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 30 - Nov 1
In two months
Dec 11 - Dec 13
In three months
Jan 8 - Jan 10
In four months
Feb 5 - Feb 7

Our top choices for West Kissimmee vacation rentals

An aerial view of a resort with multiple swimming pools, a large central pool, and surrounding greenery.

1. 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, (2,315 reviews)
"Our stay was amazing. The cottage was fantastic and the property offers so many amenities. Will definitely stay here again."
United States
Michael
$393 nightly
The price is $447
Oct 26 - Oct 27
Total with taxes and fees
Margaritaville Cottages Orlando by Rentyl with H2O Waterpark
A hotel with a symmetrical facade, a central entrance, and a covered patio area.

2. 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, (174 reviews)
"Nicely kept and very roomy. "
United States
Sheila M.
$175 nightly
The price is $196
Oct 26 - Oct 27
Total with taxes and fees
Modern Award Winning Newly Renovated, Gorgeous 2+2 Minutes Away From Disney
Interior

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, (2 reviews)
"We had a nice stay, the property is older, but very clean. The price was right for the 7nights, and it is 7 miles from park properties."
United States
Ben
$224 nightly
The price is $252
Nov 2 - Nov 3
Total with taxes and fees
Upstay: Condo Near Disney w Pool, Sauna
A modern living room with a sofa, two blue chairs, a coffee table, and a TV mounted on the wall.

4. 5 Min to Disney! 2BR Condo w/ King Bed, Pool, Fast WiFi & SmartTV+kitchen+washer

5 Min to Disney! 2BR Condo w/ King Bed, Pool, Fast WiFi & SmartTV+kitchen+washer
Kissimmee
7.4 out of 10, Good, (13 reviews)
"Very clean and stocked apartment. Great host. Easy communication and clear instructions. Had a wonderful and a convenient stay."
United States
Bhagyashree Sanjay
$230 nightly
The price is $258
Oct 26 - Oct 27
Total with taxes and fees
5 Min to Disney! 2BR Condo w/ King Bed, Pool, Fast WiFi & SmartTV+kitchen+washer
A modern living room with a glass dining table, leather sofas, and a flat-screen TV.

5. Grand Lake Resort

Grand Lake Resort
3.0 star property
Kissimmee
9.2 out of 10, Wonderful, (267 reviews)
"Place was very clean and staff was a great help very friendly and helpful."
United States
Raymond
$93 nightly
The price is $105
Oct 15 - Oct 16
Total with taxes and fees
Grand Lake Resort
A thatched-roof gazebo with a wooden fence, surrounded by white lounge chairs on a sandy area.

6. Lifetime of Vacations Resort

Lifetime of Vacations Resort
3.0 star property
Kissimmee
9.4 out of 10, Exceptional, (183 reviews)
"We absolutely love coming to lifetime and grand lake resort. This is our favorite place to stay!!"
United States
Alena
$100 nightly
The price is $111
Oct 22 - Oct 23
Total with taxes and fees
Lifetime of Vacations Resort
A spacious lobby with modern furniture, large windows, and a high ceiling.

7. Vacation Townhomes by IDILIQ at Encantada Resort

Vacation Townhomes by IDILIQ at Encantada Resort
3.0 star property
Kissimmee
8.4 out of 10, Very good, (1,479 reviews)
"Nice stay"
United States
Pamela
$257 nightly
The price is $292
Oct 29 - Oct 30
Total with taxes and fees
Vacation Townhomes by IDILIQ at Encantada Resort
Stunning Aerial View Of The Property Surrounded By Nature

8. 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.
Family Fun Condo Pool and Sauna near Disney
Interior

9. Vista Grande - Resort&spa - 15 Min to Disney!

Vista Grande - Resort&spa - 15 Min to Disney!
3.0 star property
Bahama Bay
9.4 out of 10, Exceptional, (3 reviews)
"Condo was clean and comfortable, location and amenities were nice. "
United States
Jessica
$316 nightly
The price is $326
Oct 15 - Oct 16
Total with taxes and fees
Vista Grande - Resort&spa - 15 Min 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.
$254 nightly
The price is $282
Oct 15 - Oct 16
Total with taxes and fees
Tropical Resort Condo Near Disney: Pools, Spa & Family Fun
A spacious lobby with a grand chandelier, large windows offering a view of a pool, and a second-floor balcony with a railing.

11. The Berkley, Orlando

The Berkley, Orlando
4.0 star property
Kissimmee
9.6 out of 10, Exceptional, (2,454 reviews)
"Clean rooms, great pool area, reasonably priced"
United States
Dean
$122 nightly
The price is $137
Nov 1 - Nov 2
Total with taxes and fees
The Berkley, Orlando
3205 Tranquil Trail 2.jpg

12. 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.
$403 nightly
The price is $445
Nov 1 - Nov 2
Total with taxes and fees
3 Bedrooms/ 3 Baths/ The Hub At Westside (3205TT)
A swimming pool with a brick deck, surrounded by tall trees and lounge chairs.

13. Upstay Large Family Condo w Pool, Sauna

Upstay Large Family Condo w Pool, Sauna
3.5 star property
Winter Garden
$201 nightly
The price is $226
Oct 19 - Oct 20
Total with taxes and fees
Upstay Large Family Condo w Pool, Sauna
A kitchen with grey cabinets, a microwave, a toaster, and a blender on the countertop.

14. 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.
$301 nightly
The price is $336
Oct 20 - Oct 21
Total with taxes and fees
BEAUTIFULLY remodeled 3/2 condo near DISNEY and MARGARITAVILLE RESORT!⭐️⭐️⭐️⭐️⭐️
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)
"Great value for the location. Easy access to Sunset Walk, Disney Parks, Target, etc. Easy for Ubering as well. Excellent host, highly recommend. "
United States
Kellie G.
$217 nightly
The price is $243
Oct 15 - Oct 16
Total with taxes and fees
Sweet Rental Deal !!! Just Few Minutes Away from Disney
A beach volleyball court with a net, surrounded by sand and trees.

16. Bahama Bay Resort

Bahama Bay Resort
3.5 star property
Bahama Bay
8.6 out of 10, Excellent, (2,101 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
$432 nightly
The price is $484
Oct 15 - Oct 16
Total with taxes and fees
Bahama Bay Resort
A living room with a large mural of a tropical scene, a grey sofa, and two armchairs.

17. 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.
$289 nightly
The price is $323
Oct 15 - Oct 16
Total with taxes and fees
Quiet Moana Retreat in gated community– Perfect for Disney & Universal Visitors
A hot tub area with a pool and a waterfall feature.

18. Orlando Emerald Dream House

Orlando Emerald Dream House
3.0 star property
Kissimmee
$192 nightly
The price is $218
Oct 18 - Oct 19
Total with taxes and fees
Orlando Emerald Dream House
Exterior

19. 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
$327 nightly
The price is $371
Oct 27 - Oct 28
Total with taxes and fees
Shake Shack Heated Pool & Hot Tub
Interior

20. 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
$316 nightly
The price is $347
Oct 15 - Oct 16
Total with taxes and fees
Tropical Retreat - Resort&spa - 15 Min to Disney!
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

Margaritaville Resort Orlando with H2O Waterpark

Margaritaville Resort Orlando with H2O Waterpark

10/10 Excellent
"Wonderful time!! Highly recommend"
Jacob 4-night trip
Posted 1 hour ago
Margaritaville Resort Orlando with H2O Waterpark

Price trends for vacation rentals in West Kissimmee

Less expensive
More expensive
This month
Next month
April
December
$212
$226
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 $105 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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