Search Villas in Lakeland - Winter Haven

  • 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
    today icon
    Change your mind
    Book hotels with free cancellation

Check prices for these dates

Next weekend
In two weeks
In one month
In two months

Compare 262 Villas in Lakeland - Winter Haven with updated reviews, rates, and availability.

*Tinkerbells Castle 1* Private Pool & Spa Overlooking Lake & Disney Fire Works

9.6 out of 10, Exceptional, (110)
"Excellent location, clean and spacious! Will definitely stay again!"
The price is AED 547
AED 1,593 total
includes taxes & fees
20 Apr - 21 Apr
*Tinkerbells Castle 1* Private Pool & Spa Overlooking Lake & Disney Fire Works

Adventure Villa - Beauty & Beast Dining -Themed & Customize Rooms - Private Pool

9.8 out of 10, Exceptional, (221)
"Perfect house for family of 6 making a week-long trip to Disney. Parks were a quick 10-15 min drive and kids enjoyed the play room on our day off. "
Adventure Villa - Beauty & Beast Dining -Themed & Customize Rooms - Private Pool

4 Bedroom Villa 2 Miles from Disney Entrance Kissimmee Us192

10.0 out of 10, Exceptional, (275)
"Very close to Disney parks. Clean. Large rooms. Worked out very well for 4 adults and 3 kids ages 2-5"
4 Bedroom Villa 2 Miles from Disney Entrance Kissimmee Us192

A 6 Bedroom Home at Solterra Resort with Pool & Spa with a Nice Lake View!

9.4 out of 10, Exceptional, (85)
"Our 9 night stay as a family was fantastic! We are a group of 6 adults and 3 kids ranging in age from 10-14. The feature we loved most was the set up of this home with the three master suites and the spaciousness of all the rooms. Pool and hot tub were great and worked flawlessly. We spent a fair amount of time at the resort pool as well, which we all enjoyed. The only items we were really missing and could have used more of were towels and just extra blankets. Absolutely zero issues with host,...
A 6 Bedroom Home at Solterra Resort with Pool & Spa with a Nice Lake View!

Modern Villa less than 10 minutes from Disney

10.0 out of 10, Exceptional, (109)
"We had a wonderful stay at this house. We didn't do too much outside of the resort because the warm pool and hot tub, plus the community pool and courts gave us plenty of places to go. We enjoyed walking in the community as well and there were some cute little parks. Families with littles should check out the castle park!The home was huge, clean, and had everything we wanted. We can't complain about a thing. Thanks Chris for everything you did for us, and providing a wonderful vacation home!"
Modern Villa less than 10 minutes from Disney

Ultimate New Encore Home Modern Furnishings Throughout

8.4 out of 10, Very Good, (26)
"Myself and 11 others travel south each what for Speedweeks in Daytona. We stay in the Kissimmee area because there is so much to do. This was our 4th year and by far our favorite house we have stayed in. The house was clean and just like the picture. The backyard had plenty of room for all of us to relax and just chill out. Great home!!!"
Ultimate New Encore Home Modern Furnishings Throughout

NEW LISTING! 4 Bed/4 Bath Home W/ South Facing Pool And Game room with A/C

9.8 out of 10, Exceptional, (151)
"This has been the best property we have ever stayed at. I cannot express how impressed I was with the cleanliness of this home and just how nice everything was this property. Our 15 year-old and 11-year-old sons loved having their own bedrooms with TV and it was so nice to be able to come back every day and hop in a warm pool and hot tub that we had all to ourselves. The game room entertained us many nights with the pool table and air hockey. We loved the neighborhood and being able to walk to...
NEW LISTING! 4 Bed/4 Bath Home W/ South Facing Pool And Game room with A/C

Our DisneyDreamVilla - Salt water pool! Only minutes to DisneyWorld!!!

10.0 out of 10, Exceptional, (226)
"We loved the size of the house and the spacious pool area. We were close to everywhere we wanted to go. We also liked the gated community feel for security. Everyone had their own bedroom and bathroom. It met all our needs and was a great place to stay for our family Spring Break vacation! "
Our DisneyDreamVilla - Salt water pool! Only minutes to DisneyWorld!!!

NEW OPENING! 5b4b Disney Themed Vacation Home w/Pool & BBQ ~12 min from Disney~

10.0 out of 10, Exceptional, (1)
"We loved staying here in Feb. The highlight has to be the great pool just steps away with beautiful heated water, a lazy river, giant kids zero depth play area, drinks and food purchase area, exercise room and great views of the lake just outside the pool area. Many rentals have long lines at the gate but this community never had a line. The location is close to Disney and has some wonderful restaurants nearby. You can get on the 429 6 miles above I4 which saves so much time. We would love...
NEW OPENING! 5b4b Disney Themed Vacation Home w/Pool & BBQ ~12 min from Disney~

Mickey's Mansion!7BDR Themed,Pool/Spa, near Disney

9.4 out of 10, Exceptional, (79)
"Would recommend for a large group who needs easy access to Disney. We came for our child’s competition at ESPN and it was very convenient to get back and forth. Lots of room to spread out, newly updated bathrooms, pool access and quaint neighborhood. Shopping and restaurants were easily accessible and neighborhood was quiet. "
Mickey's Mansion!7BDR Themed,Pool/Spa, near Disney

Luxury Home, Arcade, Heated Private Pool Near Disneyland. Pet Friendly.

9.4 out of 10, Exceptional, (18)
"We really enjoyed our time here. The home was clean, spacious and in a great location. The owner was responsive and communicated very clearly. "
Luxury Home, Arcade, Heated Private Pool Near Disneyland. Pet Friendly.

Glenbrook Retreat-Come in as Guests and Leave as Friends

9.6 out of 10, Exceptional, (179)
"My family and I loved our stay. The house is spacious, clean and is located in a great neighborhood . Would definitely stay here again. "
Glenbrook Retreat-Come in as Guests and Leave as Friends

Outdoor Movie System, Outdoor pool, 15 min. to Disney, Family friendly!

9.2 out of 10, Wonderful, (71)
"Upon arrival we were not given the information to get into the house. The back door was unlocked. The dishwasher was drained. The pool didn’t seem as clean as I expected. I wish we would’ve known to use the community pool(resort) was a fee. The smoker didn’t work. "
Outdoor Movie System, Outdoor pool, 15 min. to Disney, Family friendly!

The Peninsula - Villa with Pool Conservation Area View

9.4 out of 10, Exceptional, (153)
"Everything was just as described. The only recommendations would be to bring Roku sticks because the tvs are not smart tvs. Also, be aware that the cleaning crew will be there waiting for you to exit the premise. We felt rushed to leave as they arrived at around 9:30. "
The Peninsula - Villa with Pool Conservation Area View

A Star Wars themed villa for fans young and old

10.0 out of 10, Exceptional, (91)
"We had an amazing time. My daughter loved the pool and the hot tub was wonderful after those long days at Disney. The themed rooms were great. We didn't get a chance to explore the grounds this trip, but plan on returning in the future with scheduled "off days" from the parks. Chris was amazing and quick to respond to my texts before and during the trip. Highly recommended."
A Star Wars themed villa for fans young and old

Luxurious 6 bed, 5.5 bath villa, south facing, extended private pool

9.8 out of 10, Exceptional, (56)
"We rented this house for the Canadian March break. We have rented many homes over the years, and this is the best home we have ever rented. It was the nicest, cleanest and well equipped home we’ve ever rented. We enjoyed the hot tub and pool everyday and the game room was a bonus that our whole family enjoyed. The second fridge was a bonus as well came in handy with a large family. Debbie was very pleasant to deal with and her management team is amazing too. We look forward to booking this home...
Luxurious 6 bed, 5.5 bath villa, south facing, extended private pool

Brand New 10BR at Windsor Island/Pool/Spa/Firework View

2.5 star property
10.0 out of 10, Exceptional, (2)
"The house is just like the pictures . The host always replied to my messages . The house was clean and also the towels . The lady security upfront was very rude because only 1 of us in the car didnt have our id from the festival ; threaten us "
Brand New 10BR at Windsor Island/Pool/Spa/Firework View

EXQUISITE VILLA - 2 Master Suites, Pool South+Spa, Gas BBQ, Game Room, WIFI

9.6 out of 10, Exceptional, (203)
"We enjoyed our stay. The house was very clean. Everything we needed was in the house. Thank you"
EXQUISITE VILLA - 2 Master Suites, Pool South+Spa, Gas BBQ, Game Room, WIFI

Be Our Guest House ~ A Unique Disney Experience in Itself ~ Star Wars & Frozen.

10.0 out of 10, Exceptional, (236)
"Everything was clean and comfortable overall. It has plenty of space and the neighborhood was quiet. There is a grocery store at the highway 2 minutes from the house. The outdoor space is small but nice and had vests for small children. The only negative comments would be for the games. Pool cues were missing tips and there was no chalk for them. Air hockey table either wasnt moving enough air or the pucks are too worn to hover smoothly. I'm sure its tough to keep in good shape and it...
Be Our Guest House ~ A Unique Disney Experience in Itself ~ Star Wars & Frozen.

Tropical Oasis - Windsor at Westside - NEW 7 Bedroom, 5.5 Bath, Pool/Spa/WiFI

8.6 out of 10, Excellent, (60)
"This stay allowed for a relaxing getaway. The house is in a great location and in a safe neighborhood. It’s very close to Disney for those traveling for that reason. The community amenities are great (pool, gym, lounge, etc). The house itself is very spacious and well decorated, with room to fit probably 20 people comfortably. There are some upkeep issues that show signs of wear and tear but this did not take away from the experience of the trip and my vacation as a whole. The host was receptive...
Tropical Oasis - Windsor at Westside - NEW 7 Bedroom, 5.5 Bath, Pool/Spa/WiFI
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

Other property types in Lakeland - Winter Haven

Summer Bay Orlando by Exploria Resorts

3.5 star property
8.4 out of 10, Very Good, (5282)
"The Employees were courteous and the property is beautiful. We had a junior condo and it worked perfectly! The only negatives were the washer didn't work properly and the mattress wasn't super comfortable. We wouldn't hesitate to book with Summer Bay again, the next time we visit FL."
The price is AED 430
AED 599 total
includes taxes & fees
9 Apr - 10 Apr
Summer Bay Orlando by Exploria Resorts

Margaritaville Cottages Orlando with H2O Waterpark by Rentyl

4.0 star property
8.8 out of 10, Excellent, (1293)
"We stayed in a villa and it was very clean, comfy and felt just like home. The only disadvantage is that it is about a mile away from the main pool and amenities so we did need to use our car to get around. Overall, Beautiful place and great for a family getaway! We really enjoyed sunset walk as they had lots of kids activities and plenty for the adults as well. We will stay again! "
Margaritaville Cottages Orlando with H2O Waterpark by Rentyl

The Berkley, Orlando

4.0 star property
9.4 out of 10, Exceptional, (1717)
"Excellent, just wish the electric chargers for EV were included with the stay."
The price is AED 663
AED 788 total
includes taxes & fees
20 Apr - 21 Apr
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 villas in Lakeland - Winter Haven cost?
Expect to pay between AED 547 and AED 547 per night for villas in Lakeland - Winter Haven. No matter your budget, a fantastic stay is just a few clicks away on Expedia. 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 villas are there in Lakeland - Winter Haven?
Take a look at our 262 villas in Lakeland - Winter Haven and then book your favorite. Whether you’re planning a family vacation or jet-setting with friends, Expedia has got you covered.
Why book your villa in Lakeland - Winter Haven with Expedia?
Booking a villa in Lakeland - Winter Haven is as simple as deciding on your travel dates and choosing an option that checks your boxes. Looking for something upscale or budget friendly, or a stay that also offers a pool and free WiFi? Use Expedia’s search filters to narrow your results and find your perfect match.
How can I find cheap villas in Lakeland - Winter Haven?
The simplest way to compare cheap villas in Lakeland - Winter Haven is with Expedia’s handy filter tool. Narrow your search by star rating, budget and amenities to discover unbeatable bargains in just a click or two.