Vacation rentals in Kissimmee, FL

Best vacation rentals and Airbnb offers in Kissimmee, FL

10 ★ 1 reviews

Luxury Condo w/ Huge Private Balcony on Lake Bryan

Apartment, Kissimmee

Luxury Condo w/ Huge Private Balcony on Lake Bryan is a apartment in Kissimmee, with pool access, outdoor space, and kitchen access. This stay gives travelers a comfortable base for…

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About Luxury Condo w/ Huge Private Balcony on Lake Bryan

Luxury Condo w/ Huge Private Balcony on Lake Bryan is a apartment in Kissimmee, with pool access, outdoor space, and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, pool, free wifi, kitchen, and with kitchen.

Sat, Oct 3 - Sat, Oct 10 · 7 nights · total from $1,116.

From$126/night

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10 ★ 1 reviews

Family Resort Condo w/ 2 Pools: 1 Mi to Disney!

Apartment, Kissimmee

Family Resort Condo w/ 2 Pools: 1 Mi to Disney! is a apartment in Kissimmee, with pool access, kitchen access, and room for a group. This stay gives travelers a comfortable base for…

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About Family Resort Condo w/ 2 Pools: 1 Mi to Disney!

Family Resort Condo w/ 2 Pools: 1 Mi to Disney! is a apartment in Kissimmee, with pool access, kitchen access, and room for a group. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, pool, free wifi, kitchen, and with kitchen.

Sat, Oct 3 - Sat, Oct 10 · 7 nights · total from $1,395.

From$144/night

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9.4 ★ 13 reviews

St. Cloud Stay

Guest House, Kissimmee

St. Cloud Stay is a guest house in Kissimmee, with pool access and parking. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time…

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About St. Cloud Stay

St. Cloud Stay is a guest house in Kissimmee, with pool access and parking. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: pool, free wifi, parking, and free parking.

Sat, Oct 3 - Sat, Oct 10 · 7 nights · total from $646.

From$74/night

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8 ★ 1 reviews

Kissimmee Retreat w/ Pool: Near Disney & Golf!

Cottage, Kissimmee

Kissimmee Retreat w/ Pool: Near Disney & Golf! is a cottage in Kissimmee, with pool access, kitchen access, and a quieter setting. This stay gives travelers a comfortable base for exploring…

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About Kissimmee Retreat w/ Pool: Near Disney & Golf!

Kissimmee Retreat w/ Pool: Near Disney & Golf! is a cottage in Kissimmee, with pool access, kitchen access, and a quieter setting. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, pool, free wifi, kitchen, and with kitchen.

Sat, Oct 3 - Sat, Oct 10 · 7 nights · total from $1,280.

From$140/night

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Family-friendly vacation rentals in Kissimmee, FL

Plan a trip with stays that give families more room to spread out.

Family Resort Condo w/ 2 Pools: 1 Mi to Disney!

Holiday Home, Kissimmee

Family Resort Condo w/ 2 Pools: 1 Mi to Disney! is a holiday home in Kissimmee, with pool access and room for a group. This stay gives travelers a comfortable base for exploring the area,…

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About Family Resort Condo w/ 2 Pools: 1 Mi to Disney!

Family Resort Condo w/ 2 Pools: 1 Mi to Disney! is a holiday home in Kissimmee, with pool access and room for a group. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, pool, hot tub, and free wifi.

Sat, Oct 3 - Sat, Oct 10 · 7 nights · total from $1,347.

From$112/night

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Resort Retreat w/ Outdoor Oasis: 13 Mi to Disney!

Cottage, Kissimmee

Resort Retreat w/ Outdoor Oasis: 13 Mi to Disney! is a cottage in Kissimmee, with pool access, kitchen access, and a quieter setting. This stay gives travelers a comfortable base for…

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About Resort Retreat w/ Outdoor Oasis: 13 Mi to Disney!

Resort Retreat w/ Outdoor Oasis: 13 Mi to Disney! is a cottage in Kissimmee, with pool access, kitchen access, and a quieter setting. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, pool, free wifi, kitchen, and with kitchen.

Sat, Oct 3 - Sat, Oct 10 · 7 nights · total from $1,306.

From$132/night

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South Facing Pool with Lake View - Ideal for Families & Couples

Holiday Home, Kissimmee

South Facing Pool with Lake View - Ideal for Families & Couples is a holiday home in Kissimmee, with pool access. This stay gives travelers a comfortable base for exploring the area,…

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About South Facing Pool with Lake View - Ideal for Families & Couples

South Facing Pool with Lake View - Ideal for Families & Couples is a holiday home in Kissimmee, with pool access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, pool, hot tub, and free wifi.

Sat, Oct 3 - Sat, Oct 10 · 7 nights · total from $1,576.

From$144/night

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Disney Getaway w/ Private Hot Tub 14 Mi to Parks

Cottage, Kissimmee

Disney Getaway w/ Private Hot Tub 14 Mi to Parks is a cottage in Kissimmee, with pool access and kitchen access. This stay gives travelers a comfortable base for exploring the area,…

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About Disney Getaway w/ Private Hot Tub 14 Mi to Parks

Disney Getaway w/ Private Hot Tub 14 Mi to Parks is a cottage in Kissimmee, with pool access and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, pool, free wifi, kitchen, and with kitchen.

Sat, Oct 3 - Sat, Oct 10 · 7 nights · total from $2,057.

From$224/night

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Pet-friendly vacation rentals in Kissimmee, FL

Bring your pet along with stays that welcome four-legged travelers.

10 ★ 2 reviews

Willow Bend

Holiday Home, Kissimmee

Willow Bend is a holiday home in Kissimmee, with pet-friendly space and pool access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and…

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About Willow Bend

Willow Bend is a holiday home in Kissimmee, with pet-friendly space and pool access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, pool, hot tub, pet friendly, and pets friendly.

Sat, Oct 3 - Sat, Oct 10 · 7 nights · total from $2,285.

From$232/night

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Pinnacle Apartments W Amenties by Heavenly Homes

Apartment, Kissimmee

Pinnacle Apartments W Amenties by Heavenly Homes is a apartment in Kissimmee, with pet-friendly space, pool access, and parking. This stay gives travelers a comfortable base for exploring…

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About Pinnacle Apartments W Amenties by Heavenly Homes

Pinnacle Apartments W Amenties by Heavenly Homes is a apartment in Kissimmee, with pet-friendly space, pool access, and parking. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, pool, pet friendly, pets friendly, and parking.

Sat, Oct 3 - Sat, Oct 10 · 7 nights · total from $1,029.

From$100/night

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Spacious Townhouse With Resort Style Amenities, Waterview and Fitness Center

Holiday Home, Kissimmee

Spacious Townhouse With Resort Style Amenities, Waterview and Fitness Center is a holiday home in Kissimmee, with pet-friendly space and pool access. This stay gives travelers a comfortable…

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About Spacious Townhouse With Resort Style Amenities, Waterview and Fitness Center

Spacious Townhouse With Resort Style Amenities, Waterview and Fitness Center is a holiday home in Kissimmee, with pet-friendly space and pool access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, pool, free wifi, pet friendly, and pets friendly.

Sat, Oct 3 - Sat, Oct 10 · 7 nights · total from $1,360.

From$122/night

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South Facing W/ Private Pool & Spa

Holiday Home, Kissimmee

South Facing W/ Private Pool & Spa is a holiday home in Kissimmee, with pet-friendly space and pool access. This stay gives travelers a comfortable base for exploring the area, relaxing…

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About South Facing W/ Private Pool & Spa

South Facing W/ Private Pool & Spa is a holiday home in Kissimmee, with pet-friendly space and pool access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, pool, hot tub, pet friendly, and pets friendly.

Sat, Oct 3 - Sat, Oct 10 · 7 nights · total from $1,591.

From$144/night

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Vacation rentals with a pool in Kissimmee, FL

Add a pool to the search when you want an easy place to cool off between outings.

Lakeside Community, Pools, and More!

Holiday Home, Kissimmee

Lakeside Community, Pools, and More! is a holiday home in Kissimmee, with pool access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and…

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About Lakeside Community, Pools, and More!

Lakeside Community, Pools, and More! is a holiday home in Kissimmee, with pool access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: pool, free wifi, and gym.

Sat, Oct 3 - Sat, Oct 10 · 7 nights · total from $1,213.

From$109/night

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Kissimmee Condo: Community Perks, 10 Mi to Disney!

Apartment, Kissimmee

Kissimmee Condo: Community Perks, 10 Mi to Disney! is a apartment in Kissimmee, with pool access, parking, and kitchen access. This stay gives travelers a comfortable base for exploring the…

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About Kissimmee Condo: Community Perks, 10 Mi to Disney!

Kissimmee Condo: Community Perks, 10 Mi to Disney! is a apartment in Kissimmee, with pool access, parking, and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, pool, kitchen, with kitchen, and parking.

Sat, Oct 3 - Sat, Oct 10 · 7 nights · total from $1,100.

From$114/night

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Spacious Townhouse With Jetted Tub, Game Room, Heated Pool & Fitness Amenities

Holiday Home, Kissimmee

Spacious Townhouse With Jetted Tub, Game Room, Heated Pool & Fitness Amenities is a holiday home in Kissimmee, with pool access. This stay gives travelers a comfortable base for exploring…

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About Spacious Townhouse With Jetted Tub, Game Room, Heated Pool & Fitness Amenities

Spacious Townhouse With Jetted Tub, Game Room, Heated Pool & Fitness Amenities is a holiday home in Kissimmee, with pool access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, pool, hot tub, and free wifi.

Sat, Oct 3 - Sat, Oct 10 · 7 nights · total from $1,362.

From$115/night

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10 Mi to Disney: Venetian Bay Villages Retreat

Apartment, Kissimmee

10 Mi to Disney: Venetian Bay Villages Retreat is a apartment in Kissimmee, with pool access, easy beach access, and a quieter setting. This stay gives travelers a comfortable base for…

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About 10 Mi to Disney: Venetian Bay Villages Retreat

10 Mi to Disney: Venetian Bay Villages Retreat is a apartment in Kissimmee, with pool access, easy beach access, and a quieter setting. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, pool, hot tub, and free wifi.

Sat, Oct 3 - Sat, Oct 10 · 7 nights · total from $1,077.

From$132/night

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Vacation rentals with parking in Kissimmee, FL

Find vacation rentals that make arriving by car easier.

Island 1

Holiday Home, Kissimmee

Island 1 is a holiday home in Kissimmee, with pool access and parking. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with…

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About Island 1

Island 1 is a holiday home in Kissimmee, with pool access and parking. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, pool, free wifi, parking, and paid parking.

Sat, Oct 3 - Sat, Oct 10 · 7 nights · total from $1,206.

From$150/night

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Gorgeous Fully Furnished 2-Bedroom Luxury Villa

Villa, Kissimmee

Gorgeous Fully Furnished 2-Bedroom Luxury Villa is a villa in Kissimmee, with parking and room for a group. This stay gives travelers a comfortable base for exploring the area, relaxing…

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About Gorgeous Fully Furnished 2-Bedroom Luxury Villa

Gorgeous Fully Furnished 2-Bedroom Luxury Villa is a villa in Kissimmee, with parking and room for a group. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, free wifi, parking, paid parking, and ac.

Sat, Oct 3 - Sat, Oct 10 · 7 nights · total from $1,112.

From$122/night

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Newly Remodeled 1 story - 5 Bed 5 Bath with Pvt Pool Spa And Game Room

Holiday Home, Kissimmee

Newly Remodeled 1 story - 5 Bed 5 Bath with Pvt Pool Spa And Game Room is a holiday home in Kissimmee, with pool access and parking. This stay gives travelers a comfortable base for…

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About Newly Remodeled 1 story - 5 Bed 5 Bath with Pvt Pool Spa And Game Room

Newly Remodeled 1 story - 5 Bed 5 Bath with Pvt Pool Spa And Game Room is a holiday home in Kissimmee, with pool access and parking. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, free wifi, parking, paid parking, and parking::free.

Sat, Oct 3 - Sat, Oct 10 · 7 nights · total from $1,447.

From$164/night

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Blue Heron Beach II

Condo, Kissimmee

Blue Heron Beach II is a condo in Kissimmee, with pool access, easy beach access, and parking. This stay gives travelers a comfortable base for exploring the area, relaxing between outings,…

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About Blue Heron Beach II

Blue Heron Beach II is a condo in Kissimmee, with pool access, easy beach access, and parking. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, pool, free wifi, parking, and onsite parking.

Sat, Oct 3 - Sat, Oct 10 · 7 nights · total from $1,116.

From$101/night

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Vacation rentals with a kitchen in Kissimmee, FL

Compare stays with kitchen access for longer trips and easier meals.

9 ★ 2 reviews

15 Mi to Disney: Kissimmee Townhome w/ Patio

Apartment, Kissimmee

15 Mi to Disney: Kissimmee Townhome w/ Patio is a apartment in Kissimmee, with pool access, outdoor space, and kitchen access. This stay gives travelers a comfortable base for exploring the…

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About 15 Mi to Disney: Kissimmee Townhome w/ Patio

15 Mi to Disney: Kissimmee Townhome w/ Patio is a apartment in Kissimmee, with pool access, outdoor space, and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, pool, free wifi, kitchen, and with kitchen.

Sat, Oct 3 - Sat, Oct 10 · 7 nights · total from $1,661.

From$175/night

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Pool, Hot Tub & Theatre Access: Kissimmee Gem

Apartment, Kissimmee

Pool, Hot Tub & Theatre Access: Kissimmee Gem is a apartment in Kissimmee, with pool access and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing…

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About Pool, Hot Tub & Theatre Access: Kissimmee Gem

Pool, Hot Tub & Theatre Access: Kissimmee Gem is a apartment in Kissimmee, with pool access and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, pool, free wifi, kitchen, and with kitchen.

Sat, Oct 3 - Sat, Oct 10 · 7 nights · total from $1,279.

From$126/night

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Aster Cove

Holiday Home, Kissimmee

Aster Cove is a holiday home in Kissimmee, with pool access, parking, and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and…

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About Aster Cove

Aster Cove is a holiday home in Kissimmee, with pool access, parking, and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, pool, kitchen, with kitchen, and parking.

Sat, Oct 3 - Sat, Oct 10 · 7 nights · total from $1,467.

From$132/night

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~ 2 Mi to Disney & Universal: Orlando Resort Condo

Apartment, Kissimmee

~ 2 Mi to Disney & Universal: Orlando Resort Condo is a apartment in Kissimmee, with pool access and kitchen access. This stay gives travelers a comfortable base for exploring the area,…

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About ~ 2 Mi to Disney & Universal: Orlando Resort Condo

~ 2 Mi to Disney & Universal: Orlando Resort Condo is a apartment in Kissimmee, with pool access and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, pool, free wifi, kitchen, and with kitchen.

Sat, Oct 3 - Sat, Oct 10 · 7 nights · total from $1,457.

From$157/night

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