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

Holiday Homes in Kissimmee

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Check prices for these dates

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

Our top choices for Kissimmee holiday homes

Deluxe Apartment, 3 Bedrooms, Golf View | Interior

1. 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 €352
includes taxes & fees
7 Oct - 8 Oct
Sunset Greens Villa
Interior

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

Resort Stay~Near Disney~Bright~Gym~Hot Tub
Kissimmee
10.0 out of 10, Exceptional, (8 reviews)
"The place was great & convenient if going to the parks. It had everything we needed & was clean and nicely updated."
United States
Sadie H.
The price is €327
includes taxes & fees
22 Sept - 23 Sept
Resort Stay~Near Disney~Bright~Gym~Hot Tub
Outdoor pool

3. 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 €58
includes taxes & fees
22 Sept - 23 Sept
Maple Leaf Inn & Suites
Coffee/tea maker, fridge, microwave, oven

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 €271
includes taxes & fees
27 Sept - 28 Sept
Charming 2-bedroom Florida Getaway! Sleeps 6
3 bedrooms, desk, iron/ironing board, travel cot

5. 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 €341
includes taxes & fees
27 Sept - 28 Sept
Private Resort Access~King Bed~Hot Tub~Balcony
A heated pool

6. 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 €520
includes taxes & fees
28 Sept - 29 Sept
Awesome 5BR Townhouse Near Disney - Private Pool!
4 bedrooms, desk, iron/ironing board, travel cot

7. 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 €415
includes taxes & fees
23 Sept - 24 Sept
Heated Pool~Game Room~Modern~Resort~Disney Magic
A heated pool

8. 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, (27 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 €453
includes taxes & fees
22 Sept - 23 Sept
Family-Friendly 4 Bedroom 3 Bath Pool Home 271
Pool

9. Magical Family Townhome Retreat – Comfort & Convenience Near Top Attractions!

Magical Family Townhome Retreat – Comfort & Convenience Near Top Attractions!
Kissimmee
9.4 out of 10, Exceptional, (59 reviews)
"Very clean family friendly stay. I will definitely come stay again and recommend to friends and family to book their stay here."
United States
Elain S.
The price is €369
includes taxes & fees
22 Sept - 23 Sept
Magical Family Townhome Retreat – Comfort & Convenience Near Top Attractions!
Dining

10. 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 €447
includes taxes & fees
6 Oct - 7 Oct
Freshly Updated~Near Disney~Private Pool~Resort
House | Living area

11. 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 €470
includes taxes & fees
28 Sept - 29 Sept
Sunny Private Pool & Spa & Fenced Yard. Nr Parks
Outdoor dining

12. 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 €216
includes taxes & fees
22 Sept - 23 Sept
SPACIOUS 2 BEDROOM HOUSE IN DISNEY AREA 5 STAR RATED MILL CREEK RESORT 2772 W
Pool

13. 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.
The price is €397
includes taxes & fees
22 Sept - 23 Sept
Mandalorian Retreat – Private Pool Near Disney
Pool

14. 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 €290
includes taxes & fees
24 Sept - 25 Sept
Dream Home • 5BR/5BA • Private Pool & Jacuzzi • FREE Water Park • 15' to Disney
Outdoor pool, a heated pool

15. 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 €487
includes taxes & fees
30 Sept - 1 Oct
Disney-Themed Escape – Frozen & Star Wars Rooms, Pool, Games & Family Fun
Coffee/tea maker, fridge, microwave, oven

16. 4BR Villa with Free Heated Pool & Grill • Near Disney

4BR Villa with Free Heated Pool & Grill • Near Disney
Indian Point
10.0 out of 10, Exceptional, (9 reviews)
"My family of eight stayed at this house, and it was exactly as pictured. We loved the theme and colors. The house was spacious and clean, and the host replied quickly and was very accommodating. The location was great too—just a short drive to all the theme parks. We’ll definitely book here again."
United States
Aracely G.
The price is €325
includes taxes & fees
22 Sept - 23 Sept
4BR Villa with Free Heated Pool & Grill • Near Disney
Pool

17. 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 €423
includes taxes & fees
25 Sept - 26 Sept
5BD/4BA Grand Townhome w/pool close to Disney
Pool

18. 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 €352
includes taxes & fees
27 Sept - 28 Sept
Beautiful 4/3 TH w/ private pool in gated resort w/ clubhouse (10' to WDW)
Pool

19. Cozy Lakeview 4BED Townhouse close to Major Parks

Cozy Lakeview 4BED Townhouse close to Major Parks
Kissimmee
9.4 out of 10, Exceptional, (59 reviews)
"Pool was enjoyable. Stay was great! "
United States
Michael M.
The price is €358
includes taxes & fees
30 Sept - 1 Oct
Cozy Lakeview 4BED Townhouse close to Major Parks
Pool

20. 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 €311
includes taxes & fees
1 Oct - 2 Oct
2BR family retreat w/ resort access
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

The Berkley, Orlando

The Berkley, Orlando

10/10 Excellent
"The whole experience was great! Friendly staff, clean suite, and more space than we needed. I would definitely come back again"
Kristine 3-night trip
Posted 3 hours ago
The Berkley, Orlando

Find out more about Kissimmee

Kissimmee Holiday Homes information

Number of reviews
18
Accommodation
15444 Holiday Homes
Lowest Price
€58
Highest Price
€1,371

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