Location

Dates

Guests

Vacation rentals in Ocoee, Florida, United States

Themed (Star Wars & Frozen) family-friendly villa with both a private and a community pool with a gorgeous view!

1 outdoor table, lounge chairs, and an outdoor shower in the pool area. The pool area has colored LED lights for night-time use.

The formal dining room has seating for 8 (there is another informal dining room)

Master bedroom with a king-size bed and a 50-inch Roku Smart TV.

Sit back and relax in the new massage chair after a long but rewarding day at the theme park!

Disney 5 mile Private Pool, Massage Chair, Tennis!

6 bedrooms·3 baths

Kissimmee • Florida

5(36 reviews)

$1,061.23 USD total for 3 nights

Oct 27 – 30, 2026

Disney Area- Resort Hot Tub & Pools + Free Parking image 1

Disney Area- Resort Hot Tub & Pools + Free Parking image 2

Disney Area- Resort Hot Tub & Pools + Free Parking image 3

Disney Area- Resort Hot Tub & Pools + Free Parking image 4

Disney Area- Resort Hot Tub & Pools + Free Parking image 5

Disney Area- Resort Hot Tub & Pools + Free Parking

3 bedrooms·2 baths

Kissimmee • Florida

$550.00 USD total for 3 nights

Oct 27 – 30, 2026

Lovely New Pool Home at Windsor at Westside-2167TC

Lovely New Pool Home at Windsor at Westside-2167TC

Lovely New Pool Home at Windsor at Westside-2167TC

Lovely New Pool Home at Windsor at Westside-2167TC

Lovely New Pool Home at Windsor at Westside-2167TC

Lovely New Pool Home at Windsor at Westside-2167TC

8 bedrooms·6 baths

Four Corners • Florida

$1,284.71 USD total for 3 nights

Nov 4 – 7, 2026

Windsor at Westside 7Bd Hm Pool-2112MW

Windsor at Westside 7Bd Hm Pool-2112MW

Windsor at Westside 7Bd Hm Pool-2112MW

Windsor at Westside 7Bd Hm Pool-2112MW

Windsor at Westside 7Bd Hm Pool-2112MW

Windsor at Westside 7Bd Hm Pool-2112MW

7 bedrooms·5 baths

Four Corners • Florida

$1,322.17 USD total for 3 nights

Nov 6 – 9, 2026

Charming Kissimmee Townhouse

Charming Kissimmee Townhouse

Charming Kissimmee Townhouse

Charming Kissimmee Townhouse

Charming Kissimmee Townhouse

Charming Kissimmee Townhouse

3 bedrooms·2 baths

Kissimmee • Florida

4.92(26 reviews)

$804.25 USD total for 6 nights

Oct 27 – Nov 2, 2026

2312045

6 bedrooms·4 baths

Orlando • Florida

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

$1,933.02 USD total for 3 nights

Oct 27 – 30, 2026

Enjoy a beautiful sunset from your private pool with no rear neighbors and a view of the nightly fireworks from Disney. Bistro lights, palm trees, outdoor games, outdoor seating, sofa, TV and mini fridge complete this outdoor oasis!

SEEN ON TV | Themed Rooms | Arcade, Pool & Resort

professionally designed open concept living and dining room with spacious kitchen, 75" Smart TV, Nintendo switch, karaoke, and ample comfortable seating for a comfortable and fun experience.

Game room with 9 Arcade Games, a pool table, TV, full size Darth Vader and glow in the dark Custom Murals.

Windsor Island Resort & Aloha Clubhouse amenities included with your stay!

SEEN ON TV | Themed Rooms | Arcade, Pool & Resort

9 bedrooms·8 baths

Davenport • Florida

$1,420.00 USD total for 3 nights

Nov 15 – 18, 2026

Gorgeous 8BR/8Bath Windsor Island Dry Sauna

Gorgeous 8BR/8Bath Windsor Island Dry Sauna

16 seater dining room table

Living Room w/ fireplace

Gorgeous 8BR/8Bath Windsor Island Dry Sauna

8 bedrooms·8 baths

Davenport • Florida

4.87(60 reviews)

$1,693.48 USD total for 3 nights

Oct 30 – Nov 2, 2026

Turtley Awesome - Heated Spa - Themed Bedrooms - BBQ Grill

Turtley Awesome - Heated Spa - Themed Bedrooms - BBQ Grill

Turtley Awesome - Heated Spa - Themed Bedrooms - BBQ Grill

Turtley Awesome - Heated Spa - Themed Bedrooms - BBQ Grill

Turtley Awesome - Heated Spa - Themed Bedrooms - BBQ Grill

Turtley Awesome - Heated Spa - Themed Bedrooms - BBQ Grill

5 bedrooms·3 baths

Davenport • Florida

$780.99 USD total for 3 nights

Nov 29 – Dec 2, 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

Oct 27 – 30, 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

$1,489.50 USD total for 3 nights

Nov 4 – 7, 2026

in Davenport mit großem Pool

in Davenport mit großem Pool

in Davenport mit großem Pool

in Davenport mit großem Pool

4 bedrooms·3 baths

Orlando • Florida

$220/ night(excl. fees & taxes)

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

Oct 27 – 30, 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

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

$1,692.32 USD total for 6 nights

Dec 12 – 18, 2026

Gorgeous 4Bd TH Pool Windsor at Westside-2018WW

Gorgeous 4Bd TH Pool Windsor at Westside-2018WW

Gorgeous 4Bd TH Pool Windsor at Westside-2018WW

Gorgeous 4Bd TH Pool Windsor at Westside-2018WW

Gorgeous 4Bd TH Pool Windsor at Westside-2018WW

Gorgeous 4Bd TH Pool Windsor at Westside-2018WW

4 bedrooms·3 baths

Four Corners • Florida

$1,153.62 USD total for 3 nights

Oct 27 – 30, 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

$903.19 USD total for 3 nights

Nov 17 – 20, 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)

$1,197.05 USD total for 3 nights

Nov 2 – 5, 2026

Beautiful private pool deck with spa, shaded dining area, pool fence for families with children (pool/spa heat is a pre-bookable paid optional extra to be requested before check-in)

Front of this beautiful pool home with parking for two vehicles on the paved driveway (please no oversized/long-bed vehicles, no street parking)

Beautiful private pool deck with spa, shaded dining area, pool fence for families with children (pool/spa heat is a pre-bookable paid optional extra to be requested before check-in)

Family room with Smart TV, fan and views out to the pool deck

Formal dining area

Lovely 4 Bed Pool Home, Games Room, Disney 8 miles

4 bedrooms·3 baths

Davenport • Florida

4.83(47 reviews)

$750.00 USD total for 3 nights

Oct 27 – 30, 2026

Poolside Cinema: Dive into relaxation while enjoying movies under stunning sunset skies!

Circus Playroom: Dive into fun with arcade games, ping pong, and vibrant circus-themed decor!

Home Theater Oasis: Experience cinematic bliss in plush red recliners and a giant screen!

Living Room: Bright and airy space with modern decor, perfect for relaxation and fun gatherings!

Pool Hall: Play your best shot in style with a vibrant pool table and sleek bar seating!

Big Top Family Vacation Villa

9 bedrooms·6½ baths

Kissimmee • Florida

5(95 reviews)

$1,462.33 USD total for 3 nights

Nov 1 – 4, 2026

4-Schlafzimmer-Ferienhaus mit Whirlpool

Kitchen / Dining Room

4-Schlafzimmer-Ferienhaus mit Whirlpool

4 bedrooms·3 baths

Kissimmee • Florida

$214/ night(excl. fees & taxes)

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

$1,004.96 USD total for 4 nights

Oct 27 – 31, 2026

Private pool 5bd home in resort close to parks

Private pool 5bd home in resort close to parks

Private pool 5bd home in resort close to parks

Private pool 5bd home in resort close to parks

Private pool 5bd home in resort close to parks

Private pool 5bd home in resort close to parks

5 bedrooms·4½ baths

Davenport • Florida

$790.90 USD total for 3 nights

Oct 27 – 30, 2026