Search and Rent Winter Haven Condos

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Our top choices for Winter Haven condo rentals

Vacation Village Orlando, Celebration

Vacation Village Orlando, Celebration
3.0 star property
Kissimmee
8.6 out of 10, Excellent, (3142)
"Great place to stay"
United States
Jose
$133 nightly
The price is $150
Jan 13 - Jan 14, 2026
Total with taxes and fees
Vacation Village Orlando, Celebration

Lake View•Gardens•Private Balcony Suite•Legoland

Lake View•Gardens•Private Balcony Suite•Legoland
2.0 star property
Lake Wales
10.0 out of 10, Exceptional, (3)
"Great view, comfortable room for our one night stay."
United States
Vern H.
$116 nightly
The price is $127
Jan 14 - Jan 15, 2026
Total with taxes and fees
Lake View•Gardens•Private Balcony Suite•Legoland

Dazzling Newly Renovated Condo 1.5 miles to Disney

Dazzling Newly Renovated Condo 1.5 miles to Disney
Kissimmee
9.4 out of 10, Exceptional, (86)
"This place was awesome! Incredibly clean floors. I even called my sister just to show her how clean the floors were. "
United States
Elizabeth P L.
$152 nightly
The price is $170
Jan 4 - Jan 5, 2026
Total with taxes and fees
Dazzling Newly Renovated Condo 1.5 miles to Disney

Newly Remodeled 2-bedroom Family-sized condo 15 minutes to the theme park

Newly Remodeled 2-bedroom Family-sized condo 15 minutes to the theme park
2.0 star property
Champions Gate
10.0 out of 10, Exceptional, (1)
"Nice place in a great area. Plenty of restaurants nearby. We were evacuating from St Pete ahead of Milton with my wife, MIL and cat. Both bedrooms were nice and MIL and kitty really enjoyed the large couch in the living room. "
United States
David K.
$295 nightly
The price is $329
Jan 6 - Jan 7, 2026
Total with taxes and fees
Newly Remodeled 2-bedroom Family-sized condo 15 minutes to the theme park

Stylish Retreat/86`TV/King Bed/Spa Shower/Shuffleboard/Near the Lake

Stylish Retreat/86`TV/King Bed/Spa Shower/Shuffleboard/Near the Lake
Lake Wales
10.0 out of 10, Exceptional, (1)
"Had an amazing stay! Property was exactly how it was described- clean, comfortable, very safe. (As a solo woman traveling alone feeling safe always makes a trip easier) The bed and sheets were sooo comfortable! Micki was kind, attentive, incredibly responsive and happily accommodated me, making my entire experience was seamless. I felt right at home, would happily return. 5 Stars is not enough to describe how wonderful Micki is as host!"
United States
Anonymous traveler
$136 nightly
The price is $149
Jan 13 - Jan 14, 2026
Total with taxes and fees
Stylish Retreat/86`TV/King Bed/Spa Shower/Shuffleboard/Near the Lake

Parkway Palms Resort 1 bedroom condo mins to Disney World.

Parkway Palms Resort 1 bedroom condo mins to Disney World.
Kissimmee
10.0 out of 10, Exceptional, (1)
"The condo is ideally located for Disney World with many restaurants close by. The property manager was quick to respond to any questions and we would definitely stay there again."
United States
Michael G.
$357 nightly
The price is $384
Jan 7 - Jan 8, 2026
Total with taxes and fees
Parkway Palms Resort 1 bedroom condo mins to Disney World.

Resort stay~Pool Access~Peaceful Retreat~Balcony

Resort stay~Pool Access~Peaceful Retreat~Balcony
2.0 star property
Kissimmee
10.0 out of 10, Exceptional, (1)
"The host was very nice and helpful The rooms were very clean Enjoyed our stay Would stay again"
United States
Anonymous traveler
$346 nightly
The price is $350
Jan 24 - Jan 25, 2026
Total with taxes and fees
Resort stay~Pool Access~Peaceful Retreat~Balcony

BEAUTIFULLY remodeled 3/2 condo near DISNEY and MARGARITAVILLE RESORT!⭐️⭐️⭐️⭐️⭐️

BEAUTIFULLY remodeled 3/2 condo near DISNEY and MARGARITAVILLE RESORT!⭐️⭐️⭐️⭐️⭐️
Kissimmee
10.0 out of 10, Exceptional, (12)
"Enjoyed everything!"
United States
Caroline W.
$261 nightly
The price is $291
Jan 5 - Jan 6, 2026
Total with taxes and fees
BEAUTIFULLY remodeled 3/2 condo near DISNEY and MARGARITAVILLE RESORT!⭐️⭐️⭐️⭐️⭐️

Reunion Resort - Near Theme Parks & Airport

Reunion Resort - Near Theme Parks & Airport
Reunion
9.6 out of 10, Exceptional, (51)
"This was a beautiful property with all the amentities and space. "
United States
Derica N.
$329 nightly
The price is $367
Jan 2 - Jan 3, 2026
Total with taxes and fees
Reunion Resort - Near Theme Parks & Airport

Near Disney/Resort Pool, Bar & Gym

Near Disney/Resort Pool, Bar & Gym
Champions Gate
9.2 out of 10, Wonderful, (5)
"The property was great.. very clean and relaxing"
Canada
Dawn D.
$254 nightly
The price is $284
Jan 19 - Jan 20, 2026
Total with taxes and fees
Near Disney/Resort Pool, Bar & Gym

Spacious condo near Walt Disney parks & AdventHealth - Kissimmee Florida

Spacious condo near Walt Disney parks & AdventHealth - Kissimmee Florida
2.0 star property
Kissimmee
10.0 out of 10, Exceptional, (1)
"Wonderful location and great accommodations."
United States
Frank L.
Spacious condo near Walt Disney parks & AdventHealth - Kissimmee Florida

Modern Award Winning Newly Renovated, Gorgeous 2+2 Minutes Away From Disney

Modern Award Winning Newly Renovated, Gorgeous 2+2 Minutes Away From Disney
Kissimmee
9.2 out of 10, Wonderful, (150)
"Great place! Close to everything we wanted to do, hosts were easy to communicate with, place was clean and the community felt safe and secure as a woman traveling with her kiddo. I would absolutely stay again!"
United States
Hope M.
$181 nightly
The price is $203
Jan 4 - Jan 5, 2026
Total with taxes and fees
Modern Award Winning Newly Renovated, Gorgeous 2+2 Minutes Away From Disney

Sophisticated Retreat

Sophisticated Retreat
Kissimmee
9.4 out of 10, Exceptional, (6)
"Amazing! I will be staying here again!"
United States
MikeD
$174 nightly
The price is $195
Jan 12 - Jan 13, 2026
Total with taxes and fees
Sophisticated Retreat

Family-Friendly Condo with Pool & Sauna

Family-Friendly Condo with Pool & Sauna
Winter Garden
10.0 out of 10, Exceptional, (1)
"This 2 bedroom apartment was perfect for us. Clean and well kept. Very spacious rooms with comfortable beds. I would recommend this place. "
United States
Samuel L.
$240 nightly
The price is $270
Jan 6 - Jan 7, 2026
Total with taxes and fees
Family-Friendly Condo with Pool & Sauna

Valentina’s Condo-Resort Style!

Valentina’s Condo-Resort Style!
Kissimmee
10.0 out of 10, Exceptional, (6)
"Nice neighborhood, local pool and condo. Would stay again."
United States
Jason M.
$205 nightly
The price is $229
Jan 14 - Jan 15, 2026
Total with taxes and fees
Valentina’s Condo-Resort Style!

Splendid Renovated 2 + 2 Condo Near Disney with Amazing Amenities

Splendid Renovated 2 + 2 Condo Near Disney with Amazing Amenities
2.0 star property
Champions Gate
9.6 out of 10, Exceptional, (29)
"Host was very communicative, simple check in & check out. Will stay again at this property. "
United States
Anonymous traveler
Splendid Renovated 2 + 2 Condo Near Disney with Amazing Amenities

Lake View, Heated Pool, King Bed, Free Parking, Resort Condo.

Lake View, Heated Pool, King Bed, Free Parking, Resort Condo.
Kissimmee
8.0 out of 10, Very Good, (4)
"Location, privacy, security all as desired."
United States
Thomas S.
$174 nightly
The price is $195
Jan 11 - Jan 12, 2026
Total with taxes and fees
Lake View, Heated Pool, King Bed, Free Parking, Resort Condo.

Upstay Champions Gate Home w Private Pool & BBQ

Upstay Champions Gate Home w Private Pool & BBQ
2.0 star property
Davenport
9.2 out of 10, Wonderful, (7)
"It is a beautiful house, very clean, with all its comforts, 100% recommended. ❤️"
United States
Ana C.
$330 nightly
The price is $369
Jan 11 - Jan 12, 2026
Total with taxes and fees
Upstay Champions Gate Home w Private Pool & BBQ

Luxury Condominium in Kissimmee Florida near Walt Disney World

Luxury Condominium in Kissimmee Florida near Walt Disney World
Kissimmee
10.0 out of 10, Exceptional, (4)
"We did a quick overnight. The condo was beautifully decorated and very clean. Location was great and close to everything. The host Elle was wonderful and quick to respond with questions. We would definitely stay here again. "
United States
Harold W.
$198 nightly
The price is $221
Jan 3 - Jan 4, 2026
Total with taxes and fees
Luxury Condominium in Kissimmee Florida near Walt Disney World

5 Min to Disney! 2BR Condo w/ King Bed, Pool, Fast WiFi & SmartTV+kitchen+washer

5 Min to Disney! 2BR Condo w/ King Bed, Pool, Fast WiFi & SmartTV+kitchen+washer
Kissimmee
10.0 out of 10, Exceptional, (1)
$237 nightly
The price is $265
Jan 27 - Jan 28, 2026
Total with taxes and fees
5 Min to Disney! 2BR Condo w/ King Bed, Pool, Fast WiFi & SmartTV+kitchen+washer
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

Find out more about Winter Haven

Winter Haven Condo Rentals information

Number of reviews
3,431
Accommodation
3445 Condo Rentals
Lowest Price
$127
Highest Price
$384

Frequently asked questions

How much do condos in Winter Haven cost?
Condos in Winter Haven range from $127 to $384 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 vacation dates and then pick from 3445 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 travelers young and old.
Why book your condo in Winter Haven with Expedia?
Reserving a condo in Winter Haven is as easy as clicking on your travel dates and picking an option that suits your style. After something inexpensive or upscale, or a stay that also comes with a kitchen and laundry? Use Expedia's search filters to narrow your results even further and find your ideal match.
How can I find cheap condos in Winter Haven?
The simplest way to track down cheap condos in Winter Haven is with Expedia's convenient filter tool. Refine your search results by budget, amenities and star rating to discover unbeatable deals in just a few clicks.
What is there to do in Winter Haven near my condo?
Winter Haven has enough sights and activities to keep you on the hop for weeks, beginning with Indigo's Family Fun Center. Lake Henry Golf Club, Cypresswood Golf and Country Club and LEGOLAND® Florida are other renowned attractions. If you're in town for longer, Chain of Lakes Park and Theatre Winter Haven are worthwhile additions to your itinerary.

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