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

Search Condos Rentals in Winter Haven

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Save instantly and earn perks with One Key
    Learn about One Key

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
25 Sept - 27 Sept
In two months
6 Nov - 8 Nov
In three months
4 Dec - 6 Dec
In four months
1 Jan - 3 Jan

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 £304
includes taxes & fees
11 Sept - 12 Sept
Luxury 2bd/2 bath Condo Home 232
A modern living room with a flat-screen TV, a sofa, a coffee table, and a floor lamp.

2. 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 £231
includes taxes & fees
10 Sept - 11 Sept
Lovely 3-bedroom condo with AC in charming Lakeland
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.
The price is £233
includes taxes & fees
13 Sept - 14 Sept
Toria Suites Condo 924
A bedroom with a stone fireplace, a large bed, and a view of the outdoors through large windows.

4. 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 £118
includes taxes & fees
5 Oct - 6 Oct
Lake View•Gardens•Private Balcony Suite•Legoland
A resort pool area with multiple swimming pools, palm trees, and lounge chairs.

5. 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 £333
includes taxes & fees
10 Sept - 11 Sept
Luxury 3 Bedroom 2 bath Condo Home 241
A resort pool area with multiple swimming pools, palm trees, and lounge chairs.

6. 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 £311
includes taxes & fees
10 Sept - 11 Sept
Beautiful Condo 3/2 close to disney parks
A resort with a large swimming pool, lounge chairs, and a view of a large body of water.

7. 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 £197
includes taxes & fees
22 Sept - 23 Sept
Bahama Bay 515 Rum run unit 515
A swimming pool with a clear blue water, surrounded by palm trees and lounge chairs.

8. 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 £187
includes taxes & fees
13 Sept - 14 Sept
Incredible Renovated home located near all !!
A resort pool area with multiple swimming pools, palm trees, and lounge chairs.

9. Pet-Friendly Luxury Resort Condo Near Disney

Pet-Friendly Luxury Resort Condo Near Disney
Davenport
9.0 out of 10, Wonderful, (2 reviews)
"Amazing condo! It was very clean and everything looked brand new. I would definitely recommend. I would absolutely stay again."
United States
Angela F.
The price is £320
includes taxes & fees
28 Sept - 29 Sept
Pet-Friendly Luxury Resort Condo Near Disney
A swimming pool surrounded by palm trees and lounge chairs, with a building in the background.

10. 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 £216
includes taxes & fees
12 Sept - 13 Sept
Near Disney/Resort Pool, Bar & Gym
A resort pool area with multiple swimming pools, palm trees, and lounge chairs.

11. 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 £323
includes taxes & fees
10 Sept - 11 Sept
Breathtaking View 3 Bd/2 bath Resort Condo 191
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 £315
includes taxes & fees
11 Sept - 12 Sept
Beautiful 2BD/2 Bath Condo Home 221
A swimming pool with lounge chairs, palm trees, and a clear blue sky.

13. 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 £186
includes taxes & fees
8 Oct - 9 Oct
Spacious & Peaceful Condo Near Champions Gate.

14. Elegant Escape/ Gameroom & Themed Room

Elegant Escape/ Gameroom & Themed Room
Four Corners
10.0 out of 10, Exceptional, (1 review)
"Loved it!"
United States
Jakeysiya D.
The price is £248
includes taxes & fees
10 Sept - 11 Sept
Elegant Escape/ Gameroom & Themed Room

15. Scenic Resort Home Close to Disney and Universal

Scenic Resort Home Close to Disney and Universal
Kissimmee
10.0 out of 10, Exceptional, (1 review)
"Would 1000 times over stay here than in a hotel!! The location to everything is ideal. You are not in the middle of all the traffic and lime light of tourism but still close enough of a short drive. You have all the convenience unlike a cramped hotel room. The property felt safe. Would absolutely stay here again. "
United States
Lisa S.
The price is £152
includes taxes & fees
10 Sept - 11 Sept
Scenic Resort Home Close to Disney and Universal
A resort pool area with multiple swimming pools, palm trees, and lounge chairs.

16. Luxury 2BR Condo | First Floor | Balcony 169

Luxury 2BR Condo | First Floor | Balcony 169
Kissimmee
9.2 out of 10, Wonderful, (30 reviews)
"The home is located in a beautiful and peaceful neighborhood. It was very clean and accommodating. "
United States
Germaine S.
The price is £323
includes taxes & fees
21 Sept - 22 Sept
Luxury 2BR Condo | First Floor | Balcony 169
A resort pool area with multiple swimming pools, palm trees, and lounge chairs.

17. 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 £316
includes taxes & fees
30 Sept - 1 Oct
Brand New 2bd/2 bth condo 300
A hotel with a symmetrical facade, a central entrance, and a covered patio area.

18. 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, (170 reviews)
"Nicely kept and very roomy. "
United States
Sheila M.
The price is £144
includes taxes & fees
14 Sept - 15 Sept
Modern Award Winning Newly Renovated, Gorgeous 2+2 Minutes Away From Disney
A resort pool area with multiple swimming pools, palm trees, and lounge chairs.

19. 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 £309
includes taxes & fees
23 Sept - 24 Sept
Cozy, Brand-New 2BR Getaway at ChampionsGate – 291
A resort pool area with multiple swimming pools, palm trees, and lounge chairs.

20. 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.
The price is £303
includes taxes & fees
14 Sept - 15 Sept
Luxury 3 Bedroom Condo w Balcony 372
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Winter Haven Hotel Reviews

Margaritaville Resort Orlando with H2O Waterpark

Margaritaville Resort Orlando with H2O Waterpark

10/10 Excellent
"I love the feeling when I walk into Margaritaville Orlando Resort. It has a refreshing beachy, relaxing"
Damaris 3-night trip
Posted 1 hour ago
Margaritaville Resort Orlando with H2O Waterpark

Find out more about Winter Haven

Winter Haven Condo Rentals information

Number of reviews
139
Accommodation
3238 Condo Rentals
Lowest Price
£118
Highest Price
£333

Frequently asked questions

How much do condos in Winter Haven cost?
Condos in Winter Haven range from £118 to £333 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 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?
Yes, there sure are! Lock in Vsm4 Sd1947 4 Bedroom Home By Redawning — a 3.5-star option located a quick drive from downtown Winter Haven. This family-friendly condo offers convenient features like a swimming pool and WiFi. Once you've checked in and unpacked, there are plenty of family-friendly attractions to explore around Winter Haven. Eagle Ridge Mall and Cypresswood Golf and Country Club are two popular options.
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 Centre. 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.