Location

Dates

Guests

Vacation rentals in Orlando, Florida, United States

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)

$240.87 USD total for 3 nights

Sep 30 – Oct 3, 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)

$297.72 USD total for 3 nights

Oct 3 – 6, 2026

New Listing! Windsor Island-2166 8BR · Disney

New Listing! Windsor Island-2166 8BR · Disney

New Listing! Windsor Island-2166 8BR · Disney

New Listing! Windsor Island-2166 8BR · Disney

New Listing! Windsor Island-2166 8BR · Disney

New Listing! Windsor Island-2166 8BR · Disney

8 bedrooms·6 baths

Four Corners • Florida

$1,834.46 USD total for 3 nights

Sep 30 – Oct 3, 2026

The Grand Village 4BR Pool Home near Disney Parks image 1

The Grand Village 4BR Pool Home near Disney Parks image 2

The Grand Village 4BR Pool Home near Disney Parks image 3

The Grand Village 4BR Pool Home near Disney Parks image 4

The Grand Village 4BR Pool Home near Disney Parks image 5

The Grand Village 4BR Pool Home near Disney Parks

4 bedrooms·4 baths

Davenport • Florida

$629.77 USD total for 3 nights

Sep 30 – Oct 3, 2026

Luxurious Pool Home with Private Pool-2061LC

Luxurious Pool Home with Private Pool-2061LC

Luxurious Pool Home with Private Pool-2061LC

Luxurious Pool Home with Private Pool-2061LC

Luxurious Pool Home with Private Pool-2061LC

Luxurious Pool Home with Private Pool-2061LC

8 bedrooms·6 baths

Four Corners • Florida

$1,655.81 USD total for 3 nights

Oct 10 – 13, 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

Sleeps 28 | Game & Themed Rooms | Heated Pool

Sleeps 28 | Game & Themed Rooms | Heated Pool

Sleeps 28 | Game & Themed Rooms | Heated Pool

Sleeps 28 | Game & Themed Rooms | Heated Pool

Sleeps 28 | Game & Themed Rooms | Heated Pool

Sleeps 28 | Game & Themed Rooms | Heated Pool

10 bedrooms·8 baths

Davenport • Florida

$1,345.00 USD total for 3 nights

Sep 30 – Oct 3, 2026

️ Swing into the SpiderVerse! Twin & queen bunkbeds split by a Brooklyn Bridge—one side upside down for a gravity-defying Spidey illusion. Sleep like a hero, dream like a legend. ️

Relax in style, this luxe living room blends comfort and elegance with seamless indoor-outdoor flow. Step through the glass doors to a sunlit patio perfect for morning coffee or evening wine. ☀️

Live your own Encanto adventure! This themed suite blends bold colors, playful decor, and cozy charm, ideal for kids, families, and anyone who believes in magic.

Level up your stay in our Mario Game Room! Bright, bold, and packed with arcade vibes, perfect for families, gamers, and nostalgia lovers. Jump into fun and power-up your vacation! ✨

7BR Disney Villa Escape Room+Pool+Cinema + Game Rm

7BR Disney Villa Escape Room+Pool+Cinema + Game Rm

7 bedrooms·6½ baths

Kissimmee • Florida

$1,385.00 USD total for 3 nights

Oct 3 – 6, 2026

Aloha Club at Windsor Island

Mickey and Minnie relaxing after a day at the parks

Watch your favorite movies on the 85 inch 4k TV

Game room with ample seating for players and observers

Open view from lanai pool side.

Ohana Gathering House

7 bedrooms·5½ baths

Davenport • Florida

5(5 reviews)

$1,064.04 USD total for 3 nights

Sep 30 – Oct 3, 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

Sep 30 – Oct 3, 2026

Beautiful Town Home with Splash Pool-1648TPC

Beautiful Town Home with Splash Pool-1648TPC

Beautiful Town Home with Splash Pool-1648TPC

Beautiful Town Home with Splash Pool-1648TPC

Beautiful Town Home with Splash Pool-1648TPC

Beautiful Town Home with Splash Pool-1648TPC

5 bedrooms·4 baths

Four Corners • Florida

$1,084.95 USD total for 3 nights

Oct 3 – 6, 2026

Avengers has two twin beds

Plenty of sun with west facing pool and south exposure

Windsor Island water slides

Night swimming!

Chillax Inn Summer

5 bedrooms·4 baths

Davenport • Florida

$879.84 USD $813.51 USD total for 3 nights

Oct 4 – 7, 2026

Luxury 9BR Solara Pool Villa | Sleeps 20 | Disney

Solara Resort playground & sports courts — Sawyer Palm villa FL

Luxury 9BR Solara Pool Villa | Sleeps 20 | Disney

King bedroom with ensuite — Sawyer Palm 9BR villa, Solara Resort

Luxury 9BR Solara Pool Villa | Sleeps 20 | Disney

Luxury 9BR Solara Pool Villa | Sleeps 20 | Disney

9 bedrooms·6½ baths

Kissimmee • Florida

5(15 reviews)

$1,232.29 USD total for 3 nights

Oct 4 – 7, 2026

Aloha Oasis- Windsor Island Resort

Downstairs Living Room

Aloha Oasis- Windsor Island Resort

5 bedrooms·5½ baths

Davenport • Florida

5(9 reviews)

$1,284.68 USD total for 4 nights

Nov 1 – 5, 2026

SL2321 LUXURY ☆☆☆☆☆ Private Pool near to Disney♥SOLARA RESORT

SL2321 LUXURY ☆☆☆☆☆ Private Pool near to Disney♥SOLARA RESORT

SL2321 LUXURY ☆☆☆☆☆ Private Pool near to Disney♥SOLARA RESORT

SL2321 LUXURY ☆☆☆☆☆ Private Pool near to Disney♥SOLARA RESORT

SL2321 LUXURY ☆☆☆☆☆ Private Pool near to Disney♥SOLARA RESORT

SL2321 LUXURY ☆☆☆☆☆ Private Pool near to Disney♥SOLARA RESORT

6 bedrooms·4½ baths

Kissimmee • Florida

$1,488.51 USD total for 4 nights

Sep 30 – Oct 4, 2026

Private back yard pool and Hot tub

Solara Resort Solstice Bar & Grill

$Sunny Paradise Home: Heated Resort Pool\Arcade\Spa$

$Sunny Paradise Home: Heated Resort Pool\Arcade\Spa$

$Sunny Paradise Home: Heated Resort Pool\Arcade\Spa$

Sunny Paradise Home: Heated Resort Pool\Arcade\Spa

9 bedrooms·6 baths

Kissimmee • Florida

5(1 review)

$1,248.00 USD total for 3 nights

Oct 3 – 6, 2026

Orlando Resort Home✦Sleeps 21

Orlando Resort Home✦Sleeps 21

Orlando Resort Home✦Sleeps 21

Orlando Resort Home✦Sleeps 21

Orlando Resort Home✦Sleeps 21

Orlando Resort Home✦Sleeps 21

7 bedrooms·6½ baths

Kissimmee • Florida

4.98(109 reviews)

$822.90 USD total for 3 nights

Oct 4 – 7, 2026

Smart phone room

Windsor Island Resort

Upstairs livingroom

Chillax Inn Summer 2

5 bedrooms·5½ baths

Davenport • Florida

$787.70 USD total for 3 nights

Oct 21 – 24, 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)

$1,163.68 USD total for 3 nights

Sep 30 – Oct 3, 2026

Chillax by the pool

Frozen twin with trundle

Chillax Inn Aloha

5 bedrooms·4 baths

Davenport • Florida

$776.65 USD total for 3 nights

Oct 29 – Nov 1, 2026

Free arcade in the garage

Mickey and friends queen ensuite

Windsor Island slides

Toy story queen ensuite

Chillax Inn Lil Lana

5 bedrooms·5½ baths

Davenport • Florida

$1,042.00 USD $942.94 USD total for 3 nights

Sep 30 – Oct 3, 2026

New Elegant House Gateaway - Close to Parks

New Elegant House Gateaway - Close to Parks

New Elegant House Gateaway - Close to Parks

New Elegant House Gateaway - Close to Parks

New Elegant House Gateaway - Close to Parks

New Elegant House Gateaway - Close to Parks

3 bedrooms·2 baths

Kissimmee • Florida

$568.64 USD total for 3 nights

Sep 30 – Oct 3, 2026

Welcome to Ohana House

Favorite Place!

Ohana House at Windsor Island Resort

Fully Equipped Kitchen with a Patio Door to the Pool Area

Beautifully Decorated

Ohana House at Windsor Island Resort

5 bedrooms·5½ baths

Davenport • Florida

$1,524.32 USD total for 5 nights

Nov 30 – Dec 5, 2026

WI3842 LUXURY BRAND NEW Cozy Pool Townhouse near Disney

5 bedrooms·4½ baths

Davenport • Florida

$1,306.27 USD total for 4 nights

Sep 30 – Oct 4, 2026