Holiday rentals near Walt Disney World Railroad

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October 2025

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Discover a selection of private holiday rentals near Walt Disney World Railroad that can be your home away from home. Whether you're travelling with your children or with friends, holiday rentals have the best amenities for spending time at your holiday home, which might include cable TV and a washer and dryer. No matter what you're looking for, you'll be able to choose a property to rent for everyone's needs, including a place that is accessible or non-smoking.

Holiday rentals with weekly discounts - Walt Disney World Railroad

Showing deals for:26 Dec - 2 Jan

Relax By The Sparkling Private Pool In The Enclosed Patio

Excellent

(7 reviews)

Newly Renovated 6BR Family Home—Pool, BBQ & Games

Kissimmee, FL

8% off

for 7 nights, 1 home

NZ$1,915 per night

includes taxes & fees

view of sunrise from bedroom, family room, kitchen and living room

Exceptional

(62 reviews)

Near Disney and USTA tennis campus - Pool Villa on the Lake - Stunning Views!

Kissimmee, FL

8% off

for 7 nights, 1 villa

NZ$874 per night

includes taxes & fees

Exceptional

(16 reviews)

ChampionsGate Townhome + Fast WiFi, Beautiful Kitchen. Oasis Pool & Jacuzzi.

Davenport, FL

5% off

for 7 nights, 1 home

NZ$821 per night

includes taxes & fees

Exceptional

(25 reviews)

7256- Five Bedrooms All Suites, Private Pool & SPA - Solterra Resort

Davenport, FL

5% off

for 7 nights, 1 home

NZ$1,441 per night

includes taxes & fees

- Immerse in wizard themed bedrooms with enchanting details and custom woodwork
- Designed to spark imagination for both kids and adults during your Orlando stay
- A one of a kind space bringing fantasy to real life vacations

Exceptional

(19 reviews)

Mini Golf, Huge Pacman Arcade, Epic Wizards Alley, Theater: The Holiday House

Kissimmee, FL

8% off

for 7 nights, 1 home

NZ$3,928 per night

includes taxes & fees

Exceptional

(11 reviews)

Upstay 9BR Villa w Pool & Cinema—Epic Universe

Davenport, FL

8% off

for 7 nights, 1 home

NZ$2,404 per night

includes taxes & fees

Recreation Room / Bedroom 10 with two twin bunk beds

Exceptional

(46 reviews)

Lakeview Storey Lake 10BR/5BA-Pool/Spa/Rec-Close to Disney/Universal Studios

Kissimmee, FL

8% off

for 7 nights, 1 home

NZ$2,241 per night

includes taxes & fees

Large furnished sundeck with private swimming pool

Exceptional

(11 reviews)

Upstay: Resort Mansion w Pool Games Room and BBQ

Davenport, FL

8% off

for 7 nights, 1 home

NZ$1,789 per night

includes taxes & fees

Bruce the shark oversees pool, foosball, air hockey, and multiple video games.

Exceptional

(62 reviews)

*8bd Themed-Theater-Arcade-Prvt Pool/Spa-Disney!

Kissimmee, FL

8% off

for 7 nights, 1 home

NZ$1,977 per night

includes taxes & fees

Exceptional

(11 reviews)

Just Listed! 5BR Luxury Stay @ Lazy River Resort w/ Pool — Book 7 Nights & Save!

Davenport, FL

8% off

for 7 nights, 1 home

NZ$1,047 per night

includes taxes & fees

- Futuristic bunk bed room with glowing LED accents
- Built in slide adds adventure to this kids space
- Perfect family rental near Orlando with themed rooms

Wonderful

(9 reviews)

Arcades, Galactic Theater, Huge Bedroom w/ Slide, Meadow View, EV: Grand View

Davenport, FL

8% off

for 7 nights, 1 home

NZ$2,962 per night

includes taxes & fees

- Sparkling private pool with relaxing spa and loungers
- Palm trees and evening sunsets create a tropical retreat
- Orlando vacation home with outdoor entertainment space

Exceptional

(36 reviews)

Mustang Pool Table, Arcade, Huge Treehouse Bedroom, Luxury Backyard: The Oasis

Kissimmee, FL

8% off

for 7 nights, 1 home

NZ$4,153 per night

includes taxes & fees

Private heated pool with oversized pool deck

Exceptional

(63 reviews)

Big Disney Family Home! Sleeps 12! Private Pool, Spa and Game Room!

Kissimmee, FL

8% off

for 7 nights, 1 home

NZ$1,308 per night

includes taxes & fees

Garage-turned-games-room with Mario Bros theme

Wonderful

(15 reviews)

Upstay: 15BR Villa w Games Room, Pool & Cinema

Kissimmee, FL

8% off

for 7 nights, 1 home

NZ$5,059 per night

includes taxes & fees

Find spaces that suit your style

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Find the best place to stay - Walt Disney World Railroad

Incredible Arcade Game Room (All of these arcade games are FREE-TO-PLAY!)

Premier Host

Amazing-2 Movie Theaters!-Fun Game Room-Private Pool/Spa-Themed Bedrooms

Sleeps 16 · 8 bedrooms · 6 bathrooms

Premier Host

VERY CLOSE TO DISNEY! Fabulous 5 bed Home! Sleeps 12, Pool, Spa, Theater, Gated

Sleeps 12 · 5 bedrooms · 4+ bathrooms

Premier Host

PRIVATE Pool, 3mi to Disney, Forest view with total privacy, Game room

Sleeps 12 · 5 bedrooms · 4 bathrooms

Premier Host

Wonderful House at Encore Resort -Pool and SPA - 2 Gaming Rooms - Near to Disney

Sleeps 20 · 9 bedrooms · 8 bathrooms

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Enjoy full kitchens, laundry, pools, gardens and more
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