Kissimmee Vacation Rentals

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May 12 - May 13
Tomorrow
May 13 - May 14
Next weekend
May 17 - May 19

Browse Select Kissimmee Vacation Homes

The Berkley, Orlando
Lobby sitting area
The Berkley, Orlando
4.0 star property
9.4 out of 10, Exceptional, (1408)
"Perfect family spot, great location and very nice property. Would go back anytime."
The Berkley, Orlando
Orlando Renters
Individually decorated, individually furnished, iron/ironing board
Orlando Renters
3.5 star property
5.8 out of 10, (65)
"very nice house "
Orlando Renters
Formosa Valley Resort by UNE Homes
Private pool
Formosa Valley Resort by UNE Homes
4.0 star property
9.4 out of 10, Exceptional, (112)
"Downstairs bedroom bathroom had water get too cold quickly. Upstairs master bedroom had shower that had boiling hot water. No washcloths available."
Formosa Valley Resort by UNE Homes
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Splendid 5Bd Close to Disney at Storey Lake 4251
Water park
Splendid 5Bd Close to Disney at Storey Lake 4251
5.0 star property
9.4 out of 10, Exceptional, (3)
"Everything that a big family needs for a vacation, plus a great location"
Splendid 5Bd Close to Disney at Storey Lake 4251
Stunning 5 Bedroom townhome in prime location- Paradise Palms resort community!
Outdoor pool, a heated pool
Stunning 5 Bedroom townhome in prime location- Paradise Palms resort community!
9.8 out of 10, Exceptional, (154)
"We got to Orlando early, and Tim was very accomodating. There was even a slight issue with the security letting us in due to the early arrival, and Tim hopped on the phone when them super fast and it was resolved within minutes. Would love to stay here again."
Stunning 5 Bedroom townhome in prime location- Paradise Palms resort community!
Charming 4Bd W/ Private Pool @ Storey Lake Resort 2653
Aerial view
Charming 4Bd W/ Private Pool @ Storey Lake Resort 2653
2.5 star property
Charming 4Bd W/ Private Pool @ Storey Lake Resort 2653
Kissimmee Maingate Area Pool Homes by SVV
Outdoor pool
Kissimmee Maingate Area Pool Homes by SVV
3.5 star property
8.6 out of 10, Excellent, (328)
"Great would love it againn"
Kissimmee Maingate Area Pool Homes by SVV
H2631E-Resort/Single Level POOL SPA Home Disney
Pool
H2631E-Resort/Single Level POOL SPA Home Disney
9.6 out of 10, Exceptional, (14)
"We stayed the last two weeks of March 2024. We were a group of 8, ranging from 2 years to 71 years. The house was exactly as described - everyone loved it. The kids loved the games tables and the swimming pool and the adults loved the spa and the space everyone had. The resort is lovely and the location is perfect. We were there during Easter and Spring Break but never had any issues with the traffic and found getting to the Disney parks was really straightforward. Excellent communication with...
The price is CA $274
CA $867 total
includes taxes & fees
May 28 - May 29
H2631E-Resort/Single Level POOL SPA Home Disney
4Bd W/ Pool & Close To Disney @ Encantada Resort 8570
Sport court
4Bd W/ Pool & Close To Disney @ Encantada Resort 8570
2.0 star property
10.0 out of 10, Exceptional, (1)
"It was great! Very comfortable and convenient"
4Bd W/ Pool & Close To Disney @ Encantada Resort 8570
Windsor @ Westside 5 Bed, Private townhouse, Private Pool, Wonderful Amenities
Outdoor pool, a heated pool
Windsor @ Westside 5 Bed, Private townhouse, Private Pool, Wonderful Amenities
9.6 out of 10, Exceptional, (67)
"We loved the 5 bedroom townhouse. It was clean, spacious and having our own pool was great. Kathy checked on us, made arrival and departure so easy. The lazy River at the resort pool was awesome. We would definitely stay here again."
Windsor @ Westside 5 Bed, Private townhouse, Private Pool, Wonderful Amenities
Summer Discount- Brand New Themed 9BR Home @ Disney, Private Pool/SPA, Game Room
Outdoor pool, a heated pool
Summer Discount- Brand New Themed 9BR Home @ Disney, Private Pool/SPA, Game Room
10.0 out of 10, Exceptional, (18)
"Everybody enjoyed the stay. Check-in is smooth, owner even gave us early check-in so we could put our frozen items earlier. Location is 7 minutes from Walmart, and accessible to many restaurants in the area. Car access uses QR code and very convenient to pass the main gate entrance. Parking is restricted to 5 cars, but have additional parking at the Clubhouse. House facilities is what is advertised, with 2 large refrigerators, 2 sets of washer/dryer, which is good for large family gatherings....
Summer Discount- Brand New Themed 9BR Home @ Disney, Private Pool/SPA, Game Room
Outdoor TV, Air Hockey, Foosball, Epic Game Room, Basketball Arcade, 1GB: Summer Breeze
A heated pool
Outdoor TV, Air Hockey, Foosball, Epic Game Room, Basketball Arcade, 1GB: Summer Breeze
10.0 out of 10, Exceptional, (13)
"We enjoyed the friendliness of the staff the house was spacious and clean. Kyle communicates and responds back promptly. Looking to book with him more in the future"
Outdoor TV, Air Hockey, Foosball, Epic Game Room, Basketball Arcade, 1GB: Summer Breeze
Upstay - Modern Pool Home w Games - Sleeps 18!
Pool
Upstay - Modern Pool Home w Games - Sleeps 18!
10.0 out of 10, Exceptional, (4)
"Great place for guys on a golf trip, everyone really enjoyed this place."
Upstay - Modern Pool Home w Games - Sleeps 18!
Luxury Pool Home Steps to Disney, 2 Master Suites, Gated, Game Rm, BBQ Free WiFi
Outdoor pool, a heated pool
Luxury Pool Home Steps to Disney, 2 Master Suites, Gated, Game Rm, BBQ Free WiFi
10.0 out of 10, Exceptional, (88)
"I feel like we really "hit the jackpot" when we found this rental. The home is super clean, exactly as shown, and located in a central spot where it feels like you're miles away from all of the chaos, but you're really staying smack in the middle of it all. My first priority when I look for a rental is finding one with recent high cleanliness ratings. Although the home itself seems a bit older, the owner has really kept up with everything, and the cleaning crew seems to be keeping up quite...
Luxury Pool Home Steps to Disney, 2 Master Suites, Gated, Game Rm, BBQ Free WiFi
Balcony Lakeview Pool/Jacuzzi Game Room Cable TV sports channels
Outdoor dining
Balcony Lakeview Pool/Jacuzzi Game Room Cable TV sports channels
8.6 out of 10, Excellent, (58)
"After a quick ride to the grocery store for food my family and I made some wonderful meals and enjoyed the pool area with games in the game room as well as the games we brought. House and beds were very comfortable. I would stay here again."
Balcony Lakeview Pool/Jacuzzi Game Room Cable TV sports channels
Drive-In Theater, Forest Bedroom, Huge Pirate Ship, Lake Views, Pool Table, Grill: Movie Magic
A heated pool
Drive-In Theater, Forest Bedroom, Huge Pirate Ship, Lake Views, Pool Table, Grill: Movie Magic
9.8 out of 10, Exceptional, (12)
"Amazing place , very responsive Host Everything was perfect the place is beautiful!"
Drive-In Theater, Forest Bedroom, Huge Pirate Ship, Lake Views, Pool Table, Grill: Movie Magic
Summerville Vacation Homes by Columbia Management
Captiva-06 (SMV104) | Private kitchen
Summerville Vacation Homes by Columbia Management
4.0 star property
8.4 out of 10, Very good, (144)
"Very much like that each room had it's own bathroom It was not easy to contact the management company when we needed something, they did not return calls when leaving messages and seldom answered phones"
Summerville Vacation Homes by Columbia Management
Jurassic Game Room-2 Theaters (Inside & Poolside)
A heated pool
Jurassic Game Room-2 Theaters (Inside & Poolside)
9.8 out of 10, Exceptional, (51)
"The house is nice with plenty to do. It’s close to everything and in a nice neighborhood. We played 5 different golf courses and never had more than a 30 minute drive. It could’ve been a little cleaner but nothing really to complain about. They communicate well and were really easy to work with"
Jurassic Game Room-2 Theaters (Inside & Poolside)
Close to Disney 4 bedroom 3.5 bath-Unit 26 Emerald
Fridge, microwave, oven, stovetop
Close to Disney 4 bedroom 3.5 bath-Unit 26 Emerald
8.8 out of 10, Excellent, (24)
"The moment we walked into this home we felt at ease. Lots of space, lots of natural light. The home was very clean and had everything we needed. We will definitely book this home next time we are in Orlando. Thank you Manny for being attentive. You are an amazing commune. Thanks thanks again…until next time. 🙂"
Close to Disney 4 bedroom 3.5 bath-Unit 26 Emerald
6BR Home, Prime Location
Pool
6BR Home, Prime Location
10.0 out of 10, Exceptional, (3)
"The house so Beautiful and clean. We enjoyed the pool at the house and the waterpark on the premises. It is a great house for a gathering of family and friends. I do suggest updating the mattresses. I couldn’t have asked for a better place for our large group. The check in process was easy and all my emails Were answered promptly. Thank you for your hospitality."
6BR Home, Prime Location
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See all available properties in Kissimmee
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.

Price trends for Vacation Homes in Kissimmee

Less expensive
More expensive
This month
Next month
September
February
CA $148
CA $177
Month
Price
January
CA $169
February
CA $211
March
CA $211
April
CA $150
May
CA $148
June
CA $177
July
CA $181
August
CA $152
September
CA $135
October
CA $148
November
CA $155
December
CA $185
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.

Other property types in Kissimmee

Seralago Hotel & Suites Main Gate East
2 outdoor pools, a heated pool, sun loungers
Seralago Hotel & Suites Main Gate East
3.0 star property
5.2 out of 10, (5239)
"Excellent stay. Thank you"
The price is CA $55
CA $87 total
includes taxes & fees
May 13 - May 14
Seralago Hotel & Suites Main Gate East
Ramada by Wyndham Kissimmee Gateway
Exterior
Ramada by Wyndham Kissimmee Gateway
3.0 star property
7.2 out of 10, Good, (5881)
"The front desk handed us the wrong keycards so we had to trek all the way back to the lobby to get the correct keycards. You’re also told that parking in the hotel’s own parking lot is: “Park at your own risk.” Other than that, it was decent for the price."
The price is CA $75
CA $107 total
includes taxes & fees
May 13 - May 14
Ramada by Wyndham Kissimmee Gateway
Flamingo Waterpark Resort
Water park
Flamingo Waterpark Resort
3.0 star property
6.6 out of 10, (1142)
"Excelente "
The price is CA $110
CA $169 total
includes taxes & fees
May 13 - May 14
Flamingo Waterpark Resort
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.

Kissimmee Vacation Homes information

Number of reviews
2,523
Accommodation
16117 Vacation Homes
Lowest Price
CA $274
Highest Price
CA $274

Recent Reviews in Kissimmee
Expedia verified reviews

Gaylord Palms Resort & Convention Center

Gaylord Palms Resort & Convention Center

5/5 Excellent
"Nice stay"
A verified traveller stayed at Gaylord Palms Resort & Convention Center
Posted 1 hour ago
Gaylord Palms Resort & Convention Center