Compare best cottages in Kissimmee, FL from 100+ sites!

169 available cottage rental offers

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

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.

Cozy Cottage Near Disney  Pool, Hot Tub & Resort Amenities! - Kissimmee, FL
9.6 35 reviews

Cozy Cottage Near Disney Pool, Hot Tub & Resort Amenities!

cottage, Celebration
This Kissimmee cottage, part of the "4 Miles From Disney 5 Star RV Resort! Location Location !The Hidden Gem Cottage!" offer, is located near Old Town, Lake Cecile, and Fun Spot America, all within two miles, providing easy access to area attractions.
The 500-square-foot vacation home features two bedrooms, one bathroom, accommodates six guests, and includes a fully equipped kitchen, private patio, free WiFi, and access to resort amenities such as a swimming pool, spa, and water park.
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.
Cozy Tiny Home Getaway Minutes From Disney - Kissimmee, FL
10 1 review

Cozy Tiny Home Getaway Minutes From Disney

cottage, Kissimmee
This Celebration, Florida cottage is conveniently located near Walt Disney World Resort and Old Town, providing easy access to shopping and theme parks.
The one-bedroom, one-bathroom vacation home sleeps four guests comfortably, featuring a queen bed, sofa bed, fully equipped kitchen with fridge, microwave, and dishwasher, plus air conditioning, Wi-Fi, and a washer/dryer.
Ravishing 4bd With Pool And Close To Disney 4947 - Kissimmee, FL
9.6 1 review

Ravishing 4bd With Pool And Close To Disney 4947

gîte, Hunters Creek
This Hunters Creek vacation rental is conveniently located near Disney attractions, offering easy access to the theme park.
This 2000 square foot gîte features air conditioning, a swimming pool, a garden, a spa, a fitness center, and complimentary on-site parking.

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.

Mickey's Hideaway Cottage 4 Miles From Disney In Kissimmee With Wifi And Ac - Kissimmee, FL
No reviews

Mickey's Hideaway Cottage 4 Miles From Disney In Kissimmee With Wifi And Ac

cottage, Celebration
Mickey's Hideaway Cottage, a one-bedroom vacation home in Kissimmee, Florida, offers convenient access to Walt Disney World, Universal Studios, and SeaWorld.
This 1-bedroom, 1-bathroom house sleeps four guests and features a fully equipped kitchen with a fridge, microwave, and dishwasher, a private swimming pool, jacuzzi, and screened-in patio, plus access to Sherwood Forest Resort amenities including mini-golf.
Disney Getaway 4bd W Pool Resort Water Park 4983 - Kissimmee, FL
No reviews

Disney Getaway 4bd W Pool Resort Water Park 4983

gîte, Hunters Creek
This Hunters Creek vacation rental is conveniently located near Disney World, offering easy access to the theme park.
The 40-square-foot home features four bedrooms, one bathroom, a swimming pool, jacuzzi, fitness center, and a kitchen with a microwave and dishwasher, perfect for families.

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.

Tiny House Close To Disney Kissimmee - Kissimmee, FL
8.4 8 reviews

Tiny House Close To Disney Kissimmee

cottage, Celebration
This Kissimmee cottage is located a short walk from community pool and jacuzzi amenities and within driving distance of Walt Disney World Resort, Epcot, Disney's Hollywood Studios, and ESPN Wide World of Sports Complex.
This 2-bedroom, 1-bathroom rental accommodates up to 6 guests and features a microwave oven, air conditioning, and parking, with easy access to Old Town and Orlando Vineland Premium Outlets.

Best Kissimmee, FL cottages with a kitchen

Spacious Kissimmee Villa W/ Private Pool & Hot Tub - Kissimmee, FL
No reviews

Spacious Kissimmee Villa W/ Private Pool & Hot Tub

cottage, Kissimmee
This charming cottage is located in Kissimmee, just a short distance from attractions like Remington Golf Club, Osceola Center for the Arts, and Osceola Flea and Farmers Market. The cottage offers a comfortable and spacious retreat with 4.5 bathrooms, ensuring privacy for everyone. The cottage features a fully equipped kitchen with an oven, stovetop, microwave, and dishwasher, along with modern conveniences like a ceiling fan and iron/ironing board, as well as a swimming pool, barbecue grills, and free parking and WiFi.
Shiva By Avantstay Sleeps 22 Pool + Hot Tub + Great Park Access - Kissimmee, FL
No reviews

Shiva By Avantstay Sleeps 22 Pool + Hot Tub + Great Park Access

cottage, Kissimmee
This cottage is situated in Kissimmee, offering convenient access to attractions such as Shingle Creek Regional Park, Capone's Dinner Show, and Congo River Golf, all within 1.2 miles, and less than 1.9 miles from Lake Cecile and the 192 Flea Market.
This accommodation features an outdoor swimming pool, complimentary barbecues, free on-site parking, and free Wi-Fi in common areas, alongside fully equipped kitchens with refrigerators, ovens, stovetops, and microwaves, plus in-unit washer/dryer facilities and spacious patios.
Plw4277 - Kissimmee, FL
No reviews

Plw4277

cottage, Kissimmee
This non-smoking cottage is situated in Kissimmee, just 0.2 km (approximately 656 feet) from Shingle Creek Regional Park and within 5 miles of Lake Cecile and Congo River Golf.
This accommodation offers 4.5 bathrooms, a fully equipped kitchen, and Wi-Fi in common areas, with proximity to Capone's Dinner Show and the 192 Flea Market.
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.

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.

6 Mi To Disney World: Lake-view Retreat W/ Pool! - Kissimmee, FL
No reviews

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

cottage, Kissimmee
©2026 cozycozy.com