Best Lakeland - Winter Haven Condo Rental in 2026

A baseball player in a white uniform with the number 20, a catcher in an orange uniform, and an umpire standing behind the catcher.

Change your mind
Book hotels with free cancellation
Treat yourself
Save instantly and earn perks with One Key
Learn about One Key
Be picky
Search almost a million properties worldwide

Check prices for these dates

In two weeks

In two months

In three months

In four months

Our top choices for Lakeland - Winter Haven condo rentals

A bedroom with a stone fireplace, a large bed, and a view of the outdoors through large windows.

1. Lake View•Gardens•Private Balcony Suite•Legoland

Lake Wales

Vern H.

includes taxes & fees

23 Sept - 24 Sept

A room with a bed, a table with a plant, a lamp, and a window with curtains.

2. Lyrios Vacation Rentals - The Palms

Kissimmee

includes taxes & fees

3 Oct - 4 Oct

A resort pool area with multiple swimming pools, palm trees, and lounge chairs.

3. Luxury 3 Bedroom 2 bath Condo Home 241

Reunion

Christine R.

includes taxes & fees

23 Sept - 24 Sept

4. Beautiful 2BD/2 Bath Condo Home 221

Reunion

Duane S.

includes taxes & fees

23 Sept - 24 Sept

A thatched-roof gazebo with a wooden fence, surrounded by white lounge chairs on a sandy area.

5. Lifetime of Vacations Resort

Kissimmee

Alena

includes taxes & fees

23 Sept - 24 Sept

A resort with a large swimming pool, lounge chairs, and a view of a large body of water.

6. Bahama Bay 515 Rum run unit 515

Bahama Bay

Joyce

includes taxes & fees

24 Sept - 25 Sept

A swimming pool with a clear blue water, surrounded by palm trees and lounge chairs.

7. Incredible Renovated home located near all !!

Champions Gate

Susan K.

includes taxes & fees

23 Sept - 24 Sept

8. Brand New 2bd/2 bth condo 300

davenport

Jasmin

includes taxes & fees

30 Sept - 1 Oct

View all properties

Find holiday rentals that suit your style

Aparthotels

Apartments

Save an average of 15% on thousands of hotels when you're signed in

Top Lakeland - Winter Haven Hotel Reviews

The Grove Resort & Water Park Orlando

10/10 Excellent

"Absolutely great stay. The grounds were well kept, the staff was so friendly and accommodating especially TaTa who maintained great service in the rain!! We had a great time and definitely will be back!!"

Margaritaville Cottages Orlando by Rentyl with H2O Waterpark

10/10 Excellent

"This is up there with some of the best resorts I've ever visited. Positives include free parking, pet friendly (some cottages), great pools, water park access, next to Sunset walk, and close to Disney. Negatives include automatic 20% tip on all food/ drink and the pools are a drive from most cottages since the property is so large. Overall the Resort was well worth the price and I will definitely be going back!"

Meliá Orlando Celebration

10/10 Excellent

"Absolutely — here’s a tighter version that stays under 1,500 characters while keeping the fun and helpful details: This was my first time staying here, and I originally chose it because it was close to the Disney parks, but it honestly blew my expectations out of the water! At first, I thought the pool looked a little small for the size of the hotel, but there was barely anyone in it whenever we went. I also LOVED that it stayed open until 11 PM. After a long, hot day at the parks, being able to come back and cool off was perfect! The food was DELICIOUS! The turkey club was amazing. Allan, our waiter, was also fantastic—funny, friendly, and super quick. The drinks were a little pricey outside of happy hour, so definitely take advantage of the specials! They also offer shuttles to the parks, although we didn’t use them. I only have two tiny “complaints.” The shower handle was confusing because it turned both ways with no hot/cold indicator, so it took me a minute to figure out. 😂 The bed was also a little too firm for me, but that’s totally personal preference. Other than that, we had a fantastic stay. Great location, food, service, and atmosphere. I would absolutely stay here again!"

Find out more about Lakeland - Winter Haven

Lakeland - Winter Haven Condo Rentals information

Number of reviews	507
Accommodation	124 Condo Rentals
Lowest Price	£69
Highest Price	£314

Frequently asked questions

How much do condos in Lakeland - Winter Haven cost?

The price range for condos in Lakeland - Winter Haven is £69 to £314 per night. Whatever your budget, you're sure to find something that suits your needs — as well as your entire crew! 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 condos are there in Lakeland - Winter Haven?

Browse through 124 condos in Lakeland - Winter Haven and reserve your favourite. Whether you're off on a holiday with the whole fam or reuniting with friends, with Expedia, your perfect stay is just a few clicks away.

Why book your condo in Lakeland - Winter Haven with Expedia?

We think that getaways should be a walk in the park, so if you're on the lookout for condos at a great price, Expedia has your back. Keep costs down and pick something small and cosy, or splurge on a luxury condo and pamper your loved ones. Our search filters make it easy to lock in a stay in Lakeland - Winter Haven that suits you best.

How can I find cheap condos in Lakeland - Winter Haven?

A good way to uncover cheap condos in Lakeland - Winter Haven is with Expedia's convenient filter tool. Fine-tune your search results by star rating, amenities and budget to take advantage of excellent rates in a few clicks.

What is there to do in Lakeland - Winter Haven near my condo?

Whether you like sightseeing, shopping, dining or partying, Lakeland - Winter Haven offers it all, and then some! The top city of Lakeland has lots of things to see and do, including Polk Museum of Art, RP Funding Centre and Publix Field at Joker Marchant Stadium. If you're holidaying in Winter Haven, Indigo's Family Fun Centre, Chain of Lakes Park and Theatre Winter Haven should be on your to-do list.

Explore a world of travel with Expedia

Book Condo Rentals in Lakeland - Winter Haven on Expedia.com

Search Condos Rentals in Lakeland - Winter Haven

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Lakeland - Winter Haven condo rentals

1. Lake View•Gardens•Private Balcony Suite•Legoland

2. Lyrios Vacation Rentals - The Palms

3. Luxury 3 Bedroom 2 bath Condo Home 241

4. Beautiful 2BD/2 Bath Condo Home 221

5. Lifetime of Vacations Resort

6. Bahama Bay 515 Rum run unit 515

7. Incredible Renovated home located near all !!

8. Brand New 2bd/2 bth condo 300

9. Tropical Resort Condo Near Disney: Pools, Spa & Family Fun

10. Modern Award Winning Newly Renovated, Gorgeous 2+2 Minutes Away From Disney

11. Toria Suites 920

12. Ideal Condo in River Ranch • Across from the water park and near the rodeo

13. Luxury 2bd/2 bath Condo Home 232

14. 3BD/2BA Condo Near Disney | Balcony + Game Room 294

15. Cozy, Brand-New 2BR Getaway at ChampionsGate – 291

16. Quiet. Roomy. Close to Disney. Fast Wifi Parking.

17. Near Disney/Resort Pool, Bar & Gym

18. Fully Remodeled stylish 3/2 condo, close to the parks

19. Reunion Resort - Near Theme Parks & Airport

20. Luxury 3 Bedroom Condo w Balcony 372

Find holiday rentals that suit your style

Top Lakeland - Winter Haven Hotel Reviews

The Grove Resort & Water Park Orlando

Find out more about Lakeland - Winter Haven

Lakeland - Winter Haven Condo Rentals information

Frequently asked questions

Explore a world of travel with Expedia