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Check prices for these dates

Next weekend
23 May - 25 May
In two weeks
30 May - 1 Jun
In one month
13 Jun - 15 Jun
In two months
11 Jul - 13 Jul

Compare 118 Condo Rentals in Lakeland - Winter Haven with updated reviews, rates, and availability.

The Azur Resort
Townhome, 6 Bedrooms | View from room

The Azur Resort

4.0 star property
8.2 out of 10, Very Good, (32)
"Great stay, will definitely be booking again in the future! Thanks! 10/10"
The Azur Resort
Caribe Cove Resort
Outdoor pool, a heated pool

Caribe Cove Resort

3.5 star property
8.8 out of 10, Excellent, (2250)
"our stay was amazing minus the condensation pipe leaking in the laundry room "
Caribe Cove Resort
Lifetime of Vacations Resort
Lake

Lifetime of Vacations Resort

3.0 star property
9.2 out of 10, Wonderful, (131)
"This is a hidden gem! My family enjoyed our stay here and we are so happy to find it! Very clean and the grounds are beautiful! It’s a true picture of what Florida really looks like! "
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, (107)
"What a wonderful experience. The whole process was seamless from start to finish. Correspondence was always quick and the check in was made so easy. This was home from home for us, it was clean, beds comfortable, and it had everything you could wish for plus the location is just amazing near to Walmart and literally 7 minutes from Animal Kingdom. It was so good we have already booked to return later this year. Thank you to the host for making this such a wonderful stay. "
Spacious Luxury Condo in Windsor Hills Resort! 2 Miles to Disney! 3bed/2bath
Windsor Poolside Escape with Stunning Pool View-Perfect for Families!
Outdoor pool

Windsor Poolside Escape with Stunning Pool View-Perfect for Families!

2.0 star property
10.0 out of 10, Exceptional, (287)
"Great place! Lots of small details made it perfect!"
Windsor Poolside Escape with Stunning Pool View-Perfect for Families!
Great Caribbean style condo near Disney
Exterior

Great Caribbean style condo near Disney

9.6 out of 10, Exceptional, (161)
"Condo was great. Very quiet complex we had s great time and would stay again. "
Great Caribbean style condo near Disney
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, (106)
"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
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, (111)
"This place was accurately advertised. Being from out of town & not knowing the area, it was GREAT that this place was in a gated & secure area. This condo was accurately advertised, honestly, it was better! "
Newly Remodeled & Furnished! Largest Windsor Hills Condo!Kid-Friendly Water Park
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

9.0 out of 10, Wonderful, (30)
"Condo was beautiful and clean. Close to everything and very convenient to all the Disney parks. "
Ground floor 3 bed condo close to POOL and WATER PARK in Windsor Hills Resort
Modern & comfortable, 5 mins to Disney. WiFi, water slides, pool, sports.
A heated pool

Modern & comfortable, 5 mins to Disney. WiFi, water slides, pool, sports.

9.4 out of 10, Exceptional, (66)
"This place was really nice and welcoming"
Modern & comfortable, 5 mins to Disney. WiFi, water slides, pool, sports.
Dream Disney Family Vacation, Best Resort, 2 Miles To Disney, Space For 8
Exterior

Dream Disney Family Vacation, Best Resort, 2 Miles To Disney, Space For 8

9.2 out of 10, Wonderful, (131)
"We have stayed in this resort before for the proximity to Disney. The condo is clean and has enough bed space. "
Dream Disney Family Vacation, Best Resort, 2 Miles To Disney, Space For 8
CHRIS & SUE'S CONDO AT WINDSOR PALMS 3 MILES FROM DISNEY AND ALL IT'S MAGIC
A heated pool

CHRIS & SUE'S CONDO AT WINDSOR PALMS 3 MILES FROM DISNEY AND ALL IT'S MAGIC

9.6 out of 10, Exceptional, (154)
"Great clean close to parks"
CHRIS & SUE'S CONDO AT WINDSOR PALMS 3 MILES FROM DISNEY AND ALL IT'S MAGIC
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

9.0 out of 10, Wonderful, (94)
"Thank you! Clean and easy access to parks"
STAR WARS first floor 3 bedroom condo in a Galaxy just 2 miles from Disney World
Fantastic lake-view condo with pool, hot tub, balcony, AC & kitchen -near Disney
A heated pool

Fantastic lake-view condo with pool, hot tub, balcony, AC & kitchen -near Disney

8.6 out of 10, Excellent, (15)
"Great resort, roomy and great location with all amenities you need"
Fantastic lake-view condo with pool, hot tub, balcony, AC & kitchen -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, (72)
"Great condo. Everything was clean and nicely decorated. Easy to get in and check out.Great location for going to the Disney Parks! I would definitely recommend, and would stay here again myself. "
Be our Guest - 3 bedroom, sleeps 7 + Condo w/ pool view by Disney and Universal
🏝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, (249)
"We enjoyed our stay at this condo. It was clean and well appointed. The owner was quick to communicate and provided all the information we needed. "
🏝New Water Park!!! Huge Pool, 5 Minutes to Disney World!🏝
DISNEY'S FIREWORKS FROM YOUR LUXURY CONDO WITH WIRELESS INTRENET
Outdoor pool, a heated pool

DISNEY'S FIREWORKS FROM YOUR LUXURY CONDO WITH WIRELESS INTRENET

9.6 out of 10, Exceptional, (122)
"We had a great stay with plenty of room!"
DISNEY'S FIREWORKS FROM YOUR LUXURY CONDO WITH WIRELESS INTRENET
Stunning, Newly Renovated Condo, Near Disney and Universal
Pool

Stunning, Newly Renovated Condo, Near Disney and Universal

9.6 out of 10, Exceptional, (130)
"Clean, Calm and Warm. Amazing condo. "
Stunning, Newly Renovated Condo, Near Disney and Universal
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, (64)
"For the money, this place was great Positives: great pool (open til 10pm), bar, and on site store (we had to buy a roll of toilet paper, the rental only has the rolls that are on the toilet roll in each bathroom), spacious for our family of 5, great layout of the condo, plenty of parking, easy access to Disney, and comfy mattresses. Negatives: carpet needs replaced in the condo, and plumbing (toilets) were very sensitive to even just a small amount of toilet paper. All in all, I’ll say it...
5 Star Resort minutes from Disney 3 bedrooms & 2 baths, Wi-Fi, Pool, Tennis
2-102 Legacy Dunes resort, Kissimmee, close to Walt Disney World, Heated Pool
Outdoor pool, a heated pool

2-102 Legacy Dunes resort, Kissimmee, close to Walt Disney World, Heated Pool

10.0 out of 10, Exceptional, (31)
"We enjoyed this stay very much. Everything was provided, it was clean, peaceful, and lovely. We highly recommend this place to stay! "
2-102 Legacy Dunes resort, Kissimmee, close to Walt Disney World, Heated Pool
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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Other property types in Lakeland - Winter Haven

Summer Bay Orlando by Exploria Resorts
5 outdoor pools, pool umbrellas, sun loungers

Summer Bay Orlando by Exploria Resorts

3.5 star property
8.4 out of 10, Very Good, (5418)
"Great place "
The price is AED 446
AED 618 total
includes taxes & fees
28 May - 29 May
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, (1382)
"Great place to stay"
The price is AED 1,815
AED 2,983 total
includes taxes & fees
2 Jun - 3 Jun
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, (1761)
"Great stay!"
The price is AED 333
AED 416 total
includes taxes & fees
8 Jun - 9 Jun
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?
The price range for condos in Lakeland - Winter Haven is to 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 118 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.