Search and Rent Winter Haven Condos

  • Bundle & Save

    Get more, spend less whenever you see Bundle & Save deals
  • OneKeyCash

    Earn OneKeyCash on all your eligible bookings
  • Upfront pricing

    We are not like the others - we include taxes and fees

Check prices for these dates

In two weeks
In two months
In three months
In four months

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, (3,397 reviews)
"Yes .. very clean rooms and hotel chef was great"
United States
Alicia
$117 nightly
The price is $132
Mar 8 - Mar 9
Total with taxes and fees
Vacation Village Orlando, Celebration

Lake View•Gardens•Private Balcony Suite•Legoland

Lake View•Gardens•Private Balcony Suite•Legoland
Lake Wales
8.6 out of 10, Excellent, (7 reviews)
$142 nightly
The price is $157
Mar 4 - Mar 5
Total with taxes and fees
Lake View•Gardens•Private Balcony Suite•Legoland

Cute GameRoom/ Waterpark/ Clubhouses

Cute GameRoom/ Waterpark/ Clubhouses
Champions Gate
$319 nightly
The price is $351
Feb 22 - Feb 23
Total with taxes and fees
Cute GameRoom/ Waterpark/ Clubhouses

Bright Ground Floor Condo Minutes to Parks

Bright Ground Floor Condo Minutes to Parks
Kissimmee
$275 nightly
The price is $292
Feb 23 - Feb 24
Total with taxes and fees
Bright Ground Floor Condo Minutes to Parks

Upstay - Pet-Friendly Condo - Sauna, Pool

Upstay - Pet-Friendly Condo - Sauna, Pool
Winter Garden
$249 nightly
The price is $279
Feb 22 - Feb 23
Total with taxes and fees
Upstay - Pet-Friendly Condo - Sauna, Pool

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.
$172 nightly
The price is $193
Feb 23 - Feb 24
Total with taxes and fees
Scenic Resort Home Close to Disney and Universal

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
7.4 out of 10, Good, (3 reviews)
"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
$166 nightly
The price is $184
Mar 4 - Mar 5
Total with taxes and fees
Stylish Retreat/86`TV/King Bed/Spa Shower/Shuffleboard/Near the Lake

Paradise Breeze Cottage By Shine Villas Margaritaville Resort Orlando 4 Bedroom Condo

Paradise Breeze Cottage By Shine Villas Margaritaville Resort Orlando 4 Bedroom Condo
3.0 star property
Kissimmee
10.0 out of 10, Exceptional, (1 review)
$593 nightly
The price is $593
Feb 23 - Feb 24
Total with taxes and fees
Paradise Breeze Cottage By Shine Villas Margaritaville Resort Orlando 4 Bedroom Condo

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 review)
"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.
$332 nightly
The price is $356
Feb 22 - Feb 23
Total with taxes and fees
Parkway Palms Resort 1 bedroom condo mins to Disney World.

LUXURY 2 BEDROOM SECOND FLOOR (CORNER) CONDO IN SOUTHERN DUNES

LUXURY 2 BEDROOM SECOND FLOOR (CORNER) CONDO IN SOUTHERN DUNES
Haines City
9.2 out of 10, Wonderful, (63 reviews)
"We extended our stay by two weeks, please read my previous review. Can not complain about anything apart from location from theme parks, at least a 45 minute drive from attractions."
United Kingdom
Anthony M.
$422 nightly
The price is $467
Feb 25 - Feb 26
Total with taxes and fees
LUXURY 2 BEDROOM SECOND FLOOR (CORNER) CONDO IN SOUTHERN DUNES

Bahama Bay, Davenport, Florida Oversize 2 Br condo

Bahama Bay, Davenport, Florida Oversize 2 Br condo
Bahama Bay
9.6 out of 10, Exceptional, (9 reviews)
"Was good. "
United States
June C.
Bahama Bay, Davenport, Florida Oversize 2 Br condo

Brand New 2bd/2 bth condo 300

Brand New 2bd/2 bth condo 300
davenport
9.8 out of 10, Exceptional, (6 reviews)
"We have stayed here before. Good location for all your needs, excellent accommodations, gated community. Would rent again if available on our next trip. "
United States
Martin T.
Brand New 2bd/2 bth condo 300

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, (2 reviews)
"The place was perfect. Had plenty of space and everything we needed. Quiet, clean, & has a good layout. Host was great and had wonderful communication. Definitely will be back."
United States
Jessica
$244 nightly
The price is $273
Mar 11 - Mar 12
Total with taxes and fees
5 Min to Disney! 2BR Condo w/ King Bed, Pool, Fast WiFi & SmartTV+kitchen+washer

Upstay - Large Condo Near Disney w Pool and Gym

Upstay - Large Condo Near Disney w Pool and Gym
Winter Garden
$248 nightly
The price is $278
Feb 24 - Feb 25
Total with taxes and fees
Upstay - Large Condo Near Disney w Pool and Gym

Luxury 2BR Condo | First Floor | Balcony 169

Luxury 2BR Condo | First Floor | Balcony 169
Kissimmee
9.2 out of 10, Wonderful, (30 reviews)
"The property is located in a quiet community that is a reasonable driving distance from Universal Studios. It was clean, comfy, and had a decently equipped kitchen, which was nice since we cooked every night of our stay. I would definitely revisit and recommend this property. "
United States
Ariel B.
Luxury 2BR Condo | First Floor | Balcony 169

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, (153 reviews)
"Excellent accommodations."
United States
Raychelle
$225 nightly
The price is $252
Mar 1 - Mar 2
Total with taxes and fees
Modern Award Winning Newly Renovated, Gorgeous 2+2 Minutes Away From Disney

Super spacious near Disney with private pool

Super spacious near Disney with private pool
Kissimmee
9.6 out of 10, Exceptional, (4 reviews)
"Great house on a very convenient location. Communication with host was smooth and i highly recommend the house! "
United States
Fernando N.
$453 nightly
The price is $470
Feb 23 - Feb 24
Total with taxes and fees
Super spacious near Disney with private pool

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

Cozy, Brand-New 2BR Getaway at ChampionsGate – 291
Davenport
9.8 out of 10, Exceptional, (6 reviews)
"Correspondence was good, Listed accurate, clean and comfy! Thank you! Enjoyed our time there...the Oasis pools were amazing!"
United States
Thomas K.
Cozy, Brand-New 2BR Getaway at ChampionsGate – 291

Near Disney/Resort Pool, Bar & Gym

Near Disney/Resort Pool, Bar & Gym
Champions Gate
9.4 out of 10, Exceptional, (6 reviews)
"The property was great.. very clean and relaxing"
Canada
Dawn D.
$243 nightly
The price is $273
Mar 12 - Mar 13
Total with taxes and fees
Near Disney/Resort Pool, Bar & Gym

Valentina’s Condo-Resort Style!

Valentina’s Condo-Resort Style!
Kissimmee
10.0 out of 10, Exceptional, (6 reviews)
"Nice neighborhood, local pool and condo. Would stay again."
United States
Jason M.
$203 nightly
The price is $227
Mar 6 - Mar 7
Total with taxes and fees
Valentina’s Condo-Resort Style!
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.

The Annual Vacation Sale

Members save up to 40% on hotels and homes. Plan this year’s big trip and save.
Save an average of 15% on thousands of hotels when you're signed in

Top Winter Haven Hotel Reviews

Find out more about Winter Haven

Winter Haven Condo Rentals information

Number of reviews
3,538
Accommodation
3446 Condo Rentals
Lowest Price
$132
Highest Price
$593

Frequently asked questions

How much do condos in Winter Haven cost?
Condos in Winter Haven range from $132 to $593 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 3446 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.

Explore a world of travel with Expedia