Winter Park, FL Cabins & Vacation Rentals

Check prices for these upcoming dates

Winter Park Travel Guide

Contrary to its name, Winter Park is a ray of sunshine with lots to offer tourists with different interests. This historic and quaint town is family-friendly, with opportunity to enjoy arts, culture and nature all in one. There are famous museums and festivals held throughout the year, with over 70 green spaces for nature-lovers to explore. You'll also find a lot of cafes and coffee spots for the health-conscious travelers, as well as weekly farmer’s markets. It isn’t hard to see how Winter Park has become a favourite retreat in the Sunshine State for many families and couples on vacation.

Things to Do in Winter Park

You'll find one of the oldest attractions in Florida in Winter Park -- Scenic Boat Tours. A guide takes you out onto Lake Osceola to admire the flora and see if you can spot any 'gators. Winter Park Sidewalk Art Festival attracts visitors annually since it is one of the oldest and largest outdoor art festivals in the country. You can wander around Olde Winter Park and explore the traditional, brick streets and unwind in the Mead Botanical Garden, with over 48 acres of greenery. The Charles Hosmer Morse Museum of American Art also showcases the best works of artist, Louis Comfort Tiffany in the world.

Best Time to Visit Winter Park

The best time to visit Winter Park is from January to April when it's still warm but there is less rain and humidity to make it comfortable. While a lot of tourists visit this city in the Sunshine State during the summer months, Winter Park is at its hottest and most humid from May to the end of August. This is hurricane season and means the potential for storms that could affect your plans.

Cabins in Winter Park

The town of Winter Park is the perfect base village for a skiing adventure. The continental divide cuts right through Grand County, giving a stunning backdrop to all slopes in Winter Park Colorado. Winter Park Resort features 3,000 acres of award-winning terrain, with runs suitable for all abilities, as well as a large number of vacation rentals.

The fun doesn't stop in summer, and the Winter Park area becomes crowded with mountain bike enthusiasts, meaning rentals in Winter Park and nearby Fraser Valley tend to fill up during this season. The valley is surrounded by the Arapaho National Forest which is criss-crossed with a number of hiking trails -- the idea setting for any outdoor enthusiast!

Winter Park lodging fits a range of budgets. For something a little more luxurious, book a rental with a hot tub where you can soak up the surrounding mountain views. The majority of Winter Park cabin rentals have full kitchens, and many are ski-in ski-out condos, meaning you have immediate access to world-class skiing. Trailhead Lodge offers a number of 1-3 bedroom accomodations close to all of the action, or there are a number of other management companies visitors can book through.

Price and Availability in Winter Park

Most expensive
Most availability
, , , , , , , , , , , Jan , Feb , Mar , Apr , May , Jun , Jul , Aug , Sep , Oct , Nov , Dec 1 , 0.9 , 0.8 , 0.7 , 0.6 , 0.5 , 0.4 , 0.3 , 0.2 , 0.1 , 0 , , , , , , , , , , , , , , , , , , , , , , Jan , Feb , Mar , Apr , May , Jun , Jul , Aug , Sep , Oct , Nov , Dec 1 , 0.9 , 0.8 , 0.7 , 0.6 , 0.5 , 0.4 , 0.3 , 0.2 , 0.1 , 0 , , , , , , , , , , , , , , , , , , , , , , Jan , Feb , Mar , Apr , May , Jun , Jul , Aug , Sep , Oct , Nov , Dec 1 , 0.9 , 0.8 , 0.7 , 0.6 , 0.5 , 0.4 , 0.3 , 0.2 , 0.1 , 0
Powered by:
The cheapest day to stay at a vacation rental in Winter Park tends to be Monday, while the most expensive day tends to be Friday. Vacation homes in Winter Park tend to be busiest on Saturdays, while it tends to be much quieter on Mondays.
The most expensive month to stay in a vacation rental in Winter Park is in July, while the cheapest month is in April. The most popular time to book a vacation rental in Winter Park is in the high season in March. Winter Park has its low season in September, when less people are visiting and the vacation home occupancy rate drops.

The Weather in Winter Park

Rainy days
95° 69°
3
92° 68°
6
89° 49°
1
85° 42°
4
83° 38°
3
88° 48°
2
88° 42°
2
91° 56°
2
98° 66°
4
98° 71°
12
98° 72°
6
97° 73°
13
Sep
Oct
Nov
Dec
Jan
Feb
Mar
Apr
May
Jun
Jul
Aug
Rainy days

This climate histogram shows you the weather patterns in Winter Park. The warmest months in Winter Park are June and July, when temperatures reach 98 ˚F. The coolest month is December, when temperatures drop to 38 ˚F. The wettest month in Winter Park is May with 13.03 inches of rain, while the driest month is February with 1.33 inches of rain.

What Expert Travelers Think

  • — Whenever I am making travel plans I always use comparison sites to find the best accommodation for us at the best price. Whether it be for hotel stays or private rentals AllTheRooms makes this so much easier and quicker as it brings all my searches into one place, with a great offering of options

    Sarah Pool
    Sarah PoolTammymum
  • — The great thing about AllTheRooms is their ability to cover all bases. If you are travelling solo, with a partner, friends or even a larger family. There is something there for everyone and that is a hugely powerful tool that I believe it boasts moreso than competitors.

    Max Hobbs
    Max HobbsLTL Mandarin School
  • — I love All the Rooms because instead of having to check one place for home rentals, another for hotel, another for bed and breakfasts, and yet another for a room rental in a private residence, I can finally see EVERYTHING at one site; saving me considerable time

    Jeff Campbell
    Jeff CampbellMiddle Class Dad

Vacation Rentals in Winter Park

At AllTheRooms.com we have vacation rentals from all of the best providers - Airbnb, Priceline, Agoda and more. Winter Park has 496 hotels, vacation rentals and other unique places to stay, with prices to suit budget travelers, extravagant travelers and everything in between. When traveling on a budget, the most economical place to stay in Winter Park is available at $10 per night. The average price of an accommodation is $110 per night.

Those looking to get some work done during their trip to Winter Park can choose from 357 places to stay that have WiFi. We have 41 accommodations that come with breakfast included. You can maintain your workout regime by staying at one of 51 accommodations that provide gym facilities. Driving to Winter Park? Then choose one of the 347 places to stay that comes with a parking spot included. We track 135 hotels and vacation rentals that have a pool or jacuzzi.

If you're traveling with a furry friend, then be sure to select one of the 70 pet-friendly accommodations available.

376 of the accommodations in Winter Park have been reviewed and rated. 70% are rated great. You can instantly book any of 205 places to stay right now.

Destinations near Winter Park

  • Kissimmee130,113 Properties
  • Davenport52,221 Properties
  • Panama City Beach34,832 Properties
  • Champions Gate25,699 Properties
  • Destin17,395 Properties
  • Orlando14,999 Properties
  • Miramar Beach13,546 Properties
  • Fort Myers Beach12,593 Properties
  • Siesta Key9,663 Properties
  • Hollywood9,232 Properties
  • Cape Coral8,886 Properties
  • St. Augustine8,269 Properties
  • Marco Island7,819 Properties
  • Clermont6,742 Properties
  • Holmes Beach6,707 Properties
  • Santa Rosa Beach6,355 Properties
  • New Smyrna Beach6,261 Properties
  • Sanibel6,091 Properties
  • Sunny Isles Beach5,605 Properties
  • Naples5,127 Properties
  • Haines City5,080 Properties
  • Miami Beach4,959 Properties
  • Bradenton Beach4,700 Properties
  • Daytona Beach4,612 Properties
  • Bonita Springs4,356 Properties
  • Miami4,120 Properties
  • Pensacola Beach4,092 Properties
  • Celebration3,983 Properties
  • Key West3,952 Properties
  • Madeira Beach3,863 Properties
  • Bradenton3,620 Properties
  • Pompano Beach3,576 Properties
  • Indian Shores3,318 Properties
  • Treasure Island3,311 Properties
  • Sarasota3,286 Properties
  • Fort Myers3,169 Properties
  • Hallandale Beach3,135 Properties
  • St. Pete Beach3,049 Properties
  • Fort Walton Beach2,903 Properties
  • Indian Rocks Beach2,871 Properties
  • Anna Maria2,800 Properties
  • Daytona Beach Shores2,790 Properties
  • St. Augustine Beach2,557 Properties
  • Palm Coast2,547 Properties
  • Tampa2,532 Properties
  • Tallahassee2,411 Properties
  • Marathon2,301 Properties
  • Fort Lauderdale2,135 Properties
  • Key Largo2,068 Properties
  • Cocoa Beach2,018 Properties
  • Lake Buena Vista1,949 Properties
  • Longboat Key1,906 Properties
  • Captiva1,906 Properties
  • Englewood1,833 Properties
  • Ormond Beach1,804 Properties
  • Venice1,773 Properties
  • Pensacola1,741 Properties
  • Placida1,692 Properties
  • Gainesville1,666 Properties
  • Fort Pierce1,576 Properties
  • Delray Beach1,495 Properties
  • Islamorada1,482 Properties
  • Clearwater Beach1,450 Properties
  • Oakland Park1,424 Properties
  • Clearwater1,390 Properties
  • Key Colony Beach1,385 Properties
  • Deerfield Beach1,358 Properties
  • The Villages1,318 Properties
  • Dania Beach1,309 Properties
  • North Bay Village1,305 Properties
  • Cape Canaveral1,264 Properties
  • Lake Worth1,220 Properties
  • Tavernier1,209 Properties
  • Wilton Manors1,160 Properties
  • Vero Beach1,134 Properties
  • Fernandina Beach1,128 Properties
  • Rotonda West1,098 Properties
  • West Palm Beach1,098 Properties
  • Jacksonville1,057 Properties
  • Jensen Beach1,032 Properties
  • Bay Lake1,025 Properties
  • Port Charlotte1,007 Properties
  • St. George Island998 Properties
  • Weston996 Properties
  • Redington Shores970 Properties
  • Ponte Vedra Beach957 Properties
  • Dunedin947 Properties
  • Winter Garden872 Properties
  • Boca Raton856 Properties
  • Lauderdale-by-the-Sea840 Properties
  • Punta Gorda840 Properties
  • Stuart809 Properties
  • Navarre799 Properties
  • Surfside795 Properties
  • Port St. Lucie795 Properties
  • Coral Gables771 Properties
  • Port St. Joe770 Properties
  • Edgewater740 Properties
  • Aventura710 Properties
  • Boca Grande707 Properties
  • Lakeland705 Properties
  • Panama City703 Properties
  • Ocala687 Properties
  • Inverness665 Properties
  • Estero659 Properties
  • Miramar659 Properties
  • Ruskin656 Properties
  • North Captiva643 Properties
  • Gulfport643 Properties
  • Doral643 Properties
  • Melbourne622 Properties
  • Palm Beach Shores608 Properties
  • Port Orange604 Properties
  • Mexico Beach601 Properties
  • Largo598 Properties
  • Hudson593 Properties
  • Nokomis591 Properties
  • St. Petersburg582 Properties
  • Matlacha581 Properties
  • Palm Beach Gardens574 Properties
  • Flagler Beach564 Properties
  • Plantation555 Properties
  • Orange Park551 Properties
  • Palm Beach549 Properties
  • Jupiter549 Properties
  • North Redington Beach549 Properties
  • Temple Terrace543 Properties
  • Boynton Beach540 Properties
  • Crystal River524 Properties
  • Spring Hill505 Properties
  • Miami Springs495 Properties
  • Wellington490 Properties
  • New Port Richey489 Properties
  • Pembroke Pines484 Properties
  • Palm Harbor476 Properties
  • Winter Haven466 Properties
  • Homosassa460 Properties
  • Sebastian458 Properties
  • North Port458 Properties
  • North Fort Myers453 Properties
  • Brandon445 Properties
  • Sunrise437 Properties
  • Sebring433 Properties
  • Key Biscayne408 Properties
  • Redington Beach408 Properties
  • Mount Dora404 Properties
  • Davie400 Properties
  • Singer Island396 Properties
  • Altamonte Springs394 Properties
  • Tarpon Springs387 Properties
  • Seminole373 Properties
  • Wesley Chapel358 Properties
  • Melbourne Beach358 Properties
  • Belleair Beach355 Properties
  • Lehigh Acres339 Properties
  • Lutz337 Properties
  • North Miami337 Properties
  • Lake Placid334 Properties
  • Titusville328 Properties
  • Bokeelia320 Properties
  • Palm Bay319 Properties
  • Sanford319 Properties
  • Ponce Inlet314 Properties
  • Indialantic313 Properties
  • Gulf Breeze303 Properties
  • Riviera Beach298 Properties
  • Steinhatchee297 Properties
  • Satellite Beach296 Properties
  • Lake Mary283 Properties
  • Miami Shores279 Properties
  • Coral Springs274 Properties
  • Homestead267 Properties
  • Cocoa266 Properties
  • Port Richey265 Properties
  • Jacksonville Beach265 Properties
  • Lake City260 Properties
  • Bal Harbour257 Properties
  • Merritt Island257 Properties
  • Lantana254 Properties
  • Lady Lake252 Properties
  • Okeechobee242 Properties
  • Apopka236 Properties
  • Big Pine Key214 Properties
  • Port Saint Lucie213 Properties
  • Duck Key208 Properties
  • Lake Wales198 Properties
  • Juno Beach194 Properties
  • Highland Beach191 Properties
  • Cedar Key186 Properties
  • Brooksville181 Properties
  • DeLand179 Properties
  • Florida City173 Properties
  • Dunnellon170 Properties
  • Niceville163 Properties
  • Leesburg148 Properties
  • Neptune Beach132 Properties
  • Wildwood132 Properties
  • Carrabelle128 Properties
  • Ocoee125 Properties
  • Apalachicola101 Properties
  • Atlantic Beach92 Properties
  • North Miami Beach90 Properties
  • Miami Gardens82 Properties
  • Land O' Lakes71 Properties
  • Ellenton40 Properties