Vacation rentals in Winter Haven - HomeToGo base64Hash Vacation rentals in Winter Haven - HomeToGo

Vacation rentals in Winter Haven

Find 334 available offers from 11 partners
Winter Haven
Anytime
Guests
Winter Haven
Anytime
Guests

Popular Filters to find the Perfect Home Rental in Winter Haven

2 Adults
1 Bedroom
Pool
House
Pets allowed
4 Adults
Cabin

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.

Show all 334 properties

Vacation rentals with Wi-Fi

Stay connected while traveling and book a Winter Haven accommodation with high-speed internet.

House  Winter Haven
Jun 19 - Jun 26
-21%
$185
$146 per night
House ∙ 8 guests ∙ 3 bedrooms

Vacation Home in Winter Haven with Electric Fireplace + Lake Views

4.5
Excellent (48 ratings)
Winter Haven, Polk County, Florida, United States
Internet
View deal
View deal
House  Winter Haven
Sep 7 - Sep 14
$175 per night
House ∙ 7 guests ∙ 3 bedrooms

Nice House in Winter Haven with Pool & Grill

5.0
Outstanding (2 ratings)
Winter Haven, Polk County, Florida, United States
Internet
View deal
View deal
House  Winter Haven
Sep 7 - Sep 14
$215 per night
House ∙ 8 guests ∙ 4 bedrooms

Wonderful Vacation Home in Winter Haven with Pool, Yard & Grill

4.8
Outstanding (18 ratings)
Winter Haven, Polk County, Florida, United States
Internet
View deal
View deal
See all offers

Apartments and vacation rentals with a kitchen

Cook up a feast on your next vacation and book a Winter Haven rental with full kitchen.

House  Winter Haven
Jun 20 - Jun 27
$335 per night
House ∙ 7 guests ∙ 3 bedrooms

Vacation Home in Winter Haven with Free Parking

5.0
Outstanding (18 ratings)
Winter Haven, Polk County, Florida, United States
Kitchen
View deal
View deal
House  Winter Haven
Jun 19 - Jun 26
$199 per night
House ∙ 9 guests ∙ 4 bedrooms

House in Winter Haven with Yard & Patio

4.9
Outstanding (27 ratings)
Winter Haven, Polk County, Florida, United States
Kitchen
View deal
View deal
Apartment  Winter Haven
Jun 19 - Jun 26
$78 per night
Apartment ∙ 2 guests ∙ 1 bedroom

Apartment in Winter Haven

5.0
Outstanding (5 ratings)
Winter Haven, Polk County, Florida, United States
Kitchen
View deal
View deal
See all offers

Vacation rentals and apartments with air conditioning

Keep cool during your trip to Winter Haven and book a vacation rental with air conditioning.

House  Winter Haven
Jun 29 - Jul 6
$247 per night
House ∙ 12 guests ∙ 6 bedrooms

Lovely Vacation Home in Winter Haven with Yard, Patio & Grill

5.0
Outstanding (10 ratings)
Winter Haven, Polk County, Florida, United States
Air conditioning
View deal
View deal
House  Winter Haven
Aug 5 - Aug 12
$186 per night
House ∙ 10 guests ∙ 5 bedrooms

Wonderful Vacation Home in Winter Haven with Grill, Patio & Yard

5.0
Outstanding (10 ratings)
Winter Haven, Polk County, Florida, United States
Air conditioning
View deal
View deal
House  Winter Haven
Jun 19 - Jun 26
$222 per night
House ∙ 8 guests ∙ 3 bedrooms

Vacation Home in Winter Haven with Yard, Pool & Patio

4.7
Excellent (27 ratings)
Winter Haven, Polk County, Florida, United States
Air conditioning
View deal
View deal
See all offers

Best Vacation Home Deals in Winter Haven

Save up to 63%

Resort Winter Haven
Jun 22 - Jun 29
-16%
$90
$76 per night
Resort ∙ 4 guests ∙ 1 bedroom

Amusement Park in Winter Haven with Outdoor Pool

4.2
Very good
Winter Haven, Polk County, Florida, United States
Free cancellation
View deal
View deal
Apartment Winter Haven
Jun 18 - Jun 25
-63%
$170
$62 per night
Apartment ∙ 2 guests ∙ 1 bedroom

Apartment in Winter Haven

5.0
Outstanding (3 ratings)
Winter Haven, Polk County, Florida, United States
View deal
View deal
House Winter Haven
Jul 27 - Aug 3
-60%
$556
$223 per night
House ∙ 7 guests ∙ 3 bedrooms

Wonderful House in Winter Haven with Grill + Beautiful Views

Winter Haven, Polk County, Florida, United States
Free cancellation
View deal
View deal

Find a rental that fits your preferences among the 334 fantastic options from more than 11 partner websites in Winter Haven. The website HomeToGo instantaneously compares all of these rentals so you can save up to 68%!

Recommended Vacation Rentals in Winter Haven

Find your perfect vacation rental in Winter Haven: from $54 per night

House Winter Haven
Jun 19 - Jun 26
$228 per night
House ∙ 10 guests ∙ 4 bedrooms

House in Winter Haven with Grill, Yard & Patio

5.0
Outstanding (10 ratings)
Winter Haven, Polk County, Florida, United States
View deal
View deal
House Winter Haven
Jun 19 - Jun 26
$200 per night
House ∙ 4 guests ∙ 3 bedrooms

Vacation Home in Winter Haven with Patio + Lake View

4.7
Excellent (14 ratings)
Winter Haven, Polk County, Florida, United States
View deal
View deal
House Winter Haven
Sep 2 - Sep 9
-73%
$469
$125 per night
House ∙ 8 guests ∙ 3 bedrooms

House in Winter Haven with Electric Fireplace + Lake Views

4.5
Excellent (48 ratings)
Winter Haven, Polk County, Florida, United States
Free cancellation
View deal
View deal
House Winter Haven
Jul 6 - Jul 13
$200 per night
House ∙ 9 guests ∙ 4 bedrooms

Vacation Home in Winter Haven with Grill, Pool & Patio

Winter Haven, Polk County, Florida, United States
View deal
View deal
House Winter Haven
Jul 20 - Jul 27
$270 per night
House ∙ 8 guests ∙ 4 bedrooms

Vacation Home in Winter Haven with Private Pool

5.0
Outstanding (17 ratings)
Winter Haven, Polk County, Florida, United States
View deal
View deal
Apartment Winter Haven
Jun 19 - Jun 26
$91 per night
Apartment ∙ 5 guests ∙ 1 bedroom

Rental Apartment in Winter Haven + Bath View

4.6
Excellent (23 ratings)
Winter Haven, Polk County, Florida, United States
View deal
View deal
House Winter Haven
Jul 13 - Jul 20
$312 per night
House ∙ 10 guests ∙ 4 bedrooms

Vacation Home in Winter Haven with Patio, Yard & Grill

4.9
Outstanding (32 ratings)
Winter Haven, Polk County, Florida, United States
View deal
View deal
Cottage Winter Haven
Jun 19 - Jun 26
$124 per night
Cottage ∙ 6 guests ∙ 2 bedrooms

Cottage in Winter Haven

5.0
Outstanding (6 ratings)
Winter Haven, Polk County, Florida, United States
View deal
View deal
House Winter Haven
Aug 5 - Aug 12
$231 per night
House ∙ 7 guests ∙ 3 bedrooms

Family Friendly Pleasant House in Winter Haven with Grill & Patio + Great Views

4.9
Outstanding (28 ratings)
Winter Haven, Polk County, Florida, United States
View deal
View deal
See all offers

Budget-friendly Vacation Rentals in Winter Haven

Find Fantastic yet Inexpensive Offers

House Winter Haven
Aug 17 - Aug 24
-55%
$792
$356 per night
House ∙ 11 guests ∙ 5 bedrooms

Family Friendly House in Winter Haven with Screened-In Patio + Great Views

Winter Haven, Polk County, Florida, United States
Free cancellation
View deal
View deal
Cottage Winter Haven
Jun 19 - Jun 26
$238 per night
Cottage ∙ 12 guests ∙ 2 bedrooms

Cottage in Winter Haven

5.0
Outstanding (1 rating)
Winter Haven, Polk County, Florida, United States
View deal
View deal
Apartment Winter Haven
Jun 19 - Jun 26
$101 per night
Apartment ∙ 3 guests ∙ 1 bedroom

Rental Apartment in Winter Haven with Grill, Patio & Yard

4.9
Outstanding (35 ratings)
Winter Haven, Polk County, Florida, United States
View deal
View deal

Top-Rated Rentals and Accommodations in Winter Haven

Book Vacation Rental Offers with the Highest User Rating

House Winter Haven
Jul 28 - Aug 4
-53%
$436
$205 per night
House ∙ 7 guests ∙ 3 bedrooms

House in Winter Haven with Grill & Patio + Beautiful Views

5.0
Outstanding (43 ratings)
Winter Haven, Polk County, Florida, United States
View deal
View deal
Apartment Winter Haven
Jun 19 - Jun 26
$106 per night
Apartment ∙ 4 guests ∙ 1 bedroom

Beautiful Apartment in Winter Haven with Patio & Grill

4.9
Outstanding (12 ratings)
Winter Haven, Polk County, Florida, United States
View deal
View deal
House Winter Haven
Jul 12 - Jul 19
$376 per night
House ∙ 11 guests ∙ 4 bedrooms

Lovely Vacation Home in Winter Haven with Yard, Pool & Patio

5.0
Outstanding (6 ratings)
Winter Haven, Polk County, Florida, United States
View deal
View deal
2024-americas-best-customer-service-newsweek-statista-award

Popular Rental Amenities in Winter Haven

  • Pool (216)
  • Pet-friendly (54)
  • WiFi (307)
  • Kitchen (191)
  • TV (306)
  • Air conditioning (309)
  • Washing machine (223)
  • Microwave (237)
  • Parking (13)
  • No smoking (302)
  • Fishing (71)
  • Balcony/patio (79)

Select a filter to find an accommodation meeting your criteria among the 334 properties in Winter Haven. Many vacation rentals in Winter Haven offer "Pool" or "Pets allowed," which makes it a great vacation spot if you're dreaming of days spent poolside or you bring your pet everywhere. You could even look for accommodations if you want a rental providing a crib (82 rentals include "Crib" in Winter Haven) or if you need a fenced-in backyard (27 rentals in Winter Haven include "Fenced").

The Weather in Winter Haven

max.
Min.
72°
52°
8 days 8
max.
Min.
75°
55°
7 days 7
max.
Min.
79°
59°
6 days 6
max.
Min.
84°
64°
8 days 8
max.
Min.
90°
68°
8 days 8
max.
Min.
91°
73°
17 days 17
max.
Min.
91°
75°
19 days 19
max.
Min.
91°
75°
17 days 17
max.
Min.
90°
73°
14 days 14
max.
Min.
86°
68°
7 days 7
max.
Min.
79°
59°
6 days 6
max.
Min.
77°
59°
7 days 7
Jan.
Feb.
Mar.
Apr.
May
June
July
Aug.
Sep.
Oct.
Nov.
Dec.
- 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 52° The rainiest month is July while the driest month is March.

7-Day Weather Forecast in Winter Haven

Sat, 15 Jun
86°
78°

0%

1 h

8 mi/h

Sun, 16 Jun
89°
86°

0%

1 h

9 mi/h

Mon, 17 Jun
87°
84°

15%

0 h

16 mi/h

Tue, 18 Jun
89°
87°

10%

5 h

16 mi/h

Wed, 19 Jun
89°
86°

0%

6 h

16 mi/h

Thu, 20 Jun
89°
87°

10%

5 h

15 mi/h

Fri, 21 Jun
93°
87°

10%

1 h

13 mi/h

Accommodations for your vacation in Winter Haven

Many of the listings (60.55%) in Winter Haven are house rental. They are the most typical accommodations in this destination. Interestingly, type of accommodation in particular, this type of property in particular is $334 per night, with an average area of 221 m². Moreover, most house rental 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 rental, which are the other most frequent property type in Winter Haven. These properties cost $140 a night on average and have an average size of 57 m².
Where to find the best food in Winter Haven?

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.

What are the best nightlife spots in Winter Haven?

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.

Where are the unique attractions in Winter Haven?

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.

Information about vacation rentals in Winter Haven

🏡 Vacation rentals available 334 rentals
💳 Possible discounts up to 68%
🌙 Nightly prices starting at $54
⭐ Popular amenities Pool, Pets allowed and Internet
🐾 Pet friendly homes 54 homes
🏊 Vacation rentals with pools 216 homes

Frequently Asked Questions

What is the nightly price for a vacation home in Winter Haven?

The nightly price of accommodations in Winter Haven starts at $54. If you are looking for a house rental, the nightly price is $334 on average. A apartment rental Winter Haven will cost $140 per night on average.

How many vacation homes are available for booking in Winter Haven?

Currently there are 334 vacation rentals in Winter Haven to browse and book for your next trip.

What amenities are most popular for vacation rentals in Winter Haven?

Travelers search for Pool, Pets allowed, and Internet when booking a vacation rental in Winter Haven.

How many vacation rentals with a pool are there in Winter Haven?

Check out 216 vacation rentals available in Winter Haven for renting.

Are pets allowed in vacation homes in Winter Haven?

Finding a vacation home in Winter Haven that allows pets is easy, with 54 pet-friendly available.

What's the best time to travel to Winter Haven?

Winter Haven has its warmest time of year around June and July, with average nightly prices around $54.

Find the perfect Winter Haven home to match your style

Get inspired for your vacation in Winter Haven

Top cities to visit

Show more

Vacation Destinations Near Winter Haven

Show more

Top Vacation Ideas

Explore More Vacation Ideas

Show more
image-tag