Some info has been automatically translated. Show original language

Vacation rentals in Kissimmee

Book unique homes, vacation rentals, and more on Airbnb

0 of 0 items showing
1 of 3 pages

Popular amenities for Kissimmee vacation rentals

Stay near Kissimmee's top sights

The Hideaway Club House at Storey Lake5 locals recommend
Kissimmee Lakefront Park171 locals recommend
Silver Spurs Arena9 locals recommend
Kissimmee Gateway Airport4 locals recommend
Gatorland417 locals recommend
Loop West Shopping Center256 locals recommend

Private vacation rentals in Kissimmee

Superhost
The open-concept kitchen and living area feature modern appliances and sleek countertops. Bar stools provide seating at the kitchen island, and a dining table accommodates six. Natural light fills the space, highlighting the blue accent wall and comfortable seating in the living area.
Home in Davenport
5 out of 5 average rating, 4 reviews

Villa 4BD in Champions Gate for 8 – Private Pool

JoaquimRating, 5 stars4 months ago
Edney was a fantastic host! He made everything easy with clear and friendly communication, ensuring we had everything we needed for a stress-free stay. The house was amazing – spotless, roomy, and thoughtfully decorated, with every detail carefully considered. It completely surpassed our expectations! We would highly recommend staying here and look forward to coming back someday. Thank you, Edney, for an outstanding experience!
Superhost
A private pool is surrounded by a screened enclosure, capturing the evening sky's colors. Natural light filters through the adjacent glass doors, revealing a dining area with patio seating nearby. The tranquil water surface reflects the vibrant hues of sunset.
Home in Kissimmee
4.83 out of 5 average rating, 6 reviews

Cute Vacation Home Very Close to Disney

T LianneRating, 5 stars3 months ago
We really enjoyed the house and pool. It was very convenient to parks and shopping /restaurants.
Superhost
An outdoor space features a spacious pool surrounded by a sunbathing area. A covered seating area offers shade under a large umbrella, while palm trees add a touch of greenery. The screen enclosure provides protection while allowing for natural light and fresh air.
Home in Kissimmee
5 out of 5 average rating, 3 reviews

Dream vacation, near Disney

ChrisRating, 5 stars3 weeks ago
What an incredible stay we had at Rosario's place! We even extended 2 extra nights. Rosario was responsive, helpful, and so kind - she even left a birthday balloon and some treats for my mom's birthday! The house was impeccable and they were great about everything, from changing dates to heating the pool, and keeping it clean, and the pool was a perfect balmy respite. The next time we're in town (and we will be, this is our old neighborhood!), we will definitely try to book here again. Can't wait to come back!
Superhost
Home in Davenport
4.76 out of 5 average rating, 68 reviews

Vacation home

JaniquaRating, 5 stars1 month ago
Me and my Family enjoyed our days there! Miguel was very friendly and nice and welcome us to a little welcome gift I mean who dosen’t love chocolate
Guest favorite
Vacation home in Kissimmee
4.83 out of 5 average rating, 104 reviews

Nice & Cozy Home near Disney

Olga LuciaRating, 5 stars4 months ago
Everything was excellent! Especially the host's attention, she is ready to help, she responds quickly. It is close to Disney parks, supermarket, restaurants, gas station.
Guest favorite
A clear no smoking sign is displayed on the door, emphasizing a strict no smoking policy, including e-cigarettes. Through the window, a glimpse of the private heated pool can be seen, surrounded by trees and landscaped areas.
Home in Kissimmee
4.88 out of 5 average rating, 248 reviews

Private Heated Pool & Hot Tub; 6 miles to Disney

JenniferRating, 5 stars1 day ago
Thank you for allowing us to stay at your place. House is very cute and clean! Super awesome it has alarms on the doors that leads to the pool. Safety for the kiddos is always good even though mine are of age and swim well wish a lot more would have that. Will be back I’m sure!
Guest favorite
A private pool area is enclosed with mesh screening, featuring clear blue water. Two lounge chairs are positioned beside the pool on a sunlit patio. A view of a grassy area and trees is visible through the enclosure.
Home in Kissimmee
4.88 out of 5 average rating, 188 reviews

4BR,PrvtNOTOverlookedPool,FencedYard,GameRM,WiFi

MustafaRating, 5 stars3 weeks ago
Great house and host was very friendly with clear instructions on check in and check out. Pool was clean and well maintained.
Superhost
Home in Four Corners
4.88 out of 5 average rating, 48 reviews

H2412T-Windsor at Westside Resort/POOL/Water Park

EdwardRating, 5 stars1 week ago
Very nice place my family and I enjoyed staying at Michael’s place, the only thing I dislike was the fact that is too close to the Disney parks and coming back to the place after being out the traffic is kind of heavy but there is nothing anyone can do about that, Love the place!! Thank you Michael!!.

Homes in Kissimmee

Top guest favorite
A private pool area is showcased, featuring a clear blue pool surrounded by a screened enclosure. Comfortable lounge chairs in turquoise are positioned beside the pool. A serene pond and lush greenery are visible beyond the enclosure, providing a calm backdrop.
Home in Kissimmee
4.93 out of 5 average rating, 136 reviews

(Discounted Rates) Vacation Home (4 Miles Disney)

AmandaRating, 5 stars3 months ago
We had such an enjoyable time here. We highly recommend it to all. The pool was a huge winner for our kids and the location was perfect. Thanks again!
Guest favorite
Home in Kissimmee
4.95 out of 5 average rating, 21 reviews

Beautiful Gated Home near Disney and Universal

BenejahRating, 5 stars1 month ago
My stay was amazing I will be booking again
Superhost
An engaging Star Wars-themed game room features a foosball table, arcade machines, and a spacious seating area. Murals depict scenes from the franchise, with screens displaying games. The room is designed for fun and entertainment, offering a vibrant environment for guests.
Home in Kissimmee
4.83 out of 5 average rating, 136 reviews

Orlando Home with Private Pool & Game Room !

TammyRating, 5 stars2 weeks ago
This was the perfect place to stay for our family vacation. The kids loved the game room and the pool. The house was clean and in a nice, safe neighborhood. Our host was very polite and very responsive. We loved every minute of our stay and we would definitely stay here again. Highly recommend!!
Guest favorite
A spacious living area is furnished with a blue sofa and two green accent chairs. A glass coffee table sits on a patterned rug, surrounded by decorative plants. Light filters through windows with patterned curtains, creating a bright and inviting atmosphere.
Home in Orlando
4.87 out of 5 average rating, 111 reviews

Modern Home near DT&Airport/Community Pool Nearby

JamieRating, 5 stars1 month ago
I booked Valerie's accommodation for 3 of my international colleagues. Her place was exactly as pictured, very clean, organized, and had all the amenities anyone could need. As hosts, both Valerie and Jad were extremely friendly and accommodating. They were very proactive, quick to respond, communicative, and went out of their way to make the guys' experience a great one. They were very flexible - our needs changed a few times throughout their stay due to project extensions, and they were extremely helpful and graciously extended their reservation three times. The guys had nothing but wonderful things to say about their experience. 10/10 recommend if you are in the area - for the space itself and such great hosts. Thank you again Valerie and Jad!
Superhost
Two elegant marble sinks are positioned on a sleek countertop, complemented by soft gray towels neatly placed inside each bowl. A small potted plant is visible above the sink, and a round mirror reflects subtle light in the contemporary bathroom setting.
Home in Orlando
4.84 out of 5 average rating, 224 reviews

King suite , Modern house perfect for vacation

PatziRating, 5 stars1 month ago
Property was just as it was advertised and Jose was friendly and responsive. We really enjoyed our stay and will come back in the future.
Guest favorite
A vibrant water play area features a colorful pirate ship surrounded by palm trees and outdoor lounge seating. A slide extends from the ship into a shallow splash zone, inviting family fun. Bright umbrellas provide shade in the background, enhancing the lively atmosphere.
Home in Davenport
5 out of 5 average rating, 18 reviews

New Family friendly townhome.

Jean-FrancoisRating, 5 stars1 month ago
Very nice stay, proactive host and always attentive. To keep in mind for a future visit.
Guest favorite
A large two-story home is showcased with a well-maintained lawn and framed by palm trees. The exterior features a mix of light and dark colors, with a welcoming front porch and bright exterior lights. A driveway leads to a spacious garage, enhancing the home's curb appeal.
Home in Davenport
4.77 out of 5 average rating, 114 reviews

There is no other place you want to be than here.

ChrisRating, 5 stars1 week ago
We’ve just finished a fantastic family holiday at this villa and can’t recommend it highly enough. The house was spotless on arrival, with plenty of fresh towels and hotel‑quality linen. The open‑plan living area is bright and welcoming, and the kitchen has every utensil you could possibly need—including a decent sharp knife (rare in rentals!). The private pool is the real star: perfectly clean, comfortably heated, and enclosed for peace of mind with younger children. Location‑wise, it’s an easy drive to Disney and Universal, but far enough away to escape the crowds; supermarkets and restaurants are only a few minutes up the road. Communication with Frank was first‑class from booking to check‑out—quick replies and genuinely helpful advice. If you’re after a stress‑free, family‑friendly base in the Orlando area, book this place—you won’t be disappointed.
Superhost
The exterior of the villa features a light-colored facade with a distinctive archway entrance and blue front door. Lush greenery surrounds the entrance, and palm trees are visible, adding to the welcoming feel. A paved driveway leads up to the home.
Home in Davenport
4.83 out of 5 average rating, 133 reviews

Jaw Dropping 5 Bed 4 Bath Home in Hampton Lakes

JosephRating, 5 stars2 weeks ago
Luis was a very responsive host, we had small issues throughout 8 week stay and he always replied quickly and got things handled. A large part of our time there included us having our 88 year old mother with us and it was very satisfying to have Luis follow through on his promises for the pool heat level and air conditioning level at night so she could sleep comfortably. The house suited our family very well with 5 bedrooms and 4 washrooms, 3 of the bedrooms included ensuites. The pool was part of the highlight with sun shining usually from 11am to 6pm. Overall we were quite satisfied with our choice

Other great vacation rentals in Kissimmee

Guest favorite
Home in Davenport
4.84 out of 5 average rating, 32 reviews

Solterra discount slps 18/7 bdm/GR/pool/spa5485

SamanthaRating, 5 stars1 month ago
The house is brilliant. We had 11 adults and a 5 month old baby. We all flew in at different times, to different airports but access was easy for everyone. we had been given the details by the host prior to our arrival. Susan is a great host, very communicative but not intrusive. Every detail was taken care of. Passes at the gate, information about the activities and much more. I would highly recommend this AirBnB to anyone. Having a large family, it was great for space but also playing games and spending time together. We had family visit, who live in Florida, which was also easy. Susan was very helpful when my father in law couldnt be located, after visiting us. Thank you Susan, we will be back
Top guest favorite
A dining area is set with elegant tableware on a marble table. Colorful napkins are neatly arranged beside each place setting, alongside crystal glasses. Bright patterned curtains complement the decor, while a lush green plant adds a touch of nature to the atmosphere.
Home in Davenport
5 out of 5 average rating, 21 reviews

Minutes to Disney, private pool, golf, playground

ZailetRating, 5 stars2 weeks ago
Beautifully decorated house, location, and amenities!
Guest favorite
Home in Davenport
5 out of 5 average rating, 5 reviews

New! Windsor Island Resort with pool by Disney 03

IrynaRating, 5 stars16 months ago
Nice house with good layout of rooms. It is very convenient to come with children as there is a lot of entertainment on the territory of the complex. I also liked the themed design of the rooms. Overall, this is a good house for a large and friendly company.
Top guest favorite
The entrance of a resort is captured, featuring a welcoming pathway bordered by neatly trimmed landscaping. Palm trees and vibrant shrubs provide a tropical ambiance, while the building showcases a tiled roof and an inviting façade. A decorative fountain is visible near the entrance.
Condo in Davenport
5 out of 5 average rating, 28 reviews

Cozy Condo in Champions Gate

DianeRating, 5 stars2 weeks ago
We cannot say enough about how much we loved our stay during this winter. For the second year we have enjoyed a wonderful, clean, peaceful stay at this fantastic condo. There is nothing to complain about. Ana has been a very responsive and helpful host and everything was just perfect and was truly a comfortable “home sweet home”. We will surely stay at Ana’s condo again and again in the years to come.
Guest favorite
The resort area features multiple pools and lounging spaces surrounded by lush landscaping. Curved pathways guide to various amenities, including shaded cabanas and sun loungers. The vibrant blue waters contrast with the red accents of the poolside, creating an inviting recreational environment.
Townhouse in Davenport
4.9 out of 5 average rating, 10 reviews

Great Town home with lazy river

KieraRating, 5 stars1 month ago
Anthony’s place came with no hidden surprises, checkin/out was a breeze. Although we had plans to visit the local theme parks, the resort had plenty more things for our family to enjoy! Thank you Anthony for making our vacation memorable!!
Guest favorite
A large swimming pool is surrounded by lush palm trees and sun loungers, offering a refreshing escape. The clear blue water reflects the sky, with steps leading into the pool area. A spacious deck provides ample space for relaxation and enjoyment under the sun.
Home in Davenport, Orlando
4.89 out of 5 average rating, 35 reviews

Orlando Retreat: Cozy Escape for Magical Holidays

NicoleRating, 5 stars3 weeks ago
Laura’s place was the perfect spot for our Disney vacation. Close enough to be parks but just far enough that it didn’t feel so busy all the time.
Top guest favorite
A colorful water play area features a wooden pirate ship with multiple water features, including a large water bucket and a slide. Stairs lead up to the main deck, surrounded by a splash area, offering a playful environment for children.
Home in Davenport
4.96 out of 5 average rating, 25 reviews

Pelican Escape

EmiliaRating, 5 stars1 month ago
Our stay was very comfortable. Not far from Disney and other attractions. My family had everything they needed, would stay again in the future!
Superhost
Home in Four Corners
4.88 out of 5 average rating, 16 reviews

DisneyVacationHomeLazyRiver9021

SharonRating, 5 stars2 weeks ago
This beautiful home worked well for our family…4 couples and 3 small children. Pool and hot tub were great and clean! The house was large and we had a ton of fun! The host was super responsive every time we sent a message. We would definitely come back to this house and would highly recommend it!

Quick stats about vacation rentals in Kissimmee

  • Total rentals

    7.2K properties

  • Total number of reviews

    242K reviews

  • Family-friendly rentals

    6.1K properties are a good fit for families

  • Pet-friendly rentals

    1.1K properties allow pets

  • Rentals with a pool

    6.5K properties have a pool

  • Rentals with dedicated workspaces

    3.9K properties have a dedicated workspace

Your guide to Kissimmee

All About Kissimmee

Less than 30 minutes south of Orlando, the central city of Kissimmee makes for an ideal home base for visiting Florida’s most popular theme parks. The city sits on the northwest corner of Lake Tohopekaliga, also known as Lake Toho, which stretches across Kissimmee for four miles. Flat, grassy terrain complemented by tall palm trees surrounding the water make Lake Toho the unofficial centerpiece of Kissimmee. Many local activities revolve around the lake, from bass fishing to bird watching and scenic walks through its lakefront parks.

Tall mangrove trees sprouting up from the wetlands mark the official start of the infamous Florida Everglades at Kissimmee’s Shingle Creek Regional Park. These protected wetlands stretch for more than a million acres from Kissimmee to the tip of South Florida, finally emptying into the Gulf of Mexico. The park’s grassy terrain leads you to long, overwater docks hovering over the freshwater marshes, but visitors be warned: this lush foliage also provides perfect coverage for one of Kissimmee’s scaly residents, the alligator. The city takes great measures to ensure that they never cross paths with humans, but do heed the signs and do your bird spotting on the decks. On a clear day, you might find a sandhill crane or the bright pink roseate spoonbill.


The best time to stay in a vacation rental in Kissimmee

Kissimmee weather stays fairly warm throughout the year, but visitors should plan for a few rainy days here and there. Summers are usually hot and humid, and on a sunny day, a visit to Cocoa Beach is about an hour’s drive away from most Kissimmee vacation rentals. Spring weather is cooler but warm enough to kayak through the headwaters of the Florida Everglades at the Shingle Creek Regional Park. On a typical winter or fall day, the weather is cool and comfortable enough to be outdoors. During these two seasons, you can plan a picnic at the serene Brownie Wise Park facing Kissimmee’s massive Lake Tohopekaliga.


Top things to do in Kissimmee

Kissimmee Lakefront Park

The one-mile walking trail at the Kissimmee Lakefront Park is an easy walk or bike-friendly path over flat, grassy terrain. The trail follows the north shore of Lake Tohopekaliga, and at opposite ends of the trail, you can make stops at the Big Toho Marina and the eclectic Monument of States Memorial. This quirky memorial is made with stones from each of the 50 states that make up the United States.

Museum of Military History

Exhibitions featuring historic relics help tell the story of America’s military endeavors, beginning with the Revolutionary War and ending in the present day. Each of the five military branches is included too. Authentic, donated artifacts representing each major military event are on display for visitors to take in, from muskets used in 1775 to World War II service vehicles. Guided tours are often led by military veterans.

Twin Oaks Conservation Area

The 370-acre Twin Oaks Conservation Area along Lake Tohopekaliga preserves Floria’s native wildlife habitats. Tall, untamed grass pokes through the park’s freshwater marshes, and overwater piers jut out over the marshlands for visitors to take a closer look at the landscape and its inhabitants. The best wildlife lookout point is at the park’s main, elevated viewing platform, where you may be able to spot one of Florida’s most well-recognized reptiles, the alligator, or even a bald eagle.

Frequently Asked Questions

  • How is the weather in Kissimmee?

    Kissimmee boasts a tropical climate, with hot, humid summers reaching 90°F (32°C) and milder winters averaging around 60°F (15°C). Rainfall is more frequent in the summer, while winter tends to be drier.

  • What are some of the best things to do in Kissimmee?

    Popular activities in Kissimmee include exploring the Old Town, a recreated Florida town full of shops and restaurants, taking a thrilling airboat tour on Lake Tohopekaliga, or enjoying a round of golf at one of the city's many golf courses.

  • What is the best time of year to visit Kissimmee?

    The most popular time to visit Kissimmee is in the summer, particularly between March and August. During this period, the city hosts local events such as the Kissimmee Sunshine Regional Chili Cook-Off and the Silver Spurs Rodeo.

  • What are the best places to stay in Kissimmee?

    Celebrate, a family-friendly community, is often recommended for its proximity to theme parks. Downtown Kissimmee is popular for its vibrant nightlife and historic landmarks. West Kissimmee, located close to a number of natural attractions, is also frequently suggested.

  • What are the best places to visit in Kissimmee?

    Popular places to visit in Kissimmee include the Kissimmee Lakefront Park, the Osceola County Historical Society Pioneer Village, and Gatorland, a wildlife preserve and theme park.

  • What are some hiking trails in Kissimmee?

    Kissimmee has a variety of hiking trails such as the Shingle Creek Regional Trail for scenic views of natural Florida or the Disney Wilderness Preserve which is home to numerous species of plants and animals.

  • What are some family activities to do in Kissimmee?

    Families in Kissimmee can explore numerous attractions including the interactive exhibits at the Museum of Military History, a fun-filled day at Fun Spot America amusement park, or a chance to spot native Florida wildlife at the Wildlife Refuge.

  • What are some of the best day trip ideas in Kissimmee?

    Popular day trips from Kissimmee often include a visit to Orlando, just 17 miles (27 km) away, to experience its world-renowned theme parks. Alternatively, the beautiful beaches of Clearwater are just 90 miles (145 km) away.

  • What types of vacation rentals are available in Kissimmee?

    Uncover the perfect home-away-from-home with our diverse selection of vacation rentals in Kissimmee. From over 3,470 house rentals, over 490 apartment rentals to over 740 villa rentals, we've got you covered. For even more variety, explore our Airbnb Categories to find the ideal space for your getaway.

  • Are there vacation rentals with a dedicated workspace in Kissimmee?

    Yes! Work meets play with ease at over 3,930 vacation rentals in Kissimmee featuring dedicated workspaces. Stay connected and productive in your home away from home.

Destinations to explore

  1. Airbnb
  2. United States
  3. Florida
  4. Osceola County
  5. Kissimmee