Search Villas in Lakeland - Winter Haven

Start date: Check-in selected.
To Date
End date: Check-out

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

Next weekend
Jan 2 - Jan 4
In two weeks
Jan 9 - Jan 11
In one month
Jan 23 - Jan 25
In two months
Feb 20 - Feb 22

Our top choices for Lakeland - Winter Haven villas

Villa (4 Bedrooms) | Interior
Contemporary 4BR Townhome With Pool & Themed Rooms

Villa in Clermont

Contemporary 4BR Townhome With Pool & Themed Rooms
3.0 star property
The price is ￥16,482
￥51,050 total
includes taxes & fees
Jan 13 - Jan 14, 2026
Contemporary 4BR Townhome With Pool & Themed Rooms
Exterior
Fully-Equipped Villa Next to Disney!

Villa in Kissimmee

Fully-Equipped Villa Next to Disney!
9.4 out of 10, Exceptional, (75)
"It was clean and centrally located to the disney parks "
United States
Angela S.
The price is ￥18,788
￥38,724 total
includes taxes & fees
Dec 30 - Dec 31
Fully-Equipped Villa Next to Disney!
Villa, 3 Bedrooms | Aerial view
Surfstyle At Margaritaville By Shine Villas 022 3 Bedroom Villa

Villa in Kissimmee

Surfstyle At Margaritaville By Shine Villas 022 3 Bedroom Villa
3.0 star property
Surfstyle At Margaritaville By Shine Villas 022 3 Bedroom Villa
Villa | 4 bedrooms
New 4BR Villa Themed Beds Magic

Villa in Davenport

New 4BR Villa Themed Beds Magic
2.0 star property
10.0 out of 10, Exceptional, (1)
"The house was immaculate and the owners were very responsive to any needs we had."
United States
Kirsten
The price is ￥36,741
￥89,804 total
includes taxes & fees
Jan 19 - Jan 20, 2026
New 4BR Villa Themed Beds Magic
A heated pool
Spacious Luxurious 6 Bedroom 5 Bath Villa Sleeps 12 Pool, Jacuzzi, near Disney

Villa in Trafalgar Village

Spacious Luxurious 6 Bedroom 5 Bath Villa Sleeps 12 Pool, Jacuzzi, near Disney
8.8 out of 10, Excellent, (9)
"House was big enough for the whole family nice pool great area "
United States
Chrystal S.
The price is ￥15,031
￥74,229 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Spacious Luxurious 6 Bedroom 5 Bath Villa Sleeps 12 Pool, Jacuzzi, near Disney
Exterior
Family Vacation Home · 8 Minutes from Legoland Florida

Villa in Winter Haven

Family Vacation Home · 8 Minutes from Legoland Florida
10.0 out of 10, Exceptional, (1)
"Beautiful clean home. Lots of amenities. However it here were glass decorations on table. We moved them out of reach of 2 and 4 year old. Otherwise BEAUTIFUL! Definitely would stay here again."
United States
Roberta W.
The price is ￥21,333
￥55,363 total
includes taxes & fees
Jan 11 - Jan 12, 2026
Family Vacation Home · 8 Minutes from Legoland Florida
Exterior
Pelican by Migration Travel

Villa in Davenport

Pelican by Migration Travel
10.0 out of 10, Exceptional, (5)
"Everything was excellentGreat experience The house was very cleanBenjamin and Kimberly are great hostsLooking forward to staying there again"
Mexico
Ronit M.
The price is ￥20,329
￥73,357 total
includes taxes & fees
Jan 15 - Jan 16, 2026
Pelican by Migration Travel
Exterior
Completely Renovated 3/2 Close to Disney parks

Villa in Royal Palm Bay

Completely Renovated 3/2 Close to Disney parks
10.0 out of 10, Exceptional, (22)
"15 mins drive to Disney, We enjoyed our stay, clean as advertised, Owner communicates in detail, Will definitely rebook this Villa. "
United States
Elisa
The price is ￥24,311
￥54,062 total
includes taxes & fees
Dec 28 - Dec 29
Completely Renovated 3/2 Close to Disney parks
Exterior
Resort Villa with Private Pool & Spa

Villa in Trafalgar Village

Resort Villa with Private Pool & Spa
9.0 out of 10, Wonderful, (2)
"Overall the villa was lovely, beautifully clean inside with nice touches like mini toiletries, large tub of ground coffee, sugar, creamer, plenty of toilet rolls salt and pepper, olive oil, coffee filters oh and a kettle bonus for us Brits.The Lounge, dining and bedrooms were beautifully furnished and had everything we needed. Plenty of bath towels, although could have done with a few more pool towels so we didn’t have to put them in the dryer after each use, but a minor detail.Frank was an...
United States
Sarah B.
The price is ￥20,511
￥69,317 total
includes taxes & fees
Jan 22 - Jan 23, 2026
Resort Villa with Private Pool & Spa
Exterior
4875 Resort Townhouse by Disney World Orlando

Villa in Kissimmee

4875 Resort Townhouse by Disney World Orlando
The price is ￥15,360
￥48,788 total
includes taxes & fees
Jan 22 - Jan 23, 2026
4875 Resort Townhouse by Disney World Orlando
Villa (3 Bedrooms) | Interior
Upstay-luxury 3BR Home w Private Pool & Games Room

Villa in Clermont

Upstay-luxury 3BR Home w Private Pool & Games Room
3.5 star property
The price is ￥23,016
￥51,443 total
includes taxes & fees
Jan 12 - Jan 13, 2026
Upstay-luxury 3BR Home w Private Pool & Games Room
Exterior
Stunning Retreat Townhouse 10 mins to Disney with Pool

Villa in Campbell

Stunning Retreat Townhouse 10 mins to Disney with Pool
2.0 star property
The price is ￥15,903
￥54,719 total
includes taxes & fees
Jan 2 - Jan 3, 2026
Stunning Retreat Townhouse 10 mins to Disney with Pool
Villa, Multiple Bedrooms | Aerial view
Monterey Bay At Solara By Shine Villas #712 7 Bedroom Villa

Villa in Kissimmee

Monterey Bay At Solara By Shine Villas #712 7 Bedroom Villa
3.0 star property
Monterey Bay At Solara By Shine Villas #712 7 Bedroom Villa
Exterior
Mickey's Backyard Themed 6BR with Pool

Villa in Kissimmee

Mickey's Backyard Themed 6BR with Pool
2.5 star property
10.0 out of 10, Exceptional, (2)
"We had a fantastic stay at Franks place. Its absolutely perfect for familys. A really spacious property with everything you need to make it a comfortable stay. Really clean and tidy with lots of towels. The beach towels ready to be used were a great addition.Perfectly located, extremely close to Disney and the 192 which has lots of restaurants, giftshops and supermarkets. We would all 100% stay here again."
United Kingdom
Kris S.
The price is ￥22,546
￥87,878 total
includes taxes & fees
Jan 13 - Jan 14, 2026
Mickey's Backyard Themed 6BR with Pool
Outdoor pool, a heated pool
Fabulous South Facing Lakeside Villa with Private Pool, all at ground level.

Villa in Eagle Pointe South

Fabulous South Facing Lakeside Villa with Private Pool, all at ground level.
9.2 out of 10, Wonderful, (106)
"great choice"
United States
Stefanie M.
Fabulous South Facing Lakeside Villa with Private Pool, all at ground level.
Villa | 5 bedrooms
Luxury Modern Decor Best Location Private Pool

Villa in Kissimmee

Luxury Modern Decor Best Location Private Pool
2.0 star property
The price is ￥34,538
￥86,923 total
includes taxes & fees
Jan 5 - Jan 6, 2026
Luxury Modern Decor Best Location Private Pool
Outdoor dining
VedaHive Luxury Villa

Villa in Solterra Resort

VedaHive Luxury Villa
3.0 star property
6.6 out of 10, (7)
"If you enjoy your vacation with a older lady with a daughter telling you what to do and how to act in the house, then this place is for you. The hot tub at the house does not work. There's limited toilet paper so bring your own toiletries. And the bedroom I stayed in did not have sheets on the bed. Must read all the rules before staying at this house. The clubhouse water park is not included in your stay. That is an additional fee$"
United States
James
The price is ￥9,394
￥29,843 total
includes taxes & fees
Jan 2 - Jan 3, 2026
VedaHive Luxury Villa
Exterior
Kid-Friendly, themed vacation home close to Disney/Universal

Villa in Kissimmee

Kid-Friendly, themed vacation home close to Disney/Universal
10.0 out of 10, Exceptional, (5)
"Quiet, clean, and had everything we needed for our week in Orlando. Close to Disney and shops made our week easy, enjoyable, hassle free."
United States
Brittany S.
The price is ￥16,239
￥55,691 total
includes taxes & fees
Jan 12 - Jan 13, 2026
Kid-Friendly, themed vacation home close to Disney/Universal
Outdoor pool, a heated pool
Gorgeous VILLA near Disney, Private Heated South Pool

Villa in Sandy Ridge

Gorgeous VILLA near Disney, Private Heated South Pool
8.4 out of 10, Very Good, (10)
"Great place, close to everything, enjoyed the pool, appreciated everything on one floor, the owner checked in on us, which was nice. We would definitely stay here again."
Canada
Bruce P.
The price is ￥17,566
￥69,328 total
includes taxes & fees
Jan 8 - Jan 9, 2026
Gorgeous VILLA near Disney, Private Heated South Pool
Exterior
Single Level 5 Bedrm/Pool/SPA/3Miles Disney

Vacation Home in Kissimmee

Single Level 5 Bedrm/Pool/SPA/3Miles Disney
10.0 out of 10, Exceptional, (3)
"This house worked out really well for our disney trip. The layout was great for young kids. The kids really the themed rooms, pool and games!"
United States
Kari S.
The price is ￥17,717
￥87,996 total
includes taxes & fees
Jan 19 - Jan 20, 2026
Single Level 5 Bedrm/Pool/SPA/3Miles 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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Lakeland - Winter Haven Hotel Reviews

Meliá Orlando Celebration

Meliá Orlando Celebration

10/10 Excellent
"Our entire stay were excellent!!! "
Analyn 3-night trip
Posted 2 days ago
Meliá Orlando Celebration

Find out more about Lakeland - Winter Haven

Lakeland - Winter Haven Villas information

Number of reviews
212
Accommodation
253 Villas
Lowest Price
￥29,843
Highest Price
￥89,804

Frequently asked questions

How much do villas in Lakeland - Winter Haven cost?
Expect to pay between ￥29,843 and ￥89,804 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 253 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.
What is there to do near my villa in Lakeland - Winter Haven?
Whether you like food, shopping, history or sightseeing, Lakeland - Winter Haven offers it all, and more! The well-known city of Lakeland has loads of activities and attractions, including Polk Museum of Art, RP Funding Center and Publix Field at Joker Marchant Stadium. If you're escaping to Winter Haven, Indigo's Family Fun Center, Chain of Lakes Park and Theatre Winter Haven are worth putting on your itinerary.

Explore a world of travel with Expedia