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$50 OFF THEME PARK TICKETS FOR SELECT PROPERTIES!

Booking a Kissimmee house for Christmas week

A private screened pool deck at a Kissimmee vacation home in December, with patio furniture and palms under late afternoon sun

Here's the straight answer to the question people actually ask us in October and November: if you're looking for a three-bedroom house in Kissimmee over Christmas and New Year's at $150 to $250 a night, the homes we manage here are mostly four and five bedrooms, and over that particular fortnight the four-bedroom often prices closer to what you expected the three-bedroom to cost. Holiday rates move. A fourth bedroom in a house with a private pool and a full kitchen is frequently the better-value booking, not the splurge. So the list below is four- and five-bedroom Kissimmee homes worth comparing, with a note on what each one is genuinely good for, plus what to ask us about pricing before you commit.

We're locally owned and independently operated, we manage 32 properties in Kissimmee alone, and we'll tell you honestly when a home isn't the right fit for your group.

Five houses, five different trips

These are all in Kissimmee, all sleep eight or more, and all have an outdoor pool of some kind. Beyond that they're not interchangeable at all.

Why the pool question decides your December

Central Florida in late December is lovely in the afternoon and genuinely cool after dark. An unheated pool is a pool nobody swims in. That's the single biggest thing people get wrong when they book a holiday-week house here, and it's why the Eagle Pointe house carries a note in its own listing that its pool has no heating system. It's an excellent house otherwise, with the most reviews of anything on this list and a garden tub in the master, but if your kids have been promised swimming on Christmas Day, look elsewhere.

At both Lake Berkley homes, pool heat is available as an optional extra at $30 per night plus tax, ordered at least 72 hours ahead. Order it when you book, not when you arrive. Over a ten-night holiday stay it is the cheapest line item that will change how the week actually feels.

The one I'd book for a family of eight

Private Pool House w/ Spa has two master suites and a three-way split layout, which means the two sets of adults in your group sleep at opposite ends of the house and nobody has to tiptoe past a sleeping toddler at nine o'clock. Add the spa next to the pool, the game room for the night everyone refuses to go out, and a kitchen with enough counter space to cook Christmas dinner properly. Lake Berkley is guard-gated around the clock with a lakefront beach area, walking trails and a fitness centre, so there's somewhere to go on a park rest day without getting back in the car. Disney is roughly ten to fifteen minutes away off US-192.

If you're ten rather than eight, the same resort has Kissimmee Home | Private Pool | Near Disney, with five bedrooms, a screened pool and a pool table. Screened matters more than people think in December: you get the pool without the evening bugs, and you're not fishing leaves out every morning.

Townhome or house? It comes down to what you want from the week

The two Venetian Bay Villages townhomes are a different proposition from the Lake Berkley houses. No private pool, but four resort pools, a community jacuzzi, a fitness centre, four playgrounds and tennis, basketball and volleyball courts, all inside a gated community with security at the entrance. Parking is directly in front of your door. If your group's idea of a holiday is wandering to a pool in flip-flops and coming back for lunch, that's the trade, and the townhomes usually sit lower on the nightly rate than a private-pool house does.

Renovated 4BR Near Disney is the one we send multi-generational groups to. The king master is on the ground floor with its own bath, so grandparents never take a stair, and it's a short walk to the main clubhouse pool. Shingle Creek Regional Park, with its trails, is a walk away, and its weekly-car-show neighbour Old Town sits about ten minutes east on 192. Disney Springs is fifteen to twenty minutes; Universal and Epic Universe twenty-five to thirty.

Its sister property, 4.5mi to Disney World | King Suite & Jacuzzi, is the same footprint done Disney-themed, with a twin room and a bunk room for kids, board games, a stair gate, washer and dryer on both floors, and a jacuzzi tub in the downstairs master. The theming is restrained rather than overdone. For a first Disney trip with young children, the house becomes part of the holiday rather than just the place you sleep.

What $150 to $250 a night buys over the holidays

Christmas and New Year's is the most expensive fortnight of the Orlando year, and nightly rates here are set by date, not by a fixed list. Two things are worth knowing before you shop.

First, judge the total, not the headline. A house with a full kitchen, a dishwasher and a washer and dryer changes what you spend on everything else. Every home above has all three. Cooking breakfast before a park day and doing a load of laundry mid-week is the difference between a budget that holds and one that doesn't, and it's the actual reason a house beats hotel rooms for a group this size.

Second, the arithmetic of bedrooms. Three-bedroom inventory in Kissimmee is the most-searched size in the market, which is exactly why it holds its price over the holidays. Four-bedroom houses are more plentiful. Run the comparison for your specific dates before you decide that a fourth bedroom is out of reach.

Ask us about theme park tickets too. We resell discounted Walt Disney World, Universal and SeaWorld tickets, and select properties carry a $50 theme park ticket credit. We'll tell you which, for your dates.

December in Kissimmee when you're not in a park

A holiday week built entirely around park days will break your family by about the fourth morning. The good news is that the best Christmas things here are free and close.

Celebration, twenty minutes away, closes Market Street to traffic and makes it snow nightly from half five to half nine, starting at the end of November. It costs nothing, it takes an hour, and small children lose their minds over it. Disney Springs runs a Christmas Tree Trail with themed trees, a scavenger-hunt map and snowfall effects, also free to walk. Epcot's Festival of the Holidays runs from late November to the end of December. Gaylord Palms, over on Osceola Parkway near Kissimmee, hosts ICE! with its sculptures, on timed tickets, so book ahead rather than turning up.

For New Year's Eve, Magic Kingdom does Fantasy in the Sky fireworks on both the 30th and the 31st, early evening and again just before midnight, so you can see them without staying up to midnight with exhausted kids. Disney Springs doesn't do its own fireworks, though its venues run live music and parties. Old Town in Kissimmee holds a free New Year's Eve celebration of its own, about ten minutes from the Venetian Bay townhomes.

For a regular dinner out, Old Town and the 192 corridor cover most appetites: Miller's Ale House for wings and burgers after a long park day, Melao Bakery, Thai Thani, Ari Sushi. Downtown Kissimmee has Big John's Rockin' BBQ and Buchito Cuban Cafe. Winter Park, further north, puts holiday lights along Park Avenue, which is a pleasant evening if you want an hour away from theme parks entirely.

How booking with us actually works

You're booking direct, with a best rate guarantee, from a team that lives here rather than a listings platform. Every home gets a verified quality inspection and hotel-grade cleaning between guests, and guest support runs 24/7, which over a holiday week with a houseful of people is not a theoretical benefit.

Two practical notes on the homes above. Both Venetian Bay townhomes sit in a gated resort that will want your licence plate before you arrive, and the community doesn't admit commercial vehicles, work vans, RVs, boats or trailers, so if you're driving down in something unusual, tell us first. At the Lake Berkley five-bedroom, check-in is 4pm and check-out 10am, quiet hours run 9pm to 9am, the lead guest must be 25 or over, and linens and towels are provided but beach towels aren't.

Where to start

Send us your dates, your head count and whether anyone in the group needs to avoid stairs. We'll come back with what's genuinely open over Christmas and New Year's, what each one costs all-in for your exact nights including any minimum stay, and whether a four-bedroom with a heated private pool lands inside your $150 to $250 range before a three-bedroom does. Nine times out of ten over the holidays, it does.

Frequently asked questions