Search Condo Rentals in Lakeland - Winter Haven

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Check prices for these dates

In two weeks
26 Dec - 28 Dec
In two months
6 Feb - 8 Feb
In three months
6 Mar - 8 Mar
In four months
3 Apr - 5 Apr

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, (3096)
"Great place to stay"
United States
Jose
The price is AED 464
AED 618 total
includes taxes & fees
4 Jan - 5 January 2026
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.
The price is AED 340
AED 455 total
includes taxes & fees
15 Dec - 16 Dec
Lake View•Gardens•Private Balcony Suite•Legoland
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.
The price is AED 275
AED 1,672 total
includes taxes & fees
4 Jan - 5 January 2026
Pond View~Club Cortile Resort~Pool~Hot Tub~Themed
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.
The price is AED 364
AED 1,208 total
includes taxes & fees
14 Dec - 15 Dec
Lake View 2 Bed 2 Bath LOFT With Pool, Gym, Pickleball ---- L@@K FOR DISCOUNTS !
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.
The price is AED 239
AED 769 total
includes taxes & fees
15 Dec - 16 Dec
Newly Renovated, Modern Two Bedroom Condo Minutes Away From Disney
Living area
Splendid Renovated 2 + 2 Condo Near Disney with Amazing Amenities

Condo in Champions Gate

Splendid Renovated 2 + 2 Condo Near Disney with Amazing Amenities
2.0 star property
9.6 out of 10, Exceptional, (28)
"Host was very communicative, simple check in & check out. Will stay again at this property. "
United States
Anonymous traveler
The price is AED 184
AED 720 total
includes taxes & fees
14 Dec - 15 Dec
Splendid Renovated 2 + 2 Condo Near Disney with Amazing Amenities
Condo, 4 Bedrooms | Exterior
Paradise Breeze Cottage By Shine Villas Margaritaville Resort Orlando 4 Bedroom Condo

Condo in Kissimmee

Paradise Breeze Cottage By Shine Villas Margaritaville Resort Orlando 4 Bedroom Condo
3.0 star property
The price is AED 406
AED 1,960 total
includes taxes & fees
14 Dec - 15 Dec
Paradise Breeze Cottage By Shine Villas Margaritaville Resort Orlando 4 Bedroom Condo
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.
The price is AED 393
AED 1,584 total
includes taxes & fees
14 Dec - 15 Dec
LUXURY 2 BEDROOM SECOND FLOOR (CORNER) CONDO IN SOUTHERN DUNES
Private kitchen
Cozy 2-bedroom condo in a gated community in lovely Poinciana

Condo in Poinciana

Cozy 2-bedroom condo in a gated community in lovely Poinciana
The price is AED 239
AED 547 total
includes taxes & fees
19 Dec - 20 Dec
Cozy 2-bedroom condo in a gated community in lovely Poinciana
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)
"The place was in a ok location definitely not within walking distance of Disney springs. It may have been at one point but not now. It’s a 5-10 min drive. The place was not cleaned very well at all. Floors were really dirty and the place had a musty smell to it"
United States
mathew c.
The price is AED 253
AED 792 total
includes taxes & fees
9 Jan - 10 January 2026
Incredible Water View Only 1 mile from Disney
Exterior
Homelike Waterview-condo 2BR/2BA with elevator 10 min to Disney

Condo in Kissimmee

Homelike Waterview-condo 2BR/2BA with elevator 10 min to Disney
9.4 out of 10, Exceptional, (6)
"the location was excellent for our needs, just minutes from Walt Disney World. the booking was easy and precise. the check-in information was simple, but complete. all around experience was top notch."
United States
Gary S.
Homelike Waterview-condo 2BR/2BA with elevator 10 min to Disney
Lake view
Lifetime of Vacations Resort

Condo in Kissimmee

Lifetime of Vacations Resort
3.0 star property
9.4 out of 10, Exceptional, (151)
"Very nice quiet place... very polite front desk personnel "
United States
Iliana
The price is AED 387
AED 501 total
includes taxes & fees
11 Jan - 12 January 2026
Lifetime of Vacations Resort
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.
The price is AED 274
AED 1,396 total
includes taxes & fees
30 Dec - 31 Dec
Beautiful 1st Floor Condo in Gated Cane Island, Close to Parks
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.
The price is AED 246
AED 894 total
includes taxes & fees
17 Dec - 18 Dec
Upstay: Family-Friendly Getaway with Spa & Pool
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
The price is AED 488
AED 620 total
includes taxes & fees
13 Jan - 14 January 2026
Stylish Retreat/86`TV/King Bed/Spa Shower/Shuffleboard/Near the Lake
Pool
Disney 8mi~Heated Resort Pool~Hot Tub~Oasis

Condo in Kissimmee

Disney 8mi~Heated Resort Pool~Hot Tub~Oasis
The price is AED 131
AED 1,261 total
includes taxes & fees
14 Dec - 15 Dec
Disney 8mi~Heated Resort Pool~Hot Tub~Oasis
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.
The price is AED 257
AED 1,220 total
includes taxes & fees
18 Dec - 19 Dec
Newly Remodeled 2-bedroom Family-sized condo 15 minutes to the theme park
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.
The price is AED 235
AED 882 total
includes taxes & fees
17 Dec - 18 Dec
Family Fun Condo Pool and Sauna near Disney
A heated pool
Thanksgiving Special, Stylish, Relaxing, Stunning Lakeview Resort near Disney

Condo in Orlando

Thanksgiving Special, Stylish, Relaxing, Stunning Lakeview Resort near Disney
9.4 out of 10, Exceptional, (36)
"It was a nice place with a great view of the lake. The owner was very communicative and accommodating."
United States
Tim
The price is AED 404
AED 1,010 total
includes taxes & fees
8 Jan - 9 January 2026
Thanksgiving Special, Stylish, Relaxing, Stunning Lakeview Resort near Disney
Property grounds
WEEKEND DEC 13-20 95+N 2.5 BDR 2 BTH 25FT AMAZING LAKEFRONT CONDO + 25FT BALCONY

Condo in Orlando

WEEKEND DEC 13-20 95+N 2.5 BDR 2 BTH 25FT AMAZING LAKEFRONT CONDO + 25FT BALCONY
9.6 out of 10, Exceptional, (176)
"The location is very close to the Disney parks and in walking distance to food and COFFEE!"
United States
janice b.
The price is AED 410
AED 1,154 total
includes taxes & fees
17 Dec - 18 Dec
WEEKEND DEC 13-20 95+N 2.5 BDR 2 BTH 25FT AMAZING LAKEFRONT CONDO + 25FT BALCONY
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
"Pools were great. The Flo Rider was outstanding. Best instructor ever with Eric!"
Margaret 5-night trip
Posted 2 days ago
The Grove Resort & Water Park Orlando

Frequently asked questions

How much do condos in Lakeland - Winter Haven cost?
The price range for condos in Lakeland - Winter Haven is AED 455 to AED 1,960 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.

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