Vacation rentals in Kissimmee, FL

Best Vacation rentals and Airbnb offers in Kissimmee, FL

Home 1 Suites Extended Stay - Kissimmee

B & B, Kissimmee

Home 1 Suites Extended Stay - Kissimmee is a b & b in Kissimmee, with pool access and parking. This stay gives travelers a comfortable base for exploring the area, relaxing between outings,…

Read more

About Home 1 Suites Extended Stay - Kissimmee

Home 1 Suites Extended Stay - Kissimmee is a b & b 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, Aug 29 - Sat, Sep 5 · 7 nights · total from $492.

From$62/night

Show›

Budget & Pet Friendly Charming Family Suite

Holiday Home, Kissimmee

Budget & Pet Friendly Charming Family Suite is a holiday home in Kissimmee, with pet-friendly space, pool access, and parking. This stay gives travelers a comfortable base for exploring the…

Read more

About Budget & Pet Friendly Charming Family Suite

Budget & Pet Friendly Charming Family Suite is a holiday home 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, free wifi, parking, and free parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $696.

From$52/night

Show›

Disney-Area 3BR Townhome | Sleeps 9 | Pool + Gym

Holiday Home, Kissimmee

Disney-Area 3BR Townhome · Sleeps 9 · Pool + Gym is a holiday home in Kissimmee, with pet-friendly space, pool access, and kitchen access. This stay gives travelers a comfortable base for…

Read more

About Disney-Area 3BR Townhome | Sleeps 9 | Pool + Gym

Disney-Area 3BR Townhome · Sleeps 9 · Pool + Gym is a holiday home in Kissimmee, with pet-friendly space, 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, pet friendly, pets friendly, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $833.

From$63/night

Show›

11 Mi to Disney: Venetian Bay Villages Townhome!

Holiday Home, Kissimmee

11 Mi to Disney: Venetian Bay Villages Townhome! is a holiday home in Kissimmee, with pool access, easy beach access, and kitchen access. This stay gives travelers a comfortable base for…

Read more

About 11 Mi to Disney: Venetian Bay Villages Townhome!

11 Mi to Disney: Venetian Bay Villages Townhome! is a holiday home in Kissimmee, with pool access, easy beach 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, hot tub, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,089.

From$66/night

Show›

Browse 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.

Sunny Cozy Fun Home @ Disney and Universal!

Holiday Home, Kissimmee

Sunny Cozy Fun Home @ Disney and Universal! is a holiday home in Kissimmee, with pool access and parking. This stay gives travelers a comfortable base for exploring the area, relaxing…

Read more

About Sunny Cozy Fun Home @ Disney and Universal!

Sunny Cozy Fun Home @ Disney and Universal! 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, gym, parking, and free parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $736.

From$70/night

Show›

VB043 4 Bedroom, 3 Bath Townhouse

Holiday Home, Kissimmee

VB043 4 Bedroom, 3 Bath Townhouse is a holiday home in Kissimmee, with pool access, kitchen access, and room for a group. This stay gives travelers a comfortable base for exploring the…

Read more

About VB043 4 Bedroom, 3 Bath Townhouse

VB043 4 Bedroom, 3 Bath Townhouse is a holiday home 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: pool, hot tub, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $906.

From$77/night

Show›

Resort stay~Heated Pool~Gym~Near Disney~Tennis

Holiday Home, Kissimmee

Resort stay~Heated Pool~Gym~Near Disney~Tennis is a holiday home in Kissimmee, with pool access and kitchen access. This stay gives travelers a comfortable base for exploring the area,…

Read more

About Resort stay~Heated Pool~Gym~Near Disney~Tennis

Resort stay~Heated Pool~Gym~Near Disney~Tennis is a holiday home 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, kitchen, with kitchen, and gym.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,013.

From$78/night

Show›

3-bedroom apartment in welcoming Kissimmee with WiFi, AC, fitness room

Apartment, Kissimmee

3-bedroom apartment in welcoming Kissimmee with WiFi, AC, fitness room is a apartment in Kissimmee, with pool access, kitchen access, and room for a group. This stay gives travelers a…

Read more

About 3-bedroom apartment in welcoming Kissimmee with WiFi, AC, fitness room

3-bedroom apartment in welcoming Kissimmee with WiFi, AC, fitness room 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, kitchen, with kitchen, and gym.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $843.

From$80/night

Show›

Best Kissimmee, FL vacation rentals with parking

Find vacation rentals that make arriving by car easier.

Spacious & Cozy 4BR Home Near Disney

Holiday Home, Kissimmee

Spacious & Cozy 4BR Home Near Disney is a holiday home in Kissimmee, with pet-friendly space, parking, and kitchen access. This stay gives travelers a comfortable base for exploring the…

Read more

About Spacious & Cozy 4BR Home Near Disney

Spacious & Cozy 4BR Home Near Disney is a holiday home in Kissimmee, 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: pet friendly, pets friendly, kitchen, with kitchen, and parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,005.

From$74/night

Show›

2-bedroom condo 15 MIN DISNEY / FULL KITCHEN / NETFLIX / AMENITIES

Condo, Kissimmee

2-bedroom condo 15 MIN DISNEY / FULL KITCHEN / NETFLIX / AMENITIES is a condo in Kissimmee, with pet-friendly space, parking, and kitchen access. This stay gives travelers a comfortable…

Read more

About 2-bedroom condo 15 MIN DISNEY / FULL KITCHEN / NETFLIX / AMENITIES

2-bedroom condo 15 MIN DISNEY / FULL KITCHEN / NETFLIX / AMENITIES is a condo in Kissimmee, 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 $894.

From$89/night

Show›

Super Boho Waterfront Retreat w Fishing Views

Holiday Home, Kissimmee

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

Read more

About Super Boho Waterfront Retreat w Fishing Views

Super Boho Waterfront Retreat w Fishing Views is a holiday home in Kissimmee, 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 $980.

From$101/night

Show›

Amazing Waterfront Apt near Disney and Lake Tohoa

Apartment, Kissimmee

Amazing Waterfront Apt near Disney and Lake Tohoa is a apartment in Kissimmee, with pet-friendly space, easy beach access, and parking. This stay gives travelers a comfortable base for…

Read more

About Amazing Waterfront Apt near Disney and Lake Tohoa

Amazing Waterfront Apt near Disney and Lake Tohoa is a apartment in Kissimmee, with pet-friendly space, 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, pet friendly, pets friendly, parking, and free parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $861.

From$107/night

Show›

Best Pet-Friendly Vacation Rentals in Kissimmee, FL

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

VB010 Cozy Home Away From Home In Quiet Location In Venetian Bay

Villa, Kissimmee

VB010 Cozy Home Away From Home In Quiet Location In Venetian Bay is a villa in Kissimmee, with pool access, easy beach access, and kitchen access. This stay gives travelers a comfortable…

Read more

About VB010 Cozy Home Away From Home In Quiet Location In Venetian Bay

VB010 Cozy Home Away From Home In Quiet Location In Venetian Bay is a villa in Kissimmee, with pool access, easy beach 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: pool, hot tub, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $893.

From$73/night

Show›

VB011 Renovated Venetian Bay Townhome In Quiet Location

Holiday Home, Kissimmee

VB011 Renovated Venetian Bay Townhome In Quiet Location is a holiday home in Kissimmee, with pool access, easy beach access, and kitchen access. This stay gives travelers a comfortable base…

Read more

About VB011 Renovated Venetian Bay Townhome In Quiet Location

VB011 Renovated Venetian Bay Townhome In Quiet Location is a holiday home in Kissimmee, with pool access, easy beach 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: pool, hot tub, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $906.

From$77/night

Show›

VB014 Great, Quiet Venetian Bay Location

Villa, Kissimmee

VB014 Great, Quiet Venetian Bay Location is a villa in Kissimmee, with pool access, easy beach access, and kitchen access. This stay gives travelers a comfortable base for exploring the…

Read more

About VB014 Great, Quiet Venetian Bay Location

VB014 Great, Quiet Venetian Bay Location is a villa in Kissimmee, with pool access, easy beach 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, hot tub, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $906.

From$77/night

Show›

SPACIOUS 1 BEDROOM HOUSE IN DISNEY AREA 5 STAR RATED MILL CREEK RESORT 2753

Holiday Home, Kissimmee

SPACIOUS 1 BEDROOM HOUSE IN DISNEY AREA 5 STAR RATED MILL CREEK RESORT 2753 is a holiday home in Kissimmee, with pet-friendly space, pool access, and room for a group. This stay gives…

Read more

About SPACIOUS 1 BEDROOM HOUSE IN DISNEY AREA 5 STAR RATED MILL CREEK RESORT 2753

SPACIOUS 1 BEDROOM HOUSE IN DISNEY AREA 5 STAR RATED MILL CREEK RESORT 2753 is a holiday home in Kissimmee, 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, free wifi, pet friendly, and pets friendly.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $866.

From$80/night

Show›

Best Kissimmee, FL vacation rentals with a kitchen

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

Kissimmee Condo: Community Perks, 10 Mi to Disney!

Condo, Kissimmee

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

Read more

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

Kissimmee Condo: Community Perks, 10 Mi to Disney! is a condo 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, hot tub, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,087.

From$83/night

Show›

VB040 Renovated 3 Br Close To Small Pool

Holiday Home, Kissimmee

VB040 Renovated 3 Br Close To Small Pool is a holiday home in Kissimmee, with pool access, kitchen access, and room for a group. This stay gives travelers a comfortable base for exploring…

Read more

About VB040 Renovated 3 Br Close To Small Pool

VB040 Renovated 3 Br Close To Small Pool is a holiday home 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: pool, hot tub, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $967.

From$86/night

Show›

Mickey's Magical Townhome Venetian Bay Villages

Holiday Home, Kissimmee

Mickey's Magical Townhome Venetian Bay Villages is a holiday home in Kissimmee, with pet-friendly space, pool access, and easy beach access. This stay gives travelers a comfortable base for…

Read more

About Mickey's Magical Townhome Venetian Bay Villages

Mickey's Magical Townhome Venetian Bay Villages is a holiday home in Kissimmee, with pet-friendly space, pool access, and easy beach 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, pet friendly, pets friendly, and kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,087.

From$87/night

Show›

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 and kitchen access. This stay gives travelers a comfortable…

Read more

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 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, hot tub, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,205.

From$90/night

Show›

Our Favorite Family-Friendly Vacation Rentals in Kissimmee, FL

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

Family Friendly Relax Villa

Holiday Home, Kissimmee

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

Read more

About Family Friendly Relax Villa

Family Friendly Relax Villa is a holiday home in Kissimmee, 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 $905.

From$67/night

Show›

Family Friendly Relax Villa

Holiday Home, Kissimmee

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

Read more

About Family Friendly Relax Villa

Family Friendly Relax Villa is a holiday home 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, Aug 29 - Sat, Sep 5 · 7 nights · total from $939.

From$81/night

Show›

Charming 1 bed / 1 bath cottage - 700 s/f in a side by side duplex w/ carport

Holiday Home, Kissimmee

Charming 1 bed / 1 bath cottage - 700 s/f in a side by side duplex w/ carport is a holiday home in Kissimmee, with parking and kitchen access. This stay gives travelers a comfortable base…

Read more

About Charming 1 bed / 1 bath cottage - 700 s/f in a side by side duplex w/ carport

Charming 1 bed / 1 bath cottage - 700 s/f in a side by side duplex w/ carport is a holiday home in Kissimmee, with 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 $855.

From$90/night

Show›

EPIC VALUE-Disney Retreat! Magical Kid Friendly!

Holiday Home, Kissimmee

EPIC VALUE-Disney Retreat! Magical Kid Friendly! is a holiday home in Kissimmee, with pool access, parking, and kitchen access. This stay gives travelers a comfortable base for exploring…

Read more

About EPIC VALUE-Disney Retreat! Magical Kid Friendly!

EPIC VALUE-Disney Retreat! Magical Kid Friendly! 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, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,338.

From$102/night

Show›