Guesthouse holiday rentals in Kissimmee

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Top-rated Guesthouses in Kissimmee

Guests agree: These guesthouses are highly rated for location, cleanliness and more.

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Superhost

Guesthouse in Orlando

4.86 out of 5 average rating, 133 reviews

King-size Studio 4 min to Universal

Amazing location! king-size private studio, perfectly situated in the desirable Dr. Phillips area, You'll be just 4 minutes from the excitement of Universal Studios and CityWalk. "Restaurant Row," home to some of Orlando’s finest dining only 7 minutes away. The Orlando Convention Center is a quick 10-minute drive, MCO Airport is about 20 minutes away, and Disney is just 18 minutes from your doorstep. Newly remodeled bathroom, a convenient kitchenette, a fridge, a microwave, and a 65-inch TV

Superhost

Guesthouse in Orlando

4.92 out of 5 average rating, 272 reviews

Modern Guest Studio (Private) Pool / Spa available

Private Guest Studio (Not Shared ) in a Perfect Orlando location, 5 minutes from I-Drive, Universal Studios, Disney World & Premium Shopping Outlets. Very Quiet lovely neighborhood with Biking distance to "Restaurant Row" where all your favorite restaurants are located. Pool & Spa available (Not Shared) All major highways at your finger tips / ride 15 min to Disney! This space has an industrial modern look with high ceilings, Stay and cook with all the amenities including a Washer and Dryer.

Guest favourite

Guesthouse in Orlando

4.82 out of 5 average rating, 584 reviews

Spacious getaway close to Universal and Outlets!

PLEASE READ BEFORE BOOKING Checkin -4pm Checkout-10am Welcome to our home! The home is a basement apartment with private entrance ,driveway for one car, and one bedroom in your suite with 2 queen size beds, sofa pull out,and kitchen (portable burners NO STOVE) and a large bathroom with double shower head. This is your own space we have zero way to interact with you but we are a family who lives above you similar to neighbors in apartment. 5 min- universal 10 min- outlets 20 min- Disney

Guest favourite

Guesthouse in Kissimmee

4.91 out of 5 average rating, 138 reviews

Cozy&Deluxe studio for 2 near Disney & parks

Welcome to my independent apartment in my house, I have a great location and you can enjoy easy access to popular shops, restaurants and parks from this charming place to stay with a great location. I also offer the ride from/to the airport just for $30 each ride from home. MCO 30 Min Kissimmee gateway Airport 3 miles-7min Osceola hospital 2.7 miles-7min Disney world and Disney parks are 11-12 miles Universal Studios/ aventure Island is 18 miles The Loop Shopping center is 5.7 miles

Top Guest favourite

Guesthouse in Orlando

4.78 out of 5 average rating, 544 reviews

Private Studio Near Universal, Disney & Shopping!

Discover this cozy studio, completely private with its own entrance. It features a comfortable queen bed, a private bathroom, and a kitchen. It also includes a Luxurious Sofa and free parking. Just 15 minutes from Florida Mall, 15 minutes from the airport, 20 minutes from Disney, and 12 minutes from Universal Studios, as well as 8 minutes from I-Drive Orlando, Millenia Mall, and many more attractions. Perfect for a comfortable and private stay near Orlando’s top attractions!

Superhost

Guesthouse in Orlando

4.8 out of 5 average rating, 252 reviews

Luxury 5 star home 3 min Universal/ Orlando City

Discover your home away from home in this inviting 1 bedroom, 1 bathroom guesthouse, designed for comfort and modern convenience. Relax in a prime location, this cozy retreat offers easy access to popular theme parks, making it an ideal choice for fun-filled vacations. The bathroom suite has a rain shower just like you would expect in a 5-star Hotel, full kitchen, appliances and 2 TVs, one in the bedroom, and another in the living room.

Top Guest favourite

Guesthouse in Four Corners

4.98 out of 5 average rating, 492 reviews

Quiet Room Close to Disney and Attractions

Quaint and quiet retreat just minutes from attractions. Private in-law suite and bathroom, detached from main house. Features all the basic amenities of a hotel room with the feeling of home. Room is perfect for up to three persons. Queen bed and additional sleeper sofa. Located in Reunion Resort. There is a pool, gym, and spa located within the resort but not on the property and is for Reunion club members only.

Guest favourite

Guesthouse in Orlando

4.92 out of 5 average rating, 319 reviews

CLEAN & Modern 2BR w/ sunny yard, close to Disney

Our place is a 2BR, one-bath entire home, with a cozy fire pit and patio furniture space, a fun kids playground area, and a large sunny yard with mature trees for you and guests to explore and enjoy. Excellent location within 15 mins driving distance to the main Disney amusement parks. Free WiFi and HDTV with streaming services available. Please read “Guest Access” for note on other house in the property.

Guest favourite

Guesthouse in Southern Oaks

4.84 out of 5 average rating, 107 reviews

Historic lakefront guesthouse

Relax and enjoy the serenity of this historic guesthouse with large grounds and a beautiful lake. Start out your day with a cup of your favorite coffee out on the balcony or shoreside, watching the sun reflect off the lake and listening to nature. Then take out a kayak or paddle board for a bit of cardio before heading out to the parks, or enjoy some of Orlando’s hidden secrets for a bit of local fun.

Top Guest favourite

Guesthouse in Kissimmee

4.98 out of 5 average rating, 281 reviews

"Little Blue House" Getaway Near the Disney Parks

Your home away from home! Enjoy a comfortable and relaxing stay in our Casa Azul. Spacious and modern, it features a bedroom with a double bed, a private bathroom, a living room with a sofa bed, a dining room, and a fully equipped kitchen. Ideal for vacations with family or friends.