The classic snowbird plan is a condo on a beach. It is a fine plan with two problems: the coasts are expensive in winter, and a beach town in January can be a long way from everything else. Orlando makes a different case. It is in the middle of the state, an hour from the Atlantic and two from the Gulf, with a big airport for visiting family, and a house here costs less for the season than a condo with a sea view. Here is what wintering in Orlando is actually like.
The weather you came for
November through April is Orlando's dry season. Afternoons in the winter months run in the 60s and 70s, mornings can be cool enough for a sweater, and a real cold snap lasts a couple of days, not a couple of weeks. Rain is rare compared with summer. The humidity that defines Florida from June to September is largely gone. Golf, walking, tennis, gardens and outdoor dinners all work in January.
A base in the middle of everything
From our homes on the west and north sides of Orlando:
- The Atlantic: Cocoa Beach and the Space Coast are about an hour east, Daytona Beach about an hour northeast.
- The Gulf: Clearwater and St. Pete are about two hours west.
- The springs: Wekiwa Springs State Park is about 18 minutes from the Wekiwa House, and Kelly Park's Rock Springs is a little farther north. The water stays around 72 degrees, which is warm in January.
- Mount Dora, about 40 minutes northwest, for antiques and the lakefront old town.
- Winter Park, minutes from the Katherine House, for Park Avenue, the museums and the scenic boat tour.
- The parks, when the grandchildren visit: Universal 12 to 26 minutes, Disney 35 to 50.
Family visits
This is the quiet advantage. Orlando International Airport is 26 to 39 minutes from our homes, with nonstop flights from most northern cities, and a house with three bedrooms means the kids and grandchildren stay with you instead of in a hotel. The Katherine House, with its screened porch, and the Meet & Play House, with a covered patio and a game room, are the two that winter guests ask about most.
How the monthly house works
Our homes rent by the month at one rate for the whole house, furnished, with kitchens, linens and laundry in place. You bring clothes and golf clubs. Book November through March, or any stretch of it; the season is quoted as a whole when you tell us your dates. Extending into April is simple if the weather up north is slow to turn. Several homes allow pets; tell us about yours and we will confirm the policy and any deposit in writing.
Which home suits a couple
For one or two people, the Wekiwa House (two bedrooms, two bathrooms) and the 25th Street House are the easiest fits. For a couple who host, WinterPark Home and Meet. Play. Stay. give you spare rooms. All of them are single-story, which matters more than people expect. The seasonal page has the rest.
Which house fits a season
A three or four month stay asks different questions than a week at the parks. You want a bedroom you will use every night, a kitchen you can cook a real dinner in more than once, and a street quiet enough that you notice when a car pulls up. Three of our homes come up most often for a stay of a season.
West OrlandoWekiwa Home
17 min downtown · 16 min AdventHealth · 19 min Universal
South of DowntownFruit Tree Home
6 min downtown · 5 min ORMC · 13 min Universal
Northwest OrlandoWinterPark Home
13 min downtown · 10 min AdventHealth · 26 min Universal
The Wekiwa House is the smallest home in the portfolio and the simplest to run for one or two people: two bedrooms, two full bathrooms, a king bed in one room and two full beds in the other, and full-size laundry rather than a stacked unit. It sits in Hiawassee on the far west side, a stretch of quiet subdivisions with quick SR-429 access. The 25th Street House, in Holden Heights just south of downtown, is a three-bedroom bungalow with its own full-size washer and dryer, a screened front porch, keyless entry and fruit trees in the yard, a better fit if you would rather be a short drive from Lake Eola and the museums than out on the west side. The Katherine House, in Lockhart, has a screened porch, a private driveway and a community park with a playground and courts a short walk from the door, and it sits about 8 minutes from Winter Park's Park Avenue. For anyone who would rather have a hospital close by than far, Orlando Health / ORMC and AdventHealth Orlando are both under 20 minutes from any of the three. Every one of the thirteen home pages has its own 'worth knowing before you book' section, worth a look for any of these three before you commit to a season.
The drive for errands and a day at the springs
Across the thirteen homes, downtown Orlando runs 6 to 17 minutes away by road, so a grocery run, a bank visit or a doctor's appointment rarely costs you an afternoon. The far west side, where Wekiwa Home sits, adds a few minutes to most of those trips and buys the shortest run to the springs in exchange.
The chart uses the same road-routing figures published on every home page. Wekiwa Home itself has the shortest drive of the thirteen, at 18 minutes; the Londonderry and Katherine houses follow at 19 and 20; and the rest of the portfolio runs from 24 to 29 minutes, close enough that a morning at the springs is a realistic outing no matter which house you book. The park is open 8 a.m. to sunset, admission runs about $6 per carload, and the on-site concession rents canoes and kayaks for roughly $17 for the first two hours. Kelly Park's Rock Springs, in Apopka, charges about $5 per vehicle for tubing the spring, with tubes rented for a few dollars from vendors outside the gate; it can fill to capacity on a warm winter weekend, so an early start pays off.
SR-408 and SR-429, the two expressways that do most of the work getting around, are both tolled by transponder or plate, so a SunPass or E-PASS is worth carrying for a stay measured in months rather than days. The Amelia House and Fruit Tree Home are the two homes close to the LYNX Central and Church Street SunRail stations and the free downtown LYMMO bus, if you would rather leave the car parked some days.
Cooking for yourself, market by market
A season is long enough that eating out every night stops making sense, and every kitchen in the portfolio comes stocked with cookware and dishes so you can start cooking the day you arrive. Where you shop depends on which side of the portfolio you land on.
From Amelia’s Arena Retreat and Fruit Tree Home on the downtown edge, the compact Publix at The Paramount on Lake Eola is the walkable option, with a second Publix on South Orange Avenue near Holden Heights. From the Pine Hills and Lockhart cluster around the Head Avenue and Katherine houses, Presidente Supermarket on North Pine Hills Road covers the Latin groceries and the Caribbean Supercenter on West Colonial Drive has anchored that corner's Caribbean shopping for about forty years; the Walmart Supercenter on West Princeton Street covers a full American pantry. Our Pine Hills area guide has the rest of that corner.
Inside of a Publix store in MetroWest, Orlando, Florida · Nielsoncaetanosalmeron · CC BY 4.0 · resized from 6000x4000
From the west-side homes, including Wekiwa Home, the Publix at Metro West Village on South Hiawassee Road, rebuilt and reopened in 2025, is the everyday stop, and West Oaks Mall in Ocoee adds a JCPenney, a Dillard's clearance store and a fourteen-screen AMC theater with about eighty-five shops if you want more than groceries on a slow week. The Walmart Supercenter near Hiawassee keeps hours from about 6 a.m. to 11 p.m., handy if a flight lands you late or you want an early start before a morning at the springs. Pharmacies follow the same map: CVS and Walgreens sit along Silver Star Road, Pine Hills Road, Orange Blossom Trail and West Colonial Drive, and downtown has a Publix pharmacy at Lake Eola with a CVS and a Walgreens a few blocks away, so transferring a prescription for the season is a short errand rather than a project.
Gardens, museums and parks for slow days
The portfolio sits close to more indoor and outdoor culture than a week built around the theme parks would ever show you. Harry P. Leu Gardens, a fifty-acre botanical garden on the lake, is an easy way to spend a cool morning walking instead of driving. Its floral clock near the entrance is a small stop worth working into the visit.
Harry P Leu Gardens (9059614612) · KimonBerlin · CC BY-SA 2.0 · resized from 5760x3840
Loch Haven Park, north of downtown and close by, gathers the Orlando Museum of Art, the Orlando Science Center, Orlando Shakes and Orlando Family Stage in one place, with the Mennello Museum of American Art next door. Lake Eola Park downtown adds its own rhythm to a longer stay: a roughly one-mile sidewalk loop around the water, pedal-powered swan boats you can rent by the half hour, and a Sunday farmers market from 10 a.m. to 3 p.m. with food stalls, local makers and a beer garden.
On the west side, Barnett Park on West Colonial Drive is a free, 159-acre county park with walking trails, disc golf, and basketball and volleyball courts; its splash pad runs through the warmer months. Lake Lorna Doone Park, a twelve-acre park just north of Camping World Stadium, reopened in 2021 with a walking loop, outdoor fitness stations and a barrier-free playground. If you would rather watch birds than walk laps, Magnolia Park on Lake Apopka has a fishing pier, a boat ramp and free-roaming peacocks.
Game days and the winter event calendar
Winter in Orlando is also college football season. Camping World Stadium, previously known as the Florida Citrus Bowl and the Tangerine Bowl, is the current home of the Citrus Bowl, and its lots fill for a run of bowl games each December and January. Drive times to the stadium run from 2 to 15 minutes across the portfolio: City and Stadium Sanctuary Vibes is about 2 minutes away, Game Day Getaway-Downtown Orlando about 3, the Head Avenue, Entertainment and Cozy houses in Pine Hills about 8, Londonderry about 11, and WinterPark Home in Lockhart about 15.
Camping World Stadium · Quintin Soloviev · CC BY 4.0 · resized from 10599x7576
The Kia Center arena and Inter.co Stadium sit in Parramore, close to Amelia’s Arena Retreat, and both run a full winter schedule of basketball, soccer and concerts. A few minutes from our Pine Hills homes, the Central Florida Fairgrounds hosts the Central Florida Fair each spring plus concerts through the year at the attached amphitheater, worth planning around if your season runs into March or April. Every home has its own private parking, so a game night does not add a parking fee on top of the ticket. City and Stadium Sanctuary Vibes parks under a carport and Game Day Getaway-Downtown Orlando has its own driveway, both an easy spot to stage coolers and gear before kickoff. If a bowl game, a match or a show lines up with your dates, telling us early is worth it, since the streets around the venues fill up on those nights.
Bringing a dog for the season
Eight of the thirteen homes have a fenced yard: Amelia’s Arena Retreat, The Clue House, Piedmont, Game Day Getaway-Downtown Orlando, WinterPark Home, Fruit Tree Home, Meet. Play. Stay. and City and Stadium Sanctuary Vibes. A fenced yard matters more on a three-month stay than a three-night one, since a dog used to a yard at home will want one here too.
A couple of honesty notes are worth knowing before you book with a pet. City and Stadium Sanctuary Vibes's backyard is being refreshed right now, so it suits a dog on a leash but is not yet a yard to let one loose in. The yards themselves vary in how established they are; each home's own page describes the yard as it actually looks today rather than as a stock photo. If you already know your dog's size and routine, mention it when you send your dates so we can flag any yard limits ahead of time, and we will put the pet policy and any deposit in writing before your stay is confirmed. A fenced yard also means you are not walking a dog around an unfamiliar block after dark, night after night, for months.
What's already set up when you arrive
Every home comes with the same baseline, confirmed in writing when you book so nothing is a surprise on move-in day.
Exact inclusions vary a little by home and are confirmed in writing when you book.
You let yourself in with keyless entry or a lockbox, and we send the code or the key location a few days before check-in, so there is no key exchange to coordinate around a long drive down. One detail worth knowing before you pack: a sofa in any of our living rooms is furniture, not a bed, so the bedroom count published on each home's listing is the real sleeping count for a season-long booking. Wekiwa Home and Fruit Tree Home both have full-size, not stacked, washers and dryers, which matters more once you are doing your own laundry every week for months instead of once at the end of a trip. Parking is a private driveway, carport or parking pad at every home, so a season's worth of guests, deliveries and holiday visitors never means circling the block for street parking. Linens and towels are already on the beds and in the bathrooms when you arrive, the same as on a much shorter stay, just multiplied by a season's worth of laundry instead of a week's.
What guests said, and what to sort out before you book
The reviews below are real, copied from the homes' own Airbnb listings with the reviewer's name and the month they stayed.
"Michelle’s place is in a great location you can get anywhere around Orlando in 20 minutes. She responds to any questions or concerns immediately. Neighborhood is quiet and peaceful. Close to restaurants and stores would definitely recommend her place."
"This place was super clean ! Had the perfect amount of space for our group ! Would definitely stay here again next time I come to Orlando !"
"The neighborhood was very nice and the airbnb host was kind enough to leave us a full bag of water bottles for our check in. 100% would recommend if you want something chill, small, and spacious at the same time. I felt like it was just enough room for everything we wanted to accomplish during our stay for around 6 days with 5 people."
"Worked out perfect for our occasion. Thank you for having such a beautiful place.!"
Long stays get their own kind of feedback. Cristina, who stayed at the Meet & Play House in July 2026, wrote: 'Absolute great stay. The place was clean. I had everything I needed to make it a long-term stay. I was in this Airbnb for 30 days.' That is a shorter run than a winter season, but it is the same test a longer stay puts a house through.
A few questions are worth answering before you send us your dates.
- Your months. Tell us the exact start and end you have in mind; a full season is easier for us to hold open than a vague 'sometime this winter.'
- Who is coming. A couple, a family visiting for a week in the middle of your stay, or a dog. Each changes which house makes sense.
- How much you plan to drive. If Winter Park's shops or the springs matter more to you than downtown, say so, since it changes which cluster we point you to first.
- Your travel dates on each end. If you are driving down in stages or flying back north on a fixed date, tell us both dates so the house is ready exactly when you need it and cleared exactly when you leave.
- The plain parts. These are modest, older houses in working residential neighborhoods, not new construction, and each home's own page lists the yard, the kitchen and anything else worth knowing before you commit.
Two of our other guides go deeper on pieces of this: what a furnished monthly rental usually includes, and what to sort out before bringing a pet along.
Monthly Furnished Rentals: What's Usually Included
A plain rundown of the furniture, kitchen, linens, utilities, and internet you can usually expect in a furnished monthly home, and the questions worth asking before you book.
Read →
Bringing a Pet on a Work Assignment
What travel nurses and relocating professionals should sort out before bringing a dog or cat along for a month-plus stay in Orlando.
Read →
