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Check prices for these dates

Next weekend
29 Aug - 31 Aug
In two weeks
5 Sept - 7 Sept
In one month
19 Sept - 21 Sept
In two months
17 Oct - 19 Oct

Featured Condo Rentals in Winter Haven and around

Our top choices for Winter Haven condo rentals

Vacation Village at Parkway
Aerial view

Vacation Village at Parkway

3.0 star property
8.6 out of 10, Excellent, (2794)
"Lovely property will stay here everytime"
The price is €98
includes taxes & fees
25 Aug - 26 Aug
Vacation Village at Parkway
Lifetime of Vacations Resort
Lake view

Lifetime of Vacations Resort

3.0 star property
9.4 out of 10, Exceptional, (144)
"Fairly quiet, beautiful view. We would 100% stay here again."
Lifetime of Vacations Resort
Windsor Hills Condo w/all things Mickey. Pool/Waterpark and minutes from Disney!
Outdoor pool, a heated pool

Windsor Hills Condo w/all things Mickey. Pool/Waterpark and minutes from Disney!

9.4 out of 10, Exceptional, (15)
"We enjoyed our stay. The location is beautiful, private, and safe. The pool is huge and great for all ages. The condo was spacious and our children loved the kids room with the different bed options. We plan to stay here again! "
Windsor Hills Condo w/all things Mickey. Pool/Waterpark and minutes from Disney!
Windsor Palms Resort Free wifi long size pool 3 miles to Disney new listing!
Pool

Windsor Palms Resort Free wifi long size pool 3 miles to Disney new listing!

9.8 out of 10, Exceptional, (49)
"Very nice place. Great place to stay. Owner is very easy to deal with. "
Windsor Palms Resort Free wifi long size pool 3 miles to Disney new listing!
Caribe Cove Resort
Outdoor pool, a heated pool

Caribe Cove Resort

3.5 star property
8.8 out of 10, Excellent, (2257)
"We had a great family vacation "
Caribe Cove Resort
Berkley Lake Townhomes
2 outdoor pools, a heated pool, open 8:00 AM to 7:00 PM, pool loungers

Berkley Lake Townhomes

3.0 star property
8.4 out of 10, Very good, (433)
"My kids love it "
Berkley Lake Townhomes
LD8830-12-308DC - 4Beds - 2Baths - Fabulous Condo Next to Disney
Pool

LD8830-12-308DC - 4Beds - 2Baths - Fabulous Condo Next to Disney

8.8 out of 10, Excellent, (8)
"Great place to stay"
LD8830-12-308DC - 4Beds - 2Baths - Fabulous Condo Next to Disney
Great Caribbean style condo near Disney
Exterior

Great Caribbean style condo near Disney

9.6 out of 10, Exceptional, (171)
"Nice property. Very clean. "
Great Caribbean style condo near Disney
New Floor! 2BR/2Bath Condo Near Disney–gated resort, free Wifi & parking
A heated pool

New Floor! 2BR/2Bath Condo Near Disney–gated resort, free Wifi & parking

9.4 out of 10, Exceptional, (122)
"Excellent place to stay and within minutes of everything. Will be staying at the same place again . Highly recommend "
New Floor! 2BR/2Bath Condo Near Disney–gated resort, free Wifi & parking
5 Star Resort minutes from Disney 3 bedrooms & 2 baths, Wi-Fi, Pool, Tennis
A heated pool

5 Star Resort minutes from Disney 3 bedrooms & 2 baths, Wi-Fi, Pool, Tennis

9.4 out of 10, Exceptional, (74)
"This property was a perfect fit for three long days of park hopping! The beds were very comfortable. The pool and clubhouse were very fun! We would stay here again!"
5 Star Resort minutes from Disney 3 bedrooms & 2 baths, Wi-Fi, Pool, Tennis
Windsor Poolside Escape with Stunning Pool View-Perfect for Families!
Outdoor pool

Windsor Poolside Escape with Stunning Pool View-Perfect for Families!

2.0 star property
10.0 out of 10, Exceptional, (294)
"This is a perfect place if you have 2 families because of the 2 king rooms! Super clean and had everything you need!! "
Windsor Poolside Escape with Stunning Pool View-Perfect for Families!
Dream Disney Family Vacation, Best Resort, 2 Miles To Disney, Space For 8
Exterior

Dream Disney Family Vacation, Best Resort, 2 Miles To Disney, Space For 8

9.2 out of 10, Wonderful, (139)
"We have stayed in this resort before for the proximity to Disney. The condo is clean and has enough bed space. "
Dream Disney Family Vacation, Best Resort, 2 Miles To Disney, Space For 8
3 Bedrooms Condo Only Minutes From Disney!
Pool

3 Bedrooms Condo Only Minutes From Disney!

10.0 out of 10, Exceptional, (6)
"The accommodations were exactly as displayed and Steve did a great job of making sure our stay was enjoyable. The pool and water slides were great! "
3 Bedrooms Condo Only Minutes From Disney!
The Azur Resort
Townhome, 6 Bedrooms | View from room

The Azur Resort

4.0 star property
8.4 out of 10, Very good, (36)
"everything is very clean stores and dining are nearby"
The Azur Resort
Fully Remodeled~Windsor Hills~2.5 Miles from Disney World Main Entrance
Exterior

Fully Remodeled~Windsor Hills~2.5 Miles from Disney World Main Entrance

10.0 out of 10, Exceptional, (158)
"Unit was clean and very entertaing for our kids. Great location!"
Fully Remodeled~Windsor Hills~2.5 Miles from Disney World Main Entrance
Stylish 2 bed condo in Oakwater Resort just 2 miles from Disney World!
Exterior

Stylish 2 bed condo in Oakwater Resort just 2 miles from Disney World!

9.4 out of 10, Exceptional, (112)
"For my family of 4 this was our first trip to Disney World and this location is great! The condo itself was a nice, very comfortable and had everything we needed."
Stylish 2 bed condo in Oakwater Resort just 2 miles from Disney World!
'Incredible' family friendly 3 bed condo with bunk beds!!!! 5 mins from Disney.
Exterior

'Incredible' family friendly 3 bed condo with bunk beds!!!! 5 mins from Disney.

9.4 out of 10, Exceptional, (131)
"We’ve stayed at Windsor hills before and love it. I understand that it’s a self sufficient unit but we’re a bit disappointed in the few supplies in the kitchen. Other then that, it’s a great location and we plan to return. "
'Incredible' family friendly 3 bed condo with bunk beds!!!! 5 mins from Disney.
2-bedroom condo in phenomenal Kissimmee with WiFi, fitness room, AC
Microwave, oven, stovetop, dishwasher

2-bedroom condo in phenomenal Kissimmee with WiFi, fitness room, AC

9.6 out of 10, Exceptional, (4)
"Cozy place, close to the parks. Very clean and the neighborhood is very quiet. "
2-bedroom condo in phenomenal Kissimmee with WiFi, fitness room, AC
Beautiful 2 bed/2 bath condo in Windsor Hills Resort, just 2 miles to Disney!
Exterior

Beautiful 2 bed/2 bath condo in Windsor Hills Resort, just 2 miles to Disney!

8.8 out of 10, Excellent, (88)
"Very nice stay in an adequate condo. Condo had minor issues such as torn screens, prior water damage, etc. we were told that visitors such as our grandkids would not eligible to use the amenities such as the pool."
Beautiful 2 bed/2 bath condo in Windsor Hills Resort, just 2 miles to Disney!
2 Bd - 2 Ba Condo 1 1/2 Miles From Disney World and 10 miles from Universal.
Outdoor pool, a heated pool

2 Bd - 2 Ba Condo 1 1/2 Miles From Disney World and 10 miles from Universal.

9.6 out of 10, Exceptional, (144)
"Another great stay at Windsor Hill! Loved the unit & great communication with the host. "
2 Bd - 2 Ba Condo 1 1/2 Miles From Disney World and 10 miles from Universal.
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Winter Haven Hotel Reviews

Omni Orlando Resort at ChampionsGate

Omni Orlando Resort at ChampionsGate

10/10 Excellent
"Stay was so relaxing. "
Stacey 2-night trip
Posted 23 hours ago
Omni Orlando Resort at ChampionsGate

Frequently asked questions

How much do condos in Winter Haven cost?
Condos in Winter Haven range from €98 to €98 per night. These stays offer loads of space for the entire family at a price that's easy on your wallet. These prices were available on Expedia within the past 7 days, for a hotel booking with a check-in date within the next year. Prices reflect current offers and availability is subject to change. Additional terms may apply.
How many condos are there in Winter Haven?
Work out your holiday dates and then pick from 3385 condos in Winter Haven. For official business travel, a weekend escape or anything in between, Expedia can help you find the right place in just a few clicks.
Are there any family-friendly condos in Winter Haven?
You bet! Look up Vsm4 Sd1947 4 Bedroom Home By Redawning — a great 3.5-star option located a quick drive from downtown Winter Haven. This family-friendly condo comes with conveniences such as a swimming pool and WiFi. Winter Haven has no shortage of family-friendly attractions to discover that'll keep the kids entertained. LEGOLAND® Florida and Theatre Winter Haven deliver fun for travellers young and old.