Search Villas in Lakeland - Winter Haven

    calendar shield illustration
    Change your mind
    Book hotels with free cancellation
    deals illustration
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    bed illustration
    Be picky
    Search almost a million properties worldwide

Check prices for these dates

Next weekend
In two weeks
In one month
In two months

Villas in Lakeland - Winter Haven

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

9.6 out of 10, Exceptional, (118)
"Excellent location, clean and spacious! Will definitely stay again!"
The price is SAR 694
SAR 1,799 total
includes taxes & fees
6 Jul - 7 Jul
*Tinkerbells Castle 1* Private Pool & Spa Overlooking Lake & Disney Fire Works

Only 3 Miles to Disney! South Facing Private Pool 6 BDRM Villa w/ Movie Theatre

10.0 out of 10, Exceptional, (103)
"Location only got a four out of five because we needed doggie day care and the best place we could find was bass pet resort and spa, which was quite a drive from the house."
Only 3 Miles to Disney! South Facing Private Pool 6 BDRM Villa w/ Movie Theatre

Adventure Villa - Heated Pool & Spa - Themed Rooms - Min. to Disney - Game room

9.8 out of 10, Exceptional, (240)
"The home was perfect for our family vacation in Orlando "
Adventure Villa - Heated Pool & Spa - Themed Rooms - Min. to Disney - Game room

MARCH SPECIAL AVAILABLE!

9.0 out of 10, Wonderful, (72)
"We were visiting Disney and the location was great. The home is nicely appointed and well maintained. Would definitely recommend. "
MARCH SPECIAL AVAILABLE!

PRIVATE VILLA WITH SECURITY GATE, ON SUNSET LAKES-KISSIMMEE. 10MIN TO DISNEY :)

9.8 out of 10, Exceptional, (122)
"The house had everything we needed. Kids loved the pool. Parents loved the alarms on the pool doors. Lots of kitchen items to make it easy to cook some meals. Location was ideal. Will stay here again. "
PRIVATE VILLA WITH SECURITY GATE, ON SUNSET LAKES-KISSIMMEE. 10MIN TO DISNEY :)

Disney/Universal/Golf Sandyridge 4bed/3bath Villa book now Pool Heat Included

9.6 out of 10, Exceptional, (103)
"Fantastic home and owner. Wouldnt hesitate to book this home again. Rocky was an excellent host and the property is very well kept. "
Disney/Universal/Golf Sandyridge 4bed/3bath Villa book now Pool Heat Included

Amazing Villa with south facing pool and conservation view

9.8 out of 10, Exceptional, (205)
"Clean Property, pool and hot tub are heated with natural gas so it is very warm on those cool January dayswould definitely stay here again. "
Amazing Villa with south facing pool and conservation view

South Facing Pool and Spa - Resort Amenities

7.6 out of 10, Good, (19)
"Lets go positive first Listing was mostly as advertised"
South Facing Pool and Spa - Resort Amenities

Luxury 4 BR /3 BA Villa - Pool/Spa Not Overlooked, Games Room

9.8 out of 10, Exceptional, (163)
"Quite neighborhood. Busy highway around the area"
Luxury 4 BR /3 BA Villa - Pool/Spa Not Overlooked, Games Room

3 Miles from Disney!!!!! 4 Bedroom Villa with Private Pool/Game Room

10.0 out of 10, Exceptional, (15)
"Awesome place to stay. Beautiful house, wonderful private pool and safe location. Our entire family enjoyed our stay."
3 Miles from Disney!!!!! 4 Bedroom Villa with Private Pool/Game Room

4 Bedroom Villa 2 Miles from Disney Entrance Kissimmee Us192

10.0 out of 10, Exceptional, (288)
"We stayed here for proximity to Disney parks. It provided a short commute."
4 Bedroom Villa 2 Miles from Disney Entrance Kissimmee Us192

Luxury Villa Close to Disney 5br Private Pool

9.8 out of 10, Exceptional, (56)
"Comfortable stay for a few days at Disney."
Luxury Villa Close to Disney 5br Private Pool

West Facing Pool and Spa

9.0 out of 10, Wonderful, (72)
"The house was as advertised. It was spacious and comfortable and made for a great and relaxing vacation. Would definitely stay here again. "
West Facing Pool and Spa

LUXURY FOR YOU + Last-Minute-Rates: 2 Masters, Gas Grill, TV65" 4K & Game Room

9.6 out of 10, Exceptional, (144)
"Clean, comfy, and in a quiet neighborhood"
LUXURY FOR YOU + Last-Minute-Rates: 2 Masters, Gas Grill, TV65" 4K & Game Room

Family Vacation @ Resort with Private Pool, 6Bdrm

9.4 out of 10, Exceptional, (11)
"House and pool was perfect for my family we had a blast and bonus resort pool/waterpark down the street gated community very nice. Property manager was great."
Family Vacation @ Resort with Private Pool, 6Bdrm

Windsor Hills Resort 6 Bedroom South Facing Pool/ Spa Home Steps to the Magic

10.0 out of 10, Exceptional, (113)
"This house was perfect for our stay. The pool and the game room at the house were enjoyed by all. House was very well equipped and very clean. I would definitely recommend it."
Windsor Hills Resort 6 Bedroom South Facing Pool/ Spa Home Steps to the Magic

Home away from home next to Disney .

10.0 out of 10, Exceptional, (148)
"Great location, welcoming and the host was prompt with any questions we might have asked. It was perfect for our family vacation!! We would definitely stay there again. Thank you for being such great hosts!! "
Home away from home next to Disney .

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

9.6 out of 10, Exceptional, (8)
"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

9.2 out of 10, Wonderful, (82)
"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 8 Bedroom Villa, Good for 18 to 20, Pool/Spa

8.6 out of 10, Excellent, (150)
"The house was in a great location and had tons of bedrooms. I was very disappointed that the hot tub and pool heater didn't work and we didn't get a refund for that (other than the 100 we paid to heat it). We had booked this house because it was one of the few that had a hot tub. We understand that things happen but it would have been nice to have gotten a bit of a refund. The house furniture needs some help as the patio table is broken and the living room furniture is in need of repair. "
Luxury 8 Bedroom Villa, Good for 18 to 20, Pool/Spa
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.
Save an average of 15% on thousands of hotels when you're signed in

Frequently asked questions

How much do villas in Lakeland - Winter Haven cost?
Expect to pay between and 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 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.