A pathway through a park with Spanish moss hanging from trees and a body of water in the background.

Kissimmee Vacation Rentals

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Check prices for these dates

In two weeks
Oct 16 - Oct 18
In two months
Nov 27 - Nov 29
In three months
Dec 25 - Dec 27
In four months
Jan 22 - Jan 24

Our top choices for Kissimmee vacation homes

A decorative stone fountain with a twisted base, surrounded by vibrant red flowers and tropical foliage, set against a backdrop of a pool and palm trees.

1. Maple Leaf Inn & Suites

Maple Leaf Inn & Suites
2.5 star property
Kissimmee
6.8 out of 10, (72 reviews)
"The room was clean and the staff was okay "
United States
Shaneka
The price is CA $83
CA $95 total
includes taxes & fees
Sep 29 - Sep 30
Maple Leaf Inn & Suites
A modern kitchen with white cabinets, stainless steel appliances, and a marble island with bar stools.

2. Charming 2-bedroom Florida Getaway! Sleeps 6

Charming 2-bedroom Florida Getaway! Sleeps 6
Kissimmee
9.8 out of 10, Exceptional, (21 reviews)
"Great little place. We would book it again."
United States
Jack Francis G.
The price is CA $123
CA $429 total
includes taxes & fees
Sep 29 - Sep 30
Charming 2-bedroom Florida Getaway! Sleeps 6

3. Sunset Greens Villa

Sunset Greens Villa
2.0 star property
Reunion
10.0 out of 10, Exceptional, (1 review)
"Very nice property"
United States
Richard
The price is CA $112
CA $571 total
includes taxes & fees
Oct 7 - Oct 8
Sunset Greens Villa
A modern kitchen with a central island, built-in appliances, and a large window providing natural light.

4. Resort Stay~Near Disney~Bright~Gym~Hot Tub

Resort Stay~Near Disney~Bright~Gym~Hot Tub
Kissimmee
10.0 out of 10, Exceptional, (9 reviews)
"Property was very clean and convenient and host communication was excellent"
United States
John
The price is CA $120
CA $598 total
includes taxes & fees
Oct 3 - Oct 4
Resort Stay~Near Disney~Bright~Gym~Hot Tub
A bedroom with a large bed, a wooden headboard, two bedside tables with lamps, a view of a swimming pool, and a sliding door.

5. Heated Pool~Game Room~Modern~Resort~Disney Magic

Heated Pool~Game Room~Modern~Resort~Disney Magic
Lake Berkley
10.0 out of 10, Exceptional, (2 reviews)
"We absolutely loved our stay in this home. The host's were extremely kind and responsive. The home was squeaky clean and the beds were super comfy. We cannot wait to book again. Thank you Derek & Lauren!!!"
United States
Kelly F.
The price is CA $68
CA $642 total
includes taxes & fees
Sep 29 - Sep 30
Heated Pool~Game Room~Modern~Resort~Disney Magic
A living room with two sofas, a coffee table, and two lamps. There is a painting on the wall and a window with plants.

6. Sunny Private Pool & Spa & Fenced Yard. Nr Parks

Sunny Private Pool & Spa & Fenced Yard. Nr Parks
4.5 star property
Indian Point
The price is CA $289
CA $858 total
includes taxes & fees
Oct 10 - Oct 11
Sunny Private Pool & Spa & Fenced Yard. Nr Parks
An outdoor patio with a barbecue grill, a small hot tub, and a view of a lush garden.

7. Disney-Themed Escape – Frozen & Star Wars Rooms, Pool, Games & Family Fun

Disney-Themed Escape – Frozen & Star Wars Rooms, Pool, Games & Family Fun
Kissimmee
9.8 out of 10, Exceptional, (40 reviews)
"We had a good stay at the property. The description was accurate and it was clean and ready for our arrival. The host had good communication and check in was easy. We had no complaints about the stay."
United States
Susan H.
The price is CA $115
CA $775 total
includes taxes & fees
Sep 29 - Sep 30
Disney-Themed Escape – Frozen & Star Wars Rooms, Pool, Games & Family Fun

8. SPACIOUS 2 BEDROOM HOUSE IN DISNEY AREA 5 STAR RATED MILL CREEK RESORT 2772 W

SPACIOUS 2 BEDROOM HOUSE IN DISNEY AREA 5 STAR RATED MILL CREEK RESORT 2772 W
Kissimmee
9.8 out of 10, Exceptional, (17 reviews)
"Great place. Was clean and cozy. "
United States
Casey W.
The price is CA $126
CA $342 total
includes taxes & fees
Sep 29 - Sep 30
SPACIOUS 2 BEDROOM HOUSE IN DISNEY AREA 5 STAR RATED MILL CREEK RESORT 2772 W
A modern kitchen with white cabinetry, a large island with two decorative bowls, and a pendant light with multiple bulbs.

9. Freshly Updated~Near Disney~Private Pool~Resort

Freshly Updated~Near Disney~Private Pool~Resort
Crystal Cove
10.0 out of 10, Exceptional, (4 reviews)
"Everything was amazing would love to rent more properties in the future!!"
United States
Dijaun B.
The price is CA $81
CA $735 total
includes taxes & fees
Oct 26 - Oct 27
Freshly Updated~Near Disney~Private Pool~Resort
An aerial view of a resort with a winding pool, multiple lounge areas, and a separate building with a pool.

10. Family-Friendly 4 Bedroom 3 Bath Pool Home 271

Family-Friendly 4 Bedroom 3 Bath Pool Home 271
Kissimmee
8.4 out of 10, Very good, (28 reviews)
"First of all we entered and everything was off and with the broken wall and the sofa, the refrigerator was broken, the food was ruined and the pool was dirty with hair, the grill didn't work either, we didn't repeat it"
United States
Jennifer
The price is CA $90
CA $716 total
includes taxes & fees
Sep 29 - Sep 30
Family-Friendly 4 Bedroom 3 Bath Pool Home 271
A pool area with a water feature, lounge chairs, and a pergola.

11. Pond Access & Grill! Group Escape, 19 Mi to WDW

Pond Access & Grill! Group Escape, 19 Mi to WDW
Kissimmee
The price is CA $151
CA $285 total
includes taxes & fees
Oct 4 - Oct 5
Pond Access & Grill! Group Escape, 19 Mi to WDW
A residential complex with multiple two-story houses, a central swimming pool, and well-maintained lawns.

12. Disney Themed Single Family Home, Private Pool, 15 Mins From Disney & Sleeps 10

Disney Themed Single Family Home, Private Pool, 15 Mins From Disney & Sleeps 10
Lake Berkley
9.2 out of 10, Wonderful, (31 reviews)
"Awesome place and location. "
United States
Montigo W.
The price is CA $150
CA $600 total
includes taxes & fees
Oct 2 - Oct 3
Disney Themed Single Family Home, Private Pool, 15 Mins From Disney & Sleeps 10

13. Awesome 5BR Townhouse Near Disney - Private Pool!

Awesome 5BR Townhouse Near Disney - Private Pool!
Kissimmee
9.8 out of 10, Exceptional, (10 reviews)
"House is gorgeous and plenty of room, I will highly recommend this place, our family loved it "
United States
Sky K.
The price is CA $102
CA $824 total
includes taxes & fees
Sep 29 - Sep 30
Awesome 5BR Townhouse Near Disney - Private Pool!

14. 4 BD/ 4 BA/ Bella Vida (440 LF)

4 BD/ 4 BA/ Bella Vida (440 LF)
Bellavida
9.0 out of 10, Wonderful, (28 reviews)
"This was a great property conveniently located to everything. The pool was great the accommodations were perfect for our family of 6."
United States
Eric H.
The price is CA $135
CA $721 total
includes taxes & fees
Sep 29 - Sep 30
4 BD/ 4 BA/ Bella Vida (440 LF)

15. 2BR family retreat w/ resort access

2BR family retreat w/ resort access
Kissimmee
10.0 out of 10, Exceptional, (2 reviews)
"Very nice stay! I strongly recommend the stay"
United States
dwayne
The price is CA $129
CA $486 total
includes taxes & fees
Oct 14 - Oct 15
2BR family retreat w/ resort access
An aerial view of a resort with a large pool area, a water slide, and surrounding greenery.

16. *Amazing 4Bdr TH*15mins to Disney*Free Amenities!

*Amazing 4Bdr TH*15mins to Disney*Free Amenities!
Kissimmee
9.4 out of 10, Exceptional, (34 reviews)
"The owner is excellent!!!"
United States
Fabio
The price is CA $141
CA $515 total
includes taxes & fees
Sep 30 - Oct 1
*Amazing 4Bdr TH*15mins to Disney*Free Amenities!

17. Beautiful 4/3 TH w/ private pool in gated resort w/ clubhouse (10' to WDW)

Beautiful 4/3 TH w/ private pool in gated resort w/ clubhouse (10' to WDW)
Kissimmee
9.4 out of 10, Exceptional, (56 reviews)
"This home was such a wonderful space for our stay! It was clean, welcoming & in a great location! Would definitely stay here again!"
United States
Kathleen C.
The price is CA $142
CA $602 total
includes taxes & fees
Oct 20 - Oct 21
Beautiful 4/3 TH w/ private pool in gated resort w/ clubhouse (10' to WDW)
A modern living room with a sofa, ottoman, and glass dining table. There is a kitchen area with a microwave and cabinets.

18. Enchanting Newly Renovated 1.5miles to Disney and Near Tons of Restaurants 760

Enchanting Newly Renovated 1.5miles to Disney and Near Tons of Restaurants 760
Kissimmee
9.0 out of 10, Wonderful, (58 reviews)
"Loved our beautiful stay and appreciated the extra details to amenities during our stay! "
United States
Jennifer D.
The price is CA $71
CA $240 total
includes taxes & fees
Oct 7 - Oct 8
Enchanting Newly Renovated 1.5miles to Disney and Near Tons of Restaurants 760
A living room with two brown leather sofas, a beige throw blanket, and a coffee table with a decorative item. A painting of a beach landscape hangs on the wall, and a wooden clock is visible.

19. Charming 2BR/2BA Townhome with Patio near Disney

Charming 2BR/2BA Townhome with Patio near Disney
Kissimmee
8.6 out of 10, Excellent, (23 reviews)
"Very nice stay"
United States
michael h.
The price is CA $45
CA $292 total
includes taxes & fees
Oct 7 - Oct 8
Charming 2BR/2BA Townhome with Patio near Disney
A modern kitchen with white cabinets, stainless steel appliances, and a granite countertop.

20. Resort-Style Villa | Pool, Spa & Game Room!

Resort-Style Villa | Pool, Spa & Game Room!
4.0 star property
Kissimmee
8.0 out of 10, Very good, (1 review)
The price is CA $221
CA $777 total
includes taxes & fees
Sep 30 - Oct 1
Resort-Style Villa | Pool, Spa & Game Room!
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Kissimmee Hotel Reviews

Kompose Boutique Resort at Theme Parks

Kompose Boutique Resort at Theme Parks

10/10 Excellent
"My favorite! Stay here about 5 times a year."
Ingrid 3-night trip
Posted 1 hour ago
Kompose Boutique Resort at Theme Parks

Price trends for Vacation Homes in Kissimmee

Less expensive
More expensive
Next month
November
March
CA $168
Month
Price
January
CA $175
February
CA $180
March
CA $231
April
CA $161
May
CA $161
June
CA $183
July
CA $192
August
CA $165
September
CA $168
October
CA $168
November
CA $160
December
CA $217
Price trend information excludes taxes and fees and is based on base rates for a nightly stay for 2 adults found in the last 7 days on our site and averaged for commonly viewed Vacation Homes in Kissimmee. Select dates and complete search for nightly totals inclusive of taxes and fees.

Find out more about Kissimmee

Kissimmee Vacation Homes information

Number of reviews
339
Accommodation
15569 Vacation Homes
Lowest Price
CA $95
Highest Price
CA $858

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