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Featured Villas in Lakeland - Winter Haven

Large Margaritaville Villa w/ Private Pool + View

4.0 star property
8.4 out of 10, Very good, (5)
"Great property, comfortable beds, kitchen equipped with everything you need, washer and dryer, dinning table for 10 people, every room with tv, terrace tv, bathroom and small pool but very pleasant. No rooms on first floor. 3 rooms on second floor and 2 rooms on third floor. I will stay again."
Large Margaritaville Villa w/ Private Pool + View

*Nice Greenbackyard*Cozy 6BR Windsor Hills Pool Villa,2 Miles To Disney

9.2 out of 10, Wonderful, (62)
"Pretty good stay. We've always enjoyed the location of Windsor Hills; close to Disney, easy to get to, comfortable and safe. The house was roomy and more than adequate for our family of twelve. If there was anything negative it would be: only two cars can be parked in the driveway (if you have a 3rd car, it has to be parked at the main entrance area), the pool was murky and not useful for our stay. The pool maintenance guy came out twice to add chemicals, but didn't solve it. No kitchen towels....
*Nice Greenbackyard*Cozy 6BR Windsor Hills Pool Villa,2 Miles To Disney

Champions Gate Luxury 6 Bedroom Resort Villa With Spa and Games Room on Golf Course community

8.6 out of 10, Excellent, (33)
"Lovely villa, excellent area to stay, we loved the club house and all the amenities. Would definitely stay again. Any problems we had were sorted quickly, excellent service. "
Champions Gate Luxury 6 Bedroom Resort Villa With Spa and Games Room on Golf Course community

Outstanding 6 Bed Villa, Pool & Spa, Superb Lakefront Setting, 5* Windsor Hills

10.0 out of 10, Exceptional, (169)
"The home and location were just as stated on line. We paid extra for the pool to heated during our stay and it was perfect. The home is within easy access to shopping, groceries, restaurants, and theme parks. The home had lots of glasses, dishes, and cutlery. The downside to our trip was it there was not enough essentials in the home. There was 6 adults and 3 children in our group and we stayed for 9 days. We only had the 1 roll of toilet paper that was on the dispenser in each bathroom,...
Outstanding 6 Bed Villa, Pool & Spa, Superb Lakefront Setting, 5* Windsor Hills

4 Bedroom Villa 2 Miles from Disney Entrance Kissimmee Us192

10.0 out of 10, Exceptional, (272)
"The stay was really good. The host was fantastic and communicated well. The only problem we had was ants on the kitchen counter."
4 Bedroom Villa 2 Miles from Disney Entrance Kissimmee Us192

Luxury golf club Villa,cul-de-sac,close to Disney Quiet,Private Large Pool Area

9.8 out of 10, Exceptional, (117)
"Payed to have pool heated and was perfect temperature.Patio was in full sun facing south, we would have liked an umbrella for some shade. The house was as described, big glass coffee table was very wobbly and concerning with small children. But all in all great stay and comfortable home."
Luxury golf club Villa,cul-de-sac,close to Disney Quiet,Private Large Pool Area

Superb Orlando Holiday Villa WestHaven Davenport

9.2 out of 10, Wonderful, (55)
"Sorry for the delay in writing a review. This house was wonderful for our family. We found the home to be clean and comfortable. We received very clear directions for check-in. The owner was quick to respond to questions as was the property manager. Our kids liked the TV’s in their bedrooms, as they don’t have that at home! We also enjoyed the pool, especially on the 80 degree day we got. The pool heat was definitely worth it, even though we did not use the pool every day of our stay as we were...
Superb Orlando Holiday Villa WestHaven Davenport

2 King Ensuite on First Floor with Very Private Pool 5BD/5BA 10% Discount!

9.8 out of 10, Exceptional, (30)
"This home was perfect for our two family’s trip to visit local theme parks. The host was very helpful and responded quickly to any questions I had. "
The price is AU$1,040
includes taxes & fees
28 Feb - 1 Mar
2 King Ensuite on First Floor with Very Private Pool 5BD/5BA 10% Discount!

GRAND OPENING: UNLIMITED FUN! New 10BR Lux Pool/Spa Villa with Disney Magic!

10.0 out of 10, Exceptional, (3)
"Our stay in the home was very relaxing, and enjoyable. We did not leave the home to go do other things. The home had everything we needed and looked as it was pictured."
GRAND OPENING: UNLIMITED FUN! New 10BR Lux Pool/Spa Villa with Disney Magic!

Family Friendly Villa close to the attractions with Pool & Spa

9.6 out of 10, Exceptional, (113)
"Great property and plenty of room. "
Family Friendly Villa close to the attractions with Pool & Spa

Princess, Pirate & Super Hero Rooms, Mickey Pool, Toys & Game Room For All Ages

9.8 out of 10, Exceptional, (164)
"We had the best time staying here! The home was clean and had everything we needed. The princess, spider man and pirate themed rooms were perfect! The game and toy room was perfect for our kids aged 2-6 years old. The pool was perfect. The eating areas were perfect for our large group. "
Princess, Pirate & Super Hero Rooms, Mickey Pool, Toys & Game Room For All Ages

Splendid 5 Lake View Villa With Heated Pool/spa Near Disney

9.2 out of 10, Wonderful, (24)
"This was one of the most beautiful properties that we stayed at before. The pictures didn’t do it justice, including the fact that the sun set over the lake in the backyard every night. Truly stunning."
The price is AU$1,107
includes taxes & fees
19 Feb - 20 Feb
Splendid 5 Lake View Villa With Heated Pool/spa Near Disney

Luxury Orlando Villa with PrivateTheater at pool area

9.4 out of 10, Exceptional, (31)
"We had a blast enjoying the pool, hot tub and watching movies in the game room. The house was conveniently located about 20 minutes from Disney. We were a little disappointed there was only one video game available in the game room and there was no water filter/ice on the fridge but overall had a good experience."
Luxury Orlando Villa with PrivateTheater at pool area

THE ULTIMATE MOUSE HOUSE, a Spectacular Disney Themed Pool Villa for Families!!

9.0 out of 10, Wonderful, (100)
"could have been cleaned better. plus closet door fell off in one room when trying to open. dangerous. glad it was me opening it and not my 3 year old granddaughter."
THE ULTIMATE MOUSE HOUSE, a Spectacular Disney Themed Pool Villa for Families!!

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

9.8 out of 10, Exceptional, (231)
"The home was perfect for our family vacation in Orlando "
Adventure Villa - Heated Pool & Spa - Themed Rooms - Min. to Disney - Game room

Emerald Island Resort 8 Bed Pool Villa

10.0 out of 10, Exceptional, (1)
"Beautiful home. Very well kept. We really enjoyed this beautiful house! Highly recommend. 10/10 "
Emerald Island Resort 8 Bed Pool Villa

Sunny lake view villa -south facing pool -4 Beds, 2 en-suites near major parks

10.0 out of 10, Exceptional, (79)
"The home is accurately pictured and described. Some in our group said it was bigger than they expected from the pictures. The communication throughout our booking and assistance from the hosts was exceptional as well as readily accommodating as we made a couple of booking adjustments early on. The house is easily assessible to the Disney Parks, close to a Publix for groceries as well as other places to eat. Beds were comfortable and we slept very well! Fl. was having a chilly spell our week so...
Sunny lake view villa -south facing pool -4 Beds, 2 en-suites near major parks

Luxury Villa with Private Pool in Paradise Woods

9.6 out of 10, Exceptional, (113)
"Great house for a family. Kids had a great time in the heated pool. House was clean and well kept. Would highly recommend "
Luxury Villa with Private Pool in Paradise Woods

Spacious Vacation Home 5 Minutes from Disney! Sleeps 14!

9.8 out of 10, Exceptional, (109)
"We really enjoyed our stay. Everything was great, would stay here again for sure."
Spacious Vacation Home 5 Minutes from Disney! Sleeps 14!

Choose us for 2025! Spring Break Special/Near Disney

9.8 out of 10, Exceptional, (38)
"Very nice home, very clean, great pool"
Choose us for 2025! Spring Break Special/Near Disney
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

Margaritaville Resort Orlando Cottages by Rentyl

4.0 star property
8.8 out of 10, Excellent, (1198)
"Stayed at cottages. Good size homes. A bit of a drive back to the main hotel with the pools and bars. But there is a shuttle service that will take you over there and back. There were plenty of smaller side pools that were within walking distance from our cottage. We didn’t have enough towels and bedsheets and/or pillows, but they were brought over to our cottage by housekeeping. There is only housekeeping services available for an extra fee. The stay was nice and we would go back there again."
Margaritaville Resort Orlando Cottages by Rentyl

Summer Bay Orlando by Exploria Resorts

3.5 star property
8.4 out of 10, Very good, (5139)
"It was a great experience. Will come back again "
The price is AU$265
includes taxes & fees
4 Mar - 5 Mar
Summer Bay Orlando by Exploria Resorts

The Berkley, Orlando

4.0 star property
9.4 out of 10, Exceptional, (1672)
"The best staff at any resort we have ever stayed at. It was clean, very well taken care of. The pool and hot tub area was always in pristine cleanliness. My only complaint is the furniture, it’s not a comfortable couch and the living room chairs weren’t any better. "
The price is AU$421
includes taxes & fees
3 Mar - 4 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 villas in Lakeland - Winter Haven cost?
Villas in Lakeland - Winter Haven cost between AU$1,040 and AU$1,107 per night. These getaways offer the privacy to enjoy your own space at a price that fits your budget. 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 villas are there in Lakeland - Winter Haven?
Take your pick of 217 villas in Lakeland - Winter Haven. Whether you’re getting away with your family or close friends, and wherever your travels take you, Expedia makes it easy to find the perfect space.
What is there to do near my villa in Lakeland - Winter Haven?
Whether you’re here for dining, sightseeing, museums or malls, Lakeland - Winter Haven offers something for everyone! The top city of Lakeland has lots of things to do and see, including Polk Museum of Art, Polk Theatre and Explorations V Children s Museum. If you’re headed to Winter Haven, Theatre Winter Haven, Indigos Billiards, Bowling & Games and Chain of Lakes Park have to be on your itinerary.