Short Term Rentals in Kissimmee, FL

Enjoy a lavish stay in this expansive 7-bedroom, 6.5-bath villa, perfect for up to 14 guests. Features include a gourmet kitchen with stainless steel appliances, a private home theater, a fun game room, and a screened-in pool with spa. The thoughtful layout includes king and queen suites, including themed rooms for kids. Located just minutes from major attractions and amenities, this villa offers everything needed for a memorable getaway.

This 9-bed, 6-bath apartment in Kissimmee offers 4,380 sqft designed for large groups visiting Orlando attractions. The villa features two living areas, a Star Wars loft, dedicated game room with pool table, private pool and hot tub, plus full kitchen access. Located in Windsor at Westside with resort amenities including water park, lazy river, fitness center, and sports courts, just 20-25 minutes from Disney World.

Set in Kissimmee, FL, this furnished 4-bed, 3-bath townhouse accommodates up to 12 guests across two floors and 1,905 sqft. The open floor plan connects living, dining, and kitchen areas, while resort amenities include pools, hot tub, lazy river, water slides, and fitness center. A short drive from Disney and major attractions.

Set in Kissimmee, FL, this dog-friendly 2-bed, 2-bath condo sits 8-15 minutes from Walt Disney World parks. The 1,000 sqft unit features remodeled bathrooms with double vanities, a quartz countertop kitchen with large island, and a private balcony. Water, internet, and cable included. Gated community adds a pool, fitness center, dog park, and elevator access to this 3rd-floor unit.

A townhouse in Kissimmee, FL, this 3-bed, 2.5-bath corner unit in Terra Esmeralda community features an open floor plan with a spacious modern kitchen and living room designed for entertaining. The 1,379 sqft layout includes in-unit laundry, dishwasher, and tile floors, plus community pool access and a top-rated elementary school just steps away.

A condo in Lakeside Estates, this 2-bed, 2-bath unit features a renovated kitchen, brand new A/C, and large patio off the living room. The 1,090 sqft layout includes in-unit laundry and tile floors within the gated Cypress Lakes community. Rent covers lawn care and trash, plus a resident benefits package with renters insurance, monthly HVAC filters, and 24/7 maintenance.

House with 6 beds in Kissimmee, FL, this furnished 2,900 sqft home sits in the gated Terra Verde resort community with 24-hour security. The 6-bed, 6-bath layout includes a main-floor master suite, upstairs ensuites with queen beds, and jack-and-jill rooms with twin beds. A south-facing private pool backs to a pond for added privacy, plus upgraded kitchen, lanai with ceiling fans, and resort amenities like fitness center and hot tub.

House with 4 beds in Bellalago, this dog-friendly home sits 15-20 minutes from Walt Disney World with quick access to US-192 and Osceola Parkway. The 1,936 sqft, 2-bath layout includes a full kitchen with dishwasher and in-unit laundry, plus community pool and playground. Top-rated schools within walking distance make it a fit for pet owners and families.

This 5-bed, 5-bath townhouse in Kissimmee sits minutes from Disney World and Universal Studios. The 2,263 sqft layout includes a modern kitchen with large island, private heated pool with lake views, and upstairs loft with entertainment space. A fit for remote workers and fitness enthusiasts with community amenities like lazy river, fitness center, and 8,000 sqft clubhouse.

Set in Kissimmee, FL, this 3-bed, 2.5-bath corner townhouse sits directly behind the community pool in gated Compass Bay. The 1,666 sqft layout features a large living room, kitchen, and family room on the first level with front and back patios. Freshly painted with new bedroom carpets, the unit includes in-unit laundry and is 20 minutes from Orlando International Airport.

Set in Kissimmee, FL, this 3-bed, 2-bath house was built in 2020 with an open layout and tile flooring throughout. The 2,629 sqft home features granite countertops, stainless steel appliances, and a bonus room with French doors ideal for an office. Located in a gated community with playground and walking paths near Lake Toho.

This 3-bed, 2.5-bath Lakeside Estates rental offers 1,382 sqft with a community pool and dedicated laundry room. The townhouse includes full appliances (dishwasher, microwave, refrigerator), central A/C and heat, plus tile flooring throughout. Located near top-rated schools within a mile.

3-bed townhouse in Kissimmee, FL, offers 1,362 sqft in the gated Crestwynd community with easy access to Disney areas and I-4. The 3-bath layout features a main-floor bedroom and bath, plus two upstairs bedrooms with two baths and laundry area. Kitchen flows into a cozy lounge that opens to a quiet private patio.

Set in Kissimmee, FL, this 6-bed, 4-bath house sits just 2 miles from Disney World in the gated Windsor Hills Resort. The 2,812 sqft layout features a heated pool, Star Wars gaming center with movie theater, and arcade room with Xbox One and Nintendo Switch - a fit for families seeking entertainment options. Resort amenities include water slides, fitness center, and 24-hour security.

Set in Kissimmee, FL, this 5-bed, 5-bath house sits just 1.5 miles from Disney World in the gated Windsor Hills community. The 1,884 sqft villa features a heated pool and spa, state-of-the-art game room with 130" screen, and outdoor patio with TV. Full kitchen, in-unit laundry, and resort amenities including water slides complete the setup.

A house in Kissimmee, FL, this 4-bed, 5-bath vacation rental sits just 2 miles from Walt Disney World in Windsor Hills Resort. The 2,297 sqft layout features a private pool with spa, home theater with 92-inch screen, and arcade game room with seven machines. Resort amenities include community pools, fitness center, and playground access.

Quietly set in Kissimmee, FL, this fully furnished 4-bed, 3-bath townhouse offers 2,090 sqft with stunning water and conservation views from a screened porch. The Trafalgar Village location includes ceramic tile throughout living areas, luxury vinyl in bedrooms, and a convenient ground-floor guest room. Resort-style amenities feature a gated community with pool, fitness center, clubhouse, and walking trails.

This 4-bed, 3-bath house in Brighton Lakes offers 4,947 sqft of comfortable living space near shopping, dining, and major highways. The well-maintained layout provides convenient access to top-rated schools within 2 miles and easy commuting options in Kissimmee.

Right in Marydia, this 3-bed, 2-bath house offers an open living and dining layout with a well-equipped kitchen and modern appliances. The 1,576 sqft layout includes a private primary suite with ample closet space and a fully fenced yard with spacious driveway parking. Minutes from The Loop and major highways including 417, Florida Turnpike, and Osceola Parkway for quick access to Lake Nona and Orlando International Airport.

Townhouse with 3 beds in Kissimmee, FL, this brand-new 2024 townhome in the Seasons at Big Sky community offers 2.5 baths and 1,852 sqft across two stories. The open-concept layout features tile flooring downstairs, carpet upstairs, and walk-in closets in all bedrooms including the primary suite. Community pool, tennis court, and one-car garage included, with quick highway access to Advent Health and shopping.

House with 4 beds in Kissimmee, FL, this two-story waterfront home sits in Blackstone Landing with peaceful pond views from the covered lanai. The 2,846 sqft layout includes 2.5 baths and solar panels, positioned next to Poinciana High School and minutes from Disney attractions for easy access to entertainment and top-rated schools.

Set in Kissimmee, FL, this fully furnished 4-bed, 3-bath house sits in the gated Windsor Palms resort community with no rear neighbors. The 2,364 sqft layout features an updated kitchen with quartz countertops, screened pool, and bonus game room in the garage. Resort amenities include clubhouse with fitness center, tennis courts, and tiki bar pool, with rent covering lawn and pool care.

Set in Kissimmee, FL, this fully furnished 4-bed, 3-bath townhouse offers 1,470 sqft in the gated Villas at Seven Dwarfs community. The open floor plan features two master bedrooms, a sunny patio, and jetted tub. Community amenities include a clubhouse with restaurant, pool, playground, and kids water park, plus a benefits package covering cable, internet, and maintenance for $75/month.

Set in Kissimmee, FL, this 3-bed, 2-bath house features an open-concept kitchen with granite countertops and stainless steel appliances. The 1,956 sqft layout includes a huge Florida room, upgraded bathrooms, and tile and laminate flooring throughout. A fenced and paved backyard adds outdoor space, with top-rated elementary and middle schools nearby.

Set in Kissimmee, FL, this 4-bed, 3-bath townhouse sits in the gated Club Cortile community near Disney, shops, and restaurants. The 1,880 sqft layout features an open-plan kitchen, family room, and first-floor bedroom with private bath access. Resort-style amenities include a pool, spa, fitness center, tennis courts, and playground.

Set in Kissimmee, FL, this fully furnished studio apartment includes all utilities - water and electricity covered in rent. The 400 sqft space comes move-in ready with flat-screen TV, refrigerator, mini cooktop, and microwave. Located less than 30 minutes from Disney theme parks with easy access to top-rated restaurants and shopping.

Sitting in Kissimmee, FL, this 2-bed, 2.5-bath townhouse features extensive upgrades including 42" cabinets, marble countertops, and a garden tub with separate shower in the master suite. The 1,386 sqft layout adds huge walk-in closets, a laundry room, and energy-efficient appliances. Located in a gated community with a pool and water feature views, plus a top-rated high school less than a mile away.

Located in The Oaks, this 4-bed, 2-bath house sits on a conservation lot in the Shingle Creek golf community with open patio views. The 3,260 sqft layout features granite countertops, stainless steel appliances, wood-look ceramic tile, and a master suite with walk-in closet and dual vanities. Community amenities include boardwalks, nature trails, fishing pond, and athletic courts near Disney World and downtown Kissimmee.

3-bed house in Kissimmee, FL, built in 2022 with modern design and functionality. This 2,421 sqft layout includes 2.5 baths and sits just 20 minutes from the airport and 30 minutes from Disney World. The newer construction offers updated features throughout, making it a practical choice for travelers or Disney visitors.

Located in Kissimmee, FL, this newly renovated 3-bed, 2-bath condo offers 1,287 sqft with large windows overlooking a front pond. The updated kitchen features granite countertops and newer appliances, while the master suite includes a walk-in closet and renovated bath. In-unit laundry, fitness center, pool, and rent includes trash plus resident benefits package with renters insurance and maintenance.

A house in The Oaks, this 3-bed, 2-bath home offers 2,342 sqft with an open floor plan in the gated Shingle Creek Reserve community. Residents enjoy access to a golf course, tennis courts, basketball courts, and playground within the community grounds. Top-rated high school within 2 miles adds family appeal.

This 3-bed, 2.5-bath townhouse in Kissimmee features an open floor plan centered around a spacious modern kitchen and living room ideal for entertaining. The 1,352 sqft layout includes community pool access in the Terra Esmeralda community, with a top-rated elementary school just steps away.

Set in Kissimmee, FL, this 4-bed, 2-bath house features granite countertops, stainless steel appliances, and tile flooring throughout the 2,259 sqft layout. The well-maintained property includes a swimming pool and sits close to schools, shopping, theme parks, and major highways for easy access around Central Florida.

Apartment with 2 beds in Beaumont, this fully renovated 2-bed, 1-bath unit features a new kitchen with granite countertops and stainless steel appliances. The 880 sqft layout includes new flooring, ceiling fans, and AC throughout. Steps from the County Courthouse, Kissimmee Police Station, downtown shops and restaurants, plus the Sunrail station for easy commuting.

This 1,433 square-foot condo in Flora Ridge includes 3 bedrooms and 2 bathrooms just minutes from Disney World. Located near Loop Shopping Plaza with easy access to restaurants, shopping, and entertainment options. The unit offers convenient proximity to theme parks and dining, making it ideal for vacation rentals or residents wanting quick access to Orlando attractions.

House with 4 beds in The Oaks, this two-story home offers water views from the pool and backyard in a well-maintained golf community. The 2,720 sqft layout features high ceilings, open kitchen and living room, formal dining, separate family room, and upstairs loft ideal for a home office. Rent includes lawn and pool care plus washer and dryer, with convenient access to theme parks and shopping.

Quietly set in Kissimmee, FL, this spacious 4-bed, 2.5-bath house sits moments from Disney World and local attractions. The 2,957 sqft layout centers on a chef's kitchen with top-tier appliances, ample storage, and a large island. A loft space adds flexibility for entertainment or relaxation, while the den works as a home office.

House in Kissimmee, FL, this 4-bed, 2.5-bath house sits in a gated community with a 2-car garage and 2,387 sqft of space. The location offers convenient access to malls, Orlando International Airport, and major attractions, making it ideal for both daily commuting and entertainment access.

Set in Kissimmee, FL, this two-story 4-bed, 3-bath corner condo offers 1,470 sqft with an open floor plan and first-floor master suite. The unit includes in-unit laundry, dishwasher, and easy parking access. Community amenities feature a resort-style pool, clubhouse, playground, and 24-hour gated entrance.