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Kissimmee, FL cottages
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169 Best cottages in Kissimmee, FL

Discover Central Cottages in Kissimmee, FL

Position yourself near central shopping districts by selecting downtown cottages in Kissimmee, FL for easy pedestrian exploration.

Nature-packed Family Escape Near Lake Tohopekaliga - Kissimmee, FL
10 1 review

Nature-packed Family Escape Near Lake Tohopekaliga

cottage, Kissimmee
This cottage is located in Kissimmee, steps from Lake Tohopekaliga and within 6 miles of Shingle Creek Regional Park and Kissimmee Oaks Golf Course.
This rental offers a full kitchen with microwave and dishwasher, air conditioning, a garden, parking, and an arcade/game room, with complimentary WiFi in public areas and barbecue grills for guest use.
Premium Comfort - Beautiful Home, Private Pool - Kissimmee, FL
9.8 2 reviews

Premium Comfort - Beautiful Home, Private Pool

cottage, Kissimmee
This Kissimmee vacation home offers a 1170-square-foot space with a private pool, fitness center, and free parking.
The one-bathroom rental includes a fully equipped kitchen (fridge, microwave, dishwasher), air conditioning, and internet access, perfect for a relaxing Florida getaway.

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.

2616 Tranquility, Kissimmee, 6 Bed - Kissimmee, FL
No reviews

2616 Tranquility, Kissimmee, 6 Bed

cottage, Kissimmee
This cottage in Kissimmee is located less than 1.25 miles from Shingle Creek Regional Park, Capone's Dinner Show, and Congo River Golf, with Lake Cecile and Kissimmee Go-Karts also under 1.88 miles away.
This rental offers 5.5 bathrooms, a dryer, and a television, providing a comfortable stay with easy access to local entertainment and attractions.
Gorgeous, Modern Home W/private Pool! - Kissimmee, FL
No reviews

Gorgeous, Modern Home W/private Pool!

gîte, Hunters Creek
This house is situated in the Hunters Creek district, offering convenient access to local attractions.
This 3290 square foot residence features air conditioning, a private swimming pool and spa, a full kitchen with a fridge, microwave, and dishwasher, and on-site dining options, making it ideal for families with internet and parking included.
Entertaining Game Room 4br Near Disney - Kissimmee, FL
No reviews

Entertaining Game Room 4br Near Disney

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
No reviews

Private Pool & Game Room: Family Vacation Rental

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.

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.

Popular destinations

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.

Upstay 32 Guest Mansion - Pool, Hot Tub, Games - Kissimmee, FL
No reviews

Upstay 32 Guest Mansion - Pool, Hot Tub, Games

cottage, Kissimmee
This cottage in Kissimmee is located less than 2 miles from Shingle Creek Regional Park, Capone's Dinner Show, and Lake Cecile.
This vacation rental offers a swimming pool, barbecue facilities, free Wi-Fi in common areas, free parking, and a fully equipped kitchen with a microwave and dishwasher.
Chic Modern Escape, 12br, Pool And Game Room - Kissimmee, FL
No reviews

Chic Modern Escape, 12br, Pool And Game Room

cottage, Kissimmee
This cottage in Kissimmee is located within a 15-minute walk of Shingle Creek Regional Park and Give Kids the World Village, and approximately 1.9 miles from the 192 flea market and Medieval Times Dinner & Tournament.
This 12-bedroom vacation home offers a private outdoor swimming pool, hot tub, gas grill, and picnic area, along with a fully equipped kitchen and complimentary Wi-Fi.
Upstay: 15br Villa W Games Room, Pool & Cinema - Kissimmee, FL
No reviews

Upstay: 15br Villa W Games Room, Pool & Cinema

cottage, Kissimmee
This Kissimmee cottage is located a 5-minute walk from Shingle Creek Regional Park and a 2-minute drive from Medieval Times.
This spacious 15-bedroom, 15.5-bathroom home offers air conditioning, complimentary WiFi, a full kitchen with microwave and freezer, a swimming pool, and a jacuzzi, ideal for large groups.
Upstay Sleeps 26 W Private Pool, Hot Tub, Games - Kissimmee, FL
No reviews

Upstay Sleeps 26 W Private Pool, Hot Tub, Games

cottage, Kissimmee
This non-smoking cottage in Kissimmee is located within 2 miles of Capone's Dinner Show, Lake Cecile, and Shingle Creek Regional Park.
This vacation rental offers a swimming pool, barbecue facilities, complimentary Wi-Fi in common areas, and free non-voiturier parking, along with a well-equipped kitchen featuring a microwave and dishwasher.

Best Kissimmee, FL cottages with a kitchen

Disney Getaway W/ Private Hot Tub 14 Mi To Parks - Kissimmee, FL
No reviews

Disney Getaway W/ Private Hot Tub 14 Mi To Parks

cottage, Buenaventura Lakes
This cottage in Buenaventura Lakes is located within 6 miles of the Osceola Performing Arts Center, Houston Astros Spring Training facilities, and the Tupperware Center.
This rental offers a functional kitchen, air conditioning, a swimming pool, parking, and complimentary WiFi in common areas, with 2 bathrooms for guest comfort.
Tiny House In Kissimmee Sleeps 4, Only 20 Minutes To Disney/universal - Kissimmee, FL
No reviews

Tiny House In Kissimmee Sleeps 4, Only 20 Minutes To Disney/universal

cottage, Kissimmee
This Kissimmee cottage is conveniently located, offering a local perspective near major theme parks like Aquatica and Universal Epic Universe, with Old Town and Florida Mall just short drives away.
This 400 sq ft cottage features 1 bedroom and 1 bathroom, accommodating up to 4 guests with a queen bed and sofa bed, and includes amenities such as WiFi, a full kitchen, and a swimming pool.
Heated Pool & Bathtub 4br Near Disney - Kissimmee, FL
No reviews

Heated Pool & Bathtub 4br Near Disney

cottage, Kissimmee
This Indian Point vacation home in Kissimmee is located less than 1.25 miles from Give Kids the World Village and Shingle Creek Regional Park, and less than 1.88 miles from 192 Flea Market and Medieval Times.
This cottage offers air conditioning, a microwave oven, a dishwasher, a swimming pool, a garden, and parking, with complimentary WiFi available in public areas.
Sl4359 - 5br House With Pool Near Disney - Kissimmee, FL
No reviews

Sl4359 - 5br House With Pool Near Disney

cottage, Kissimmee
This Kissimmee cottage is situated within 2 miles of Shingle Creek Regional Park, Capone's Dinner Show, and Congo River Golf.
This vacation rental offers air conditioning, a full kitchen with a microwave and dishwasher, an outdoor swimming pool, and free WiFi.

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.

Spacious Vacation Rental W/ Yard In Kissimmee! - Kissimmee, FL
8.0 2 reviews

Spacious Vacation Rental W/ Yard In Kissimmee!

cottage, Poinciana
Garden View 6br Escape With Pool, Hot Tub & Games - Kissimmee, FL
No reviews

Garden View 6br Escape With Pool, Hot Tub & Games

cottage, Kissimmee
3br Townhome W/ Pool & Bbq Near Disney - Kissimmee, FL
No reviews

3br Townhome W/ Pool & Bbq Near Disney

cottage, Kissimmee
Family Home With Pool, Bbq & Cinema Near Disney - Kissimmee, FL
No reviews

Family Home With Pool, Bbq & Cinema Near Disney

cottage, Kissimmee
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