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1,526 vacation rentals

(4) Excellent 

41

Jan 23-27&Jan 31-Feb 4 special-Windsor Hills Luxury pool house/2 miles to Disney

Central Florida / Kissimmee

Kissimmee house

6 13 min stay varies

  • 6 bedrooms
  • sleeps 13
  • min stay varies
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$186

Responds fast!
avg. 1 hour 42 minutes

Price per night from

$186

(22) Very Good 

21

Furnished apartment - weekly & monthly Orlando rental.

Central Florida / Kissimmee

Kissimmee hotel apartment

3 6 min stay varies

  • 3 bedrooms
  • sleeps 6
  • min stay varies
  • Nearest beach 64 mi
  • Swimming pool
  • Child Friendly
“Wonderful Place to stay” I stayed at the Island Club for a period of 3 months and was very happy with my stay. It was quiet, and comfortable. I liked the layout of my condo which was on one floor. My family of 5 had plenty of room to enjoy. I also
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Price per night from

$80

Price per night from

$80

(27) Excellent 

24

Jan 14-19 & 25-31Special.~Windsor Hills 3BD/3BA w/FREE Pool Ht & Welcome Package

Central Florida / Kissimmee

Kissimmee house

3 8 min stay varies

  • 3 bedrooms
  • sleeps 8
  • min stay varies
  • Nearest beach 97 mi
  • Swimming pool
  • Child Friendly
“A Magical Stay” What's not to love about this home! First and foremost Brandie herself is a genuine person who really cares about the people who stay at her home. From the initial contact of a personal phone call, to her follow ups on every little qu
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Price per night from

$126

Responds fast!
avg. 2 hours 4 minutes

Price per night from

$126

(20) Very Good 

31

New! Townhouse. 4Bed/4Bath ""Super Promotion LAST DAYS JANUARY 2018""

Kissimmee / Compass Bay

Kissimmee townhouse

4 8 1 night min

  • 4 bedrooms
  • sleeps 8
  • 1 night min
  • Beach / lakeside relaxation
  • Swimming pool
  • Child Friendly

Price per night from

$52

Price per night from

$52

50

Disney Contemporary 3

Central Florida / Kissimmee

Kissimmee house

4 16 min stay varies

  • 4 bedrooms
  • sleeps 16
  • min stay varies
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$194

Responds fast!
avg. 6 minutes

Price per night from

$194

22

Disney Vacation Rental, Private Townhouse in gated community

Kissimmee / Venetian Bay Villages

Kissimmee townhouse

4 10 5 nights min

  • 4 bedrooms
  • sleeps 10
  • 5 nights min
  • Nearest beach 97 mi
  • Swimming pool
  • Child Friendly

Price per night from

$120

Responds fast!
avg. 8 minutes

Price per night from

$120

(1) Excellent 

42

Scotman's Retreat

Central Florida / Kissimmee

Kissimmee villa

5 11 6 nights min

  • 5 bedrooms
  • sleeps 11
  • 6 nights min
  • Child Friendly

Price per night from

$157

Price per night from

$157

21

SunLake 3126B luxury condo one mile from Disney

Central Florida / Kissimmee

Kissimmee condo

3 6 5 nights min

  • 3 bedrooms
  • sleeps 6
  • 5 nights min
  • Beach / lakeside relaxation
  • Nearest beach 92 mi
  • Swimming pool

Price per night from

$102

Price per night from

$102

(5) Excellent 

56

Top Rated Disney Adventure Villa at Windsor Hills Luxury Villa New Water Park!!’

Central Florida / Kissimmee

Kissimmee villa

6 16 min stay varies

  • 6 bedrooms
  • sleeps 16
  • min stay varies
  • Nearest beach 89 mi
  • Swimming pool
  • Child Friendly
“Would highly recommend this home for family vacation!” We had a great stay. It is such a great location! The owners were very accommodating for anything we needed. Available at anytime if needed. Will definitely be back again in a couple years. We wou
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Price per night from

$228

Responds fast!
avg. 1 hour 18 minutes

Price per night from

$228

(5) Very Good 

31

Regal Oaks - The Official CLC World Resort - Two bedroom Townhome

Kissimmee / Regal Oaks

Kissimmee townhouse

2 6 2 nights min

  • 2 bedrooms
  • sleeps 6
  • 2 nights min
  • Child Friendly
  • Air conditioning
  • Private garden

Price per night from

$194

Price per night from

$194

(20) Very Good 

Certificate of Excellence

37

DISNEY WORLD SWEETWATER CLUB CONDOMINIUM

Central Florida / Kissimmee

Kissimmee condo

3 6 min stay varies

  • 3 bedrooms
  • sleeps 6
  • min stay varies
  • Swimming pool
  • Child Friendly
  • Air conditioning
“Great vacation stay!!!!” EVERYTHING was above what I expected! The condo was very nice and comfortable I couldn't have stayed in a better area I give this vacation home a 10 all around! I will stay here again and again if/when I visit Florida again!!!
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Certificate of Excellence

Price per night from

$75

Price per night from

$75

(1) Excellent 

23

Charming Condo near Disney!!

Central Florida / Kissimmee

Kissimmee condo

3 8 4 nights min

  • 3 bedrooms
  • sleeps 8
  • 4 nights min
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$90

Price per night from

$90

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

(2) Excellent 

38

NEW Storey Lake Resort Disney 4821 Crusoe Street FREE WIFI and PARKING- 5BR/4BA

Central Florida / Kissimmee

Kissimmee townhouse

5 13 6 nights min

  • 5 bedrooms
  • sleeps 13
  • 6 nights min
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$147

Responds fast!
avg. 2 hours 42 minutes

Price per night from

$147

25

Orbit One Vacation Villas: 2-BR, Sleeps up to 6

Central Florida / Kissimmee

Kissimmee condo

2 6 7 nights min

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

Price per night from

$274

Price per night from

$274

(1) Excellent 

75

Great new townhouse 1 mile from Disney in Orlando-9

Central Florida / Kissimmee

Kissimmee townhouse

3 8 2 nights min

  • 3 bedrooms
  • sleeps 8
  • 2 nights min
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$95

Responds fast!
avg. 3 hours 10 minutes

Price per night from

$95

(10) Excellent 

Certificate of Excellence

90

Windsor Palms Resort/southwestPool/GamesRoom/Gated

Central Florida / Kissimmee

Kissimmee house

4 8 min stay varies

  • 4 bedrooms
  • sleeps 8
  • min stay varies
  • Nearest beach 50 mi
  • Swimming pool
  • Child Friendly
“Cozy and great location” Stayed for wife's birthday and it was great. Cozy home with all the extras. Big screen TV to watch the games, gameroom to keep the kids entertained, pool was nice size.10 to 15 mins away from the mouse named Mickey. I Will com
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Certificate of Excellence

Price per night from

$132

Responds fast!
avg. 1 hour 15 minutes

Price per night from

$132

(5) Very Good 

Certificate of Excellence

26

Family Golf Resort 'Villa Bonita' Southern Dunes

Central Florida / Kissimmee

Kissimmee villa

3 6 2 nights min

  • 3 bedrooms
  • sleeps 6
  • 2 nights min
  • Nearest beach 96 mi
  • Swimming pool
  • Child Friendly
“nice house” everything was updated and nice ,except for the mattress they are very old every time we when to sleep and got up we had back paint everybody, and everyroom they need to updated...other then that it was very nice
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Certificate of Excellence

Price per night from

$91

Responds fast!
avg. 48 minutes

Price per night from

$91

(7) Very Good 

40

Spectacular LAKE VIEW Compass Bay Condo,699$p/week

Kissimmee / Compass Bay

Kissimmee townhouse

3 6 4 nights min

  • 3 bedrooms
  • sleeps 6
  • 4 nights min
  • Beach / lakeside relaxation
  • Nearest beach 81 mi
  • Swimming pool

Price per night from

$114

Responds fast!
avg. 3 hours 40 minutes

Price per night from

$114

(6) Very Good 

Certificate of Excellence

60

2601 Windsor Hills 6 bedroom villa with movie / game room / pool / spa

Central Florida / Kissimmee

Kissimmee house

6 14 min stay varies

  • 6 bedrooms
  • sleeps 14
  • min stay varies
  • Swimming pool
  • Child Friendly
  • Air conditioning

Certificate of Excellence

Price per night from

$190

Responds fast!
avg. 1 hour 48 minutes

Price per night from

$190

(43) Excellent 

19

Visit Memory Lane of Celebration|Affordable Home|Central Location+Premium Resort

Central Florida / Kissimmee

Kissimmee house

3 7 min stay varies

  • 3 bedrooms
  • sleeps 7
  • min stay varies
  • Nearest beach 90 mi
  • Swimming pool
  • Child Friendly
“Gem in an ocean of homes” This is truly a gem in the vast ocean of vacation homes available in Florida. Despite not being in the most luxurious neighborhood or having the most luxurious of decorations and furnishings, all the basics and essentials wer
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Price per night from

$66

Responds fast!
avg. 49 minutes

Price per night from

$66

(6) Excellent 

29

Windsor Palms - Luxury Villa with SW Facing Pool

Central Florida / Kissimmee

Kissimmee villa

4 8 min stay varies

  • 4 bedrooms
  • sleeps 8
  • min stay varies
  • Nearest beach 120 mi
  • Swimming pool
  • Child Friendly

Price per night from

$161

Price per night from

$161

(4) Excellent 

12

Wow Factor-Interior Designers Own 5 bed/5bath Home

Kissimmee / Windsor Hills Resort

Kissimmee house

5 10 min stay varies

  • 5 bedrooms
  • sleeps 10
  • min stay varies
  • Nearest beach 129 mi
  • Swimming pool
  • Child Friendly

Price per night from

$201

Price per night from

$201

15

3 BR WINDSOR HILLS 204

Central Florida / Kissimmee

Kissimmee apartment

3 8 min stay varies

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

Price per night from

$86

Price per night from

$86

11

CONDO FOR RENT AT WESTGATE TOWN CENTER ORLANDO FLO

Central Florida / Kissimmee

Kissimmee condo

2 8 7 nights min

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

Price per night from

$173

Price per night from

$173

49

Trendy Orlando Vacation Home-2.5 Miles From Disney

Central Florida / Kissimmee

Kissimmee hotel apartment

3 6 3 nights min

  • 3 bedrooms
  • sleeps 6
  • 3 nights min
  • Beach / lakeside relaxation
  • Swimming pool
  • Child Friendly

Price per night from

$115

Price per night from

$115

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

$100

Price per night from

$100

(6) Excellent 

Certificate of Excellence

22

Nice House in Kissimmee Free Wi FI. The house has 4 BEDROOMS/ Free Pool Heated

Central Florida / Kissimmee

Kissimmee house

3 10 3 nights min

  • 3 bedrooms
  • sleeps 10
  • 3 nights min
  • Nearest beach 120 mi
  • Swimming pool
  • Child Friendly
“Perfect house for relaxing” The location of this excellent house was what we were expecting ,quiet and good neighborhood . What impressed me the most was that the house was super clean , of course I included in that clean the pool . In gene
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Certificate of Excellence

Price per night from

$131

Responds fast!
avg. 2 hours 2 minutes

Price per night from

$131

(28) Very Good 

39

NEWEST Furnished Townhouse 3B&3B. 699 $ p/w

Kissimmee / Compass Bay

Kissimmee townhouse

3 6 4 nights min

  • 3 bedrooms
  • sleeps 6
  • 4 nights min
  • Beach / lakeside relaxation
  • Swimming pool
  • Child Friendly
“Excellent” The house was beautiful and clean. My family and myself really enjoyed our stay. We would definitely book this home again for our future vacations to Florida.
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Price per night from

$99

Responds fast!
avg. 3 hours 8 minutes

Price per night from

$99

(1) Very Good 

12

Large Private Pool Home - Minutes from Disney

Central Florida / Kissimmee

Kissimmee house

4 8 4 nights min

  • 4 bedrooms
  • sleeps 8
  • 4 nights min
  • Child Friendly
  • Air conditioning

Price per night from

$111

Responds fast!
avg. 50 minutes

Price per night from

$111

(4) Very Good 

61

New 9Br/6Ba luxurious Pool House from $300/nt, Close To Disney

Central Florida / Kissimmee

Kissimmee house

9 20 min stay varies

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

Price per night from

$321

Responds fast!
avg. 3 hours 46 minutes

Price per night from

$321

(11) Excellent 

Certificate of Excellence

21

***NEWLY RENOVATED! Private Pool - Gated Resort - Free WIFI - Near DISNEY!!

Central Florida / Kissimmee

Kissimmee house

4 10 min stay varies

  • 4 bedrooms
  • sleeps 10
  • min stay varies
  • Nearest beach 80 mi
  • Swimming pool
  • Child Friendly
“Great family rental with plenty of space!” Great rental! Lots of space for our family to spread out and our kids loved the private pool! We will never stay in a hotel again!! We stayed during Hurricane Matthew and felt very safe! Super close to any st
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Certificate of Excellence

Price per night from

$124

Responds fast!
avg. 1 hour 47 minutes

Price per night from

$124

(1) Excellent 

18

SunLake 3117A Luxury condo one mile from Disney

Central Florida / Kissimmee

Kissimmee condo

3 8 5 nights min

  • 3 bedrooms
  • sleeps 8
  • 5 nights min
  • Nearest beach 89 mi
  • Child Friendly

Price per night from

$90

Price per night from

$90

(20) Excellent 

28

SUPER Close To Disney, Gameroom, Private Backyard, Lake, Free WiFi, Pool, Spa

Kissimmee / Rolling Hills at Formosa

Kissimmee house

6 15 min stay varies

  • 6 bedrooms
  • sleeps 15
  • min stay varies
  • Swimming pool
  • Child Friendly
  • Air conditioning
“Very welcoming and worth it !” Me and my family absolutely loved this vacation house everything was so welcoming and near perfect ! This house is definitely something we will never forget and hopefully when we come back we will be able to rent from ki
…see more

Price per night from

$217

Responds fast!
avg. 1 hour 25 minutes

Price per night from

$217

13

2 BR WINDSOR HILLS 402! CLOSEST CONDO TO DISNEY!

Central Florida / Kissimmee

Kissimmee house

2 6 min stay varies

  • 2 bedrooms
  • sleeps 6
  • min stay varies
  • Nearest beach 50 mi
  • Swimming pool
  • Ask about children

Price per night from

$91

Price per night from

$91

(7) Excellent 

77

BLUE HORIZON 5-Bed 5-bath not Overlooked on Sunset Lakes

Central Florida / Kissimmee

Kissimmee villa

5 12 min stay varies

  • 5 bedrooms
  • sleeps 12
  • min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 113 mi
  • Swimming pool
“Fabulous holiday home in a fabulous location.” The Villa was the best we have stayed in both for comfort and location.It was just a short 10 minute drive to most attractions and even closer to a choice of supermarkets.The outdoor barbecue area was lov
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Price per night from

$201

Price per night from

$201

(3) Very Good 

23

HOUSE IN NEW COMPLEX NEAR DISNEY GAME ROOM POOL

Central Florida / Kissimmee

Kissimmee house

6 12 min stay varies

  • 6 bedrooms
  • sleeps 12
  • min stay varies
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$292

Responds fast!
avg. 1 hour 14 minutes

Price per night from

$292

7

1 Bedroom Resort Condo in the Heart of Kissimmee

Central Florida / Kissimmee

Kissimmee hotel apartment

1 4 5 nights min

  • 1 bedroom
  • sleeps 4
  • 5 nights min
  • Swimming pool
  • Child Friendly

Price per night from

$151

Price per night from

$151