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Search and Rent Lakeland - Winter Haven Condos

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Our top choices for Lakeland - Winter Haven condo rentals

Exterior
Vacation Village Orlando, Celebration

Condo in Kissimmee

Vacation Village Orlando, Celebration
3.0 star property
8.6 out of 10, Excellent, (3113)
"Great place to stay"
United States
Jose
$113 nightly
The price is $128
Dec 24 - Dec 25
Total with taxes and fees
Vacation Village Orlando, Celebration
WiFi, bed sheets
Lake View•Gardens•Private Balcony Suite•Legoland

Condo in Lake Wales

Lake View•Gardens•Private Balcony Suite•Legoland
2.0 star property
10.0 out of 10, Exceptional, (2)
"Great view, comfortable room for our one night stay."
United States
Vern H.
$117 nightly
The price is $129
Jan 13 - Jan 14, 2026
Total with taxes and fees
Lake View•Gardens•Private Balcony Suite•Legoland
Pool
Beautiful 1st Floor Condo in Gated Cane Island, Close to Parks

Condo in Kissimmee

Beautiful 1st Floor Condo in Gated Cane Island, Close to Parks
9.4 out of 10, Exceptional, (19)
"Spacious unit, great proximity to the parks. Close to stores and restaurants. "
United States
Erika D.
$351 nightly
The price is $379
Dec 30 - Dec 31
Total with taxes and fees
Beautiful 1st Floor Condo in Gated Cane Island, Close to Parks
Pool
Fantastic Award Winning Newly Renovated Condo (4 miles to Disney) 2+2

Condo in Kissimmee

Fantastic Award Winning Newly Renovated Condo (4 miles to Disney) 2+2
9.6 out of 10, Exceptional, (193)
"We absolutely LOVED staying here for our vacation! The master bed is so comfy, and everything looks just like the pictures. We loved being able to relax in the pool after long days outside. I would definitely stay here again, thank you!!"
United States
Kristi C.
$218 nightly
The price is $244
Dec 28 - Dec 29
Total with taxes and fees
Fantastic Award Winning Newly Renovated Condo (4 miles to Disney) 2+2
Outdoor pool, a heated pool
Incredible Water View Only 1 mile from Disney

Condo in Orlando

Incredible Water View Only 1 mile from Disney
9.6 out of 10, Exceptional, (65)
"Perfect location and great view which is not something I typically expect on a Disney vacation."
United States
Jennifer M.
$196 nightly
The price is $218
Jan 9 - Jan 10, 2026
Total with taxes and fees
Incredible Water View Only 1 mile from Disney
Exterior
Disney & Universal Condo Grand Opening Specials! Amazing Views, Spacious 2B 2BA

Condo in Orlando

Disney & Universal Condo Grand Opening Specials! Amazing Views, Spacious 2B 2BA
2.0 star property
10.0 out of 10, Exceptional, (1)
"Truly an incredible space"
United States
Sean Parker S.
$267 nightly
The price is $297
Jan 5 - Jan 6, 2026
Total with taxes and fees
Disney & Universal Condo Grand Opening Specials! Amazing Views, Spacious 2B 2BA
Property grounds
Sensational Water View 1 Mile to Disney Newly Renovated Superb Location

Condo in Orlando

Sensational Water View 1 Mile to Disney Newly Renovated Superb Location
9.8 out of 10, Exceptional, (198)
"Very smooth process checking in and out. Property was clean, and host provided all the necessary information to make our stay enjoyable. "
United States
Beverly C.
$231 nightly
The price is $257
Dec 29 - Dec 30
Total with taxes and fees
Sensational Water View 1 Mile to Disney Newly Renovated Superb Location
Outdoor pool, a heated pool
PAY LATER!! SALE!! Beautiful lake view, newly decorated, next to Disney & FUN!!

Condo in Orlando

PAY LATER!! SALE!! Beautiful lake view, newly decorated, next to Disney & FUN!!
9.2 out of 10, Wonderful, (60)
"we had a wonderful stay "
United States
Paul D.
$247 nightly
The price is $274
Jan 17 - Jan 18, 2026
Total with taxes and fees
PAY LATER!! SALE!! Beautiful lake view, newly decorated, next to Disney & FUN!!
Room
Stylish Retreat/86`TV/King Bed/Spa Shower/Shuffleboard/Near the Lake

Condo in Lake Wales

Stylish Retreat/86`TV/King Bed/Spa Shower/Shuffleboard/Near the Lake
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
$142 nightly
The price is $157
Jan 13 - Jan 14, 2026
Total with taxes and fees
Stylish Retreat/86`TV/King Bed/Spa Shower/Shuffleboard/Near the Lake
Golf
LUXURY 2 BEDROOM SECOND FLOOR (CORNER) CONDO IN SOUTHERN DUNES

Condo in Haines City

LUXURY 2 BEDROOM SECOND FLOOR (CORNER) CONDO IN SOUTHERN DUNES
9.2 out of 10, Wonderful, (63)
"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.
$424 nightly
The price is $469
Dec 24 - Dec 25
Total with taxes and fees
LUXURY 2 BEDROOM SECOND FLOOR (CORNER) CONDO IN SOUTHERN DUNES
Interior
Lake View 2 Bed 2 Bath LOFT With Pool, Gym, Pickleball ---- L@@K FOR DISCOUNTS !

Condo in Brandon

Lake View 2 Bed 2 Bath LOFT With Pool, Gym, Pickleball ---- L@@K FOR DISCOUNTS !
9.8 out of 10, Exceptional, (203)
"Excellent location, perfect little condo with all the necessities. Had a wonderful time. Loved the added bonus of having a washer and dryer"
United States
Steve H.
$314 nightly
The price is $352
Dec 24 - Dec 25
Total with taxes and fees
Lake View 2 Bed 2 Bath LOFT With Pool, Gym, Pickleball ---- L@@K FOR DISCOUNTS !
Interior
Pond View~Club Cortile Resort~Pool~Hot Tub~Themed

Condo in Kissimmee

Pond View~Club Cortile Resort~Pool~Hot Tub~Themed
2.0 star property
10.0 out of 10, Exceptional, (1)
"Thanks to Derek and Lauren being such great Hosts our stay was amazing. Great communication from start to finish, the price is beautiful and amazing very comfortable and a great atmosphere. My family and I will definitely be revisiting next visit to Orlando."
United States
Eriq B.
$468 nightly
The price is $473
Dec 24 - Dec 25
Total with taxes and fees
Pond View~Club Cortile Resort~Pool~Hot Tub~Themed
TV, foosball, table tennis
Magical Newly Renovated,1.5 miles to Disney with Tons of Eateries Near By 754

Condo in Kissimmee

Magical Newly Renovated,1.5 miles to Disney with Tons of Eateries Near By 754
9.0 out of 10, Wonderful, (20)
"Clean place and had everything we needed for the stay."
United States
Antonio
$177 nightly
The price is $198
Jan 3 - Jan 4, 2026
Total with taxes and fees
Magical Newly Renovated,1.5 miles to Disney with Tons of Eateries Near By 754
Pool
Newly Remodeled 2-bedroom Family-sized condo 15 minutes to the theme park

Condo in Champions Gate

Newly Remodeled 2-bedroom Family-sized condo 15 minutes to the theme park
2.0 star property
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.
$297 nightly
The price is $332
Jan 7 - Jan 8, 2026
Total with taxes and fees
Newly Remodeled 2-bedroom Family-sized condo 15 minutes to the theme park
1 bedroom, in-room safe, desk, iron/ironing board
Sophisticated Retreat

Condo in Kissimmee

Sophisticated Retreat
9.4 out of 10, Exceptional, (6)
"Amazing! I will be staying here again!"
United States
MikeD
$173 nightly
The price is $194
Jan 6 - Jan 7, 2026
Total with taxes and fees
Sophisticated Retreat
Pool
Newly Renovated, Modern Two Bedroom Condo Minutes Away From Disney

Condo in Kissimmee

Newly Renovated, Modern Two Bedroom Condo Minutes Away From Disney
9.6 out of 10, Exceptional, (115)
"We had such a wonderful stay! Everything was so clean and well organized. Will stay here again if it is available!!!"
United States
Logan S.
$261 nightly
The price is $292
Jan 2 - Jan 3, 2026
Total with taxes and fees
Newly Renovated, Modern Two Bedroom Condo Minutes Away From Disney
Pool
Upstay: Family-Friendly Getaway with Spa & Pool

Condo in Orlando

Upstay: Family-Friendly Getaway with Spa & Pool
9.2 out of 10, Wonderful, (5)
"Great place to stay. Close to all the major theme parks"
United States
marci m.
$247 nightly
The price is $276
Jan 13 - Jan 14, 2026
Total with taxes and fees
Upstay: Family-Friendly Getaway with Spa & Pool
Exterior
Family Fun Condo Pool and Sauna near Disney

Condo in Winter Garden

Family Fun Condo Pool and Sauna near Disney
10.0 out of 10, Exceptional, (2)
"Clean, nicely appointed apartment close to Disney. Great pet friendly location. Will stay again. Highly recommend! "
United States
John and Dawn R.
$240 nightly
The price is $269
Jan 12 - Jan 13, 2026
Total with taxes and fees
Family Fun Condo Pool and Sauna near Disney
Pool
Buena Vista Resort Condo w/ Pool & Private Patio

Condo in Orlando

Buena Vista Resort Condo w/ Pool & Private Patio
8.6 out of 10, Excellent, (14)
"Condo was as advertised clean and close to everything. Would highly recommend this property for any Disney vacation."
Canada
Derek M.
$244 nightly
The price is $273
Jan 13 - Jan 14, 2026
Total with taxes and fees
Buena Vista Resort Condo w/ Pool & Private Patio
Pool
Fabulous Award Winning Newly Renovated Condo 2+2 Near Disney 5 Stars!

Condo in Kissimmee

Fabulous Award Winning Newly Renovated Condo 2+2 Near Disney 5 Stars!
9.4 out of 10, Exceptional, (134)
"Clean, nice property, location was nice"
United States
Sara R.
$239 nightly
The price is $267
Dec 29 - Dec 30
Total with taxes and fees
Fabulous Award Winning Newly Renovated Condo 2+2 Near Disney 5 Stars!
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 Lakeland - Winter Haven Hotel Reviews

The Grove Resort & Water Park Orlando

The Grove Resort & Water Park Orlando

10/10 Excellent
"Everything was great about my expectations "
Hazel 1-night trip
Posted 8 hours ago
The Grove Resort & Water Park Orlando

Find out more about Lakeland - Winter Haven

Lakeland - Winter Haven Condo Rentals information

Number of reviews
4,125
Accommodation
123 Condo Rentals
Lowest Price
$128
Highest Price
$473

Frequently asked questions

How much do condos in Lakeland - Winter Haven cost?
The price range for condos in Lakeland - Winter Haven is $128 to $473 per night. Whatever your budget, you're sure to find something that suits your needs — as well as your entire crew! 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 Lakeland - Winter Haven?
Browse through 123 condos in Lakeland - Winter Haven and reserve your favorite. Whether you're off on a vacation with the whole fam or reuniting with friends, with Expedia, your perfect stay is just a few clicks away.
Why book your condo in Lakeland - Winter Haven with Expedia?
We think that getaways should be a walk in the park, so if you're on the lookout for condos at a great price, Expedia has your back. Keep costs down and pick something small and cozy, or splurge on a luxury condo and pamper your loved ones. Our search filters make it easy to lock in a stay in Lakeland - Winter Haven that suits you best.
How can I find cheap condos in Lakeland - Winter Haven?
A good way to uncover cheap condos in Lakeland - Winter Haven is with Expedia's convenient filter tool. Fine-tune your search results by star rating, amenities and budget to take advantage of excellent rates in a few clicks.
What is there to do in Lakeland - Winter Haven near my condo?
Whether you like sightseeing, shopping, dining or partying, Lakeland - Winter Haven offers it all, and then some! The top city of Lakeland has lots of things to see and do, including Polk Museum of Art, RP Funding Center and Publix Field at Joker Marchant Stadium. If you're vacationing in Winter Haven, Indigo's Family Fun Center, Chain of Lakes Park and Theatre Winter Haven should be on your to-do list.

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