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Kissimmee, FL cottages
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12 Best cottages in Kissimmee, FL

Top Family-Friendly Cottages in Kissimmee, FL

Getting the cottage right makes all the difference for a family trip to Kissimmee, FL, with city attractions located within easy reach of every option.

5003 Windermere Avenue - Kissimmee, FL
10 3 reviews
Kissimmee, FL
10/26 – 11/09
$220/nighttotal: $3080 (14 )

5003 Windermere Avenue

1 3
cottage , Hunters Creek
This Hunters Creek cottage is located just 1.2 miles from Capone's Dinner Show, Kissimmee Go-Karts, and Shingle Creek Regional Park, and 2.5 miles from Old Town.
The family-friendly cottage features a fully equipped kitchen, a swimming pool, and free Wi-Fi, making it ideal for a relaxing vacation.
Entertaining Game Room 4br Near Disney - Kissimmee, FL
Kissimmee, FL
08/31 – 09/17
$225/nighttotal: $3825 (17 )

Entertaining Game Room 4br Near Disney

1 3
cottage , Kissimmee
This cottage in Seasons, Kissimmee, is located within 1.2 miles of Medieval Times and the 192 Flea Market, and within 3.1 miles of Give Kids the World Village.
This pet-friendly, family-friendly rental offers air conditioning, free WiFi in public areas, a full kitchen with an oven and microwave, a video game console, cable TV, and on-site gas grills and a 24-hour fitness center, with free self-parking available.
Private Pool & Game Room: Family Vacation Rental - Kissimmee, FL
Kissimmee, FL
10/10 – 10/17
$427/nighttotal: $2989 (7 )

Private Pool & Game Room: Family Vacation Rental

1 3
cottage , Hunters Creek
This Hunters Creek cottage is conveniently located near major Orlando attractions, approximately 3 miles from Capone's Dinner Show, 6 miles from Walt Disney World® Resort, and 3 miles from Lake Buena Vista Factory Stores.
Each cottage unit boasts multiple bathrooms (5), fully equipped kitchens with microwaves and dishwashers, and in-unit entertainment including TVs and video game consoles, plus access to an on-site pool, business center, and video game room.
2758bd · Dazzling 5br Villa In Storey Lake With Pool & Spa - Kissimmee, FL
Kissimmee, FL
10/10 – 10/17
$492/nighttotal: $3444 (7 )

2758bd · Dazzling 5br Villa In Storey Lake With Pool & Spa

1 3
cottage , Kissimmee
This non-smoking cottage in Kissimmee is located within 2 miles of Shingle Creek Regional Park and Lake Cecile, and less than 5 miles from Kissimmee Go-Karts and Medieval Times.
This vacation rental offers complimentary Wi-Fi in common areas, a full kitchen, air conditioning, and cable television, with 5.5 bathrooms.

Best Kissimmee, FL cottages with a kitchen

10 Mi To Disney: Home W/ Game Room & Lanai! - Kissimmee, FL
Kissimmee, FL
10/26 – 11/09
$222/nighttotal: $3108 (14 )

10 Mi To Disney: Home W/ Game Room & Lanai!

1 3
cottage , Kissimmee
This Bellavida cottage in Kissimmee offers convenient access to Give Kids the World Village and Shingle Creek Regional Park, both within 1.2 miles, and is also close to the 192 Flea Market and Medieval Times dinner show (within 1.9 miles).
The three-bathroom vacation home features a fully equipped kitchen with microwave and dishwasher, a private patio, on-site pool access, and a nearby arcade.
4184pd Weekly Stay 5br Free Water Park - Kissimmee, FL
Kissimmee, FL
06/20 – 06/27
$544/nighttotal: $3808 (7 )

4184pd Weekly Stay 5br Free Water Park

1 2
house , Kissimmee
This non-smoking cottage in Kissimmee is located 0.3 km (approximately 984 feet) from Shingle Creek Regional Park and within 5 miles of Lake Cecile and Capone's Dinner Show.
This rental offers complimentary Wi-Fi in common areas, air conditioning, a fully functional kitchen, and a television with cable channels, featuring 4 bathrooms for your convenience.
Home 6br - Prime Location - Kissimmee, FL
Kissimmee, FL
08/31 – 09/17
$258/nighttotal: $4386 (17 )

Home 6br - Prime Location

1 3
cottage , Hunters Creek
This cottage is located in Kissimmee, within 1 mile of Shingle Creek Regional Park and Lake Cecile, and 2 miles from Capone's Dinner Show and Kissimmee Go-Karts.
This rental offers air conditioning, free WiFi in public areas, and an outdoor swimming pool, with gas grills and a 24-hour fitness center available for guest use.
6 Mi To Disney World: Lake-view Retreat W/ Pool! - Kissimmee, FL
Kissimmee, FL
08/31 – 09/17
$209/nighttotal: $3553 (17 )

6 Mi To Disney World: Lake-view Retreat W/ Pool!

1 3
cottage , Kissimmee
This Kissimmee vacation home in the Montego Bay area is less than 1.2 miles from Kissimmee Go-Karts and Capone's Dinner Show, and under 1.9 miles from Medieval Times and Lake Cecile.
The two-bathroom cottage features a fully equipped kitchen with microwave and dishwasher, a cozy fireplace, a private patio, free Wi-Fi in common areas, and access to a free outdoor pool and free parking.

Frequently Asked Questions about cottages in Kissimmee, FL

  • What part of Kissimmee is ideal for renting a cottage?

    Many cottages can be found in the areas around the theme parks like Celebration, Reunion, and Windsor Hills. These communities are close to the attractions and offer a more residential feel compared to staying in a hotel.
  • What are the best cottages in Kissimmee, FL?

  • What are the top eco-tourism attractions in Kissimmee?

    Kissimmee offers top eco-tourism attractions like the Forever Florida Eco-Attraction, the Kissimmee Lakefront Park, and the Shingle Creek Regional Park, which provide opportunities to connect with nature and learn about environmental conservation.
  • When is the best time to rent a cottage in Kissimmee?

    The best time to visit Kissimmee is during the spring (March-May) or fall (September-November) when the weather is pleasant and the crowds are smaller. If you're looking for a more affordable option, consider visiting during the off-season (January-February or August-September) but be aware that some attractions may have limited hours or availability.
  • What are the best cottages with a pool in Kissimmee, FL?

  • What are the best ways to travel to Kissimmee eco-consciously?

    Traveling to Kissimmee eco-consciously can be done by choosing fuel-efficient transportation options, such as hybrid or electric vehicles, using public transportation, or even opting for biking or walking when exploring the area.
  • What are the can't-miss sights in Kissimmee?

    You definitely need to visit the theme parks like Walt Disney World Resort, Universal Orlando Resort, and SeaWorld Orlando. For a unique experience, check out the Celebration Town Center, a charming planned community with a European-style town square. And don't forget to explore the natural beauty of the area at the Shingle Creek Regional Park or the Osceola Heritage Park.
  • What are the best cottages with a jacuzzi in Kissimmee, FL?

  • Is Kissimmee pedestrian and cyclist-friendly?

    While Kissimmee is more car-centric, there are areas and trails like the Kissimmee Lakefront Park and the Shingle Creek Regional Park that offer pedestrian and cyclist-friendly environments for those looking to explore the area in a more eco-friendly way.
  • Why consider renting a cottage in Kissimmee for your stay?

    Cottages in Kissimmee offer a more spacious and private accommodation option compared to hotels. They often come with amenities like a kitchen, laundry facilities, and a private pool, making them ideal for families or groups. You can also find cottages with different themes and styles to suit your preferences.
  • What are the best cottages for families and kids in Kissimmee, FL?

  • Are there opportunities to learn about traditional ways of life that have a lighter environmental footprint in Kissimmee?

    Yes, visitors to Kissimmee can learn about traditional ways of life with a lighter environmental footprint by exploring eco-attractions like the Forever Florida Eco-Attraction, taking part in educational programs, or engaging with local conservation organizations.
  • Can you easily explore Kissimmee on foot or by bike?

    While Kissimmee is a car-dependent city, you can explore some areas on foot or by bike. The Celebration Town Center and the Shingle Creek Regional Park are great for walking or biking. However, for exploring the wider area, renting a car is recommended.
  • What are the best pet friendly cottages in Kissimmee, FL?

  • What are the best nature conservation activities one can participate in while visiting Kissimmee?

    While visiting Kissimmee, one can participate in nature conservation activities like volunteering for clean-up initiatives, joining local conservation organizations, or supporting initiatives like the Kissimmee River Restoration Project to help protect and preserve the environment.
  • What family-friendly activities are available in Kissimmee?

    Kissimmee is a great destination for families. Besides the theme parks, you can enjoy activities like visiting the Gatorland, playing mini-golf at one of the many courses, or exploring the Osceola Heritage Park, which features a museum and a petting zoo.
  • What are the best cottages with parking in Kissimmee, FL?

  • Are there any eco-friendly shops or markets in Kissimmee that sell local, sustainable products?

    Kissimmee offers eco-friendly shops and markets like the Celebration Farmers Market, the Whole Foods Market, or local boutiques that promote local and sustainable products, providing options for those looking to shop consciously.
  • What are some of the best walking or cycling routes in Kissimmee?

    Some of the best walking or cycling routes in Kissimmee include the Kissimmee Lakefront Park Trail, the Shingle Creek Regional Trail, and the Celebration Trail, offering scenic views and opportunities to connect with nature.
  • Are there any local initiatives or projects in Kissimmee that support environmental sustainability?

    Kissimmee has several local initiatives and projects supporting environmental sustainability, such as water conservation efforts, community gardens, and educational programs that promote environmental awareness and sustainable practices.

Destinations nearby

Guest-Favorite Cottages with a Hot Tub in Kissimmee, FL

Experience the ultimate recovery after a day in the city with a private hot tub at these cottages in Kissimmee, FL.

Amazing House At Bella Vida 5br - Kissimmee, FL
Kissimmee, FL
07/24 – 08/03
$386/nighttotal: $3860 (10 )

Amazing House At Bella Vida 5br

1 2
cottage , Kissimmee
This cottage in Kissimmee is located within a 15-minute walk of Give Kids the World Village and Shingle Creek Regional Park, and less than 2 miles from Medieval Times and 192 Flea Market.
This rental offers a private pool, an outdoor pool with a children's pool, a 24-hour fitness center, a well-equipped kitchen with a freezer and microwave, air conditioning, internet, and gas grills.

Traveler-Approved Pet-Friendly Cottages in Kissimmee, FL

Bringing your dog to Kissimmee, FL? Every pet-friendly cottage here offers dog parks nearby and city walks on the doorstep.

Dog-friendly Kissimmee Home W/ Lanai + Pool! - Kissimmee, FL
Kissimmee, FL
10/26 – 11/09
$226/nighttotal: $3164 (14 )

Dog-friendly Kissimmee Home W/ Lanai + Pool!

1 3
cottage , Kissimmee
This Kissimmee cottage is located in Crystal Cove, within a mile of Medieval Times and the 192 Flea Market, and within three miles of Shingle Creek Regional Park and Give Kids the World Village, making it a convenient base for exploring the area's attractions. The home is ideal for families or groups, with 4.5 bathrooms offering ample space and privacy.
The cottage features a private pool, an arcade/game room, barbecue grills, and a peaceful patio, perfect for relaxing after a day of exploring. The fully equipped kitchen includes an oven, stovetop, microwave, and dishwasher, and guests can enjoy complimentary Wi-Fi in public areas and free self parking.
Ground Floor Gathering Up To 9 Guests Bl387 - Kissimmee, FL
Kissimmee, FL
06/20 – 06/27
$345/nighttotal: $2415 (7 )

Ground Floor Gathering Up To 9 Guests Bl387

1 2
cottage , Kissimmee
This cottage in Kissimmee is a 15-minute walk from Shingle Creek Regional Park and Give Kids the World Village, with the 192 Flea Market and Medieval Times within 2 miles.
This pet-friendly, family-friendly rental features a full kitchen with a freezer and microwave, air conditioning, a swimming pool, fitness center, and parking, plus a video game console.
3br Townhome W/ Pool & Bbq Near Disney - Kissimmee, FL
Kissimmee, FL
07/24 – 08/03
$214/nighttotal: $2140 (10 )

3br Townhome W/ Pool & Bbq Near Disney

1 2
cottage , Kissimmee
This vacation rental in Venetian Bay Villages, Kissimmee, is located within 3 miles of Shingle Creek Regional Park, the 192 Flea Market, and Medieval Times, with HCA Florida Osceola Hospital also nearby.
This pet-friendly cottage offers a full kitchen with a microwave and dishwasher, air conditioning, a swimming pool, parking, and free Wi-Fi in public areas.
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