
Online booking available

$200 - $300
Per Night

$1400 - $2100
Per Week

8954 Majesty Palm Road

Kissimmee
Welcome to this stunning 4 bedroom, 3 bathroom townhome in the popular resort community of Paradise ...
Home 4 / 3 / 8

*
Online booking available

$200 - $300
Per Night

$1400 - $2100
Per Week

8979 Cat Palm Road

Kissimmee
Let us give your next vacation that wow factor with this beautiful townhouse located in the resort c...
Home 4 / 3 / 8

*
Online booking available

$200 - $300
Per Night

$1400 - $2100
Per Week

 

More Getaway Locations and Properties