Photo by Visit Central Florida

Search Condos in Lakeland - Winter Haven

Start date: Check-in selected.
To Date
End date: Check-out

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
9 Jan - 11 Jan
In two months
20 Feb - 22 Feb
In three months
20 Mar - 22 Mar
In four months
17 Apr - 19 Apr

Our top choices for Lakeland - Winter Haven condo rentals

Aerial view
Vacation Village Orlando, Celebration

Condo in Kissimmee

Vacation Village Orlando, Celebration
3.0 star property
8.6 out of 10, Excellent, (3121)
"Great place to stay"
United States
Jose
The price is NZ$236
includes taxes & fees
8 Jan - 9 Jan 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 NZ$212
includes taxes & fees
13 Jan - 14 Jan 2026
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.
The price is NZ$649
includes taxes & fees
30 Dec - 31 Dec
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.
The price is NZ$418
includes taxes & fees
28 Dec - 29 Dec
Fantastic Award Winning Newly Renovated Condo (4 miles to Disney) 2+2
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.
The price is NZ$546
includes taxes & fees
4 Jan - 5 Jan 2026
Disney & Universal Condo Grand Opening Specials! Amazing Views, Spacious 2B 2BA
Exterior
Parkway Palms Resort 1 bedroom condo mins to Disney World.

Condo in Kissimmee

Parkway Palms Resort 1 bedroom condo mins to Disney World.
10.0 out of 10, Exceptional, (1)
"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.
The price is NZ$598
includes taxes & fees
4 Jan - 5 Jan 2026
Parkway Palms Resort 1 bedroom condo mins to Disney World.
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)
"The location was great. We were only there 2 nights, and everything we needed and wanted was within a 10 minutee drive. Would highly recommend. "
United States
Lisa R.
The price is NZ$440
includes taxes & fees
29 Dec - 30 Dec
Sensational Water View 1 Mile to Disney Newly Renovated Superb Location
Property grounds
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.
The price is NZ$373
includes taxes & fees
9 Jan - 10 Jan 2026
Incredible Water View Only 1 mile from Disney
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.
The price is NZ$480
includes taxes & fees
17 Jan - 18 Jan 2026
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 traveller
The price is NZ$260
includes taxes & fees
13 Jan - 14 Jan 2026
Stylish Retreat/86`TV/King Bed/Spa Shower/Shuffleboard/Near the Lake
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 NZ$583
includes taxes & fees
3 Jan - 4 Jan 2026
Lake View 2 Bed 2 Bath LOFT With Pool, Gym, Pickleball ---- L@@K FOR DISCOUNTS !
Outdoor dining
Sophisticated Retreat

Condo in Kissimmee

Sophisticated Retreat
9.4 out of 10, Exceptional, (6)
"Amazing! I will be staying here again!"
United States
MikeD
The price is NZ$336
includes taxes & fees
8 Jan - 9 Jan 2026
Sophisticated Retreat
Outdoor pool
Amazing Water View, 1 Mile to Disney,Newly Renovated

Condo in Orlando

Amazing Water View, 1 Mile to Disney,Newly Renovated
9.6 out of 10, Exceptional, (122)
"Very nice resort ! We had a great time "
United States
Sara P.
The price is NZ$440
includes taxes & fees
1 Jan - 2 Jan 2026
Amazing Water View, 1 Mile to Disney,Newly Renovated
TV, table football, ping pong
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
The price is NZ$340
includes taxes & fees
3 Jan - 4 Jan 2026
Magical Newly Renovated,1.5 miles to Disney with Tons of Eateries Near By 754
Smart TV, DVD player
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 loved our stay. The place was wonderfully kept. "
United States
Mo W.
The price is NZ$502
includes taxes & fees
2 Jan - 3 Jan 2026
Newly Renovated, Modern Two Bedroom Condo Minutes Away From Disney
Smart TV
Toria Suites 922

Condo in East Lake Morton

Toria Suites 922
The price is NZ$406
includes taxes & fees
4 Jan - 5 Jan 2026
Toria Suites 922
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 NZ$472
includes taxes & fees
13 Jan - 14 Jan 2026
Upstay: Family-Friendly Getaway with Spa & Pool
Pool
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 NZ$459
includes taxes & fees
12 Jan - 13 Jan 2026
Family Fun Condo Pool and Sauna near Disney
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 NZ$579
includes taxes & fees
7 Jan - 8 Jan 2026
Newly Remodeled 2-bedroom Family-sized condo 15 minutes to the theme park
Fridge, microwave, oven, stovetop
Resort stay~Pool Access~Peaceful Retreat~Balcony

Condo in Kissimmee

Resort stay~Pool Access~Peaceful Retreat~Balcony
2.0 star property
10.0 out of 10, Exceptional, (1)
"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 NZ$597
includes taxes & fees
24 Jan - 25 Jan 2026
Resort stay~Pool Access~Peaceful Retreat~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.
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 Lakeland - Winter Haven Hotel Reviews

The Grove Resort & Water Park Orlando

The Grove Resort & Water Park Orlando

10/10 Excellent
"Room was spacious clean and great overall. "
Gabriel 3-night trip
Posted 2 days ago
The Grove Resort & Water Park Orlando

Find out more about Lakeland - Winter Haven

Lakeland - Winter Haven Condo Rentals information

Number of reviews
4,104
Accommodation
123 Condo Rentals
Lowest Price
NZ$212
Highest Price
NZ$649

Frequently asked questions

How much do condos in Lakeland - Winter Haven cost?
The price range for condos in Lakeland - Winter Haven is NZ$212 to NZ$649 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 favourite. Whether you're off on a holiday with the whole fam or reuniting with friends, with Expedia, your perfect stay is just a few clicks away.
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 Centre and Publix Field at Joker Marchant Stadium. If you're holidaying in Winter Haven, Indigo's Family Fun Centre, Chain of Lakes Park and Theatre Winter Haven should be on your to-do list.

Explore a world of travel with Expedia