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

West 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 West Kissimmee vacation 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, (2,424 reviews)
"Great place"
Canada
Stefanny
$133 nightly
The price is $150
Oct 1 - Oct 2
Total with taxes and fees
The Berkley, Orlando
An aerial view of a resort with a central swimming pool, surrounded by palm trees and a variety of buildings.

2. Fantastic Award Winning Newly Renovated Condo 4 miles to Disney 2+2

Fantastic Award Winning Newly Renovated Condo 4 miles to Disney 2+2
Kissimmee
9.6 out of 10, Exceptional, (214 reviews)
"Great property."
United States
Paula M.
$181 nightly
The price is $204
Sep 26 - Sep 27
Total with taxes and fees
Fantastic Award Winning Newly Renovated Condo 4 miles to Disney 2+2
A modern living room with a glass dining table, leather sofas, and a flat-screen TV.

3. Grand Lake Resort

Grand Lake Resort
3.0 star property
Kissimmee
9.2 out of 10, Wonderful, (253 reviews)
"I enjoyed my stay at this hotel and the pool was clean and refreshing"
United States
LeeAnna
$90 nightly
The price is $101
Sep 23 - Sep 24
Total with taxes and fees
Grand Lake Resort

4. 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
$217 nightly
The price is $244
Oct 20 - Oct 21
Total with taxes and fees
Upstay: Condo Near Disney w Pool, Sauna
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
$92 nightly
The price is $102
Sep 23 - Sep 24
Total with taxes and fees
Lifetime of Vacations Resort

6. 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
$297 nightly
The price is $325
Sep 23 - Sep 24
Total with taxes and fees
Tropical Retreat - Resort&spa - 15 Min to Disney!
A spacious lobby with modern furniture, large windows, and a high ceiling.

7. 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
$276 nightly
The price is $313
Sep 27 - Sep 28
Total with taxes and fees
Encantada Resort Vacation Townhomes by IDILIQ
A hotel with a symmetrical facade, a central entrance, and a covered patio area.

8. 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, (172 reviews)
"Nicely kept and very roomy. "
United States
Sheila M.
$170 nightly
The price is $190
Sep 28 - Sep 29
Total with taxes and fees
Modern Award Winning Newly Renovated, Gorgeous 2+2 Minutes Away From Disney
An aerial view of a residential property with a large swimming pool, multiple houses, and a well-maintained garden.

9. 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.
$254 nightly
The price is $281
Sep 23 - Sep 24
Total with taxes and fees
Tropical Resort Condo Near Disney: Pools, Spa & Family Fun
A multi-story building with a beige facade, balconies, and a staircase leading to an upper level.

10. 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.
$169 nightly
The price is $189
Sep 23 - Sep 24
Total with taxes and fees
Quiet. Roomy. Close to Disney. Fast Wifi Parking.
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, (2,273 reviews)
"nice place to stay!"
United States
Victor
$435 nightly
The price is $494
Sep 28 - Sep 29
Total with taxes and fees
Margaritaville Cottages Orlando by Rentyl with H2O Waterpark
A dining area with a chandelier, a framed picture on the wall, and a view into another room.

12. Lovely apartment, near Disney, Fits 8 people

Lovely apartment, near Disney, Fits 8 people
Grand Palms
9.6 out of 10, Exceptional, (7 reviews)
"Great location to everything you need and Disney stuff, very quiet neighborhood and place was very clean and spacious and the rate was very affordable. "
United States
Michele S.
$245 nightly
The price is $275
Sep 26 - Sep 27
Total with taxes and fees
Lovely apartment, near Disney, Fits 8 people
A kitchen with grey cabinets, a microwave, a toaster, and a blender on the countertop.

13. 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.
$299 nightly
The price is $334
Sep 27 - Sep 28
Total with taxes and fees
BEAUTIFULLY remodeled 3/2 condo near DISNEY and MARGARITAVILLE RESORT!⭐️⭐️⭐️⭐️⭐️
A spacious lobby with leather sofas, a central coffee table, and large windows offering a view of greenery outside.

14. Modern 3BR Resort Condo With Pool Near Disney

Modern 3BR Resort Condo With Pool Near Disney
4.0 star property
Winter Garden
$216 nightly
The price is $243
Sep 23 - Sep 24
Total with taxes and fees
Modern 3BR Resort Condo With Pool Near Disney
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.
$217 nightly
The price is $243
Sep 23 - Sep 24
Total with taxes and fees
Sweet Rental Deal !!! Just Few Minutes Away from Disney

16. Family Fun Condo Pool and Sauna near Disney

Family Fun Condo Pool and Sauna near Disney
Winter Garden
9.6 out of 10, Exceptional, (5 reviews)
"Clean, nicely appointed apartment close to Disney. Great pet friendly location. Will stay again. Highly recommend! "
United States
John and Dawn R.
$246 nightly
The price is $275
Sep 24 - Sep 25
Total with taxes and fees
Family Fun Condo Pool and Sauna near Disney

17. 3 Bedrooms/ 3 Baths/ The Hub At Westside (3205TT)

3 Bedrooms/ 3 Baths/ The Hub At Westside (3205TT)
Kissimmee
9.8 out of 10, Exceptional, (34 reviews)
"Yes we were in great condition, thanks again for the stay."
United States
Ernestine M.
$383 nightly
The price is $422
Sep 27 - Sep 28
Total with taxes and fees
3 Bedrooms/ 3 Baths/ The Hub At Westside (3205TT)
A swimming pool with a central fountain, surrounded by palm trees and lounge chairs.

18. 1st Floor • Free Parking • No Resort Fees • 14 minutes to Disney • 5 min shops

1st Floor • Free Parking • No Resort Fees • 14 minutes to Disney • 5 min shops
Kissimmee
10.0 out of 10, Exceptional, (6 reviews)
$257 nightly
The price is $287
Sep 23 - Sep 24
Total with taxes and fees
1st Floor • Free Parking • No Resort Fees • 14 minutes to Disney • 5 min shops
A beach with thatched umbrellas, blue lounge chairs, and a sandy area.

19. Andy's Hideaway at Bahama Bay | Sage Vacations

Andy's Hideaway at Bahama Bay | Sage Vacations
Bahama Bay
9.0 out of 10, Wonderful, (17 reviews)
"It was so convenient to Disney and it was fun"
United States
Melissa R.
$277 nightly
The price is $306
Sep 24 - Sep 25
Total with taxes and fees
Andy's Hideaway at Bahama Bay | Sage Vacations
A large swimming pool with lounge chairs and palm trees, surrounded by buildings with a Mediterranean architectural style.

20. Disney Days & Sunset Nights – Your Kissimmee Adventure Starts Here!

Disney Days & Sunset Nights – Your Kissimmee Adventure Starts Here!
Kissimmee
9.2 out of 10, Wonderful, (116 reviews)
"Clean nice area close to D.W."
United States
Vern L.
$209 nightly
The price is $233
Sep 23 - Sep 24
Total with taxes and fees
Disney Days & Sunset Nights – Your Kissimmee Adventure Starts Here!
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

Summer Bay Orlando MOD Collection by Sonesta

Summer Bay Orlando MOD Collection by Sonesta

10/10 Excellent
"Staff was very kind and helpful."
kieren 2-night trip
Posted 1 hour ago
Summer Bay Orlando MOD Collection by Sonesta

Price trends for vacation rentals in West Kissimmee

Less expensive
More expensive
Next month
April
December
$212
Month
Price
January
$266
February
$250
March
$213
April
$192
May
$195
June
$209
July
$210
August
$210
September
$210
October
$212
November
$226
December
$268
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 rentals in West Kissimmee. Select dates and complete search for nightly totals inclusive of taxes and fees.

Find out more about West Kissimmee

Everything you need to know about West Kissimmee vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the West Kissimmee vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect West Kissimmee vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

West Kissimmee vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in West Kissimmee. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit West Kissimmee in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $101 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on West Kissimmee rentals

At Expedia, we put the best West Kissimmee vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top West Kissimmee rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream West Kissimmee vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around West Kissimmee. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

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