Location

Dates

Guests

Vacation rentals in Ocoee, Florida, United States

Close to the parks! 5bd/4ba home & pool in resort

Close to the parks! 5bd/4ba home & pool in resort

Close to the parks! 5bd/4ba home & pool in resort

Close to the parks! 5bd/4ba home & pool in resort

Close to the parks! 5bd/4ba home & pool in resort

Close to the parks! 5bd/4ba home & pool in resort

5 bedrooms·4½ baths

Davenport • Florida

$618.32 USD total for 3 nights

Oct 27 – 30, 2026

Themed 5bd home w/ private Pool & Arcade in Resort

Themed 5bd home w/ private Pool & Arcade in Resort

Themed 5bd home w/ private Pool & Arcade in Resort

Themed 5bd home w/ private Pool & Arcade in Resort

Themed 5bd home w/ private Pool & Arcade in Resort

Themed 5bd home w/ private Pool & Arcade in Resort

5 bedrooms·4½ baths

Davenport • Florida

$1,133.75 USD total for 3 nights

Nov 21 – 24, 2026

Moderne Villa mit Seeblick nur wenige Minuten von Disney entfernt

Moderne Villa mit Seeblick nur wenige Minuten von Disney entfernt

4 bedrooms·2 baths

Kissimmee • Florida

$212/ night(excl. fees & taxes)

Smart phone room

Windsor Island Resort

Upstairs livingroom

Chillax Inn Summer 2

5 bedrooms·5½ baths

Davenport • Florida

$791.39 USD total for 3 nights

Nov 15 – 18, 2026

Chillax by the pool

Frozen twin with trundle

Chillax Inn Aloha

5 bedrooms·4 baths

Davenport • Florida

$776.65 USD $720.63 USD total for 3 nights

Nov 3 – 6, 2026

Wunderschönes Haus mit 4 Schlafzimmern und privatem Pool

Wunderschönes Haus mit 4 Schlafzimmern und privatem Pool

Wunderschönes Haus mit 4 Schlafzimmern und privatem Pool

4 bedrooms·3 baths

Kissimmee • Florida

Keep everyone occupied!

Mickey & Minnie double and single

Windsor at Westside lazy river and splash area

Chillax Inn the spa

Chillax Inn Qin Loop

8 bedrooms·6 baths

Kissimmee • Florida

$1,170.78 USD total for 3 nights

Nov 8 – 11, 2026

Living room area

Front of the house

Amazing Pool and View with no neighbors in the back

Harry potter room, game room, upstairs movie/gathering room, mickey room

Mickey mouse themed room

Brand New 7BR Home in Windsor Island Resort

7 bedrooms·5½ baths

Davenport • Florida

4.9(52 reviews)

$1,130.08 USD total for 3 nights

Nov 8 – 11, 2026

Car pool table and movie room

Free arcade garage conversion

Chillax at night

Windsor Island slides

Home theater area with 85" TV

Chillax Inn Lana

8 bedrooms·6 baths

Davenport • Florida

$1,321.81 USD $1,204.61 USD total for 3 nights

Oct 27 – 30, 2026

Star wars twins bedroom #8

Game room in air conditioned garage

The force is strong in this one!

Windsor Island water slides

Shoot some pool and chillax

Chillax Inn Lilac

10 bedrooms·8 baths

Davenport • Florida

$2,339.77 USD $2,122.17 USD total for 4 nights

Oct 27 – 31, 2026

"Mahalo Magical" mit Whirlpool

Kitchen / Dining Room

"Mahalo Magical" mit Whirlpool

10 bedrooms·7 baths

Orlando • Florida

$444/ night(excl. fees & taxes)

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)

$316.74 USD total for 3 nights

Nov 1 – 4, 2026

1b Disney Adventures Start at This Cozy Suite

1b Disney Adventures Start at This Cozy Suite

1b Disney Adventures Start at This Cozy Suite

1b Disney Adventures Start at This Cozy Suite

1b Disney Adventures Start at This Cozy Suite

1b Disney Adventures Start at This Cozy Suite

2 bedrooms·1 bath

Kissimmee • Florida

4.67(69 reviews)

$300.79 USD total for 3 nights

Oct 27 – 30, 2026

Kingswood

5 bedrooms·4½ baths

Davenport • Florida

4.64(88 reviews)

$755.04 USD total for 3 nights

Oct 27 – 30, 2026

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)

$212.04 USD total for 3 nights

Oct 27 – 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!

Watch the sunset under the all-inclusive amenities to you!

This is a bird's eye view of the main clubhouse. It is walking distance from your resort stay. This includes water park, tennis courts, lounge areas, arcade area and so much more!

Magic is calling!

The south facing pool gives you an extended abundance of sunlight to enjoy and relax poolside.

Windsor's Avengers Villa, SF Pool, 6mi to Disney!

5 bedrooms·5 baths

Kissimmee • Florida

4.7(166 reviews)

$623.30 USD total for 3 nights

Oct 29 – Nov 1, 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)

$282.84 USD total for 3 nights

Oct 27 – 30, 2026

Orlando Resort Home✦Sleeps 24

Orlando Resort Home✦Sleeps 24

Orlando Resort Home✦Sleeps 24

Orlando Resort Home✦Sleeps 24

Orlando Resort Home✦Sleeps 24

Orlando Resort Home✦Sleeps 24

9 bedrooms·6½ baths

Kissimmee • Florida

4.99(154 reviews)

$1,230.44 USD total for 3 nights

Nov 2 – 5, 2026

Largest private pool and pool deck in Windsor Island Resort

Largest private pool and pool deck in Windsor Island Resort! The neighbors are jealous!

Windsor Island slides

Complete relaxation all day!

Chillax Inn Kaipo

7 bedrooms·5½ baths

Davenport • Florida

$1,203.88 USD $1,118.01 USD total for 3 nights

Nov 1 – 4, 2026

Stunning Themed 7 Bed Pool Home with Theater-3229L

Stunning Themed 7 Bed Pool Home with Theater-3229L

Stunning Themed 7 Bed Pool Home with Theater-3229L

Stunning Themed 7 Bed Pool Home with Theater-3229L

Stunning Themed 7 Bed Pool Home with Theater-3229L

Stunning Themed 7 Bed Pool Home with Theater-3229L

7 bedrooms·6 baths

Four Corners • Florida

$2,370.38 USD total for 3 nights

Oct 27 – 30, 2026

WI927- ♥LUXURY BRAND NEW Cozy Pool Townhouse near to Disney♥

5 bedrooms·4½ baths

Davenport • Florida

$1,106.51 USD total for 4 nights

Oct 27 – 31, 2026

CRYSTAL COVE (4725BD) - 5BR 3.5BA Pool home with Lake View

CRYSTAL COVE (4725BD) - 5BR 3.5BA Pool home with Lake View

CRYSTAL COVE (4725BD) - 5BR 3.5BA Pool home with Lake View

Large Living Area

Large open Kitchen

CRYSTAL COVE (4725BD) - 5BR 3.5BA Pool home with Lake View

5 bedrooms·3½ baths

Kissimmee • Florida

$814.42 USD $792.11 USD total for 3 nights

Oct 27 – 30, 2026

Seasons Retreat mit privatem Pool in der Nähe von Disney

Aerial photography

Aerial photography

Seasons Retreat mit privatem Pool in der Nähe von Disney

5 bedrooms·4 baths

Kissimmee • Florida

$234/ night(excl. fees & taxes)

CRYSTAL COVE (4730BD) - 5BR 3.5BA Pool Home & Spa, Fenced Yard

CRYSTAL COVE (4730BD) - 5BR 3.5BA Pool Home & Spa, Fenced Yard

CRYSTAL COVE (4730BD) - 5BR 3.5BA Pool Home & Spa, Fenced Yard

CRYSTAL COVE (4730BD) - 5BR 3.5BA Pool Home & Spa, Fenced Yard

CRYSTAL COVE (4730BD) - 5BR 3.5BA Pool Home & Spa, Fenced Yard

CRYSTAL COVE (4730BD) - 5BR 3.5BA Pool Home & Spa, Fenced Yard

5 bedrooms·3½ baths

Kissimmee • Florida

$814.42 USD $792.11 USD total for 3 nights

Oct 27 – 30, 2026