Winter Haven Vacation Rentals

Compare 2,663 available properties from 34 providers
Winter Haven
Save up to 41%

Best Vacation Home Deals in Winter Haven

-41%
e.g. 2/2 - 2/9
House ∙ 4 guests ∙ 1 bedroom
Cypress Gardens, Polk County, Florida, United States
from $155 $260
e-domizil
4.6
View deal
-33%
e.g. 1/5 - 1/12
House ∙ 6 guests ∙ 2 bedrooms
Cypress Gardens, Polk County, Florida, United States
from $177 $266
e-domizil
4.6
View deal
-33%
e.g. 5/4 - 5/11
House ∙ 7 guests ∙ 2 bedrooms
Cypress Gardens, Polk County, Florida, United States
from $177 $266
e-domizil
4.5
View deal

Find a rental that fits your preferences among the 2,646 fantastic options from more than 34 partner websites in Winter Haven. The website HomeToGo instantaneously compares all of these rentals so you can save up to 41%!

Recommended Vacation Rentals in Winter Haven

Rent a vacation accommodation in Winter Haven: from $64 per night

House ∙ 6 guests ∙ 3 bedrooms
Winter Haven, Polk County, Florida, United States
from $100
VRBO
5.0
View deal
House ∙ 4 guests ∙ 2 bedrooms
Lake Wales, Polk County, Florida, United States
from $90
VRBO
5.0
View deal
House ∙ 6 guests ∙ 2 bedrooms
Lake Wales, Polk County, Florida, United States
from $257
VRBO
5.0
View deal
House ∙ 6 guests ∙ 3 bedrooms
Cypress Gardens, Polk County, Florida, United States
from $278
VRBO
4.7
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House ∙ 8 guests ∙ 3 bedrooms
Jan Phyl Village, Polk County, Florida, United States
from $177
HomeAway
5.0
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House ∙ 10 guests ∙ 3 bedrooms
Dundee, Polk County, Florida, United States
from $119
HomeAway
4.6
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House ∙ 6 guests ∙ 3 bedrooms
Haines City, Polk County, Florida, United States
from $103
VRBO
4.3
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House ∙ 11 guests ∙ 5 bedrooms
Auburndale, Polk County, Florida, United States
from $202
HomeAway
5.0
View deal
House ∙ 14 guests ∙ 4 bedrooms
Winter Haven, Polk County, Florida, United States
from $223
VRBO
5.0
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Vacation Houses With Pools

Pool
Apartment ∙ 4 guests ∙ 2 bedrooms
Winter Haven, Polk County, Florida, United States
from $61
VRBO
5.0
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Pool
House ∙ 6 guests ∙ 3 bedrooms
Winter Haven, Polk County, Florida, United States
from $226
VRBO
5.0
View deal
Pool
Resort ∙ 4 guests
Winter Haven, Polk County, Florida, United States
from $71
Booking.com
4.1
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Vacation Homes With Fishing Spots Nearby

Fishing
House ∙ 4 guests
Lake Wales, Polk County, Florida, United States
from $85
VRBO
4.5
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Fishing
House ∙ 8 guests ∙ 3 bedrooms
Winter Haven, Polk County, Florida, United States
from $162
VRBO
5.0
View deal
Fishing
House ∙ 4 guests ∙ 1 bedroom
Winter Haven, Polk County, Florida, United States
from $83
Booking.com
4.6
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Apartments With Balconies or Patios

Balcony/Patio
House ∙ 12 guests ∙ 4 bedrooms
Eagle Lake, Polk County, Florida, United States
from $256
VRBO
4.3
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Balcony/Patio
House ∙ 8 guests ∙ 3 bedrooms
Haines City, Polk County, Florida, United States
from $201
Booking.com
4.6
View deal
Balcony/Patio
House ∙ 8 guests ∙ 3 bedrooms
Haines City, Polk County, Florida, United States
from $182
Booking.com
4.3
View deal
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Popular Rental Amenities in Winter Haven

  • Kitchen (2,574)
  • No smoking (2,217)
  • Pool (2,207)
  • Internet (2,161)
  • AC (2,150)
  • TV (2,115)
  • No pets (1,990)
  • Parking (1,520)
  • Washer (1,424)
  • Microwave (1,416)
  • Dishwasher (1,400)
  • Grill (565)
Select a filter to find an accommodation meeting your criteria among the 2,646 properties in Winter Haven. Many vacation rentals in Winter Haven offer "internet" or "pools," which makes it a great vacation spot if you need internet access during your vacation or you're dreaming of days spent poolside. You could even look for accommodations if you want to sweat it out in a sauna (30 rentals include "saunas" in Winter Haven) or if you want a rental providing a crib (3 rentals in Winter Haven include "cribs").

Price and Availability Index in Winter Haven

Vacation Rental Price Information in Winter Haven

We analyzed price data and rendered them in this graph, which shows vacation rental prices for the next twelve months in Winter Haven. Prices in a week of February (2/16 - 2/23) go up to $206 per night, which is the highest average price in the next 12 months. Prices decrease in a week of May (5/4 - 5/11), where average prices are $157.

Rental Availability Information in Winter Haven

The availability graph shows the percentage of available rentals in Winter Haven. It is in December that you will find the week with the least available rentals (12/22 - 12/29). On the contrary, you will find the highest number of available rentals in a week of November (11/2 - 11/9).

The Weather in Winter Haven

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- Rainy days

Check out the climate diagram for Winter Haven. The highest average temperatures are in the month of June. Conversely, January is the coolest month in Winter Haven, with temperatures going under 51° The rainiest month is June while the driest month is March.

Accommodations in Winter Haven

Most of the listings (86.8%) in Winter Haven are house rentals. They are the most typical accommodations in this destination. Interestingly, type of accommodation in particular, this type of property in particular is $226 per night, with an average area of 2,170 ft². Moreover, most house rentals in this destination can welcome 9 guests, which makes it a perfect destination for large groups. If you would prefer to book another accommodation type, you could check apartment rentals, which are the other most frequent property type in Winter Haven. These properties cost $216 a night on average and have an average size of 1,840 ft².

Discover beautiful vacation rentals in Winter Haven, Florida

Located in Central Florida, Winter Haven is home to 50 lakes, making it an ideal destination for waterskiing and fishing enthusiasts. So if you are visiting for some fun on the lake, there is a broad range of vacation homes to choose from in Winter Haven. Depending on your budget, you can get a luxury condo, villa or an apartment that offers the ultimate comfort and convenience. There are vacation houses that feature spectacular lakeside views while providing welcoming neighborhood charm.

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Food & Drinks

Where to find delicious local food

If you are into seafood, Harry's Old Place offers local favorites such as sweet and spicy shrimp, fried gator bites, and baked oysters. For those who love steak, Manny's Original Chophouse is a family-friendly spot for roasted prime ribs, country fried steak and boneless chops. Carrabba's Italian Grill is a popular joint for guests who want to try Italian cuisines, such as Chicken Bryan, Pollo Sorrento, and Pollo Rosa Maria.

Nightlife

Get out for some fun

Make the most of your stay by trying out some of the locals clubs and sports bars. Somewhere Sports Bar & Grill is popular for karaoke music and boasts an extensive drink list of wine, beer and more. If you want to have fun with friends, Jessie's Lounge is the go-to spot for live music and dance nights. Or, you could try Apple Lounge if you want a cool place to eat, hang out, play pool and listen to music.

Local Attractions

Things to Do

Enjoy a spot of beauty with serene gardens by visiting Bok Tower Gardens which boasts a 205-foot Singing Tower Carillon with a bell that plays every day. Sherman's Antique features a 5,000 sq. ft. of treasures for guests to see. If you love musicals or stage readings, Theater Winter Haven offers shows and main stage productions to make your visit enjoyable.

We compare more than 300 providers, including:

Booking.com Vacation Rentals in Winter Haven VRBO Vacation Rentals in Winter Haven HomeAway Vacation Rentals in Winter Haven TripAdvisor Vacation Rentals in Winter Haven VacationRentals.com Vacation Rentals in Winter Haven HouseTrip Vacation Rentals in Winter Haven FlipKey Vacation Rentals in Winter Haven 9flats.com Vacation Rentals in Winter Haven VaycayHero Vacation Rentals in Winter Haven PerfectPlaces.com Vacation Rentals in Winter Haven Homestay.com Vacation Rentals in Winter Haven Only-apartments Vacation Rentals in Winter Haven Interhome Vacation Rentals in Winter Haven Bedycasa Vacation Rentals in Winter Haven Novasol Vacation Rentals in Winter Haven HomeEscape Vacation Rentals in Winter Haven

Things to See and Do in Winter Haven

Vacation Destinations Near Winter Haven