Vacation Rentals with Pool in Kissimmee

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Filtering by: Swimming pool

21,667 vacation rentals

(35) Very Good 

17

Luxurious 3 Bedroom Townhome-1.5 miles from Disney

Central Florida / Kissimmee

Kissimmee villa

3 7 min stay varies

  • 3 bedrooms
  • sleeps 7
  • min stay varies
  • Swimming pool
  • Child Friendly
  • Air conditioning
“Great Experience” The villa did not disappoint and was a great place for my family and I to stay during our world wind visit to Disney. I would recommend this place to anyone who is going to Orlando with a large group :-)
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Price per night from

$79

Responds fast!
avg. 2 hours 43 minutes

Price per night from

$79

(16) Excellent 

28

** SEPT & OCT SPECIAL ($1000 for Week) (TAXES INCLUDED IN PRICE) **********

Central Florida / Kissimmee

Kissimmee house

4 10 min stay varies

  • 4 bedrooms
  • sleeps 10
  • min stay varies
  • Swimming pool
  • Child Friendly
  • Air conditioning
“Awesome Stay!” Can't say enough great things about this property. It was everything as described and pictured. The location was perfect being only about 20 minutes from the Disney parks. The pool, which is beautiful, was a welcome addition after s
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Price per night from

$129

Price per night from

$129

(15) Very Good 

26

Kissimmee Townhouse 4 bedrooms

Central Florida / Kissimmee

Kissimmee townhouse

4 8 3 nights min

  • 4 bedrooms
  • sleeps 8
  • 3 nights min
  • Swimming pool
  • Child Friendly
  • Air conditioning
“Great Place” This vacation home is absolutely beautiful and convenient to everything. Still here and having a great time.
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Price per night from

$120

Price per night from

$120

(25) Excellent 

15

Luxury 4 Bedroom Villa w/pool, 2 Miles from Disney

Central Florida / Kissimmee

Kissimmee house

4 8 4 nights min

  • 4 bedrooms
  • sleeps 8
  • 4 nights min
  • Swimming pool
  • Child Friendly
  • Air conditioning
“Beautiful Home, It was so relaxing and comfortable!!” Our family had a wonderful time on our Vacation. The location was very convenient. The pool and hot tub was great. The house was amazing, and my children loved it, I like the entrance to the pool a
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Price per night from

$101

Price per night from

$101

(7) Very Good 

40

Lakefront, gated 4Br/3Ba, 6mile to Disney, Private Jacuzzi, Free WiFi/Cable TV

Central Florida / Kissimmee

Kissimmee villa

4 10 min stay varies

  • 4 bedrooms
  • sleeps 10
  • min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 72 mi
  • Swimming pool
“Very pleased” We were very pleased with the house and the attention given by the owner, I emailed a concern and 1 hour later it was resolved. House is good for parents with kids.
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Price per night from

$67

Responds fast!
avg. 1 hour 31 minutes

Price per night from

$67

(30) Very Good 

49

Pat and Ron's Holiday Home, Relaxing Retreat

Central Florida / Kissimmee

Kissimmee villa

3 6 4 nights min

  • 3 bedrooms
  • sleeps 6
  • 4 nights min
  • Swimming pool
  • Child Friendly
  • Air conditioning
“Great accommodations for the price!” My best friend, her daughter, and I stayed in Pat and Ron's Holiday Home in June. Overall, for the price you can't really beat it. The house was clean and inviting and in a great location. The neighborhood appears
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Price per night from

$88

Price per night from

$88

(33) Very Good 

27

1.5 M to Disney,From $70/nt,3BR 1600 sqft Townhome

Central Florida / Kissimmee

Kissimmee apartment

3 8 min stay varies

  • 3 bedrooms
  • sleeps 8
  • min stay varies
  • Nearest beach 97 mi
  • Swimming pool
  • Child Friendly
“Spacious family friendly condo close to Disney.” Perfect location to visit Disney. Very spacious with a full kitchen . A great family friendly condo.
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Price per night from

$70

Responds fast!
avg. 2 hours 22 minutes

Price per night from

$70

(19) 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

$79

Price per night from

$79

(26) Very Good 

26

3 Bedroom Vacation Home in Kissimmee Pet-Friendly

Central Florida / Kissimmee

Kissimmee house

3 6 2 nights min

  • 3 bedrooms
  • sleeps 6
  • 2 nights min
  • Swimming pool
  • Child Friendly
  • Air conditioning
“Vacation 2017” The house is really beautiful, clean and well maintained. We had a wonderful time and really felt at home. The owner Philip was very friendly and helpful. Thanks to Al for setting up the internet for us. Hoping to come back again next y
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Price per night from

$80

Price per night from

$80

(4) Excellent 

46

Caribe Cove Resort - 2 BR * Unit Top floor * New Mattress - WiFi/Parking free

Central Florida / Kissimmee

Kissimmee apartment

2 6 min stay varies

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

Price per night from

$99

Price per night from

$99

(17) Excellent 

53

'Casa Linda' Beautiful Lakeside Home with Gym and Hot Tub

Central Florida / Kissimmee

Kissimmee house

3 8 4 nights min

  • 3 bedrooms
  • sleeps 8
  • 4 nights min
  • Beach / lakeside relaxation
  • Nearest beach 121 mi
  • Swimming pool
“Amazing” Beautiful :) This was definitely a great place to stay My daughter and I had a nice relaxing vacation while staying here Definitely would recommend this to anyone looking for a nice place to stay Thank you :)
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Price per night from

$90

Price per night from

$90

(14) Excellent 

35

Terra Verde 5 Bedroom with Conservation View

Central Florida / Kissimmee

Kissimmee villa

5 10 min stay varies

  • 5 bedrooms
  • sleeps 10
  • min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 56 mi
  • Swimming pool
“Very nice” The home was just as promised. It was clean and well kept. The location was a straight shot to disney. We didn't have to go on the toll road. Terra verde was great also. I liked the idea of a safe and secure place to stay in a home away fro
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Price per night from

$180

Responds fast!
avg. 1 hour 39 minutes

Price per night from

$180

(7) Very Good 

55

New Opening 8br/6ba pool villa from $260/nt ,Close to Disney

Central Florida / Kissimmee

Kissimmee house

8 18 min stay varies

  • 8 bedrooms
  • sleeps 18
  • min stay varies
  • Swimming pool
  • Child Friendly
  • Air conditioning
“Family vacation” This by far was the best we went to. There is something for everyone to do down to the kids, the house was beautiful.
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Price per night from

$250

Responds fast!
avg. 2 hours 22 minutes

Price per night from

$250

(4) Excellent 

41

Dec 10-22 Special --Windsor Hills Luxury pool house/Wifi/1.5 mile 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

$165

Responds fast!
avg. 1 hour 51 minutes

Price per night from

$165

(6) Very Good 

25

From $80/nt,Close to Disney,Seaworld,Convention Center,4br Townhome with Hot Tub

Central Florida / Kissimmee

Kissimmee townhouse

4 10 min stay varies

  • 4 bedrooms
  • sleeps 10
  • min stay varies
  • Nearest beach 97 mi
  • Swimming pool
  • Child Friendly
“Great Family Friendly Home” We had a blast. It felt safe and secure. It was clean and spacious. I have a large family of 9 and everyone had plenty of space. Quiet but friendly neighbors. Amenities were awesome. Hot tub was so relaxing. We had a great
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Price per night from

$80

Responds fast!
avg. 2 hours 22 minutes

Price per night from

$80

4

Furnished 4 Bedroom Villa for Rent

Central Florida / Kissimmee

Kissimmee villa

4 10 2 nights min

  • 4 bedrooms
  • sleeps 10
  • 2 nights min
  • Swimming pool
  • Air conditioning

Price per night from

$200

Price per night from

$200

(7) Very Good 

16

The Charming Mickey's Tree House,

Central Florida / Kissimmee

Kissimmee villa

4 9 min stay varies

  • 4 bedrooms
  • sleeps 9
  • min stay varies
  • Swimming pool
  • Child Friendly
  • Air conditioning
“Awesome vacation!!” My husband and I took our 3 year old daughter and had a wonderful time. The house had everything we needed and more. We felt right at home from the time we got there until the time we went home. The pool and hot tub were perfect
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Price per night from

$100

Price per night from

$100

(3) Very Good 

47

Kissimmee Windsor at Westside's "The Second Star to the Right" vacation home

Central Florida / Kissimmee

Kissimmee villa

7 18 min stay varies

  • 7 bedrooms
  • sleeps 18
  • min stay varies
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$239

Price per night from

$239

(2) Very Good 

49

☀ One Time Offer ☀ perfect for families! Spacious pool villa with spa near parks

Kissimmee / Paradise Palms

Kissimmee townhouse

6 14 min stay varies

  • 6 bedrooms
  • sleeps 14
  • min stay varies
  • Nearest beach 97 mi
  • Swimming pool
  • Child Friendly

Price per night from

$114

Price per night from

$114

11

Beautiful 3bedroom/ 2 bath villa on Veranda Palms Resort with own pool & spa

Central Florida / Kissimmee

Kissimmee villa

3 6 3 nights min

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

Price per night from

$80

Price per night from

$80

(22) Very Good 

29

Inexpensive Disney Luxury Home, Pet-Friendly, 1 mile from Parks-2

Central Florida / Kissimmee

Kissimmee apartment

3 8 2 nights min

  • 3 bedrooms
  • sleeps 8
  • 2 nights min
  • Swimming pool
  • Child Friendly
  • Air conditioning
“Pet friendly gated community” We enjoyed or stay at Manny's townhouse. The neighborhood was quiet, clean, and the neighbors were very friendly. I love that the pool was very close to where we stayed and all the activities we had planned was close by.
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Price per night from

$95

Price per night from

$95

(2) Excellent 

56

New Opening 9 Br/6 Ba 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

$300

Responds fast!
avg. 2 hours 22 minutes

Price per night from

$300

(2) Excellent 

37

2636TW- Veranda Palms

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

$218

Price per night from

$218

(13) Very Good 

27

New Opening 5Br/3Ba Hot Tub/Lake View,Close Disney,Seaworld,Convention Center

Central Florida / Kissimmee

Kissimmee townhouse

5 12 min stay varies

  • 5 bedrooms
  • sleeps 12
  • min stay varies
  • Beach / lakeside relaxation
  • Swimming pool
  • Child Friendly
“Ok” Overall it was fine..checkout was at 11 and at 10 cleaners knocked on door and then preceded to sit in driveway waiting for us to leave. There was no dish soap or soap in bathrooms which would have been nice.
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Price per night from

$90

Responds fast!
avg. 2 hours 22 minutes

Price per night from

$90

(20) Excellent 

27

From $80/nt,4br/3ba townhome with hot tub/lake view,Near Disney,Seaworld

Central Florida / Kissimmee

Kissimmee apartment

4 8 min stay varies

  • 4 bedrooms
  • sleeps 8
  • min stay varies
  • Beach / lakeside relaxation
  • Swimming pool
  • Child Friendly

Price per night from

$80

Responds fast!
avg. 2 hours 22 minutes

Price per night from

$80

49

NEW! 4/3 Private Town Home at Storey Lake Resort-Near Disney Theme Parks

Central Florida / Kissimmee

Kissimmee townhouse

4 8 min stay varies

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

Price per night from

$149

Responds fast!
avg. 40 minutes

Price per night from

$149

(3) Excellent 

24

Private Home near Disney with Pool

Central Florida / Kissimmee

Kissimmee house

4 10 3 nights min

  • 4 bedrooms
  • sleeps 10
  • 3 nights min
  • Swimming pool
  • Child Friendly
  • Air conditioning
“Super Home!!” Our stay was wonderful. The home was clean and well organized. The owner thought of everything from towels to pans to pool floats to extra pillows. We especially enjoyed the quiet neighborhood and safe environment. The price was right an
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Price per night from

$100

Price per night from

$100

17

Christine’s Villa

Central Florida / Kissimmee

Kissimmee villa

3 6 min stay varies

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

Price per night from

$81

Price per night from

$81

(4) Average 

20

7631 Heritage Crossing Way - 101

Central Florida / Kissimmee

Kissimmee apartment

3 6 2 nights min

  • 3 bedrooms
  • sleeps 6
  • 2 nights min
  • Swimming pool
  • Child Friendly
  • Air conditioning
“condo” the only thing we didn!t like about the condo was there was no dinning room and did not like sitting at the kitchen counter other tan that the place was great.
…see more

Price per night from

$95

Price per night from

$95

(6) Very Good 

22

Dolce Vita

Kissimmee / Bellavida Resort

Kissimmee townhouse

3 6 min stay varies

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

Price per night from

$79

Price per night from

$79

(16) Very Good 

35

Spacious 4-bed lakeside pool villa near Disney

Central Florida / Kissimmee

Kissimmee villa

4 10 min stay varies

  • 4 bedrooms
  • sleeps 10
  • min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 97 mi
  • Swimming pool
“Peaceful location with stunning views” We had a wonderful holiday in this lovely villa. It is spacious and well appointed everything was beautifully clean. The estate is quiet and peaceful considering how close it is to the 192 and all it has to offer
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Price per night from

$109

Responds fast!
avg. 2 hours 53 minutes

Price per night from

$109

(12) Very Good 

21

100 Aker Woods

Central Florida / Kissimmee

Kissimmee house

4 8 min stay varies

  • 4 bedrooms
  • sleeps 8
  • min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning
“AMAZING!!!” This house was Wonderful! Exactly as described! Loyalty USA was GREAT to work with!!! Very pleased all around!!!!
…see more

Price per night from

$129

Price per night from

$129

(3) Very Good 

43

Close2theMagic 3br/3ba Townhouse Windsor Hills

Central Florida / Kissimmee

Kissimmee house

3 7 2 nights min

  • 3 bedrooms
  • sleeps 7
  • 2 nights min
  • Swimming pool
  • Child Friendly
  • Air conditioning
“Vacation comfort at its Best!” This was a family vacation to bring my 5 yr old granddaughter to Disney for her first time. It was spectacular! The condo was so close to Disney that we could be there in a few minutes. The heated splash pool was so a
…see more

Price per night from

$119

Price per night from

$119

(12) Very Good 

51

Brand New 8br/6ba pool villa from $260/nt ,Close to Disney

Central Florida / Kissimmee

Kissimmee house

8 18 min stay varies

  • 8 bedrooms
  • sleeps 18
  • min stay varies
  • Swimming pool
  • Child Friendly
  • Air conditioning
“Mrs” Me and my family really enjoyed staying at the property rental it was ever thing we need in a vaction rental.
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Price per night from

$250

Responds fast!
avg. 2 hours 22 minutes

Price per night from

$250

20

Star Island: A Perfect Paradise!

Central Florida / Kissimmee

Kissimmee apartment

1 4 3 nights min

  • 1 bedroom
  • sleeps 4
  • 3 nights min
  • Swimming pool
  • Ask about children
  • Air conditioning

Price per night from

$84

Price per night from

$84

(12) Very Good 

29

From $90/nt,5br/3ba townhome with hot tub,Near Disney,Seaworld,Convention center

Central Florida / Kissimmee

Kissimmee apartment

5 12 min stay varies

  • 5 bedrooms
  • sleeps 12
  • min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 97 mi
  • Swimming pool
“Vacation rental” The overall experience was nice. The hot was only hot for one day and wouldn't get hot again there after. The cookware needs to be updated but overall we had a great time. I wouldn't definitely rent this rental again.
…see more

Price per night from

$90

Responds fast!
avg. 2 hours 23 minutes

Price per night from

$90

24

Enjoy Beautiful Cypress Palms in Florida!

Central Florida / Kissimmee

Kissimmee apartment

1 4 2 nights min

  • 1 bedroom
  • sleeps 4
  • 2 nights min
  • Swimming pool
  • Ask about children
  • Air conditioning

Price per night from

$89

Price per night from

$89

31

DISNEY AREA 5 BEDROOM PRIVATE POOL VILLA

Central Florida / Kissimmee

Kissimmee villa

5 10 min stay varies

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

Price per night from

$100

Responds fast!
avg. 2 hours 34 minutes

Price per night from

$100