A restaurant and bar with a distinctive tower and palm trees.

West Kissimmee Holiday Rentals

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Check prices for these dates

In two weeks
25 Sept - 27 Sept
In two months
6 Nov - 8 Nov
In three months
4 Dec - 6 Dec
In four months
1 Jan - 3 Jan

Our top choices for West Kissimmee holiday rentals

A spacious lobby with a grand chandelier, large windows offering a view of a pool, and a second-floor balcony with a railing.

1. The Berkley, Orlando

The Berkley, Orlando
4.0 star property
Kissimmee
9.6 out of 10, Exceptional, (2,406 reviews)
"Great place"
Canada
Stefanny
The price is HK$887
HK$1,086 total
includes taxes & fees
24 Sept - 25 Sept
The Berkley, Orlando
A spacious lobby with modern furniture, large windows, and a high ceiling.

2. Encantada Resort Vacation Townhomes by IDILIQ

Encantada Resort Vacation Townhomes by IDILIQ
3.0 star property
Kissimmee
8.4 out of 10, Very good, (1,471 reviews)
"Nice stay"
United States
Pamela
The price is HK$506
HK$2,123 total
includes taxes & fees
15 Sept - 16 Sept
Encantada Resort Vacation Townhomes by IDILIQ

3. Upstay: Condo Near Disney w Pool, Sauna

Upstay: Condo Near Disney w Pool, Sauna
4.0 star property
Winter Garden
10.0 out of 10, Exceptional, (1 review)
"The unit was very clean and organized when we arrived. All the amenities and appliances that come with the unit worked amazing. The only exception was the WiFi. It was a bit slow, however this could be easily fixed and should not discourage from booking this property. Being at the pool was the highlight of staying at this property. It was clean and came with fun pool sized amenities like pool basketball and connect 4. Being in the lobby was also fun with the ping pong table and pool table. The...
United States
Nancy
The price is HK$541
HK$1,923 total
includes taxes & fees
13 Sept - 14 Sept
Upstay: Condo Near Disney w Pool, Sauna
A modern living room with a glass dining table, leather sofas, and a flat-screen TV.

4. Grand Lake Resort

Grand Lake Resort
3.0 star property
Kissimmee
9.2 out of 10, Wonderful, (244 reviews)
"Great price and size"
United States
Scott
The price is HK$559
HK$705 total
includes taxes & fees
13 Sept - 14 Sept
Grand Lake Resort
A thatched-roof gazebo with a wooden fence, surrounded by white lounge chairs on a sandy area.

5. Lifetime of Vacations Resort

Lifetime of Vacations Resort
3.0 star property
Kissimmee
9.4 out of 10, Exceptional, (182 reviews)
"We absolutely love coming to lifetime and grand lake resort. This is our favorite place to stay!!"
United States
Alena
The price is HK$521
HK$725 total
includes taxes & fees
13 Sept - 14 Sept
Lifetime of Vacations Resort

6. Bahama Bay Resort

Bahama Bay Resort
3.5 star property
Bahama Bay
8.6 out of 10, Excellent, (2,100 reviews)
"Had a wonderful stay at Bahama Bay Resort. The property was clean, comfortable, and had everything we needed for a relaxing stay. The resort itself was beautiful and peaceful, and the location was convenient. Everything went smoothly from check-in to check-out. Would definitely stay here again!"
United States
Kavya
The price is HK$1,500
HK$3,592 total
includes taxes & fees
13 Sept - 14 Sept
Bahama Bay Resort

7. Tropical Retreat - Resort&spa - 15 Min to Disney!

Tropical Retreat - Resort&spa - 15 Min to Disney!
4.0 star property
Bahama Bay
10.0 out of 10, Exceptional, (2 reviews)
"Schone kamers en iedereen is zeer vriendelijk!"
Netherlands
Rowan
The price is HK$602
HK$2,669 total
includes taxes & fees
14 Sept - 15 Sept
Tropical Retreat - Resort&spa - 15 Min to Disney!
A multi-story building with a beige facade, balconies, and a staircase leading to an upper level.

8. Quiet. Roomy. Close to Disney. Fast Wifi Parking.

Quiet. Roomy. Close to Disney. Fast Wifi Parking.
Grand Palms
9.4 out of 10, Exceptional, (9 reviews)
"Great stay! Very quiet and bigger than I expected... rooms where on the opposite side of the house, so that was super nice! It's super close to everything!! I will definitely stay again!"
United States
Sheri J.
The price is HK$550
HK$1,484 total
includes taxes & fees
14 Sept - 15 Sept
Quiet. Roomy. Close to Disney. Fast Wifi Parking.
A bedroom with a large bed, two bedside tables, a chandelier, and a view of the outdoors.

9. ON SALE! 4BD 3BTH 1.5 MILES TO DISNEY!

ON SALE! 4BD 3BTH 1.5 MILES TO DISNEY!
Kissimmee
9.6 out of 10, Exceptional, (132 reviews)
"The condo was exactly as described. Well equipped, comfortable beds and great location."
United States
Scott F.
The price is HK$1,012
HK$3,051 total
includes taxes & fees
14 Sept - 15 Sept
ON SALE! 4BD 3BTH 1.5 MILES TO DISNEY!
An aerial view of a residential property with a large swimming pool, multiple houses, and a well-maintained garden.

10. Tropical Resort Condo Near Disney: Pools, Spa & Family Fun

Tropical Resort Condo Near Disney: Pools, Spa & Family Fun
Bahama Bay
9.6 out of 10, Exceptional, (139 reviews)
"Was a simple and excellent stay"
United States
Nathan M.
The price is HK$635
HK$2,196 total
includes taxes & fees
13 Sept - 14 Sept
Tropical Resort Condo Near Disney: Pools, Spa & Family Fun
An aerial view of a resort with multiple swimming pools, a large central pool, and surrounding greenery.

11. Margaritaville Cottages Orlando by Rentyl with H2O Waterpark

Margaritaville Cottages Orlando by Rentyl with H2O Waterpark
4.0 star property
Kissimmee
9.0 out of 10, Wonderful, (2,254 reviews)
"nice place to stay!"
United States
Victor
The price is HK$1,600
HK$3,920 total
includes taxes & fees
13 Sept - 14 Sept
Margaritaville Cottages Orlando by Rentyl with H2O Waterpark
A hotel with a symmetrical facade, a central entrance, and a covered patio area.

12. Modern Award Winning Newly Renovated, Gorgeous 2+2 Minutes Away From Disney

Modern Award Winning Newly Renovated, Gorgeous 2+2 Minutes Away From Disney
Kissimmee
9.2 out of 10, Wonderful, (171 reviews)
"Nicely kept and very roomy. "
United States
Sheila M.
The price is HK$392
HK$1,492 total
includes taxes & fees
14 Sept - 15 Sept
Modern Award Winning Newly Renovated, Gorgeous 2+2 Minutes Away From Disney
A bedroom with a bed, nightstand, wall art, ceiling fan, and a mirror.

13. Upstay Large Family Condo w Pool, Sauna

Upstay Large Family Condo w Pool, Sauna
3.5 star property
Winter Garden
The price is HK$588
HK$1,976 total
includes taxes & fees
29 Sept - 30 Sept
Upstay Large Family Condo w Pool, Sauna

14. Shake Shack Heated Pool & Hot Tub

Shake Shack Heated Pool & Hot Tub
3.5 star property
Kissimmee
10.0 out of 10, Exceptional, (1 review)
"We had a great time. The location was amazing and the convenience of a home is unmeasurable. Cheers! "
United States
Keith
The price is HK$1,005
HK$2,912 total
includes taxes & fees
19 Sept - 20 Sept
Shake Shack Heated Pool & Hot Tub
A swimming pool area with a hot tub, lounge chairs, and palm trees.

15. Sweet Rental Deal !!! Just Few Minutes Away from Disney

Sweet Rental Deal !!! Just Few Minutes Away from Disney
Grand Palms
9.4 out of 10, Exceptional, (140 reviews)
"I was a bit thrown off when I didn't receive any check in information on day of arrival. Call to Ms. Maria and communication with VRBO, everything was settled. The townhouse is a little out dated but enough space for my family. Good location and easy to get around. If in the area again, I would book."
United States
Cometrist P.
The price is HK$745
HK$1,903 total
includes taxes & fees
13 Sept - 14 Sept
Sweet Rental Deal !!! Just Few Minutes Away from Disney
A kitchen with grey cabinets, a microwave, a toaster, and a blender on the countertop.

16. BEAUTIFULLY remodeled 3/2 condo near DISNEY and MARGARITAVILLE RESORT!⭐️⭐️⭐️⭐️⭐️

BEAUTIFULLY remodeled 3/2 condo near DISNEY and MARGARITAVILLE RESORT!⭐️⭐️⭐️⭐️⭐️
Kissimmee
10.0 out of 10, Exceptional, (13 reviews)
"Home was clean, loved the wine when we arrived late and easy access"
United States
Denis B.
The price is HK$805
HK$2,635 total
includes taxes & fees
23 Sept - 24 Sept
BEAUTIFULLY remodeled 3/2 condo near DISNEY and MARGARITAVILLE RESORT!⭐️⭐️⭐️⭐️⭐️

17. Emerald Garden - Resort - 15 Min to Disney - Pets

Emerald Garden - Resort - 15 Min to Disney - Pets
3.0 star property
Kissimmee
10.0 out of 10, Exceptional, (1 review)
The price is HK$797
HK$3,123 total
includes taxes & fees
13 Sept - 14 Sept
Emerald Garden - Resort - 15 Min to Disney - Pets
A swimming pool with a 5½ FT depth marker, surrounded by lounge chairs and palm trees.

18. Unit 19 | 3BR Home | 2 Mi to Disney | Pet Friendly | Gated Resort

Unit 19 | 3BR Home | 2 Mi to Disney | Pet Friendly | Gated Resort
Kissimmee
9.4 out of 10, Exceptional, (45 reviews)
"Great location and great host!"
United States
Matt W.
Unit 19 | 3BR Home | 2 Mi to Disney | Pet Friendly | Gated Resort
A two-story house with a red-tiled roof, a covered porch with columns, and a well-maintained garden with various shrubs and palm trees.

19. Unit 26 | 4BR Home | 2 Mi to Disney | Pet Friendly |

Unit 26 | 4BR Home | 2 Mi to Disney | Pet Friendly |
Kissimmee
9.0 out of 10, Wonderful, (66 reviews)
"Clean home, very comfy beds, 2 king size bedrooms with full master baths, plus another full bath and half bath a bonus! Great for a weekend getaway to Disney with the family! Very comfortable living area to hang out. "
United States
Shonda L.
Unit 26 | 4BR Home | 2 Mi to Disney | Pet Friendly |
A living room with a large mural of a tropical scene, a grey sofa, and two armchairs.

20. Quiet Moana Retreat in gated community– Perfect for Disney & Universal Visitors

Quiet Moana Retreat in gated community– Perfect for Disney & Universal Visitors
Kissimmee
10.0 out of 10, Exceptional, (33 reviews)
"Everything was amazing, pool was fantastic with baby gators in the pond"
Canada
Tim K.
The price is HK$747
HK$2,711 total
includes taxes & fees
14 Sept - 15 Sept
Quiet Moana Retreat in gated community– Perfect for Disney & Universal Visitors
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 West Kissimmee Hotel Reviews

Holiday Inn Club Vacations at Orange Lake Resort by IHG

Holiday Inn Club Vacations at Orange Lake Resort by IHG

10/10 Excellent
"check in took forever. we noticed at 4pm people were leaving the check in counter (workers) or those workers just standing there not checking anyone in. there was about 40+ ppl in line. other than that, the stay was nice. clean! and we really enjoyed the beds."
Melissa 2-night trip
Posted less than an hour ago
Holiday Inn Club Vacations at Orange Lake Resort by IHG

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