A castle entrance with flags and banners, including a LEGO Kingdoms banner.

Search Condos Rentals in Winter Haven from CA $128

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Check prices for these dates

In two weeks
Sep 18 - Sep 20
In two months
Oct 30 - Nov 1
In three months
Nov 27 - Nov 29
In four months
Dec 25 - Dec 27

Our top choices for Winter Haven condo rentals

A resort pool area with multiple swimming pools, palm trees, and lounge chairs.

1. Luxury 2bd/2 bath Condo Home 232

Luxury 2bd/2 bath Condo Home 232
davenport
8.0 out of 10, Very good, (7 reviews)
"Place was great. "
United States
Brad K.
The price is CA $96
CA $603 total
includes taxes & fees
Sep 26 - Sep 27
Luxury 2bd/2 bath Condo Home 232
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
9.0 out of 10, Wonderful, (12 reviews)
"Great view, comfortable room for our one night stay."
United States
Vern H.
The price is CA $167
CA $215 total
includes taxes & fees
Oct 5 - Oct 6
Lake View•Gardens•Private Balcony Suite•Legoland
An aerial view of a resort with a large central swimming pool, multiple lounge areas, and a small lake.

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

Cozy 3BR condo w/ pool, hot tub & balcony
Poinciana
The price is CA $104
CA $468 total
includes taxes & fees
Sep 13 - Sep 14
Cozy 3BR condo w/ pool, hot tub & balcony
A resort pool area with multiple swimming pools, palm trees, and lounge chairs.

4. Brand New 2bd/2 bth condo 300

Brand New 2bd/2 bth condo 300
davenport
9.8 out of 10, Exceptional, (10 reviews)
"Super clean. ~5min drive to all essentials. Quiet and private!"
United States
Jasmin
The price is CA $93
CA $594 total
includes taxes & fees
Sep 30 - Oct 1
Brand New 2bd/2 bth condo 300
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
The price is CA $144
CA $369 total
includes taxes & fees
Sep 8 - Sep 9
Bahama Bay 515 Rum run unit 515
A resort pool area with multiple swimming pools, palm trees, and lounge chairs.

6. Cozy, Brand-New 2BR Getaway at ChampionsGate – 291

Cozy, Brand-New 2BR Getaway at ChampionsGate – 291
Davenport
9.6 out of 10, Exceptional, (7 reviews)
"Correspondence was good, Listed accurate, clean and comfy! Thank you! Enjoyed our time there...the Oasis pools were amazing!"
United States
Thomas K.
The price is CA $68
CA $561 total
includes taxes & fees
Sep 8 - Sep 9
Cozy, Brand-New 2BR Getaway at ChampionsGate – 291
A resort pool area with multiple swimming pools, palm trees, and lounge chairs.

7. Beautiful Condo 3/2 close to disney parks

Beautiful Condo 3/2 close to disney parks
Kissimmee
10.0 out of 10, Exceptional, (1 review)
"We had a lovely stay and truly enjoyed the quiet, cute atmosphere of the home. The Oasis Club, and kids waterpark were highlights. Unfortunately we didn't make time for the park located right in front of the house but it was a great park! The management team was incredibly accommodating, easily handling last-minute guest requests for my son’s birthday. Check-in was a breeze. However, the property fell short regarding cleanliness and maintenance. The carpets felt greasy and stained, and the...
United States
Tiffany O.
The price is CA $67
CA $566 total
includes taxes & fees
Sep 9 - Sep 10
Beautiful Condo 3/2 close to disney parks
A modern living room with a flat-screen TV, a sofa, a coffee table, and a floor lamp.

8. 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, (2 reviews)
"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.
The price is CA $199
CA $424 total
includes taxes & fees
Sep 8 - Sep 9
Lovely 3-bedroom condo with AC in charming Lakeland
A resort pool area with multiple swimming pools, palm trees, and lounge chairs.

9. Luxury 3 Bedroom 2 bath Condo Home 241

Luxury 3 Bedroom 2 bath Condo Home 241
Reunion
9.8 out of 10, Exceptional, (6 reviews)
"Lovely place, very clean and comfortable."
United States
Christine R.
The price is CA $89
CA $625 total
includes taxes & fees
Sep 9 - Sep 10
Luxury 3 Bedroom 2 bath Condo Home 241
A swimming pool with a clear blue water, surrounded by palm trees and lounge chairs.

10. Incredible Renovated home located near all !!

Incredible Renovated home located near all !!
Champions Gate
6.0 out of 10, (8 reviews)
"We really enjoyed Melissa’s condo Deja Blue. Quite pretty inside and quiet surroundings. Beds are comfortable, plenty of towels available, most things you need for a stay are provided. A few things in the condo could be updated but overall we had a great month in this unit and love the Champions Gate area for walking and dining."
United States
Susan K.
The price is CA $100
CA $343 total
includes taxes & fees
Sep 8 - Sep 9
Incredible Renovated home located near all !!
A hallway with a white door, a mounted television, a dark wooden bench with storage, and a light-colored rug.

11. 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.
The price is CA $173
CA $438 total
includes taxes & fees
Sep 17 - Sep 18
Toria Suites 920
A resort pool area with multiple swimming pools, palm trees, and lounge chairs.

12. Beautiful 2BD/2 Bath Condo Home 221

Beautiful 2BD/2 Bath Condo Home 221
Reunion
8.4 out of 10, Very good, (16 reviews)
"Didn't use the pool.Very nice, a little over priced"
United States
Duane S.
The price is CA $81
CA $584 total
includes taxes & fees
Sep 13 - Sep 14
Beautiful 2BD/2 Bath Condo Home 221
A swimming pool surrounded by palm trees and lounge chairs, with a building in the background.

13. 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.
The price is CA $118
CA $400 total
includes taxes & fees
Sep 8 - Sep 9
Near Disney/Resort Pool, Bar & Gym
A large, light blue building with a central entrance and a small balcony.

14. Reunion Resort - Near Theme Parks & Airport

Reunion Resort - Near Theme Parks & Airport
Reunion
9.6 out of 10, Exceptional, (61 reviews)
"Very comfortable and convenient!"
United States
NQuavah V.
The price is CA $125
CA $469 total
includes taxes & fees
Sep 13 - Sep 14
Reunion Resort - Near Theme Parks & Airport
A swimming pool with lounge chairs, palm trees, and a clear blue sky.

15. Spacious & Peaceful Condo Near Champions Gate.

Spacious & Peaceful Condo Near Champions Gate.
Champions Gate
10.0 out of 10, Exceptional, (4 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.
The price is CA $103
CA $321 total
includes taxes & fees
Sep 8 - Sep 9
Spacious & Peaceful Condo Near Champions Gate.
A room with a bed, a table with a plant, a lamp, and a window with curtains.

16. Lyrios Vacation Rentals - The Palms

Lyrios Vacation Rentals - The Palms
4.0 star property
Kissimmee
The price is CA $137
CA $280 total
includes taxes & fees
Sep 8 - Sep 9
Lyrios Vacation Rentals - The Palms
A resort pool area with multiple swimming pools, palm trees, and lounge chairs.

17. Brand New Luxury 2 Bedroom Condo (321)

Brand New Luxury 2 Bedroom Condo (321)
DAVENPORT
10.0 out of 10, Exceptional, (2 reviews)
"Nice location that is in a gated community "
United States
Amanda O.
The price is CA $92
CA $598 total
includes taxes & fees
Sep 28 - Sep 29
Brand New Luxury 2 Bedroom Condo (321)
A two-story residential building with a well-maintained lawn, a covered patio, and a small outdoor seating area.

18. Resort stay~Pool Access~Peaceful Retreat~Balcony

Resort stay~Pool Access~Peaceful Retreat~Balcony
Kissimmee
10.0 out of 10, Exceptional, (3 reviews)
"The host was very nice and helpful The rooms were very clean Enjoyed our stay Would stay again"
United States
Anonymous traveller
The price is CA $93
CA $508 total
includes taxes & fees
Oct 1 - Oct 2
Resort stay~Pool Access~Peaceful Retreat~Balcony
A resort pool area with multiple swimming pools, palm trees, and lounge chairs.

19. Luxury 3 Bedroom Condo w Balcony 372

Luxury 3 Bedroom Condo w Balcony 372
DAVENPORT
9.6 out of 10, Exceptional, (5 reviews)
"Very nice place to stay"
United States
ricky h.
Luxury 3 Bedroom Condo w Balcony 372
A resort pool area with multiple swimming pools, palm trees, and lounge chairs.

20. 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.
The price is CA $62
CA $587 total
includes taxes & fees
Sep 8 - Sep 9
Breathtaking View 3 Bd/2 bath Resort Condo 191
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

The Grove Resort & Water Park Orlando

The Grove Resort & Water Park Orlando

10/10 Excellent
"Really enjoyed our stay. This resort is highly recommended. My family really enjoyed their selves."
Nancy 2-night trip
Posted 1 hour ago
The Grove Resort & Water Park Orlando

Find out more about Winter Haven

Winter Haven Condo Rentals information

Number of reviews
357
Accommodation
3419 Condo Rentals
Lowest Price
CA $128
Highest Price
CA $369

Frequently asked questions

How much do condos in Winter Haven cost?
Condos in Winter Haven range from CA $128 to CA $369 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 3419 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.
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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