Kissimmee, FL Short term rentals

6491 available short term rental offers

7 nights
2
1
  • airbnb
  • booking
  • vrbo
  • expedia
  • sonder
  • priceline
  • tripadvisor
  • tripcom
  • homestay
  • hotelscom
  • orbitz
  • vacasa
Kissimmee, FL short term rentals
Choose the perfect vacation accommodation
Price per night
Accommodation type
Rating

Best Short term and Weekly rentals in Kissimmee, FL

Top Luxury Short-Term Rentals in Kissimmee, FL

For those who appreciate quality, a high-end short-term rental in Kissimmee, FL delivers on every front.

The Berkley Retreat  3br Home With Pool Near Disney - Kissimmee, FL
9.2 94 reviews
Kissimmee, FL
06/29 – 07/03
$287/nighttotal: $1148 (4 )

The Berkley Retreat 3br Home With Pool Near Disney

3 6
apartment , Kissimmee
This Lake Berkley vacation home in Kissimmee offers convenient access to Give Kids The World Village and Shingle Creek Regional Park (under 1 mile), 192 Flea Market, and Medieval Times (within 3 miles).
The three-bedroom, two-bathroom house sleeps six and boasts a private pool, jacuzzi, game room, fully equipped kitchen, laundry facilities, and free parking.

Best Kissimmee, FL Short term rentals with a jacuzzi

Among the 6491 accommodations in Kissimmee, FL, here are the 4 best rentals with a jacuzzi

️ 5br/5ba Home W/ Private Pool & Spa, Themed Kids Rooms & Resort Fun | Storey Lake Near Disney - Kissimmee, FL
9.8 36 reviews
Kissimmee, FL
07/07 – 07/12
$396/nighttotal: $1980 (5 )

️ 5br/5ba Home W/ Private Pool & Spa, Themed Kids Rooms & Resort Fun | Storey Lake Near Disney

5 10
apartment , Kissimmee
This family-friendly vacation home is located in Kissimmee, Florida, within easy reach of popular attractions like Give Kids the World Village and Kissimmee Go-Karts. Guests consistently rate this property as excellent, highlighting its comfortable and convenient features.
This 5-bedroom, 5-bathroom home provides ample space for up to 12 guests, with a spacious 3,080 square feet of living area. Enjoy amenities like a private pool, a fully equipped kitchen, a game room, and easy access to a water park, fitness center, and limo/town car service.
Family Condo Near Disney, Pool, Gym, Parking & Spa - Kissimmee, FL
9.8 102 reviews
Kissimmee, FL
08/10 – 08/24
$101/nighttotal: $1414 (14 )

Family Condo Near Disney, Pool, Gym, Parking & Spa

1 2
apartment , Kissimmee
This Kissimmee vacation rental is conveniently located near major attractions such as Disney World, Universal Studios, and SeaWorld, with easy access to local entertainment options within a 10-minute drive.
The two-bedroom, two-bathroom condo sleeps six, features a fully equipped kitchen, a 50" Smart TV, a dedicated workspace, and resort-style amenities including pools, a jacuzzi, and a fitness center; allergy-friendly tiled floors throughout.
3 Bedroom Townhome In Gated Community. Pet Friendly! - Kissimmee, FL
9.6 137 reviews
Kissimmee, FL
08/14 – 08/16
$210/nighttotal: $420 (2 )

3 Bedroom Townhome In Gated Community. Pet Friendly!

3 6
apartment , Kissimmee
This Kissimmee vacation home is located within three miles of Medieval Times, the 192 Flea Market, and Give Kids the World Village, and 2.5 miles from Shingle Creek Regional Park.
This 1,190-square-foot property boasts three bedrooms, six bathrooms, and accommodates up to six guests, featuring a private pool, jacuzzi, sauna, fitness center, and tennis court, plus a fully equipped kitchen and in-house laundry.
All New Renovated 3/2 Condo Close To Parks - Kissimmee, FL
9.8 298 reviews
Kissimmee, FL
07/03 – 07/13
$148/nighttotal: $1480 (10 )

All New Renovated 3/2 Condo Close To Parks

3 4
apartment , Kissimmee
This Kissimmee vacation rental is situated in a villa community, just a short walk from parks, shops, and entertainment options. It has consistently received excellent ratings for location, cleanliness, and overall experience.
The three-bedroom apartment comfortably accommodates up to six guests, offering a spacious and relaxing retreat. Enjoy amenities like a private balcony, a swimming pool, and a fitness center, making your stay both comfortable and enjoyable.

Frequently Asked Questions about short term rentals in Kissimmee, FL

  • Which top landmarks you shouldn't miss in Kissimmee?

    Kissimmee is known for its theme parks, so you definitely want to check out Walt Disney World, Universal Orlando Resort, and SeaWorld. But if you're looking for something a little different, head over to the Old Town, a historic district with shops, restaurants, and a classic amusement park. You can even ride a vintage carousel!
  • What are the best short term rentals in Kissimmee, FL?

  • What are the top nightlife spots and party destinations in Kissimmee?

    Kissimmee offers top nightlife spots and party destinations like Old Town Kissimmee, Cowboys Orlando, and the House of Blues at Disney Springs, which provide a lively atmosphere and entertainment for party lovers.
  • What kind of weather can travelers expect in Kissimmee?

    Kissimmee has a subtropical climate, so expect warm temperatures year-round. Summers are hot and humid, with temperatures in the 90s. Winters are mild, with average temperatures in the 60s. We get a lot of sunshine, so pack your sunscreen!
  • What are the best short term rentals with a pool in Kissimmee, FL?

  • Which restaurants and bars in Kissimmee offer the best party atmosphere?

    Restaurants and bars like Bahama Breeze, Yard House, and Splitsville Luxury Lanes offer a fun and vibrant party atmosphere in Kissimmee, with live music, dancing, and a lively ambiance.
  • What are the most popular festivals and events in Kissimmee?

    You'll find tons of fun events throughout the year in Kissimmee. The Osceola County Fair is a big one, with rides, games, and live music. The Kissimmee Air Show is another popular event, featuring impressive aerial displays. And don't forget about the annual Chili Cook-Off, where you can sample some of the best chili in the area.
  • What are the best short term rentals with a jacuzzi in Kissimmee, FL?

  • Are there organized bar crawls or pub tours for a fun way to explore the nightlife in Kissimmee?

    While organized bar crawls or pub tours may not be as prevalent in Kissimmee as in other cities, visitors can still enjoy a fun way to explore the nightlife by hopping between the various bars and venues in areas like Old Town Kissimmee or Disney Springs.
  • Are there any famous stadiums or sports arenas in Kissimmee?

    Kissimmee doesn't have any major league stadiums or arenas, but we do have the Silver Spurs Arena, which hosts a variety of events, including concerts, rodeos, and sporting events. It's a great place to catch a local game or see a big-name performer.
  • What are the best short term rentals for families and kids in Kissimmee, FL?

  • Is it easy to get around at night in Kissimmee?

    Yes, it is relatively easy to get around at night in Kissimmee, especially if you have your own transportation or use rideshare services like Uber or Lyft. However, it's always advisable to plan your transportation in advance, especially if you plan to enjoy the nightlife and consume alcohol.
  • What notable natural landmarks are near Kissimmee?

    Kissimmee is close to some beautiful natural areas. You can visit the Kissimmee Prairie Preserve State Park, which is a great place for hiking, camping, and wildlife viewing. Or head over to the Lake Tohopekaliga, where you can go boating, fishing, and swimming. The area is also known for its beautiful sunsets, so be sure to catch one during your trip.
  • What are the most popular festivals and events in Kissimmee for party lovers?

    Some popular festivals and events in Kissimmee for party lovers include the Mardi Gras celebration at Universal Orlando Resort, the Epcot International Food & Wine Festival, and various themed parties and events hosted by local bars and venues throughout the year.
  • What part of Kissimmee is ideal for finding lodging?

    You'll find plenty of hotels and resorts near the theme parks, which is a great option if you plan to spend most of your time at Disney World, Universal, or SeaWorld. If you're looking for something a little more affordable, check out the areas near Old Town or the Kissimmee Lakefront. You'll find a variety of options, from budget-friendly motels to upscale hotels.
  • Are there any shops in Kissimmee that sell party essentials and unique souvenirs?

    Yes, visitors can find shops in Kissimmee like Party City, Celebration Town Center, or local gift shops that offer party essentials and unique souvenirs, allowing you to bring home memories of your party experience in Kissimmee.

Destinations nearby

Traveler-Approved Family Short-Term Rentals in Kissimmee, FL

Keep the little ones entertained in Kissimmee, FL by choosing a family rental located just steps away from the city’s top attractions.

Your Dream Apartment Stay - Kissimmee, FL
9.8 49 reviews
Kissimmee, FL
07/01 – 07/02
$204/nightfor 1 night

Your Dream Apartment Stay

1 2
apartment , Kissimmee
This one-bedroom Kissimmee apartment rental is ideally located in the Loop district, offering easy access to Walt Disney World, Universal Orlando Resort, and SeaWorld Orlando, all within a 15- to 25-minute drive.
The unit sleeps four guests comfortably, boasting a queen-size bed, a futon, a fully equipped kitchen with modern appliances, in-unit laundry, high-speed Wi-Fi, and access to a community pool, fitness center, and clubhouse.
3 Bedrooms 2.5 Bathrooms Luxury Family Retreat Minutes To Parks & Airport - Kissimmee, FL
10 4 reviews
Kissimmee, FL
07/03 – 07/05
$286/nighttotal: $572 (2 )

3 Bedrooms 2.5 Bathrooms Luxury Family Retreat Minutes To Parks & Airport

3 7
apartment , Kissimmee
This 3-bedroom townhome is situated in the Buena Ventura Lakes neighborhood of Kissimmee, offering proximity to Old Town (approximately 3 miles), Disney Springs™ (approximately 5 miles), and major attractions like Aquatica and the Orange County Convention Center.
This family-friendly rental sleeps up to 8 guests with a king bed, two full beds, and two twin beds, featuring 2 bathrooms, a full kitchen with a dishwasher, air conditioning, a swimming pool, and tennis courts for your convenience.
5 Br 3ba Pool Spa Gated, Lakeview ;Star Wars Arcade; Epci 12 Miles Disney 5 Mile - Kissimmee, FL
8.6 94 reviews
Kissimmee, FL
08/28 – 09/05
$185/nighttotal: $1480 (8 )

5 Br 3ba Pool Spa Gated, Lakeview ;Star Wars Arcade; Epci 12 Miles Disney 5 Mile

5 12
apartment , Kissimmee
This vacation rental is conveniently located in Kissimmee, just a short distance from popular attractions like Kissimmee Go-Karts, 192 Flea Market, and Shingle Creek Regional Park. The home has received very good user ratings, indicating a comfortable and enjoyable stay for guests.
This 5-bedroom, 3-bathroom home comfortably accommodates up to 12 guests in its 1800 square feet of space. Enjoy the lakefront location, on-site amenities like a swimming pool, Jacuzzi, spa, and fitness center, as well as a fully equipped kitchen and a terrace/balcony.
4 Bedrooms, 3 Bathrooms Townhouse - Kissimmee, FL
9.4 6 reviews
Kissimmee, FL
07/07 – 07/12
$364/nighttotal: $1820 (5 )

4 Bedrooms, 3 Bathrooms Townhouse

4 10
apartment , Kissimmee
This luxury, brand-new townhouse is located in the gated Storey Lake Resort community in Kissimmee, offering prime access just 8 miles from Walt Disney World and minutes from Universal Studios Florida and SeaWorld Orlando, with convenient proximity to The Mall at Millenia, Florida Mall, and Vineland Premium Outlets.
This 1920 square foot vacation home accommodates up to 12 guests with 4 bedrooms and 3 bathrooms, featuring a private screened-in pool, free access to a water park with water slides and a lazy river, and exclusive use of resort amenities including a fitness center, spa, jacuzzi, mini golf, and a tiki bar/restaurant.

Best Kissimmee, FL lodging with parking

15 Minute Drive Disney Vacation Home W/hot Tub - Kissimmee, FL
8.6 21 reviews
Kissimmee, FL
07/07 – 07/12
$216/nighttotal: $1080 (5 )

15 Minute Drive Disney Vacation Home W/hot Tub

4 10
apartment , Kissimmee
This Kissimmee vacation home boasts a central location, less than a mile from Shingle Creek Regional Park, Kissimmee Go-Karts, and the 192 Flea Market, and within two miles of Capone's Dinner Show and Medieval Times.
The 4-bedroom, 3-bathroom house sleeps 10 guests and features a private pool, jacuzzi, fitness center, and fully equipped kitchen; enjoy free WiFi and on-site parking.
Spacious Family Villa W/ Private Pool Near Disney - Kissimmee, FL
9.2 38 reviews
Kissimmee, FL
12/25 – 01/07
$304/nighttotal: $3952 (13 )

Spacious Family Villa W/ Private Pool Near Disney

4 7
apartment , Kissimmee
This Kissimmee vacation home, located in Eagle Pointe South, is less than a 10-minute drive from shopping and dining and a short drive from Walt Disney World Resort, Disney's Hollywood Studios, and Epcot.
This 1820-square-foot house features four bedrooms, three bathrooms, sleeps ten guests, and includes a private pool, fully equipped kitchen, and in-house laundry facilities.
Sunny Pool, Game Room, Only 8 Mi To Disney, Walk To #Gktw! - Kissimmee, FL
9.7 149 reviews
Kissimmee, FL
07/11 – 07/20
$259/nighttotal: $2331 (9 )

Sunny Pool, Game Room, Only 8 Mi To Disney, Walk To #Gktw!

3 4
apartment , Kissimmee
This smoke-free Kissimmee vacation home is located in the Creekside district, a 5-minute walk from Shingle Creek Regional Park and Give Kids the World Village, and within 2 miles of the 192 Flea Market and Medieval Times.
This 1,380-square-foot house features three bedrooms, two bathrooms, and accommodates six guests, boasting a private pool, a fully equipped kitchen, free Wi-Fi, and proximity to numerous attractions.
Villas At Seven Dwarfs - 4br, 3ba, 2 Ensuite King - Kissimmee, FL
9.2 107 reviews
Kissimmee, FL
06/29 – 07/03
$197/nighttotal: $788 (4 )

Villas At Seven Dwarfs - 4br, 3ba, 2 Ensuite King

4 6
apartment , Kissimmee
This 4-bedroom, 3-bathroom vacation rental is located in Kissimmee, within walking distance of Capone's Dinner Show and Kissimmee Go-Karts, and within a 3-mile radius of 192 Flea Market and Lake Buena Vista Factory Stores. The home features a fully equipped kitchen, a fitness center, and a shared bathroom, making it ideal for families or groups of up to 8 guests.
©2026 cozycozy.com