Kissimmee City Rentals

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24,013 Houses

(1) Excellent 

26

Disney Vacation Pool Home/Villa in Deluxe Resort

Kissimmee / Kissimmee City

Kissimmee townhouse

4 10 1 night min

  • 4 bedrooms
  • sleeps 10
  • 1 night min
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$160

Responds fast!
avg. 2 hours 41 minutes

Price per night from

$160

24

Oakwater the nearest resort from Disney !

Kissimmee / Kissimmee City

Kissimmee townhouse

3 6 5 nights min

  • 3 bedrooms
  • sleeps 6
  • 5 nights min
  • Child Friendly
  • Air conditioning

Price per night from

$114

Price per night from

$114

(4) Excellent 

49

AMAZING HOUSE IN DISNEY

Kissimmee / Kissimmee City

Kissimmee house

5 10 4 nights min

  • 5 bedrooms
  • sleeps 10
  • 4 nights min
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$401

Responds fast!
avg. 3 hours 44 minutes

Price per night from

$401

(4) Very Good 

21

8 bedrooms villa only 3 miles from Disney World

Kissimmee / Kissimmee City

Kissimmee villa

8 20 min stay varies

  • 8 bedrooms
  • sleeps 20
  • min stay varies
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$286

Responds fast!
avg. 2 hours 33 minutes

Price per night from

$286

8

Westgate Town Center Villa-Timesharing 12/30/17-01/06/18

Kissimmee / Kissimmee City

Kissimmee villa

1 4 7 nights min

  • 1 bedroom
  • sleeps 4
  • 7 nights min
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$115

Responds fast!
avg. 1 hour 59 minutes

Price per night from

$115

(17) Excellent 

Certificate of Excellence

25

Oakhill Disney Villa

Kissimmee / Kissimmee City

Kissimmee villa

4 10 min stay varies

  • 4 bedrooms
  • sleeps 10
  • min stay varies
  • Nearest beach 120 mi
  • Swimming pool
  • Child Friendly

Certificate of Excellence

Price per night from

$177

Responds fast!
avg. 1 hour 20 minutes

Price per night from

$177

(1) Very Good 

20

Lovely Condo,NEW MATTRESSES,WIFI,4 miles to Disney

Kissimmee / Kissimmee City

Kissimmee condo

3 6 3 nights min

  • 3 bedrooms
  • sleeps 6
  • 3 nights min
  • Beach / lakeside relaxation
  • Nearest beach 100 mi
  • Swimming pool

Price per night from

$103

Price per night from

$103

(21) Very Good 

43

Funshine Magical Villa with Gameroom and WiFi

Kissimmee / Kissimmee City

Kissimmee villa

4 9 min stay varies

  • 4 bedrooms
  • sleeps 9
  • min stay varies
  • Nearest beach 95 mi
  • Swimming pool
  • Child Friendly

Price per night from

$146

Responds fast!
avg. 1 hour 7 minutes

Price per night from

$146

(2) Excellent 

41

8164 Windsor Palms Resort

Kissimmee / Kissimmee City

Kissimmee house

4 8 min stay varies

  • 4 bedrooms
  • sleeps 8
  • min stay varies
  • Nearest beach 100 mi
  • Swimming pool
  • Child Friendly

Price per night from

$138

Responds fast!
avg. 2 hours 21 minutes

Price per night from

$138

Great rentals within 20 miles that match your search

Distance approx 17.5 km from Kissimmee City Show on Map

(36) Very Good 

14

Poolsidevilla Glenbrook Rolling Green Dr CLERMONT

Lake County / Clermont

Clermont villa

4 8 4 nights min

  • 4 bedrooms
  • sleeps 8
  • 4 nights min
  • Swimming pool
  • Child Friendly
  • Air conditioning
“Relaxing Stay with family in condo” we had a relaxing stay at the condo mainly the kids had good time in the heated pool and game room. Condo had all the amenities exactly stated in the ad and looked same as in the pictures. It is closer to the Disney
…see more

Price per night from

$111

Responds fast!
avg. 1 hour 32 minutes

Price per night from

$111

Distance approx 17.47 km from Kissimmee City Show on Map

(9) Very Good 

24

Luxurious 6 bed/ 4 bath Disney villa on Glenbrook,

Central Florida / Orlando

Orlando villa

6 12 min stay varies

  • 6 bedrooms
  • sleeps 12
  • min stay varies
  • Nearest beach 72 mi
  • Swimming pool
  • Child Friendly

Price per night from

$201

Responds fast!
avg. 3 hours 23 minutes

Price per night from

$201

Distance approx 15.06 km from Kissimmee City Show on Map

(3) Excellent 

16

Orlando area: affordable 2bed+2bath villas 6min to Disney

Central Florida / Kissimmee

Kissimmee apartment

2 6 3 nights min

  • 2 bedrooms
  • sleeps 6
  • 3 nights min
  • Nearest beach 121 mi
  • Swimming pool
  • Child Friendly

Price per night from

$102

Responds fast!
avg. 3 hours 32 minutes

Price per night from

$102

Distance approx 17.83 km from Kissimmee City Show on Map

27

Monica's Southern Dunes House

Central Florida / Haines City

Haines City villa

3 6 min stay varies

  • 3 bedrooms
  • sleeps 6
  • min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning

Price per night from

$107

Responds fast!
avg. 2 hours 36 minutes

Price per night from

$107

Distance approx 14.95 km from Kissimmee City Show on Map

47

Wonderful 4 bed, 3 bath home in Paradise Palms!

Central Florida / Kissimmee

Kissimmee house

4 10 min stay varies

  • 4 bedrooms
  • sleeps 10
  • min stay varies
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$138

Price per night from

$138

Distance approx 10 km from Kissimmee City Show on Map

14

WESTGATE LAKES RESORT & SPA-Orlando Florida

Central Florida / Orlando

Orlando villa

3 12 7 nights min

  • 3 bedrooms
  • sleeps 12
  • 7 nights min
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$217

Responds fast!
avg. 1 hour 35 minutes

Price per night from

$217

Distance approx 6.95 km from Kissimmee City Show on Map

24

NEW! 3BR Orlando House - 11 Miles to Disney Parks!

Florida Panhandle / Southport

Southport house

3 8 min stay varies

  • 3 bedrooms
  • sleeps 8
  • min stay varies
  • Child Friendly
  • Air conditioning

Price per night from

$126

Responds fast!
avg. 10 minutes

Price per night from

$126

Distance approx 5.56 km from Kissimmee City Show on Map

(1) Very Good 

19

Comfy 2 Bed Vacation Villa Minutes from DISNEY!!!

Central Florida / Kissimmee

Kissimmee villa

2 4 1 night min

  • 2 bedrooms
  • sleeps 4
  • 1 night min
  • Nearest beach 69 mi
  • Swimming pool
  • Child Friendly

Price per night from

$79

Price per night from

$79

Distance approx 7.8 km from Kissimmee City Show on Map

9

The Fountains Resort

Central Florida / Orlando

Orlando villa

2 6 7 nights min

  • 2 bedrooms
  • sleeps 6
  • 7 nights min
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$201

Price per night from

$201

Distance approx 15.06 km from Kissimmee City Show on Map

16

ABSOLUTELY AMAZING CARIBE COVE 2 BEDROOM

Central Florida / Kissimmee

Kissimmee condo

2 6 3 nights min

  • 2 bedrooms
  • sleeps 6
  • 3 nights min
  • Swimming pool
  • Air conditioning

Price per night from

$106

Price per night from

$106

Distance approx 14.85 km from Kissimmee City Show on Map

33

SPECIAL RATE IN THIS AMAZING JOY HOME SMILE50

Kissimmee / Paradise Palms

Kissimmee house

5 11 5 nights min

  • 5 bedrooms
  • sleeps 11
  • 5 nights min
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$227

Price per night from

$227

Distance approx 15.57 km from Kissimmee City Show on Map

(1) Excellent 

7

419 Fox Loop GAMES ROOM

Central Florida / Davenport

Davenport villa

4 8 3 nights min

  • 4 bedrooms
  • sleeps 8
  • 3 nights min
  • Swimming pool
  • Ask about children
  • Pet Friendly

Price per night from

$121

Price per night from

$121

Distance approx 15.71 km from Kissimmee City Show on Map

27

Remodeled 3 bed / 2 bath villa & pool in gated community, 10 mins to Disney

Central Florida / Four Corners

Four Corners villa

3 6 min stay varies

  • 3 bedrooms
  • sleeps 6
  • min stay varies
  • Nearest beach 110 mi
  • Swimming pool
  • Child Friendly

Price per night from

$97

Responds fast!
avg. 1 hour 42 minutes

Price per night from

$97

Distance approx 12.57 km from Kissimmee City Show on Map

(22) Very Good 

38

Luxury 3 bedroom 2 bathroom Condo in Orlando near Disney (Coconut Condo)

Central Florida / Kissimmee

Kissimmee apartment

3 8 min stay varies

  • 3 bedrooms
  • sleeps 8
  • min stay varies
  • Nearest beach 75 mi
  • Swimming pool
  • Child Friendly
“Great Stay” Great play to stay! Close to Disney, gated community, nice 3 bedroom condo. Very clean and secure. Owner was excellent to work with and kept us informed. Would highly recommend staying here. Even during holiday time, traffic wasn't b
…see more

Price per night from

$91

Responds fast!
avg. 2 hours 11 minutes

Price per night from

$91

Distance approx 11.8 km from Kissimmee City Show on Map

15

2 Bed Deluxe (Condo)

Central Florida / Kissimmee

Kissimmee condo

2 8 7 nights min

  • 2 bedrooms
  • sleeps 8
  • 7 nights min
  • Child Friendly
  • Air conditioning

Price per night from

$303

Price per night from

$303

Distance approx 4 km from Kissimmee City Show on Map

(12) Very Good 

39

Affordably Priced Luxury Townhouse within Fiesta Key Resort located near Disney

Central Florida / Kissimmee

Kissimmee villa

3 8 min stay varies

  • 3 bedrooms
  • sleeps 8
  • min stay varies
  • Swimming pool
  • Child Friendly
  • Air conditioning
“Great value, very nice home” Thanks, your house is very nice and in the future I recommend to the other persons.
…see more

Price per night from

$91

Responds fast!
avg. 3 hours 2 minutes

Price per night from

$91

Distance approx 12.13 km from Kissimmee City Show on Map

18

Dreamland-Beautiful lakeside 6 bedroom house with private pool- 5 min to Disney

Central Florida / Kissimmee

Kissimmee house

6 12 4 nights min

  • 6 bedrooms
  • sleeps 12
  • 4 nights min
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$227

Price per night from

$227

Distance approx 15.03 km from Kissimmee City Show on Map

7

626 Majesty Drive

Central Florida / Davenport

Davenport villa

3 6 3 nights min

  • 3 bedrooms
  • sleeps 6
  • 3 nights min
  • Swimming pool
  • Ask about children
  • Pet Friendly

Price per night from

$104

Price per night from

$104

Distance approx 4.07 km from Kissimmee City Show on Map

38

7 Bedroom/5 Bathroom Terra Verde (112MB)

Central Florida / Kissimmee

Kissimmee house

7 16 min stay varies

  • 7 bedrooms
  • sleeps 16
  • min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning

Price per night from

$446

Price per night from

$446

Distance approx 4.23 km from Kissimmee City Show on Map

16

4 Bedroom/ 3 Bathroom Seven Dwarfs (19-102)

Central Florida / Kissimmee

Kissimmee house

4 10 min stay varies

  • 4 bedrooms
  • sleeps 10
  • min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning

Price per night from

$122

Price per night from

$122

Distance approx 14.24 km from Kissimmee City Show on Map

34

⭐ Beautiful, Spacious ⭐ 4BR Villa 6 Mi. to Disney!

Central Florida / Four Corners

Four Corners house

4 10 1 night min

  • 4 bedrooms
  • sleeps 10
  • 1 night min
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$130

Responds fast!
avg. 2 hours 46 minutes

Price per night from

$130

Distance approx 4.23 km from Kissimmee City Show on Map

28

4 Bedroom/ 3 Bathroom Seven Dwarfs (22-102)

Central Florida / Kissimmee

Kissimmee house

4 12 min stay varies

  • 4 bedrooms
  • sleeps 12
  • min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning

Price per night from

$122

Price per night from

$122

Distance approx 15.05 km from Kissimmee City Show on Map

(6) Very Good 

24

Lake View Villa, WiFi, and Pool

Kissimmee / Tuscany, Florida

Kissimmee villa

3 8 1 night min

  • 3 bedrooms
  • sleeps 8
  • 1 night min
  • Beach / lakeside relaxation
  • Swimming pool
  • Child Friendly
“great area to stay” House was very clean and great location. The 2 couples who stayed are golfers and location to many of our favorite courses was helpful. Variety of nice restaurants nearby.
…see more

Price per night from

$80

Price per night from

$80

Distance approx 17.17 km from Kissimmee City Show on Map

(25) Very Good 

30

Special - 7bd/5ba, Pool/spa, Near Disney. Contact owner for booking < 3 days.

Central Florida / Orlando

Orlando house

7 16 min stay varies

  • 7 bedrooms
  • sleeps 16
  • min stay varies
  • Swimming pool
  • Child Friendly
  • Air conditioning
“Excellent stay!” The house is great for big groups (10 - 14). It is conveniently located near Disney parks. It has ample space. Our group enjoyed it plentiful. Any issues, we resolved them quickly with the owner. Highly recommended for anyone planning
…see more

Price per night from

$164

Responds fast!
avg. 36 minutes

Price per night from

$164

Distance approx 10.79 km from Kissimmee City Show on Map

(11) Excellent 

93

Most private backyard in Orlando! Minutes 2 Disney

Central Florida / Loughman

Loughman villa

4 8 min stay varies

  • 4 bedrooms
  • sleeps 8
  • min stay varies
  • Nearest beach 126 mi
  • Swimming pool
  • Child Friendly

Price per night from

$171

Responds fast!
avg. 8 minutes

Price per night from

$171

Distance approx 16.19 km from Kissimmee City Show on Map

(1) Excellent 

39

Awesome Condo with wrap Around Balcony

Davenport / Bella Piazza

Davenport condo

3 8 min stay varies

  • 3 bedrooms
  • sleeps 8
  • min stay varies
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$104

Responds fast!
avg. 58 minutes

Price per night from

$104

Distance approx 4.1 km from Kissimmee City Show on Map

(2) Very Good 

16

Splended Bed 3 Villa

Central Florida / Kissimmee

Kissimmee villa

3 6 min stay varies

  • 3 bedrooms
  • sleeps 6
  • min stay varies
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$101

Price per night from

$101

Distance approx 4.22 km from Kissimmee City Show on Map

46

Mickeys Retreat Villa Windward Cay Near Disney

Central Florida / Kissimmee

Kissimmee villa

3 6 1 night min

  • 3 bedrooms
  • sleeps 6
  • 1 night min
  • Beach / lakeside relaxation
  • Nearest beach 120 mi
  • Swimming pool

Price per night from

$172

Price per night from

$172

Distance approx 12.36 km from Kissimmee City Show on Map

71

TRANQUILITY AT REUNION RESORT- OFFERING FANTASTIC AMENITIES

Central Florida / Reunion

Reunion villa

12 28 7 nights min

  • 12 bedrooms
  • sleeps 28
  • 7 nights min
  • Child Friendly

Price per night from

$2,036

Price per night from

$2,036