Search Lakeland - Winter Haven Condo Rentals

  • Plan, book, stay with confidence

    • bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    Sign in
    today icon
    Change your mind
    Book hotels with free cancellation

Check prices for these dates

Next weekend
21 Mar - 23 Mar
In two weeks
28 Mar - 30 Mar
In one month
11 Apr - 13 Apr
In two months
9 May - 11 May

Featured Condo Rentals in Lakeland - Winter Haven

The Azur Resort
Townhome, 6 Bedrooms | View from room

The Azur Resort

4.0 star property
8.4 out of 10, Very good, (26)
"Everything was perfect only thing missing was dish soap in the kitchen area. We were very comfortable here everything was clean. Highly recommend!"
The Azur Resort
Lifetime of Vacations Resort
Lake

Lifetime of Vacations Resort

3.0 star property
9.2 out of 10, Wonderful, (124)
"The property was clean and comfy. We loved the staff and the view. "
Lifetime of Vacations Resort
Spacious Luxury Condo in Windsor Hills Resort! 2 Miles to Disney! 3bed/2bath
A heated pool

Spacious Luxury Condo in Windsor Hills Resort! 2 Miles to Disney! 3bed/2bath

10.0 out of 10, Exceptional, (98)
"The place was perfect for our big family! The kids loved their room! The bathrooms are nicely updated loved the masters shower. Would stay there again anytime. April was really nice and she answers so quickly. Thanks for a great week at your beautiful condo!"
Spacious Luxury Condo in Windsor Hills Resort! 2 Miles to Disney! 3bed/2bath
Dream Disney Family Vacation,one of best resort 2 miles to Disney, space for 8
Exterior

Dream Disney Family Vacation,one of best resort 2 miles to Disney, space for 8

9.0 out of 10, Wonderful, (119)
"Great location close to Disney and pool area was great! Host was great and very responsive. The condo unit could use some maintenance work inside but other than that it was great!"
Dream Disney Family Vacation,one of best resort 2 miles to Disney, space for 8
Ground floor 3 bed condo close to pool and WATER PARK in Windsor Hills Resort
Sport court

Ground floor 3 bed condo close to pool and WATER PARK in Windsor Hills Resort

9.6 out of 10, Exceptional, (101)
"It's a well maintained beautiful property at a great location.Location is prefect, 15 minutes drive from Magic Kingdom, near Walmart and other aminities. "
Ground floor 3 bed condo close to pool and WATER PARK in Windsor Hills Resort
Ground floor 3 bed condo close to POOL and WATER PARK in Windsor Hills Resort
Pool

Ground floor 3 bed condo close to POOL and WATER PARK in Windsor Hills Resort

9.2 out of 10, Wonderful, (25)
"We enjoyed our stay there. Was very clean and comfy. Was surprised on some things not included, like paper towels, kitchen towels and dish soap, kid friendly dishes, (there was a couple plastic plates but no plastic cups)All in all we had a great time. "
Ground floor 3 bed condo close to POOL and WATER PARK in Windsor Hills Resort
5 Star Resort minutes from Disney 3 bedrooms & 2 baths, Wi-Fi, Pool, Tennis
A heated pool

5 Star Resort minutes from Disney 3 bedrooms & 2 baths, Wi-Fi, Pool, Tennis

9.6 out of 10, Exceptional, (54)
"We had a nice stay, but we were only there to sleep. We did not use any of the amenities. My only complaint is not really even a complaint, but there was a lot of hair in the bathroom. it was even on the walls. This was in the master bathroom. I'm not sure about the other bathroom and everything else was super clean! Location was excellent and Disney was only a short drive away which is what we were there for. The king bed was super comfortable. My sister slept in the queen bed and said it was...
5 Star Resort minutes from Disney 3 bedrooms & 2 baths, Wi-Fi, Pool, Tennis
STAR WARS first floor 3 bedroom condo in a Galaxy just 2 miles from Disney World
Exterior

STAR WARS first floor 3 bedroom condo in a Galaxy just 2 miles from Disney World

9.2 out of 10, Wonderful, (88)
"As always, Windsor Hills is a wonderful community to stay in! Location to WDW is great. Loved being on the first floor - no steps after long day in the park. Communication from owners was great. Would definitely stay here again. "
STAR WARS first floor 3 bedroom condo in a Galaxy just 2 miles from Disney World
Caribe Cove Resort
Outdoor pool, a heated pool

Caribe Cove Resort

3.5 star property
8.8 out of 10, Excellent, (2245)
"Condo is spacious, beds aren’t comfortable but for the price it’s understandable. If they could change the mattress would be amazing! Pool area is really nice. "
Caribe Cove Resort
Great Caribbean style condo near Disney
Exterior

Great Caribbean style condo near Disney

9.6 out of 10, Exceptional, (155)
"Condo was well decorated and stocked with everything you need. If I had only one complaint, it would be the television situation. They don't have smart TVs, so streaming services are a no go, and the cable service constantly drops out or freezes. There was also no service in the master bedroom. Other than theses issues, we had an enjoyable stay. "
Great Caribbean style condo near Disney
Welcome to Dream Weaver, 3/2 top floor condo with elevators, 3 miles from Disney
Outdoor pool, a heated pool

Welcome to Dream Weaver, 3/2 top floor condo with elevators, 3 miles from Disney

9.8 out of 10, Exceptional, (73)
"I would recommend this property for future renters! This property provided the very basics to allow our vacation to be enjoyable. "
Welcome to Dream Weaver, 3/2 top floor condo with elevators, 3 miles from Disney
3 Bed Luxury Premium Rated At Bahama Bay
Pool

3 Bed Luxury Premium Rated At Bahama Bay

9.2 out of 10, Wonderful, (154)
"Description is accurate. Host was available for questions. Easy in and out. Great complex everyone was very friendly. "
The price is AU$415
includes taxes & fees
5 Apr - 6 Apr
3 Bed Luxury Premium Rated At Bahama Bay
Newly Remodeled & Furnished! Largest Windsor Hills Condo!Kid-Friendly Water Park
Outdoor pool, a heated pool

Newly Remodeled & Furnished! Largest Windsor Hills Condo!Kid-Friendly Water Park

9.4 out of 10, Exceptional, (106)
"Great place to stay, plenty of space for a family. Everything you need to make it a home from home. Very clean internally and the surrounding amenities are kept clean and tidy. Would certainly stay again. "
Newly Remodeled & Furnished! Largest Windsor Hills Condo!Kid-Friendly Water Park
🏝New Water Park!!! Huge Pool, 5 Minutes to Disney World!🏝
Outdoor pool, a heated pool

🏝New Water Park!!! Huge Pool, 5 Minutes to Disney World!🏝

9.8 out of 10, Exceptional, (241)
"We stayed here to bring our daughter to the parks nearby. The house was condo was clean and welcoming. They provided some necessities which was nice. We went during a chilly week in FL so we didn’t get to take advantage of the pool area really. We did go in the hot tub for a little bit one night. Seemed clean. The onsite store had weird hours which was disappointing. They didn’t open until 10 and closed at like 7pm. Was hoping to be able to buy coffee in the mornings there but couldn’t. But I...
🏝New Water Park!!! Huge Pool, 5 Minutes to Disney World!🏝
FULLY REMODELED! Windsor Hills 402! A Must See, 2 Bedroom Condo!
A heated pool

FULLY REMODELED! Windsor Hills 402! A Must See, 2 Bedroom Condo!

9.2 out of 10, Wonderful, (51)
"This property was very clean and well appointed with everything you could possibly need. We enjoyed the pool and grille on site. The condo was a very short walk to the pool. Check in process was easy and communication was very efficient. We loved the close proximity to Disney as well as Celebration. Would return. "
FULLY REMODELED! Windsor Hills 402! A Must See, 2 Bedroom Condo!
Stunning, Newly Renovated Condo, Near Disney and Universal
Pool

Stunning, Newly Renovated Condo, Near Disney and Universal

9.6 out of 10, Exceptional, (121)
"Overall, place was well appointed with dishes and cooking utensils, washer/dryer, tv’s ect. Against the traffic when travelling to Disney which was great as all other routes were backed up. Good size condo. Complex was nice with amenities such as pool, work out centre and hot tub although we did not have time to enjoy them. Mark was very responsive. I would book again. "
The price is AU$355
includes taxes & fees
24 Mar - 25 Mar
Stunning, Newly Renovated Condo, Near Disney and Universal
Modern Award Winning Newly Renovated, Gorgeous 2+2 Minutes Away From Disney
A heated pool

Modern Award Winning Newly Renovated, Gorgeous 2+2 Minutes Away From Disney

9.2 out of 10, Wonderful, (135)
"We enjoyed our stay. No issues. We liked the location and the fact that it’s a gated community. Would stay here again. Thanks!"
The price is AU$348
includes taxes & fees
13 Mar - 14 Mar
Modern Award Winning Newly Renovated, Gorgeous 2+2 Minutes Away From Disney
Get away from it all in a place that's close to it ALL! Renovated - near Disney!
Outdoor pool, a heated pool

Get away from it all in a place that's close to it ALL! Renovated - near Disney!

10.0 out of 10, Exceptional, (108)
"Great time at Disney. Location of unit was good. Cons: Additional Pillows in master bedroom were thin and probably needs replacing. There is a musky smell when you enter the unit. Possibly from dishwasher or laundry room. Pros: location is great. Pool is warm. Hot tub nice. Disney plus nice. Unit had everything needed. Overall we would come again "
Get away from it all in a place that's close to it ALL! Renovated - near Disney!
Be our Guest - 3 bedroom, sleeps 7 + Condo w/ pool view by Disney and Universal
Pool

Be our Guest - 3 bedroom, sleeps 7 + Condo w/ pool view by Disney and Universal

9.8 out of 10, Exceptional, (67)
"This was the perfect spot for a Disney visit. We just wished we had had more time to enjoy all the amenities!"
Be our Guest - 3 bedroom, sleeps 7 + Condo w/ pool view by Disney and Universal
2 Bed Condo Close to Disney Watch the Fireworks Resort Access with Amenities
Pool

2 Bed Condo Close to Disney Watch the Fireworks Resort Access with Amenities

2.0 star property
8.0 out of 10, Very good, (2)
"Lovely stay and fireworks as it says! Close to the parks and close to other entertainment. Good resort pools and amenities. Thank you "
2 Bed Condo Close to Disney Watch the Fireworks Resort Access with Amenities
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.
Don't see what you're looking for?
See all available properties in Lakeland - Winter Haven
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Other property types in Lakeland - Winter Haven

Summer Bay Orlando by Exploria Resorts
5 outdoor pools

Summer Bay Orlando by Exploria Resorts

3.5 star property
8.4 out of 10, Very good, (5214)
"Lack of communication when you checked in"
The price is AU$247
includes taxes & fees
25 Mar - 26 Mar
Summer Bay Orlando by Exploria Resorts
Margaritaville Cottages Orlando with H2O Waterpark by Rentyl
Interior

Margaritaville Cottages Orlando with H2O Waterpark by Rentyl

4.0 star property
8.8 out of 10, Excellent, (1247)
"We loved our stay!"
Margaritaville Cottages Orlando with H2O Waterpark by Rentyl
The Berkley, Orlando
Lobby sitting area

The Berkley, Orlando

4.0 star property
9.4 out of 10, Exceptional, (1701)
"This location was great for a large family with kids, spacious apartments and very comfortable beds. Very close and convenient to the parks. "
The price is AU$373
includes taxes & fees
13 Mar - 14 Mar
The Berkley, Orlando
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.

Frequently asked questions

How much do condos in Lakeland - Winter Haven cost?
You’ll pay from AU$348 to AU$415 per night for condos in Lakeland - Winter Haven. Whatever your budget, an ideal stay is a click away on Expedia. This price was 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?
Lakeland - Winter Haven has 100 condos on offer. Enter your destination and dates and lock in your next escape today.
What is there to do in Lakeland - Winter Haven near my condo?
The best accessory to pack for your Lakeland - Winter Haven adventure is a good itinerary! Polk Museum of Art, Polk Theatre and Explorations V Children s Museum are some of the leading sights if you’re heading to Lakeland. Winter Haven also lures visitors with its terrific attractions, such as Theatre Winter Haven. Want to add to your to-do list? Visit Indigos Billiards, Bowling & Games and Chain of Lakes Park too.