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 9 - Oct 11
In two months
Nov 20 - Nov 22
In three months
Dec 18 - Dec 20
In four months
Jan 15 - Jan 17

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 27 - Sep 28
Maple Leaf Inn & Suites
A modern kitchen with a central island, built-in appliances, and a large window providing natural light.

2. 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 $124
CA $604 total
includes taxes & fees
Oct 3 - Oct 4
Resort Stay~Near Disney~Bright~Gym~Hot Tub
A pool area with a water feature, lounge chairs, and a pergola.

3. 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 modern kitchen with white cabinets, stainless steel appliances, and a marble island with bar stools.

4. 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 $108
CA $410 total
includes taxes & fees
Sep 27 - Sep 28
Charming 2-bedroom Florida Getaway! Sleeps 6

5. 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 bedroom with a large bed, a ceiling fan, and a view of a pool and building.

6. Private Resort Access~King Bed~Hot Tub~Balcony

Private Resort Access~King Bed~Hot Tub~Balcony
Kissimmee
10.0 out of 10, Exceptional, (3 reviews)
"Great host and fantastic pool"
United States
paul m.
The price is CA $49
CA $513 total
includes taxes & fees
Sep 28 - Sep 29
Private Resort Access~King Bed~Hot Tub~Balcony
An aerial view of a resort with a winding pool, multiple lounge areas, and a separate building with a pool.

7. 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 $91
CA $717 total
includes taxes & fees
Sep 28 - Sep 29
Family-Friendly 4 Bedroom 3 Bath Pool Home 271
A bedroom with a large bed, a wooden headboard, two bedside tables with lamps, a view of a swimming pool, and a sliding door.

8. 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 $75
CA $650 total
includes taxes & fees
Sep 30 - Oct 1
Heated Pool~Game Room~Modern~Resort~Disney Magic
A resort with multiple swimming pools, palm trees, and a large building complex in the background.

9. Dream Home • 5BR/5BA • Private Pool & Jacuzzi • FREE Water Park • 15' to Disney

Dream Home • 5BR/5BA • Private Pool & Jacuzzi • FREE Water Park • 15' to Disney
Kissimmee
9.4 out of 10, Exceptional, (9 reviews)
"We loved this home."
United States
Denzil
The price is CA $283
CA $686 total
includes taxes & fees
Oct 12 - Oct 13
Dream Home • 5BR/5BA • Private Pool & Jacuzzi • FREE Water Park • 15' to Disney

10. 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 $339 total
includes taxes & fees
Sep 27 - Sep 28
SPACIOUS 2 BEDROOM HOUSE IN DISNEY AREA 5 STAR RATED MILL CREEK RESORT 2772 W
A pool area with lounge chairs and a fountain.

11. Mandalorian Retreat – Private Pool Near Disney

Mandalorian Retreat – Private Pool Near Disney
Bellavida
9.8 out of 10, Exceptional, (39 reviews)
"Great location"
United States
Gene M.
Mandalorian Retreat – Private Pool Near Disney
A living room with two sofas, a coffee table, and two lamps. There is a painting on the wall and a window with plants.

12. 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 $202
CA $754 total
includes taxes & fees
Sep 28 - Sep 29
Sunny Private Pool & Spa & Fenced Yard. Nr Parks
A resort with a large pool, water slides, and lounge areas.

13. Incredible Fantasy World Nr Disney, Amazing Amenities.Free Shuttle to the Parks

Incredible Fantasy World Nr Disney, Amazing Amenities.Free Shuttle to the Parks
Kissimmee
9.4 out of 10, Exceptional, (82 reviews)
"Fantastic stay! The condo was clean, comfortable, and exactly as advertised. The full kitchen made it easy to prepare breakfast before heading to the parks, and the amenities—including the pools, lazy river, and hot tub—were a great way to relax. Mark was an outstanding host who communicated well and checked in to make sure we had everything we needed. The property was family-friendly, conveniently located, and truly felt like a home away from home. We would definitely stay here again. "
United States
Manuel F.
Incredible Fantasy World Nr Disney, Amazing Amenities.Free Shuttle to the Parks
A modern kitchen with white cabinetry, a large island with two decorative bowls, and a pendant light with multiple bulbs.

14. 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 $106
CA $774 total
includes taxes & fees
Oct 19 - Oct 20
Freshly Updated~Near Disney~Private Pool~Resort

15. 5BD/4BA Grand Townhome w/pool close to Disney

5BD/4BA Grand Townhome w/pool close to Disney
Kissimmee
9.8 out of 10, Exceptional, (15 reviews)
"Everything was great pool property cleanliness"
United States
Frank V.
The price is CA $177
CA $709 total
includes taxes & fees
Oct 5 - Oct 6
5BD/4BA Grand Townhome w/pool close to Disney

16. 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 $719 total
includes taxes & fees
Sep 27 - Sep 28
4 BD/ 4 BA/ Bella Vida (440 LF)
A residential complex with multiple two-story houses, a central swimming pool, and well-maintained lawns.

17. 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

18. Stylish Home With Pool Hot Tub and Parking

Stylish Home With Pool Hot Tub and Parking
2.0 star property
Reunion
10.0 out of 10, Exceptional, (1 review)
Stylish Home With Pool Hot Tub and Parking

19. 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 $490 total
includes taxes & fees
Oct 13 - Oct 14
2BR family retreat w/ resort access
An outdoor patio with a barbecue grill, a small hot tub, and a view of a lush garden.

20. 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 27 - Sep 28
Disney-Themed Escape – Frozen & Star Wars Rooms, Pool, Games & Family Fun
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

8/10 Good
"Nice pool great for kids food during lunch was great. Breakfast not so great had everything you needed but not as appetizing but does the job. They do not clean your room until the third day."
Farah 2-night trip
Posted 3 hours 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
326
Accommodation
15569 Vacation Homes
Lowest Price
CA $95
Highest Price
CA $775

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