Luxury Lakeland - Winter Haven Villas for 2026

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Our top choices for Lakeland - Winter Haven villas

Solara Resort Home With Pool 15min to Disney World

Kissimmee

includes taxes & fees

9 Jun - 10 Jun

Emerald Garden - Resort - 15 Min to Disney - Pets

Kissimmee

includes taxes & fees

26 May - 27 May

Bahama Bay Resort - Ground Floor

Bahama Bay

includes taxes & fees

20 Jun - 21 Jun

VedaHive Luxury Villa

Solterra Resort

Nelson

includes taxes & fees

25 May - 26 May

Magical Hideaway At Kissimmee By Shine Villas 4 Bedroom Villa

Lindfields

includes taxes & fees

26 May - 27 May

Contemporary 4BR Townhome With Pool & Themed Rooms

Clermont

includes taxes & fees

27 May - 28 May

Bahama Bay Resort - Grand Bahama Penthouse

Bahama Bay

includes taxes & fees

5 Jun - 6 Jun

Tranquil Hideaway At Sandy Ridge 4 Bedroom Home

Sandy Ridge

includes taxes & fees

26 May - 27 May

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Top Lakeland - Winter Haven Hotel Reviews

Howard Johnson by Wyndham Lakeland

10/10 Excellent

"The room was clean staff was very nice."

Margaritaville Resort Orlando with H2O Waterpark

10/10 Excellent

"This is my second time staying here and each time I couldn't wait to go back ! The place is clean and the staff is wonderful . There's a rental car in the lobby and even that gentleman was very helpful . Each time I have traveled there , there was a big event going on so it gets a big congested at the front desk but everyone still makes you feel special and greets you with a smile ."

Hilton Vacation Club Aqua Sol Orlando West

6/10 Okay

"If Aqua Sol did not have an excellent maintenance staff I would've gave it two stars. The maintenance staff saved this for me the elevator in building 400 broke several times in the week I was here. Luckily every time it went down, I found a maintenance person, and it was back up and running later, but it kept being a problem throughout the week. The property is well maintained and the staff is excellent. It's a little dated I will admit that. That doesn't make it bad it gives it an old Florida charm that I appreciated. I will say there is a terrible issue with the water pressure here. My shower always felt like it was struggling to push water out and the soaking tub took 20 minutes to fill up. Everything else about the hotel was fine. It's in a great location and while I don't see people spending a whole lot of time on the property there is stuff for you to do if you're having a day in Orlando that isn't filled with the Mouse. A lot more kid friendly so if you have a family, this might be the place for you. Overall, I enjoyed my stay but I probably wouldn't stay here again"

Margaritaville Cottages Orlando by Rentyl with H2O Waterpark

8/10 Good

"Three bedroomed cottage beautiful, spacious and clean. However it was a 15 minute walk to the hotel amenities, sunset walk etc which was too much for the 4yr old in nearly 100 degrees heat. So we ended up going to and fro to the pool, dining etc in the car all the time. Check in staff had no idea on WiFi password for our cottage and we had no Internet access for 2 days which was unacceptable. Our front door lock was broken on our second day and we were locked out, reception staff, one lady specifically was very rude and offhand with us. However once these issues were all sorted we loved our stay there. Pool area is beautiful, sunset walk is lovely and the waterpark next door which we got free access to was fab. We would definitely stay there again but would book the cottage via a company tjat allows us to choose which area we stay in as this resort is huge."

Find out more about Lakeland - Winter Haven

Lakeland - Winter Haven Villas information

Number of reviews	12
Accommodation	8 Villas
Lowest Price	S$222
Highest Price	S$797

Frequently asked questions

How much do villas in Lakeland - Winter Haven cost?

Expect to pay between S$222 and S$797 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 8 villas in Lakeland - Winter Haven and then book your favourite. Whether you're planning a family holiday 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 Centre and Publix Field at Joker Marchant Stadium. If you're escaping to Winter Haven, Indigo's Family Fun Centre, Chain of Lakes Park and Theatre Winter Haven are worth putting on your itinerary.

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Our top choices for Lakeland - Winter Haven villas

Solara Resort Home With Pool 15min to Disney World

Emerald Garden - Resort - 15 Min to Disney - Pets

Bahama Bay Resort - Ground Floor

VedaHive Luxury Villa

Magical Hideaway At Kissimmee By Shine Villas 4 Bedroom Villa

Contemporary 4BR Townhome With Pool & Themed Rooms

Bahama Bay Resort - Grand Bahama Penthouse

Tranquil Hideaway At Sandy Ridge 4 Bedroom Home

Find holiday rentals that suit your style

Top Lakeland - Winter Haven Hotel Reviews

Howard Johnson by Wyndham Lakeland

The Grove Resort & Water Park Orlando

Margaritaville Resort Orlando with H2O Waterpark

Quality Inn & Suites By the Parks

Hilton Vacation Club Mystic Dunes Orlando

Hilton Vacation Club Aqua Sol Orlando West

Meliá Orlando Celebration

Margaritaville Cottages Orlando by Rentyl with H2O Waterpark

Days Inn & Suites by Wyndham Lakeland

Find out more about Lakeland - Winter Haven

Lakeland - Winter Haven Villas information

Frequently asked questions

Explore a world of travel with Expedia

Villas in Lakeland - Winter Haven

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Lakeland - Winter Haven villas

Solara Resort Home With Pool 15min to Disney World

Emerald Garden - Resort - 15 Min to Disney - Pets

Bahama Bay Resort - Ground Floor

VedaHive Luxury Villa

Magical Hideaway At Kissimmee By Shine Villas 4 Bedroom Villa

Contemporary 4BR Townhome With Pool & Themed Rooms

Bahama Bay Resort - Grand Bahama Penthouse

Tranquil Hideaway At Sandy Ridge 4 Bedroom Home

Find holiday rentals that suit your style

Top Lakeland - Winter Haven Hotel Reviews

Howard Johnson by Wyndham Lakeland

Find out more about Lakeland - Winter Haven

Lakeland - Winter Haven Villas information

Frequently asked questions

Explore a world of travel with Expedia