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Check prices for these dates

Next weekend
28 Feb - 2 Mar
In two weeks
7 Mar - 9 Mar
In one month
21 Mar - 23 Mar
In two months
18 Apr - 20 Apr

Compare 217 Villas in Lakeland - Winter Haven with updated reviews, rates, and availability.

Large Margaritaville Villa w/ Private Pool + View
Pool

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
Pool

*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
1538-moon-valley-drive--davenport--fl-33896---01.jpg

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
Pool

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
Villa

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
Dining

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
Our Villa

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!
Spa and Waterpark

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 AED 735
AED 2,380 total
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!
Children's area

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

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
Princess room with princess dresses

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

9.8 out of 10, Exceptional, (164)
"Everyone in our family was impressed with the property! We can’t say enough good things. It perfectly accommodated our party of 12, ages 8months- 65yrs for week that included Disney World. Everything was very clean, host was responsive when we needed help finding a couple random things. Community pool and playground were a big plus on down days!"
Princess, Pirate & Super Hero Rooms, Mickey Pool, Toys & Game Room For All Ages
Splendid 5 Lake View Villa With Heated Pool/spa Near Disney
Miscellaneous

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

9.2 out of 10, Wonderful, (25)
"Large Home- Pretty View- Great Location "
The price is AED 680
AED 2,473 total
includes taxes & fees
24 Feb - 25 Feb
Splendid 5 Lake View Villa With Heated Pool/spa Near Disney
Luxury Orlando Villa with PrivateTheater at pool area
Pool

Luxury Orlando Villa with PrivateTheater at pool area

9.4 out of 10, Exceptional, (32)
"House was perfect for our getaway, close to everything downtown was a short uber ride. Hosts were the best to deal with and give a huge thumbs up to them for making our stay one to remember!"
Luxury Orlando Villa with PrivateTheater at pool area
THE ULTIMATE MOUSE HOUSE, a Spectacular Disney Themed Pool Villa for Families!!
Enjoy our bright and spacious open kitchen, equipped with everything you need.

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
Adventure Villa - Safe & Private location & only Minutes to all the action

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

9.8 out of 10, Exceptional, (231)
"This house was everything! Great location! Clean! The pool was so awesome! Very clean! Prompt response from host every time! Thank you! We will be back!!! The star wars room was so so cool! "
Adventure Villa - Heated Pool & Spa - Themed Rooms - Min. to Disney - Game room
Emerald Island Resort 8 Bed Pool Villa
8583-sunrise-key-drive--kissimmee--fl-34747---01

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
south facing pool area with Spa

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

10.0 out of 10, Exceptional, (79)
"We really enjoyed our stay and the location of the home! The extras for our granddaughter, high chair, playpen and stroller, were a huge bonus! "
Sunny lake view villa -south facing pool -4 Beds, 2 en-suites near major parks
Luxury Villa with Private Pool in Paradise Woods
Outside front of Villa Paradise Woods

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!
Welcome home: Your vacation oasis awaits at the front door! 🏡✨

Spacious Vacation Home 5 Minutes from Disney! Sleeps 14!

9.8 out of 10, Exceptional, (110)
"we stayed here for a family vacation to all the parks. its within 15 to 20min. of anything you want to do. close to the Disney locations. there is all the amenities you need very close like groceries and eating out. we ate at a Brazilian restaurant that was awesome and recommend. it was only a 2 min. drive from house. everything was clean and the owner stays in touch so everything works out to the best. would stay again if we came back. "
Spacious Vacation Home 5 Minutes from Disney! Sleeps 14!
Choose us for 2025! Spring Break Special/Near Disney
Nemo

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
Front of property

Margaritaville Resort Orlando Cottages by Rentyl

4.0 star property
8.8 out of 10, Excellent, (1209)
"We had a fantastic stay at Margaritaville Resort Orlando Cottages! The cottages were incredibly spacious and perfect for our family of seven—everyone was comfortable, and we never felt cramped. The location was ideal for our Disney World trip, with easy access to the parks while also providing a peaceful and relaxing retreat after long days of adventure. The atmosphere was wonderful, and it truly felt like a home away from home. We would absolutely stay here again and highly recommend it to...
Margaritaville Resort Orlando Cottages by Rentyl
Summer Bay Orlando by Exploria Resorts
Property amenity

Summer Bay Orlando by Exploria Resorts

3.5 star property
8.4 out of 10, Very Good, (5160)
"Me and my bf stay for 5 days in the junior suite, it was very accommodating and lots of pools and activities for families, we felt very safe and welcomed. Rooms were very clean, the only thing that we didn’t care for was the living room, it’s very big with small tv and furniture but that’s nothing we just spent most of our time in the nice comfy king bed, will definitely stay again but may just upgrade our room next time! "
The price is AED 463
AED 636 total
includes taxes & fees
23 Mar - 24 Mar
Summer Bay Orlando by Exploria Resorts
Holiday Inn Club Vacations Orlando Breeze Resort
Property amenity

Holiday Inn Club Vacations Orlando Breeze Resort

3.5 star property
9.4 out of 10, Exceptional, (414)
"Loved the big space in the apartment-sized living room/kitchen/eating area and bedroom and bathroom. Having a full sized kitchen and stove was wonderful. We really enjoyed the large pool and hot tub one evening. Close to lots of restaurants and shopping. Not too far from the highway. "
The price is AED 474
AED 586 total
includes taxes & fees
24 Feb - 25 Feb
Holiday Inn Club Vacations Orlando Breeze Resort
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 range between AED 680 and AED 735 per night. These getaways provide the privacy to enjoy your own space at a price that’s friendly to your wallet. 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?
Lakeland - Winter Haven has 217 villas to choose from. Enter your dates and destination and plan your perfect stay today.
Why book your villa in Lakeland - Winter Haven with Expedia?
Expedia makes it easy to find your ideal villa in Lakeland - Winter Haven. Traveling with the kids? Take advantage of our filters to look for stays with amenities like a pool and WiFi. If you have a budget in mind, choose how much you’d like to spend and the star rating of the property. We’ll help you find the perfect pad that matches your style and taste.
How can I find cheap villas in Lakeland - Winter Haven?
Expedia can help you easily source cheap villas in Lakeland - Winter Haven. Simply use our filter tool to choose star rating, budget and amenities to refine your search and find a fantastic place to stay in just a few clicks.