Vacation rentals in Osceola County, FL

Best vacation rentals and Airbnb offers in Osceola County, FL

Fluorescent Village

B & B, Osceola County

Fluorescent Village is a b & b in Osceola County, with parking. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family…

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About Fluorescent Village

Fluorescent Village is a b & b in Osceola County, with 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, free parking, and ac.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $565.

From$66/night

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St. Cloud Stay

Guest House, Osceola County

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

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About St. Cloud Stay

St. Cloud Stay is a guest house in Osceola County, 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, Aug 29 - Sat, Sep 5 · 7 nights · total from $655.

From$75/night

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Pet friendly + in Dwtn + 20mi to Disney & Parks!

Holiday Home, Osceola County

Pet friendly + in Dwtn + 20mi to Disney & Parks! is a holiday home in Osceola County, with pet-friendly space, parking, and kitchen access. This stay gives travelers a comfortable base for…

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About Pet friendly + in Dwtn + 20mi to Disney & Parks!

Pet friendly + in Dwtn + 20mi to Disney & Parks! is a holiday home in Osceola County, with pet-friendly space, 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, pet friendly, pets friendly, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $537.

From$77/night

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Family Friendly Relax Villa

Holiday Home, Osceola County

Family Friendly Relax Villa is a holiday home in Osceola County, with pool access, kitchen access, and room for a group. This stay gives travelers a comfortable base for exploring the area,…

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About Family Friendly Relax Villa

Family Friendly Relax Villa is a holiday home in Osceola County, 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, Aug 29 - Sat, Sep 5 · 7 nights · total from $946.

From$82/night

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Vacation rentals with a pool in Osceola County, 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, Osceola County

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

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About Lakeside Community, Pools, and More!

Lakeside Community, Pools, and More! is a holiday home in Osceola County, 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, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,118.

From$97/night

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Peaceful townhouse in Kissimmee Florida

Holiday Home, Osceola County

Peaceful townhouse in Kissimmee Florida is a holiday home in Osceola County, with pool access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings,…

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About Peaceful townhouse in Kissimmee Florida

Peaceful townhouse in Kissimmee Florida is a holiday home in Osceola County, 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, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,321.

From$110/night

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Bright & Cozy 2BR Condo Minutes from Disney Parks

Condo, Osceola County

Bright & Cozy 2BR Condo Minutes from Disney Parks is a condo in Osceola County, with pool access, kitchen access, and room for a group. This stay gives travelers a comfortable base for…

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About Bright & Cozy 2BR Condo Minutes from Disney Parks

Bright & Cozy 2BR Condo Minutes from Disney Parks is a condo in Osceola County, 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, Aug 29 - Sat, Sep 5 · 7 nights · total from $928.

From$133/night

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Gilded Parasol By Shine Villas Remington Golf #410 4 Bedroom Home

Villa, Osceola County

Gilded Parasol By Shine Villas Remington Golf #410 4 Bedroom Home is a villa in Osceola County, with pool access and room for a group. This stay gives travelers a comfortable base for…

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About Gilded Parasol By Shine Villas Remington Golf #410 4 Bedroom Home

Gilded Parasol By Shine Villas Remington Golf #410 4 Bedroom Home is a villa in Osceola County, 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, free wifi, and gym.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,580.

From$142/night

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Vacation rentals with parking in Osceola County, FL

Find vacation rentals that make arriving by car easier.

Super Boho Waterfront Retreat w Fishing Views

Holiday Home, Osceola County

Super Boho Waterfront Retreat w Fishing Views is a holiday home in Osceola County, with easy beach access, parking, and a quieter setting. This stay gives travelers a comfortable base for…

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About Super Boho Waterfront Retreat w Fishing Views

Super Boho Waterfront Retreat w Fishing Views is a holiday home in Osceola County, with easy beach access, parking, 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, free wifi, parking, free parking, and accessible.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $970.

From$99/night

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Kissimmee Retreat w/ Pool: Near Disney & Golf!

Holiday Home, Osceola County

Kissimmee Retreat w/ Pool: Near Disney & Golf! is a holiday home in Osceola County, with pool access, parking, and a quieter setting. This stay gives travelers a comfortable base for…

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

Kissimmee Retreat w/ Pool: Near Disney & Golf! is a holiday home in Osceola County, with pool access, parking, 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, parking, and paid parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,245.

From$109/night

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Gilded Parasol by Shine Villas Remington Golf #410 home

Villa, Osceola County

Gilded Parasol by Shine Villas Remington Golf #410 home is a villa in Osceola County, with pool access and parking. This stay gives travelers a comfortable base for exploring the area,…

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About Gilded Parasol by Shine Villas Remington Golf #410 home

Gilded Parasol by Shine Villas Remington Golf #410 home is a villa in Osceola County, 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, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,529.

From$146/night

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Three bedrooms, full kitchen, clean, quiet and relaxing.

Holiday Home, Osceola County

Three bedrooms, full kitchen, clean, quiet and relaxing. is a holiday home in Osceola County, with parking, kitchen access, and room for a group. This stay gives travelers a comfortable…

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About Three bedrooms, full kitchen, clean, quiet and relaxing.

Three bedrooms, full kitchen, clean, quiet and relaxing. is a holiday home in Osceola County, with parking, 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, free wifi, kitchen, with kitchen, and parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,166.

From$167/night

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Pet-friendly vacation rentals in Osceola County, FL

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

Super Boho - Lake Toho Timeless Charm

Holiday Home, Osceola County

Super Boho - Lake Toho Timeless Charm is a holiday home in Osceola County, with pet-friendly space. This stay gives travelers a comfortable base for exploring the area, relaxing between…

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About Super Boho - Lake Toho Timeless Charm

Super Boho - Lake Toho Timeless Charm is a holiday home in Osceola County, with pet-friendly space. 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, pet friendly, pets friendly, and internet.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $910.

From$88/night

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A Comfortable home away from home. In kissimmee close to Disney World

Holiday Home, Osceola County

A Comfortable home away from home. In kissimmee close to Disney World is a holiday home in Osceola County, with pet-friendly space and kitchen access. This stay gives travelers a…

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About A Comfortable home away from home. In kissimmee close to Disney World

A Comfortable home away from home. In kissimmee close to Disney World is a holiday home in Osceola County, with pet-friendly 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, free wifi, pet friendly, pets friendly, and kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $956.

From$137/night

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Private home and entrance, stocked kitchen, fenced yard, Pets, boats ok,Parking

Holiday Home, Osceola County

Private home and entrance, stocked kitchen, fenced yard, Pets, boats ok,Parking is a holiday home in Osceola County, with pet-friendly space, pool access, and parking. This stay gives…

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About Private home and entrance, stocked kitchen, fenced yard, Pets, boats ok,Parking

Private home and entrance, stocked kitchen, fenced yard, Pets, boats ok,Parking is a holiday home in Osceola County, 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, free wifi, pet friendly, and pets friendly.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,082.

From$155/night

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Welcome to the “Little ‘Toa” Ideal for short & long term stays!

Holiday Home, Osceola County

Welcome to the “Little ‘Toa” Ideal for short & long term stays! is a holiday home in Osceola County, with pet-friendly space and kitchen access. This stay gives travelers a comfortable base…

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About Welcome to the “Little ‘Toa” Ideal for short & long term stays!

Welcome to the “Little ‘Toa” Ideal for short & long term stays! is a holiday home in Osceola County, with pet-friendly 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, free wifi, pet friendly, pets friendly, and kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,101.

From$157/night

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Vacation rentals with a kitchen in Osceola County, FL

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

Lakeside Community, pools, and more!

Holiday Home, Osceola County

Lakeside Community, pools, and more! is a holiday home in Osceola County, with pool access, parking, and kitchen access. This stay gives travelers a comfortable base for exploring the area,…

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About Lakeside Community, pools, and more!

Lakeside Community, pools, and more! is a holiday home in Osceola County, 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, Aug 29 - Sat, Sep 5 · 7 nights · total from $977.

From$140/night

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Vacation in luxury! Welcome to your home away from home.

Holiday Home, Osceola County

Vacation in luxury! Welcome to your home away from home. is a holiday home in Osceola County, with kitchen access. This stay gives travelers a comfortable base for exploring the area,…

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About Vacation in luxury! Welcome to your home away from home.

Vacation in luxury! Welcome to your home away from home. is a holiday home in Osceola County, with 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, kitchen, with kitchen, gym, and washer.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $985.

From$141/night

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Family Deluxe Lodge Suite: full kitchen + arcade + walk to pool and rodeo

Condo, Osceola County

Family Deluxe Lodge Suite: full kitchen + arcade + walk to pool and rodeo is a condo in Osceola County, with pool access, kitchen access, and room for a group. This stay gives travelers a…

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About Family Deluxe Lodge Suite: full kitchen + arcade + walk to pool and rodeo

Family Deluxe Lodge Suite: full kitchen + arcade + walk to pool and rodeo is a condo in Osceola County, 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, hot tub, and free wifi.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,032.

From$147/night

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Spacious home, private pool (heatable), gated community, TV in all bedrooms

Holiday Home, Osceola County

Spacious home, private pool (heatable), gated community, TV in all bedrooms is a holiday home in Osceola County, with pool access, parking, and kitchen access. This stay gives travelers a…

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About Spacious home, private pool (heatable), gated community, TV in all bedrooms

Spacious home, private pool (heatable), gated community, TV in all bedrooms is a holiday home in Osceola County, 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: pool, kitchen, with kitchen, parking, and free parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,103.

From$158/night

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Family-friendly vacation rentals in Osceola County, FL

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

Family Friendly Relax Villa

Holiday Home, Osceola County

Family Friendly Relax Villa is a holiday home in Osceola County, with pet-friendly space, pool access, and room for a group. This stay gives travelers a comfortable base for exploring the…

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About Family Friendly Relax Villa

Family Friendly Relax Villa is a holiday home in Osceola County, with pet-friendly space, 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, pet friendly, and pets friendly.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $812.

From$116/night

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New & Updated Peaceful family townhouse in Kissimmee, FL

Holiday Home, Osceola County

New & Updated Peaceful family townhouse in Kissimmee, FL is a holiday home in Osceola County, with pool access, kitchen access, and room for a group. This stay gives travelers a comfortable…

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About New & Updated Peaceful family townhouse in Kissimmee, FL

New & Updated Peaceful family townhouse in Kissimmee, FL is a holiday home in Osceola County, 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: pool, hot tub, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $971.

From$139/night

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Charming 1-bedroom house in pleasant St. Cloud within close distance to Parks

Holiday Home, Osceola County

Charming 1-bedroom house in pleasant St. Cloud within close distance to Parks is a holiday home in Osceola County, with pet-friendly space, kitchen access, and room for a group. This stay…

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About Charming 1-bedroom house in pleasant St. Cloud within close distance to Parks

Charming 1-bedroom house in pleasant St. Cloud within close distance to Parks is a holiday home in Osceola County, with pet-friendly space, 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, pet friendly, pets friendly, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,213.

From$173/night

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Pool Access: Cozy St Cloud Getaway!

Cottage, Osceola County

Pool Access: Cozy St Cloud Getaway! is a cottage in Osceola County, with pool access, parking, and kitchen access. This stay gives travelers a comfortable base for exploring the area,…

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About Pool Access: Cozy St Cloud Getaway!

Pool Access: Cozy St Cloud Getaway! is a cottage in Osceola County, 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, free wifi, kitchen, with kitchen, and parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,845.

From$206/night

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