Location

Dates

Guests

Vacation rentals in Kissimmee

Amazing Condo Getaway

Amazing Condo Getaway

Amazing Condo Getaway

Amazing Condo Getaway

Amazing Condo Getaway

Amazing Condo Getaway

2 bedrooms·2 baths

Kissimmee • Florida

$628.46 USD total for 3 nights

Jan 29 – Feb 1, 2027

Modern Condo Near Disney

Modern Condo Near Disney

Modern Condo Near Disney

Modern Condo Near Disney

Modern Condo Near Disney

Modern Condo Near Disney

2 bedrooms·2 baths

Kissimmee • Florida

$530.26 USD total for 3 nights

Oct 21 – 24, 2026

Condo in the Heart of Orlando - 10 Min from Disney

Condo in the Heart of Orlando - 10 Min from Disney

Condo in the Heart of Orlando - 10 Min from Disney

Condo in the Heart of Orlando - 10 Min from Disney

Condo in the Heart of Orlando - 10 Min from Disney

Condo in the Heart of Orlando - 10 Min from Disney

2 bedrooms·2 baths

Kissimmee • Florida

$517.56 USD total for 3 nights

Oct 17 – 20, 2026

ST308 - BRAND NEW Storey Lake APT 6/2022 ♥ LUXURY ☆☆☆☆☆ Disney ♥

3 bedrooms·2 baths

Kissimmee • Florida

$1,001.70 USD total for 4 nights

Oct 13 – 17, 2026

Resort Condo 10 Min to Disney

Resort Condo 10 Min to Disney

Resort Condo 10 Min to Disney

Resort Condo 10 Min to Disney

Resort Condo 10 Min to Disney

Resort Condo 10 Min to Disney

2 bedrooms·2 baths

Kissimmee • Florida

$517.56 USD total for 3 nights

Oct 19 – 22, 2026

3121-406 · Stylish Apartment with Privilage Location & View

3121-406 · Stylish Apartment with Privilage Location & View

3121-406 · Stylish Apartment with Privilage Location & View

3121-406 · Stylish Apartment with Privilage Location & View

3121-406 · Stylish Apartment with Privilage Location & View

3121-406 · Stylish Apartment with Privilage Location & View

2 bedrooms·2 baths

Kissimmee • Florida

$526.76 USD total for 3 nights

Oct 18 – 21, 2026

Disney 10 Min, Family 3BR Condo, Pool

3 bedrooms·2 baths

Orlando • Florida

$582.26 USD total for 3 nights

Nov 7 – 10, 2026

VC207 - Luxury Apartament - 6 minutes to Universal Studios

VC207 - Luxury Apartament - 6 minutes to Universal Studios

VC207 - Luxury Apartament - 6 minutes to Universal Studios

VC207 - Luxury Apartament - 6 minutes to Universal Studios

VC207 - Luxury Apartament - 6 minutes to Universal Studios

VC207 - Luxury Apartament - 6 minutes to Universal Studios

4 bedrooms·2 baths

Orlando • Florida

$1,377.48 USD total for 4 nights

Oct 13 – 17, 2026

VC203 - Cozy Apartament - 6 minutes to Universal Studios

VC203 - Cozy Apartament - 6 minutes to Universal Studios

VC203 - Cozy Apartament - 6 minutes to Universal Studios

VC203 - Cozy Apartament - 6 minutes to Universal Studios

VC203 - Cozy Apartament - 6 minutes to Universal Studios

VC203 - Cozy Apartament - 6 minutes to Universal Studios

3 bedrooms·2 baths

Orlando • Florida

$1,059.14 USD total for 4 nights

Oct 13 – 17, 2026

Themed Luxury Apartment With Pools/Jacuzzi

Themed Luxury Apartment With Pools/Jacuzzi

Themed Luxury Apartment With Pools/Jacuzzi

Themed Luxury Apartment With Pools/Jacuzzi

Themed Luxury Apartment With Pools/Jacuzzi

Themed Luxury Apartment With Pools/Jacuzzi

3 bedrooms·2 baths

Kissimmee • Florida

5(11 reviews)

$750.00 USD total for 3 nights

Oct 13 – 16, 2026

Surprise your family with a trip to Disney and world class theme parks! ...while enjoying all the enormous amount of amenities that this resort offers!

Kids of all ages will love this waterpark all day! Enjoy access to pools, a water park, game room and more!

Spend your best memories under amenities galore!

Magic is calling!

Enjoy the decorated gallery walls and the largest, completely open floor plan available at Windsor Hills!

New! Windsor Hills Galaxy's Edge, 2mi to Disney!

3 bedrooms·2 baths

Kissimmee • Florida

4.84(205 reviews)

$1,200.67 USD total for 5 nights

Nov 25 – 30, 2026

Surprise your family with a trip to Disney and world class theme parks! ...while enjoying all the enormous amount of amenities that this resort offers!

One is faster, the other more adventurous!

Spend your best memories under amenities galore!

Magic is calling!

New! Windsor Hills Magical Retreat, 2mi to Disney!

3 bedrooms·2 baths

Kissimmee • Florida

5(12 reviews)

$520.80 USD total for 3 nights

Nov 3 – 6, 2026

Surprise your family with a trip to Disney and world class theme parks! ...while enjoying all the enormous amount of amenities that this resort offers!

Spend your best memories under amenities galore!

One is faster, the other more adventurous!

Magic is calling!

Enjoy an expansive dining room that flows into a Mickey Themed living room.

Windsor Hills Mickey’s Dream Home, 2mi to Disney!

3 bedrooms·2 baths

Kissimmee • Florida

4.84(267 reviews)

$527.82 USD total for 3 nights

Oct 25 – 28, 2026

Big Condo 3 bedrooms, Pool

Big Condo 3 bedrooms, Pool

Big Condo 3 bedrooms, Pool

Big Condo 3 bedrooms, Pool

Big Condo 3 bedrooms, Pool

Big Condo 3 bedrooms, Pool

3 bedrooms·2 baths

Kissimmee • Florida

1A Magical Disney Getaway in Gated Community 8mi

1A Magical Disney Getaway in Gated Community 8mi

1A Magical Disney Getaway in Gated Community 8mi

1A Magical Disney Getaway in Gated Community 8mi

1A Magical Disney Getaway in Gated Community 8mi

1A Magical Disney Getaway in Gated Community 8mi

1 bedroom·1 bath

Kissimmee • Florida

4.9(29 reviews)

$231.79 USD total for 3 nights

Oct 13 – 16, 2026

1C Magical Family Stay Near Disney 8mi/Pool/Resort

1C Magical Family Stay Near Disney 8mi/Pool/Resort

1C Magical Family Stay Near Disney 8mi/Pool/Resort

1C Magical Family Stay Near Disney 8mi/Pool/Resort

1C Magical Family Stay Near Disney 8mi/Pool/Resort

1C Magical Family Stay Near Disney 8mi/Pool/Resort

2 bedrooms·1 bath

Kissimmee • Florida

4.41(22 reviews)

$290.88 USD total for 3 nights

Oct 13 – 16, 2026

1D Disney Fun Steps Away – Pool & Kids’ Activities

1D Disney Fun Steps Away – Pool & Kids’ Activities

1D Disney Fun Steps Away – Pool & Kids’ Activities

1D Disney Fun Steps Away – Pool & Kids’ Activities

1D Disney Fun Steps Away – Pool & Kids’ Activities

1D Disney Fun Steps Away – Pool & Kids’ Activities

2 bedrooms·1 bath

Kissimmee • Florida

4.65(79 reviews)

$259.03 USD total for 3 nights

Oct 25 – 28, 2026

Harry's Hangout

Harry's Hangout

Harry's Hangout

Harry's Hangout

Harry's Hangout

Harry's Hangout

1 bedroom·1 bath

Kissimmee • Florida

$411.27 USD total for 3 nights

Oct 31 – Nov 3, 2026

Bahama Bay Resort - Privacy - No rear neighbor

Bahama Bay Resort - Privacy - No rear neighbor

Bahama Bay Resort - Privacy - No rear neighbor

Bahama Bay Resort - Privacy - No rear neighbor

Bahama Bay Resort - Privacy - No rear neighbor

Bahama Bay Resort - Privacy - No rear neighbor

3 bedrooms·2 baths

Davenport • Florida

$798.19 USD total for 4 nights

Oct 13 – 17, 2026

Historic Home Lake Eola 1 Bedroom oasis Thornton Park

Historic Home Lake Eola 1 Bedroom oasis Thornton Park

Historic Home Lake Eola 1 Bedroom oasis Thornton Park

Historic Home Lake Eola 1 Bedroom oasis Thornton Park

Historic Home Lake Eola 1 Bedroom oasis Thornton Park

Historic Home Lake Eola 1 Bedroom oasis Thornton Park

1 bedroom·1 bath

Orlando • Florida

5(26 reviews)

$411.25 USD $393.92 USD total for 3 nights

Oct 31 – Nov 3, 2026

Thornton park paradise 1 bedroom Lake Eola

Thornton park paradise 1 bedroom Lake Eola

Thornton park paradise 1 bedroom Lake Eola

Thornton park paradise 1 bedroom Lake Eola

Thornton park paradise 1 bedroom Lake Eola

Thornton park paradise 1 bedroom Lake Eola

1 bedroom·1 bath

Orlando • Florida

$364.25 USD $349.27 USD total for 3 nights

Oct 13 – 16, 2026