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Check prices for these dates

In two weeks
Sep 4 - Sep 6
In two months
Oct 16 - Oct 18
In three months
Nov 13 - Nov 15
In four months
Dec 11 - Dec 13

Our top choices for Winter Haven condo rentals

An aerial view of a resort with a large central swimming pool, multiple lounge areas, and a small lake.

1. Cozy 3BR condo w/ pool, hot tub & balcony

Cozy 3BR condo w/ pool, hot tub & balcony
Poinciana
$332 nightly
The price is $341
Aug 24 - Aug 25
Total with taxes and fees
Cozy 3BR condo w/ pool, hot tub & balcony
A bedroom with a stone fireplace, a large bed, and a view of the outdoors through large windows.

2. Lake View•Gardens•Private Balcony Suite•Legoland

Lake View•Gardens•Private Balcony Suite•Legoland
Lake Wales
9.2 out of 10, Wonderful, (11 reviews)
"Great view, comfortable room for our one night stay."
United States
Vern H.
$139 nightly
The price is $154
Sep 3 - Sep 4
Total with taxes and fees
Lake View•Gardens•Private Balcony Suite•Legoland
A living room with a dark grey sofa set, a dining table with chairs, and a patterned rug.

3. Toria Suites Condo 924

Toria Suites Condo 924
East Lake Morton
9.0 out of 10, Wonderful, (2 reviews)
"Centrally located in the city, quiet. "
United States
Brian L.
$280 nightly
The price is $310
Aug 26 - Aug 27
Total with taxes and fees
Toria Suites Condo 924
A modern living room with a flat-screen TV, a sofa, a coffee table, and a floor lamp.

4. Lovely 3-bedroom condo with AC in charming Lakeland

Lovely 3-bedroom condo with AC in charming Lakeland
Lakeland
10.0 out of 10, Exceptional, (1 review)
"My family and I booked this property for a couple of days. Upon arrival, the property was clean and well maintained. The linens and towels were immaculate and abundant. We did not have any difficulties communicating with the owner, check in was seamless. For safety reasons, we would suggest dusk to dawn lightening at the entrance. Over all, our stay was pleasant and we look forward to booking this property again when in town!!!!!!"
United States
Norman S.
$316 nightly
The price is $349
Aug 23 - Aug 24
Total with taxes and fees
Lovely 3-bedroom condo with AC in charming Lakeland
A resort with a large swimming pool, lounge chairs, and a view of a large body of water.

5. Bahama Bay 515 Rum run unit 515

Bahama Bay 515 Rum run unit 515
2.0 star property
Bahama Bay
10.0 out of 10, Exceptional, (2 reviews)
"The apartment is very nice, closed to Disney World resort, while in a quiet community."
United States
Joyce
$238 nightly
The price is $266
Aug 24 - Aug 25
Total with taxes and fees
Bahama Bay 515 Rum run unit 515

6. Cute GameRoom/ Waterpark/ Clubhouses

Cute GameRoom/ Waterpark/ Clubhouses
Champions Gate
$306 nightly
The price is $343
Aug 24 - Aug 25
Total with taxes and fees
Cute GameRoom/ Waterpark/ Clubhouses
A resort with a central swimming pool, palm trees, and a building with a red-tiled roof.

7. Luxurious Living at Your Fingertips with King bed

Luxurious Living at Your Fingertips with King bed
Champions Gate
10.0 out of 10, Exceptional, (1 review)
"This was a last minute booking but it turned out great. We were in town for a trade show and this fit me and my colleague perfectly. "
United States
Theresa M.
$317 nightly
The price is $354
Aug 29 - Aug 30
Total with taxes and fees
Luxurious Living at Your Fingertips with King bed
A large, light blue building with a central entrance and a small balcony.

8. Reunion Resort - Near Theme Parks & Airport

Reunion Resort - Near Theme Parks & Airport
Reunion
9.6 out of 10, Exceptional, (61 reviews)
"the pool and gated access made the stay even better. Communication was smooth, and the check-in process was simple and stress-free. The space felt welcoming and worked perfectly for a relaxing getaway. We’d definitely recommend it to anyone looking for a comfortable place to stay."
United States
mupenzi b.
$286 nightly
The price is $319
Aug 24 - Aug 25
Total with taxes and fees
Reunion Resort - Near Theme Parks & Airport
An aerial view of a resort with multiple swimming pools, sun loungers, and palm trees.

9. Harry Potter/ Water Fun / Console-Ready Stay

Harry Potter/ Water Fun / Console-Ready Stay
Four Corners
10.0 out of 10, Exceptional, (1 review)
$306 nightly
The price is $343
Aug 26 - Aug 27
Total with taxes and fees
Harry Potter/ Water Fun / Console-Ready Stay
An outdoor seating area with wicker furniture, a fire feature, and palm trees.

10. New! Seven Eagles Hideaway at Reunion Resort

New! Seven Eagles Hideaway at Reunion Resort
Reunion
$317 nightly
The price is $354
Aug 22 - Aug 23
Total with taxes and fees
New! Seven Eagles Hideaway at Reunion Resort
A swimming pool with a central fountain, surrounded by palm trees and lounge chairs.

11. 1st Floor • Free Parking • No Resort Fees • 14 minutes to Disney • 5 min shops

1st Floor • Free Parking • No Resort Fees • 14 minutes to Disney • 5 min shops
Kissimmee
10.0 out of 10, Exceptional, (3 reviews)
"This was a great location it was close to all the places we wanted to visit. Looking forward to our next trip."
United States
Tammy H.
$240 nightly
The price is $269
Aug 24 - Aug 25
Total with taxes and fees
1st Floor • Free Parking • No Resort Fees • 14 minutes to Disney • 5 min shops
A swimming pool surrounded by palm trees and lounge chairs, with a building in the background.

12. Near Disney/Resort Pool, Bar & Gym

Near Disney/Resort Pool, Bar & Gym
Champions Gate
8.6 out of 10, Excellent, (9 reviews)
"The place was very nice. The hostess was very attentive and quick to respond. It is close to restaurants and everything you need. We would definitely stay here again. "
United States
Saul T.
$259 nightly
The price is $289
Aug 25 - Aug 26
Total with taxes and fees
Near Disney/Resort Pool, Bar & Gym
An aerial view of a resort with multiple swimming pools, sun loungers, and palm trees.

13. Cozy Family ThemedRoom/Waterpark/Garage

Cozy Family ThemedRoom/Waterpark/Garage
Reunion
8.0 out of 10, Very Good, (3 reviews)
"Awesome could not get tv to work without putting my personal information not enough toilet paper or trash bags for the stay but otherwise great pool a little cool but would stay again"
United States
Adelita j.
$306 nightly
The price is $343
Aug 23 - Aug 24
Total with taxes and fees
Cozy Family ThemedRoom/Waterpark/Garage
An aerial view of a resort with multiple swimming pools, sun loungers, and palm trees.

14. Four Corners Condo: Parks, Pool & Family Fun!

Four Corners Condo: Parks, Pool & Family Fun!
Four Corners
$303 nightly
The price is $340
Aug 25 - Aug 26
Total with taxes and fees
Four Corners Condo: Parks, Pool & Family Fun!

15. 2 Bedrooms/ 2 Bathrooms/ Champions Gate (897 OA)

2 Bedrooms/ 2 Bathrooms/ Champions Gate (897 OA)
Davenport
$332 nightly
The price is $369
Sep 2 - Sep 3
Total with taxes and fees
2 Bedrooms/ 2 Bathrooms/ Champions Gate (897 OA)
An aerial view of a resort with multiple swimming pools, sun loungers, and palm trees.

16. Dreamy ThemedRoom/GameRoom/Waterpark

Dreamy ThemedRoom/GameRoom/Waterpark
Four Corners
$302 nightly
The price is $339
Aug 26 - Aug 27
Total with taxes and fees
Dreamy ThemedRoom/GameRoom/Waterpark
A hallway with a white door, a mounted television, a dark wooden bench with storage, and a light-colored rug.

17. Toria Suites 920

Toria Suites 920
East Lake Morton
9.8 out of 10, Exceptional, (6 reviews)
"Was a great area to be in with food and nice places to walk within walking distance"
United States
Troy M.
$291 nightly
The price is $322
Aug 24 - Aug 25
Total with taxes and fees
Toria Suites 920

18. King Bed. Heated Pool. Fast Wi-Fi. Free Parking. Near Disney/Universal.

King Bed. Heated Pool. Fast Wi-Fi. Free Parking. Near Disney/Universal.
Kissimmee
10.0 out of 10, Exceptional, (1 review)
"The property was perfect! Matched the description right on. Julie was great at communicating with us. We will definitely stay here again next time we visit our daughter. Thanks Julie"
United States
scott l.
$179 nightly
The price is $200
Aug 23 - Aug 24
Total with taxes and fees
King Bed. Heated Pool. Fast Wi-Fi. Free Parking. Near Disney/Universal.
A resort pool area with multiple swimming pools, palm trees, and lounge chairs.

19. Breathtaking View 3 Bd/2 bath Resort Condo 191

Breathtaking View 3 Bd/2 bath Resort Condo 191
Kissimmee
9.0 out of 10, Wonderful, (22 reviews)
"So cozy and clean and the view was beautiful! Will definitely stay here again!"
United States
Karina R.
$408 nightly
The price is $445
Aug 29 - Aug 30
Total with taxes and fees
Breathtaking View 3 Bd/2 bath Resort Condo 191
A swimming pool with lounge chairs, palm trees, and a clear blue sky.

20. Spacious & Peaceful Condo Near Champions Gate.

Spacious & Peaceful Condo Near Champions Gate.
Champions Gate
10.0 out of 10, Exceptional, (3 reviews)
"Andrea did a wonderful job keeping us infoormed of what we needed to know for our stay. She was helpful and very accommodating to our needs.We would highly recommend her condo for anyone wanting to stay just a short drive from all that Orlando has to offer."
United States
Alicia T.
$207 nightly
The price is $232
Sep 8 - Sep 9
Total with taxes and fees
Spacious & Peaceful Condo Near Champions Gate.
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

Holiday Inn Club Vacations at Orange Lake Resort by IHG

Holiday Inn Club Vacations at Orange Lake Resort by IHG

8/10 Good
"All the staff I encountered were super friendly except some pool staff who treated guests like little kids when it was time to close the pool for the day."
Sarah 10-night trip
Posted less than an hour ago
Holiday Inn Club Vacations at Orange Lake Resort by IHG

Find out more about Winter Haven

Winter Haven Condo Rentals information

Number of reviews
125
Accommodation
3238 Condo Rentals
Lowest Price
$154
Highest Price
$445

Frequently asked questions

How much do condos in Winter Haven cost?
Condos in Winter Haven range from $154 to $445 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 3238 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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