We noticed that you're using an unsupported browser. The Tripadvisor website may not display properly.We support the following browsers:
Windows: Internet Explorer, Mozilla Firefox, Google Chrome. Mac: Safari.

Smoking Allowed Holiday Rentals in Kissimmee

List your property
Owner log in
Check-in
— / — / —
Check-out
— / — / —
Guests
0 rooms, 2+ guests
Distance from
1 km
Price per night
AU$0
AU$1,000+
Suitability
Show more
Bathrooms
Any
Amenities
Show more
Property type
Show more
Distinctive Features
Show more
Neighbourhood
Show more
3214 rentals in Kissimmee.
Sort by:
Tripadvisor Sort
Superb 4 Bedroom Home, just 3 minutes from Disney
50 reviews
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
Disney 5 Star Vacations / The Osprey Villa
77 reviews
5 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
Villa Linton - Beautiful Florida Home with Themed Bedrooms
29 reviews
5 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
Belle's Cove, Family-Friendly Villa with Gameroom and Hot Tub
43 reviews
4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
Fantasy Pool Home
54 reviews
4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
villanirvana
46 reviews
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
Star Lake Villa, close to Disney with pool
45 reviews
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
Debbie's Florida Retreat a Luxury Vacation Home
60 reviews
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
Colonial type Villa in a beautiful setting.
62 reviews
6 bedrooms
6 bathrooms
Sleeps 14
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
Spacious 4-bed lakeside pool villa near Disney
20 reviews
4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
Save time - get the best Kissimmee rentals sent straight to your email!
DISNEY WORLD! LOW $'S! ENTIRE NEW Home! Harry Potter Theme, Sleeps 8!
126 reviews
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
The Emerald Dolphin, Kissimmee Rental with WiFi, Hot Tub and Pool
8 reviews
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
The Charming Mickey's Tree House,
15 reviews
4 bedrooms
2 bathrooms
Sleeps 9
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
Family-Friendly Large Villa with a Pool, Jacuzzi,
51 reviews
5 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
BRUSONS RETREAT, 5 Bed Villa, South Facing Pool & Terrace.
18 reviews
5 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
Kissimmee Disney Villa with Wireless Internet
31 reviews
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
Executive Villa with Stunning Lakeviews & South Facing Pool and Spa / Jacuzzi - a dream vacation home
14 reviews
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
New Opening 9 Br/6 Ba luxurious Pool House from $300/nt, Close To Disney
6 reviews
9 bedrooms
6 bathrooms
Sleeps 18
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
Roughtallys Villa
20 reviews
7 bedrooms
4 bathrooms
Sleeps 14
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
Book that deserved vacation now !
18 reviews
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
Palm Tree Villa Florida, 5 Star Review Rating with Pool Lift & Wheel in Shower.
33 reviews
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
A stunning pool home in Kissimmee, Disney Paradi
21 reviews
4 bedrooms
3 bathrooms
Sleeps 9
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
Sonshines Florida Villa, Peaceful Getaway and Pool
72 reviews
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
Disney Family Villa pool/spa/games room, 5 bds 4 bathrooms, 15 Mins to Disney
37 reviews
5 bedrooms
4 bathrooms
Sleeps 12
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
DORAL WOODS SECLUDED VILLA
58 reviews
4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
A HOLIDAY HOME IN BEAUTIFUL LAKE MARION RESORT.
23 reviews
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
Executive 4 Bedroom / 3 Bathroom Lake View Home in Gated Resort Community
31 reviews
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
2675CA - Sonoma Resort
2 reviews
6 bedrooms
6 bathrooms
Sleeps 14
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
Lovely Affordable Ground Floor Condo at Cane Island Resort
41 reviews
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
Disney Dream Villa At CLC Encantada Resort
134 reviews
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
Lake Berkley Holiday Villa with FREE pool heating.
29 reviews
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
Large Condo close to Disney World & all of the other Orlando theme parks
70 reviews
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Stayz.com.au logo
Check-in
Check-out
Superior Home with Private Pool, 4307
2 reviews
6 bedrooms
4 bathrooms
Sleeps 12
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
Beautiful 5 bed/3.5 bath-2 En-suites, Free SPA Heat, WiFi, Disney/Universal.
12 reviews
5 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
Bass Lake Beauty with a Pool, WiFi and Air Conditioning
23 reviews
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
Mickeys Clubhouse Windsor Palm Frozen & New Minion themed rooms
19 reviews
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
Stunning 5 Bd w/ Pool Close to Disney * Storey Lake 2767
5 bedrooms
5 bathrooms
Sleeps 16
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
Magical Pool Villa - 4 Miles to Disney!
13 reviews
7 bedrooms
4 bathrooms
Sleeps 15
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
Ultimate luxury 15 bedroom suites for 30 guests
1 review
15 bedrooms
15 bathrooms
Sleeps 30
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
*****..'Emerald Hunny Pot Villa'..*****
17 reviews
4 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
4BR-2 King-Large Pool/Spa-GamesRm-ROKU-WiFi
23 reviews
4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
⭐⭐⭐Disney Contemporary 3 ⭐⭐⭐
2 reviews
4 bedrooms
3 bathrooms
Sleeps 15
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
9 Bedroom Home w-Pool Storey Lake -1672
1 review
9 bedrooms
5 bathrooms
Sleeps 26
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
Pet Friendly Home with Private Pool, 4405
3 reviews
4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
Chris and Sue's Disney Condo at Windsor Palms Resort
41 reviews
3 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
Tranquil Holiday Home-Games Room, Private Pool, WiFi, Disney/Orlando
15 reviews
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
R1 Luxury resort,3 miles to Disney, Great 3 bd,& more
1 review
3 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
Grandmas's Ami (4907TV) - Trafalgar Village
1 review
5 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
Spacious Windward Cay 3 Bed
3 reviews
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
Hideaway Villa,Terra Verde Resort - Xbox,PS2,Games Room, Pool
24 reviews
5 bedrooms
4 bathrooms
Sleeps 12
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
PreviousNext
123456…