Search Villas in Lakeland - Winter Haven

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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, (111)
"We absolutely loved this property and had an amazing time enjoying the pool and game room. After staying here, we don't see ourselves staying on Disney property again because a house such as this offers so much more freedom and truly feels like a vacation! The house was spotless, and the host was incredibly responsive.The only issue we encountered was discovering on Tuesday that the refrigerator wasn't working. We initially suspected something was wrong when our ice cream never fully froze. I...
The price is AED 533
AED 1,540 total
includes taxes & fees
18 May - 19 May
*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, (228)
"Great location. Owner communicates quickly. Would definitely stay again."
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, (277)
"In a great location, close to the parks and anything we needed. Owners were fantastic and helpful. Place was exactly what we needed, 2 masters and 2 more rooms with queen beds. Worked well for my dad, my husband, daughter, brother in law and mother in law. Owners were always quick to answer. Will stay here again "
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, (110)
"We had a great stay at this vacation home! The house was mostly clean and had everything we needed for a comfortable trip. The kids especially loved the Mickey-themed game room — it kept them entertained for hours! The location was a huge plus — super convenient to both Disney and Universal, which made getting around really easy. Overall, it was a nice spot to relax after long days at the parks. "
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, (154)
"This was a senior trip for our 17 year old, and everything about it was perfect. The house was immaculate when we arrived, and the location was never more than 15 minutes from any Disney park we wanted to visit. Thank you for being our "home base" and helping make this trip a great one!"
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, (229)
"I stayed in this home for one week with my family of 10. The home was exactly as described and shown in photos. The host was easily accessible and gracious with my questions. Will definitely be staying here again. "
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, (4)
"This was a great location for our family trip for 12. The home was spacious and had everything we needed for an enjoyable stay. The neighborhood had a pool with a separate kids area. There was also a lazy river and a kids activity room that was open during the day. Our rental had its own pool, which you could request to be heated. This was great for the kids with us who enjoyed swimming even after the larger neighborhood pool closed. We were in a great shopping area as well at about 15 minutes...
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, (81)
"The location and the house was beautiful. "
Mickey's Mansion!7BDR Themed,Pool/Spa, near Disney

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

9.4 out of 10, Exceptional, (19)
"We have been blown away by how lovely the dream house is. We stayed here for 2 weeks to do all the Walt Disney World that we could manage and the location is perfect, so close to the parks, a genuine 20 minutes drive from the main gates of Disney.The host has been amazing throughout with helpful communication and thoughtful things we didn't even ask for or expect.The pool was a great temperature, the BBQ was a huge benefit, and the house is in great, clean condition throughout. Plenty of...
Luxury Home, Arcade, Heated Private Pool Free, Near Disneyland. Pet Friendly.

Glenbrook Retreat-Come in as Guests and Leave as Friends

9.6 out of 10, Exceptional, (183)
"The property is conveniently located to the attractions of Orlando, but far enough away to not be a constant nuisance. The property is well equipped with everything you might need. The decor of the home is a little tired. I imagine it gets a lot of use so the paint on the walls could be spruced up, and some of the furnishings have been worn. For example, there’s burn marks on the countertops where people have placed hot pots. The one thing I would recommend is to fix the safety fence around...
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, (72)
"We had 18 people in our group ranging from 3 to 73 years old. This property was perfect for our group. We never felt like we were right on top of each other. We took advantage of all the amenities that we paid for. The pool/spa area, and the game room were used every day. The clubhouse was very nice, but we were only able to take advantage of it a few times. The two refrigerators, dishwashers, and washers/dryers came in very handy. For large groups this place is worth it. "
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, (154)
"Nice place to stay for our family vacation "
The Peninsula - Villa with Pool Conservation Area View

A Star Wars themed villa for fans young and old

10.0 out of 10, Exceptional, (94)
"The house was awesome! The amenities were slammed busy so we didn’t get to use them but it was very nice to have the private pool! Plenty of room for all of us and beds were very comfortable! "
A Star Wars themed villa for fans young and old

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

2.5 star property
10.0 out of 10, Exceptional, (4)
"The house was amazing. Chuck was a terrific manager and responded quickly when we had a question. Waterpark was outstanding. Thanks for the wonderful vacation."
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, (208)
"This was a nice place and we enjoyed our stay. The four bedrooms were nice and had enough beds four our family. The pool was nice and we enjoyed the spa. We opted for the pool heat which was well worth it. The house was as the pictures shown. "
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, (240)
"The home was perfect for our family of 5! The game room, pool, machine, and arcade made it fun for my kids when we weren't enjoying the beach and parks. Everything was super clean and Keith was very responsive and helpful! Thanks"
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, (61)
"Poor communication when questions were asked."
Tropical Oasis - Windsor at Westside - NEW 7 Bedroom, 5.5 Bath, Pool/Spa/WiFI

Luxury 8 Bedroom Villa, Good for 18 to 20, Pool/Spa

8.6 out of 10, Excellent, (146)
"The house is in a great location. Close to the big parks. 25 to 45 minutes depending which one. Theres lots of grocery stores around and many restaurants. The house overall was good. A little banged up in places. There is no working air conditioning upstairs. So it was very hot. We had small children and the plates and bowls were all heavy ceramic. They need plastic ones. Overall it all was good."
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.
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Other property types in Lakeland - Winter Haven

Summer Bay Orlando by Exploria Resorts

3.5 star property
8.4 out of 10, Very Good, (5371)
"First time taking my daughter out of country as a single mom. There is so much to do on resort, transportation to the theme parks, hospitable, clean, excellent communication and overall exceptional service. The staff here go above and beyond, will be rebooking in the future"
The price is AED 397
AED 563 total
includes taxes & fees
7 May - 8 May
Summer Bay Orlando by Exploria Resorts

Margaritaville Cottages Orlando with H2O Waterpark by Rentyl

4.0 star property
8.8 out of 10, Excellent, (1351)
"Excellent accommodations. Very clean."
The price is AED 2,531
AED 3,795 total
includes taxes & fees
24 May - 25 May
Margaritaville Cottages Orlando with H2O Waterpark by Rentyl

The Berkley, Orlando

4.0 star property
9.4 out of 10, Exceptional, (1747)
"Rooms were amazing...staff very friendly"
The price is AED 407
AED 500 total
includes taxes & fees
5 May - 6 May
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 533 and AED 533 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.