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

Map
Satellite
Map updates are paused. Zoom in to see updated info.
Reset zoom
Updating Map...
Your filters are still active.
Check In Check Out
    There are no pins in your viewport. Try moving the map or changing your filters.
    • {providername} {price}
    {providername} {price}
      {listitems}
    {sold_out_text}
    We can't find prices for this accommodation
    From {rate_price} {rate_periodicity}
    View Map
    Location
    Any Distance
    from
    Price
    per night
    $228 Average
    |||
    |||
    $0$1,000+
    Suitability
    Suitability
    More filters
    Travellers to Kissimmee are booking January dates now. Secure your holiday rental today, and have the perfect trip.
    23 Matching Rentals in KissimmeeView all 5,600 rentals
    Sort by:
    Default
    Magical Memories, Pet-Friendly Home with WiFi1 / 18
    (34)Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
    other travellers have booked this property
    Certificate of Excellence
    Check in Check out
    Show Prices
    Payment Protection
    Superb 4 Bedroom Home, just 3 minutes from Disney1 / 75
    (41)Excellent
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
    other travellers have booked this property
    Certificate of Excellence
    Check in Check out
    Show Prices
    Payment Protection
    5 Bedrooms, 4 Bathrooms, Sleeps 15 Quick View
    other travellers have booked this property
    Check in Check out
    Show Prices
    Payment Protection
    RVH_130R Heritage Crossing Retreat1 / 27
    (1)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
    other traveller has booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Property Reference # RVH_130 This second floor 3 bed, 2 bath 1,344 sq ft. condo is located in the Heritage Crossing neighborhood of Reunion Resort. Enjoy amazing views of the Arnold Palmer Legacy golf course and beautiful sunsets from your own private balconies with two magnificent pools close by....
    View all property information
    Location Information
    Kissimmee, Central Florida 34747
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    Make Enquiry
    2CLOSE TO ALL ATTRACTIONS! RESORT LUXURY LIVING ON A BUDGET!1 / 37
    (1)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 12 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Air Conditioning
    • Cable/satellite TV
    • Hot Tub
    • Children's Pool
    • Wi-Fi
    • Patio
    • Grill
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 25 September 2018
    We have previously stayed in Amrit’s other 2 properties and this one was just as stunning as the others. She is alway quick to respond to our questions within minutes. I have...
    See all reviews
    About this property
    LOCATION LOCATION LOCATION!!! CLOSE TO DISNEY, Universal Studios, Sea World, and yes even Busch Gardens and the beaches, not to mention the world famous shopping outlets! Security controlled access very safe and private! Our townhouse boasts ample space for 1-11 guests quite comfortably. Our...
    View all property information
    Location Information
    Kissimmee, Central Florida 34747
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 12
    Make Enquiry
    Orange Lake Country Club1 / 5
    (1)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Wi-Fi
    • Hot Tub
    • Cable/satellite TV
    • DVD Player
    • Air Conditioning
    • Children's Pool
    • Washer
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Villa located at Orange Lake Country Club - Golf Resort, in west Kissimmee, Florida. Is is a beautiful family resort, with a river island, golf courses, daily water and earth activities. You will have an unforgivable experience. The villa has all the comforts and you will find in and around the...
    View all property information
    Location Information
    Kissimmee, Central Florida 34747
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 8
    Make Enquiry
    Casa Luna - Kissimmee 4 Bedroom 2 Bath, Pool, Wi-Fi1 / 36
    (2)Excellent
    4 Bedrooms, 2 Bathrooms, Sleeps 12 Quick View
    other travellers have booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Patio
    • Private Outdoor Pool (Heated)
    • Washer
    • Parking
    • Air Conditioning
    • Wi-Fi
    • Cable/satellite TV
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 10 July 2018
    Just home for a 15 day stay here. Had a fabulous time. It’s a beautiful property in a beautiful location and there is everything there that you could possibly need to make your...
    See all reviews
    About this property
    Recently renovated, BEAUTIFUL 4 bedroom, 2 bath home in Kissimmee, FL available for vacation rental. Home is located 25 minutes to Disney and 35 minutes to Sea World and Universal Studios. Central location lets you easily get to Cocoa Beach or Tampa Beach in just 75 minutes. Sleeps 10-12 people....
    View all property information
    Location Information
    Kissimmee, Central Florida 34758
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 12
    Make Enquiry
    2 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Washer
    • Central Heating
    • Balcony
    • Patio
    • Hot Tub
    • Grill
    • Terrace
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This large and luxurious space won’t leave you cramped and feeling claustrophobic like most regular hotel rooms. You’ll appreciate the many comforts of home such as a fully equipped kitchen, private balcony or patio, in-room washer and dryer, large screen television, jetted tub and more. You’ll...
    View all property information
    Location Information
    Kissimmee, Central Florida 34746
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 8
    Make Enquiry
    2 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Hot Tub
    • Wi-Fi
    • Children's Pool
    • Cable/satellite TV
    • Balcony
    • Air Conditioning
    • Washer
    • Housekeeping Included
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    I rent my condo in Orlando - Florida. Location directly from the owner. Condo fully furnished and sleeps 8. Chek in/out is in friday, saturday or sunday for 7 days. Availability : 23 december to 30 december 2019 You can choose another week but the availability has to be confirmed with the ressort....
    View all property information
    Location Information
    Kissimmee, Central Florida 34747
    Condo/Apartment - 2 Bedrooms, 3 Bathrooms, Sleeps 8
    Make Enquiry
    2 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Hot Tub
    • Internet Access
    • Balcony
    • Air Conditioning
    • DVD Player
    • Parking
    • Cable/satellite TV
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    You will get all the comforts of a fully furnished home with accommodations all within minutes of Orlando's world-famous theme parks and attractions. With a variety of onsite amenities and dining options. After a fun-filled day exploring Kissimmee area attractions, escape to the brilliantly...
    View all property information
    Location Information
    Kissimmee, Central Florida 34747
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 8
    Make Enquiry
    Save time - get the best Kissimmee rentals sent straight to your email!
    Get the List
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Terrace
    • Hot Tub
    • Sauna
    • Balcony
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    View all property information
    Location Information
    Kissimmee, Central Florida 34747
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
    Make Enquiry
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Waterfront
    • Cable/satellite TV
    • Air Conditioning
    • Washer
    • Private Garden
    • Grill
    • Wi-Fi
    • Secure Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    4 bedroom home, built in the late 90's, that sits on half an acre by a huge lake filled with fish and other wild life. Location is surrounded by shops and restaurants within a 5 mile radius; i.e. Publix (closes 10pm daily) Walmart Supercenter (24 hrs.) Walgreens (24 hrs.) Denny's (24 hrs.) Zaxby's,...
    View all property information
    Location Information
    Kissimmee, Central Florida 34758 3506
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
    Make Enquiry
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Air Conditioning
    • Washer
    • Hot Tub
    • Shared Outdoor Pool (Unheated)
    • Wi-Fi
    • Cable/satellite TV
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Beautiful and Stylish Townhouse by the lake with a unique groovy and jazzy vibe. MESMERIZE YOURSELF IN THIS CHIC VACATION HOME FULL OF ARTS AND COLORS. The whole place brand new is completely yours, Enjoy ! Make your reservation Now ! DETAILS -Gated Community -Clubhouse Amenities -Covered Lanai...
    View all property information
    Location Information
    Kissimmee, Central Florida 34746
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
    Make Enquiry
    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Air Conditioning
    • Shared Outdoor Pool (Unheated)
    • Washer
    • Grill
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Townhouse totally new and ready for your enjoyment ! CLOSE TO ALL DISNEY AND UNIVERSAL PARKS. Is a property decorated and inspired to receive each client in a place that they can feel in their own home. The whole place brand new is completely yours Enjoy ! Make your reservation Now ! DETAILS -Gated...
    View all property information
    Location Information
    Kissimmee, Central Florida 34746
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
    Make Enquiry
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Private Outdoor Pool (Unheated)
    • Washer
    • Wi-Fi
    • Cable/satellite TV
    • Balcony
    • Air Conditioning
    • Terrace
    • Hot Tub
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This Brand New Condo is just 5 min from Disney !! The condo is decorated and inspired to receive each client in a place that they can feel in their own home. The whole place brand new is completely yours,Enjoy ! Make your reservation NOW! DETAILS -Gated Community -Fresh Towels/Linens -Clubhouse...
    View all property information
    Location Information
    Kissimmee, Central Florida 34746
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
    Make Enquiry
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Wi-Fi
    • Air Conditioning
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Gorgeous Brand New 2 Bedrooms, 2 Bathrooms Vacation Rental Condo located in Storey Lake Resort, will ensure you have an amazing vacation. The bedrooms consist one King bedroom on suite & one bedroom with 2 single beds. Closest community from Disney, Disney Springs, Malls, Walmart. Clubhouse Resort...
    View all property information
    Location Information
    Kissimmee, Central Florida 34746
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
    Make Enquiry
    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Grill
    • Wi-Fi
    • Shared Outdoor Pool (Unheated)
    • Washer
    • Patio
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Townhouse totally new and ready for your enjoyment ! CLOSE TO ALL DISNEY AND UNIVERSAL PARKS. Is a property decorated and inspired to receive each client in a place that they can feel in their own home. The whole place brand new is completely yours Enjoy ! Make your reservation Now ! DETAILS -Gated...
    View all property information
    Location Information
    Kissimmee, Central Florida 34746
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
    Make Enquiry
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Grill
    • Wi-Fi
    • Washer
    • Patio
    • Cable/satellite TV
    • Shared Outdoor Pool (Unheated)
    • Air Conditioning
    • Hot Tub
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    HOME SWEET HOME It is a property decorated and inspired to receive each client in a place that they can feel in their own home. The whole place brand new is completely yours Enjoy ! Make your reservation Now ! DETAILS -Gated Community -Clubhouse Amenities -Covered Lanai -Safety Pool Fence For Child...
    View all property information
    Location Information
    Kissimmee, Central Florida 34746
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
    Make Enquiry
    5 Bedrooms, 5 Bathrooms, Sleeps 10 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Washer
    • Grill
    • Wi-Fi
    • Cable/satellite TV
    • Air Conditioning
    • Patio
    • Shared Outdoor Pool (Unheated)
    • Hot Tub
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    PARADISE HOUSE is in one of the best locations of the city THE NEW STOREY LAKE RESORT. New Luxurious Single Family home, prepared for you to live an unforgettable and relaxed vacation. You will find an amazing surprise once you get house as we want to give you a warm welcome to you and your family...
    View all property information
    Location Information
    Kissimmee, Central Florida 34746
    Holiday Rental House - 5 Bedrooms, 5 Bathrooms, Sleeps 10
    Make Enquiry
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Patio
    • Wi-Fi
    • Air Conditioning
    • Shared Outdoor Pool (Unheated)
    • Washer
    • Cable/satellite TV
    • Hot Tub
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This Brand New Condo is just 9 min from Disney !! The condo is decorated and inspired to receive each client in a place that they can feel in their own home. The whole place brand new is completely yours,Enjoy ! Make your reservation NOW!! DETAILS -Gated Community -Fresh Towels/Linens -Clubhouse...
    View all property information
    Location Information
    Kissimmee, Central Florida 34746
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
    Make Enquiry
    List your property for free!
    List your holiday rental where TripAdvisor travellers can find it.
    Add a Listing
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Shared Outdoor Pool (Unheated)
    • Cable/satellite TV
    • Wi-Fi
    • Air Conditioning
    • Patio
    • Hot Tub
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Brand New Condo ! The condo is decorated and inspired to receive each client in a place that they can feel in their own home. The whole place brand new is completely yours,Enjoy ! Make your reservation NOW! DETAILS -Gated Community -Fresh Towels/Linens -Clubhouse Amenities -Equipped Kitchen...
    View all property information
    Location Information
    Kissimmee, Central Florida 34746
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
    Make Enquiry
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Shared Outdoor Pool (Unheated)
    • Hot Tub
    • Washer
    • Wi-Fi
    • Patio
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Staying at Storey Lake resort guests can easily access all the word-famous attraction parks, restaurants, shopping malls, and more within minutes. Is on Osceola Parkway and has a convenient access to the main Florida highways such as SR 535, I-4, 417, US 192, I-Drive, and Poinciana Blvd. You will...
    View all property information
    Location Information
    Kissimmee, Central Florida 34746
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
    Make Enquiry
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Patio
    • Air Conditioning
    • Wi-Fi
    • Shared Outdoor Pool (Unheated)
    • Washer
    • Hot Tub
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This Brand New Condo is just 5 min from Disney !! The condo is decorated and inspired to receive each client in a place that they can feel in their own home. The whole place brand new is completely yours,Enjoy ! Make your reservation NOW! DETAILS -Gated Community -Fresh Towels/Linens -Clubhouse...
    View all property information
    Location Information
    Kissimmee, Central Florida 34746
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
    Make Enquiry
    List your property
    Owner log in