AllTheRooms.

Winter Haven Vacation Rentals

  1. Vacation Rental Search
  2. United States of America
  3. Florida
  4. Winter Haven

Check prices for these upcoming dates

Winterhaven Travel Guide

Set between Tampa and Orlando, Winterhaven is home to the largest LEGOLAND in the world, as well as stunning canal linked lakes, forest trails, and lush botanical gardens. Visitors can find so many places to discover, explore, and enjoy during their time here.

Things to Do in Winterhaven

Bok Tower Gardens are a tranquil area of luscious tropical gardens and bird sanctuary, known for their majestic singing tower. The bells of the tower are rung several times a day and the area is just wonderful to walk around.There are 50 lakes here, either within or just outside the city limits, where you can fish, take a boat ride, go paddle boarding or fly boarding, or join a guided cruise through the canals. A trip to LEGOLAND is a must if you're with little ones, and different events take place here all year round.

Best Time to Visit Winterhaven

January to April are the best months to plan a trip to Winterhaven.

More+

Price and Availability in Winter Haven

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 Haven tends to be Wednesday, while the most expensive day tends to be Sunday. Vacation homes in Winter Haven tend to be busiest on Saturdays, while it tends to be much quieter on Tuesdays.
The most expensive month to stay in a vacation rental in Winter Haven is in April, while the cheapest month is in September. The most popular time to book a vacation rental in Winter Haven is in the high season in March. Winter Haven has its low season in September, when less people are visiting and the vacation home occupancy rate drops.
More+

The Weather in Winter Haven

Rainy days
97° 63°
0
96° 71°
6
96° 73°
10
98° 70°
4
94° 68°
4
94° 59°
1
86° 49°
3
86° 46°
1
83° 40°
0
88° 37°
6
93° 49°
0
91° 48°
4
May
Jun
Jul
Aug
Sep
Oct
Nov
Dec
Jan
Feb
Mar
Apr
Rainy days

This climate histogram shows you the weather patterns in Winter Haven. The warmest months in Winter Haven are May and August, when temperatures reach 98 ˚F. The coolest month is November, when temperatures drop to 37 ˚F. The wettest month in Winter Haven is June with 9.98 inches of rain, while the driest month is August with 0.05 inches of rain.

More+

What Expert Travelers Think

  • — Site is easy to use; clean, laid out well, good colors and branding, fun logo and title that connects to the purpose of the brand. The blog, vacation destinations, and rental destinations is a great feature and really make the brand stand apart from other sites!

    Laurelle McVicker
    Laurelle McVickerLaurelle McVicker
    Laurelle McVicker

  • — My favorite thing about AllTheRooms is that it combines both rentals and hotels available so you can see an entire view of what is available in a certain area. I was able to see listings on AllTheRooms that I never even saw on other travel sites!

    Daniella Flores
    Daniella FloresILIKETODABBLE
    Visit ILIKETODABBLE

  • — 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
    Middle Class Dad

Vacation Rentals in Winter Haven

At AllTheRooms.com we have rentals from all of your favorite providers - Airbnb, Priceline, Agoda and more. We have 466 vacation rentals, hotels and other accommodation types in Winter Haven ranging from inexpensive options to luxury places to stay. If you are trying to keep costs down, the cheapest place to stay in Winter Haven is just $17 per night. In general, a place to stay in Winter Haven will cost you $93 per night.

If you need to stay connected during your trip, then you can choose from over 170 accommodations in Winter Haven that have WiFi. We have 18 accommodations that come with breakfast included. Fitness fanatics can get a workout in during their stay by choosing from 11 accommodations that have gyms. If you are driving to Winter Haven, you'll want to pick from 174 places to stay that provide parking. 66 accommodations come with a pool or jacuzzi

If you're traveling with your best friend, then be sure to choose one of the 37 pet-friendly accommodations available.

AllTheRooms compares vacation rentals, hotels and other bespoke accommodation types from many providers in Winter Haven, including 163 places to stay from Airbnb, 18 accommodations from Priceline and 7 places to stay from Agoda

254 accommodations in Winter Haven have been reviewed; 61% are rated excellent or good. You can instantly book any of 131 places to stay right now.

More+

Destinations near Winter Haven

  • 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
  • West Palm Beach1,098 Properties
  • Rotonda West1,098 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
  • Gulfport643 Properties
  • North Captiva643 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
  • North Redington Beach549 Properties
  • Palm Beach549 Properties
  • Jupiter549 Properties
  • Temple Terrace543 Properties
  • Boynton Beach540 Properties
  • Crystal River524 Properties
  • Spring Hill505 Properties
  • Winter Park496 Properties
  • Miami Springs495 Properties
  • Wellington490 Properties
  • New Port Richey489 Properties
  • Pembroke Pines484 Properties
  • Palm Harbor476 Properties
  • Homosassa460 Properties
  • North Port458 Properties
  • Sebastian458 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
  • Melbourne Beach358 Properties
  • Wesley Chapel358 Properties
  • Belleair Beach355 Properties
  • Lehigh Acres339 Properties
  • Lutz337 Properties
  • North Miami337 Properties
  • Lake Placid334 Properties
  • Titusville328 Properties
  • Bokeelia320 Properties
  • Sanford319 Properties
  • Palm Bay319 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
  • Jacksonville Beach265 Properties
  • Port Richey265 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