AllTheRooms.

Winter Haven Vacation Rentals

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

Our Favorite Vacation Rentals in Winter Haven

  • Haines City Pool Homes
     Country House
    Booking.com
    From
    $126
  • Pool Home in a Luxury Resort
     4br Home/Apartment
    HolidayLettings
    From
    $390
  • Beautiful Vacation Home, Private Room Close to Disney!!
     Home/Apartment
    HolidayLettings
    From
    $43
  • Calabay Parc at Tower Lake Getaway
    Good6br Country House
    Flipkey
    From
    $536
  • Sweet Cottage- 5 mi to Legoland & 0.5 mi to dwntwn
    Excellent2br Home/Apartment
    Airbnb
    From
    $154
  • The Paradise Hide Away
    ExcellentHome/Apartment
    Airbnb
    From
    $97
  • LOFT HAVEN in WINTER HAVEN minutes to LEGOLAND
     Home/Apartment
    Airbnb
    From
    $170
  • Lego my Bungalow
    ExcellentHome/Apartment
    Airbnb
    From
    $55
Show all

Check prices for these upcoming dates

Winter Haven Vacation Rentals with a Pool

  • Winter Haven Pool Cabana- 3 doors from Legoland.
    ExcellentHome/Apartment
    Airbnb
    From
    $198
  • 全新！阳光温馨联排度假别墅，离奥兰多迪士尼10分钟车程，游泳池健身房会所，温暖舒适
     3br Home/Apartment
    Airbnb
    From
    $209
  • Estate Home in the center of it all.
     4br Home/Apartment
    Airbnb
    From
    $678
  • House for rent in Orlando area with basketball ct
    Excellent6br Home/Apartment
    Airbnb
    From
    $1,966
Show all

Winter Haven Vacation Rentals with Wi-Fi

  • Walton House - New 2BR/2BA Cottage on Lake Alfred!
    Excellent2br Home/Apartment
    Airbnb
    From
    $253
  • Zetta's Hide-a-Way
    ExcellentHome/Apartment
    Airbnb
    From
    $82
  • Disney relaxing Tree House
    ExcellentHome/Apartment
    Airbnb
    From
    $101
  • Bartow's Hidden Gem
    NiceHome/Apartment
    Airbnb
    From
    $77
Show all

Winter Haven Pet-Friendly Vacation Rentals

  • RV/CAMPER PARKING w/ Indoor Bathroom & Laundry!!
     Home/Apartment
    Airbnb
    From
    $32
  • Clothing Optional campsite in Central Florida #1
    ExcellentHome/Apartment
    Airbnb
    From
    $11
  • Calabay Parc at Tower Lake Getaway
    Good6br Home/Apartment
    Airbnb
    From
    $345
  • Clothing Optional Campsite in Central Florida #2
    ExcellentHome/Apartment
    Airbnb
    From
    $17
Show all

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
83° 40°
3
90° 49°
2
88° 44°
1
91° 55°
2
98° 68°
1
100° 73°
10
99° 73°
12
97° 75°
8
98° 69°
4
95° 70°
5
90° 49°
3
86° 41°
3
Jan
Feb
Mar
Apr
May
Jun
Jul
Aug
Sep
Oct
Nov
Dec
Rainy days

This climate histogram shows you the weather patterns in Winter Haven. The warmest months in Winter Haven are July and June, when temperatures reach 100 ˚F. The coolest month is December, when temperatures drop to 40 ˚F. The wettest month in Winter Haven is June with 11.89 inches of rain, while the driest month is October with 1.43 inches of rain.

More+

What Expert Travelers Think

  • — 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

  • — I love AllTheRooms because it enables me to compare a range of providers in just one search. I'd normally spend time checking prices across a range of platforms by visiting different websites one-by-one, so this helps me to save time on my accommodation searches while planning my upcoming trips

    Kacie Morgan
    Kacie MorganThe Rare Welsh Bit
    The Rare Welsh Bit

  • — As a mom of 5 kids who enjoy traveling, I love AllTheRooms! It is quick and easy to find the best deal on lodging that fits our family, in the area we'd like. AllTheRooms really does save you time, money, and hassle.

    Becky
    BeckyKid World Citizen
    Kid World Citizen

Vacation Rentals in Winter Haven

Browse accommodations from all your favorite providers including Airbnb, Priceline, Agoda and others at AllTheRooms.com. AllTheRooms has 435 rentals, hotels and other great places to stay during your time in Winter Haven, with everything from inexpensive hostels and homestays to luxury Airbnbs and hotels. A trip to Winter Haven can be budget-friendly - the lowest price rental is available at $15 a night. On average, an accommodation in Winter Haven will cost you $96 per night.

If you need internet access during your stay in Winter Haven, then you can choose from over 157 places to stay that provide WiFi internet. 17 places to stay include a breakfast. Fitness addicts can get a workout in during their stay by choosing from 11 accommodations that have gyms. If you're planning on arriving in Winter Haven by car, be sure to choose from 161 accommodations that provide parking. We have 64 accommodations that have a pool or jacuzzi.

Those traveling with a dog, cat or some other animal can stay in one of 35 accommodations that are designated as pet-friendly.

We combine a wide variety of Winter Haven accommodations including vacation rentals, home stays, hostels and other unique places to stay into one easy search. We show results from more than 3 providers, including 149 places to stay from Airbnb, 18 accommodations from Priceline and 7 places to stay from Agoda.

228 accommodations in Winter Haven have been reviewed; 59% are rated excellent or good. 121 places to stay in are instantly bookable.

More+

Destinations near Winter Haven

  • Kissimmee119,002 Properties
  • Davenport48,426 Properties
  • Panama City Beach31,005 Properties
  • Champions Gate22,029 Properties
  • Destin16,186 Properties
  • Orlando13,852 Properties
  • Miramar Beach12,461 Properties
  • Fort Myers Beach11,436 Properties
  • Siesta Key9,215 Properties
  • Hollywood8,338 Properties
  • Cape Coral7,848 Properties
  • St. Augustine7,547 Properties
  • Marco Island7,312 Properties
  • Clermont6,305 Properties
  • Holmes Beach6,162 Properties
  • New Smyrna Beach5,909 Properties
  • Sanibel5,703 Properties
  • Santa Rosa Beach5,604 Properties
  • Sunny Isles Beach5,200 Properties
  • Naples4,861 Properties
  • Miami Beach4,757 Properties
  • Haines City4,615 Properties
  • Bradenton Beach4,324 Properties
  • Daytona Beach4,246 Properties
  • Bonita Springs4,103 Properties
  • Miami3,978 Properties
  • Celebration3,938 Properties
  • Key West3,864 Properties
  • Pensacola Beach3,854 Properties
  • Madeira Beach3,687 Properties
  • Pompano Beach3,335 Properties
  • Bradenton3,288 Properties
  • Treasure Island3,157 Properties
  • Indian Shores3,123 Properties
  • Sarasota3,090 Properties
  • Fort Myers2,910 Properties
  • St. Pete Beach2,852 Properties
  • Fort Walton Beach2,836 Properties
  • Indian Rocks Beach2,730 Properties
  • Hallandale Beach2,679 Properties
  • Anna Maria2,611 Properties
  • Daytona Beach Shores2,552 Properties
  • Palm Coast2,419 Properties
  • St. Augustine Beach2,371 Properties
  • Tampa2,340 Properties
  • Tallahassee2,279 Properties
  • Marathon2,066 Properties
  • Fort Lauderdale2,049 Properties
  • Key Largo1,951 Properties
  • Cocoa Beach1,916 Properties
  • Longboat Key1,835 Properties
  • Captiva1,717 Properties
  • Englewood1,706 Properties
  • Ormond Beach1,672 Properties
  • Placida1,663 Properties
  • Lake Buena Vista1,656 Properties
  • Venice1,633 Properties
  • Pensacola1,624 Properties
  • Gainesville1,540 Properties
  • Fort Pierce1,517 Properties
  • Clearwater Beach1,413 Properties
  • Islamorada1,410 Properties
  • Delray Beach1,371 Properties
  • Oakland Park1,333 Properties
  • Key Colony Beach1,318 Properties
  • Clearwater1,303 Properties
  • Deerfield Beach1,252 Properties
  • The Villages1,249 Properties
  • North Bay Village1,231 Properties
  • Dania Beach1,222 Properties
  • Cape Canaveral1,199 Properties
  • Tavernier1,147 Properties
  • Fernandina Beach1,117 Properties
  • Wilton Manors1,088 Properties
  • Lake Worth1,055 Properties
  • Vero Beach1,053 Properties
  • Rotonda West1,050 Properties
  • Jacksonville1,049 Properties
  • West Palm Beach1,021 Properties
  • Weston965 Properties
  • St. George Island965 Properties
  • Jensen Beach960 Properties
  • Bay Lake956 Properties
  • Redington Shores931 Properties
  • Port Charlotte915 Properties
  • Dunedin888 Properties
  • Ponte Vedra Beach862 Properties
  • Boca Raton811 Properties
  • Winter Garden802 Properties
  • Stuart767 Properties
  • Navarre766 Properties
  • Lauderdale-by-the-Sea760 Properties
  • Punta Gorda756 Properties
  • Port St. Lucie751 Properties
  • Surfside731 Properties
  • Port St. Joe731 Properties
  • Edgewater707 Properties
  • Coral Gables688 Properties
  • Panama City675 Properties
  • Boca Grande668 Properties
  • Aventura649 Properties
  • Ocala642 Properties
  • Estero639 Properties
  • Inverness624 Properties
  • Lakeland613 Properties
  • Gulfport612 Properties
  • Ruskin592 Properties
  • North Captiva579 Properties
  • Port Orange578 Properties
  • Mexico Beach571 Properties
  • Melbourne567 Properties
  • Nokomis564 Properties
  • Matlacha561 Properties
  • Palm Beach Shores560 Properties
  • St. Petersburg555 Properties
  • Miramar552 Properties
  • Doral550 Properties
  • Hudson545 Properties
  • Palm Beach Gardens540 Properties
  • Largo535 Properties
  • Orange Park534 Properties
  • Flagler Beach533 Properties
  • Jupiter527 Properties
  • North Redington Beach522 Properties
  • Temple Terrace517 Properties
  • Plantation497 Properties
  • Palm Beach497 Properties
  • Crystal River486 Properties
  • Boynton Beach479 Properties
  • Miami Springs471 Properties
  • Spring Hill469 Properties
  • Wellington462 Properties
  • New Port Richey461 Properties
  • Winter Park453 Properties
  • Palm Harbor443 Properties
  • Sebastian438 Properties
  • Brandon429 Properties
  • North Port427 Properties
  • North Fort Myers425 Properties
  • Homosassa417 Properties
  • Pembroke Pines403 Properties
  • Sebring399 Properties
  • Sunrise394 Properties
  • Mount Dora383 Properties
  • Redington Beach381 Properties
  • Key Biscayne378 Properties
  • Altamonte Springs378 Properties
  • Singer Island372 Properties
  • Tarpon Springs364 Properties
  • Davie351 Properties
  • Seminole343 Properties
  • Belleair Beach337 Properties
  • Melbourne Beach331 Properties
  • Wesley Chapel326 Properties
  • Lehigh Acres322 Properties
  • Lake Placid314 Properties
  • Lutz310 Properties
  • Titusville310 Properties
  • Bokeelia305 Properties
  • North Miami296 Properties
  • Sanford296 Properties
  • Indialantic294 Properties
  • Palm Bay293 Properties
  • Ponce Inlet293 Properties
  • Satellite Beach290 Properties
  • Riviera Beach283 Properties
  • Steinhatchee282 Properties
  • Gulf Breeze272 Properties
  • Lake Mary270 Properties
  • Jacksonville Beach259 Properties
  • Homestead254 Properties
  • Bal Harbour250 Properties
  • Lake City249 Properties
  • Cocoa248 Properties
  • Miami Shores244 Properties
  • Coral Springs243 Properties
  • Lady Lake241 Properties
  • Port Richey239 Properties
  • Lantana234 Properties
  • Okeechobee234 Properties
  • Merritt Island223 Properties
  • Apopka221 Properties
  • Port Saint Lucie196 Properties
  • Big Pine Key196 Properties
  • Lake Wales191 Properties
  • Highland Beach190 Properties
  • Juno Beach188 Properties
  • Duck Key186 Properties
  • Brooksville173 Properties
  • Cedar Key173 Properties
  • Florida City169 Properties
  • DeLand167 Properties
  • Dunnellon152 Properties
  • Niceville149 Properties
  • Leesburg138 Properties
  • Neptune Beach125 Properties
  • Carrabelle120 Properties
  • Ocoee118 Properties
  • Wildwood114 Properties
  • Apalachicola100 Properties
  • Atlantic Beach92 Properties
  • North Miami Beach80 Properties
  • Miami Gardens77 Properties
  • Land O' Lakes65 Properties
  • Ellenton33 Properties