Lakeland - Winter Haven, FL Cottages from AED 287

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
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

In two weeks

In two months

In three months

In four months

Our top choices for Lakeland - Winter Haven cottages

1. Lake Ida Beach Resort

Winter Haven

Heather

AED 287 total

includes taxes & fees

7 Oct - 8 Oct

2. Hook, Line & Leisure: Lakefront Gem w/ Porch!

Florence Villa

"We stayed here because our soccer team had a tournament in the area. We had a couple families stay and the price was much cheaper than hotels around the area. The house is beautiful and spacious inside. Has alot of upgrades. At first we thought the neighborhood looked a little off, but we had no issues at all with our stay. We have some other tournaments in this area later in the year and we will definitely be booking to stay here again."

John

AED 1,484 total

includes taxes & fees

23 Sep - 24 Sep

3. This old Florida feeling getaway is 420 friendly and a great place to just relax

Avon Park

Debi D.

AED 534 total

includes taxes & fees

23 Sep - 24 Sep

4. Charming Lakeside Cottage

Winter Haven

Ron O.

AED 605 total

includes taxes & fees

23 Sep - 24 Sep

5. Lakefront Tiny Cottage 4 Miles to LEGOLAND.

winter have

Kyle P.

AED 513 total

includes taxes & fees

23 Sep - 24 Sep

6. Sweet Cottage 5 mi to Legoland & 0.5 mi to dwntwn

Winter Haven

Rachel B.

AED 994 total

includes taxes & fees

23 Sep - 24 Sep

7. Family Resort Home w Pool, BBQ & Game Room

Solana

AED 1,205 total

includes taxes & fees

23 Sep - 24 Sep

8. Peaceful 2-bedroom Tiny House with private parking lot in charming Lakeland

Lakeland

AED 841 total

includes taxes & fees

21 Oct - 22 Oct

View all properties

Find vacation 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

8/10 Good

"The apartments are great! However, the halls and rugs need to be cleaned and washed as there is a strong smell coming from them on every floor."

Embassy Suites By Hilton Orlando Sunset Walk

10/10 Excellent

"Absolutely loved this hotel! The atmosphere was amazing, and the complimentary breakfast and drinks were definitely the best part. Everything about our stay was wonderful, and the hotel exceeded my expectations. I can’t wait to go 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!"

Frequently asked questions

How much do cottages in Lakeland - Winter Haven cost?

Cottages in Lakeland - Winter Haven range between AED 287 and AED 2,065 per night. These properties offer a chance to get in touch with nature — at a price you can afford. 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 cottages are there in Lakeland - Winter Haven?

Choose from 30 cottages in Lakeland - Winter Haven. Whether you're traveling with the whole family, as a twosome or with a group of besties, Expedia can help you secure your perfect fit.

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

Reserving a cottage in Lakeland - Winter Haven is as simple as entering your travel dates and choosing an ideal place for outdoor relaxation and recreation. From chic retreats to inexpensive properties and cottages that offer conveniences like a kitchen, Expedia has something for all traveler styles. As for irresistible deals? We've got you covered!

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

Expedia can help you locate cheap cottages in Lakeland - Winter Haven. To reserve your perfect stay in just a few clicks, use our convenient filter tool to refine your search results by amenities, budget and star rating.

Explore a world of travel with Expedia

Florida Vacations

Room 1

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Lakeland - Winter Haven cottages

1. Lake Ida Beach Resort

2. Hook, Line & Leisure: Lakefront Gem w/ Porch!

3. This old Florida feeling getaway is 420 friendly and a great place to just relax

4. Charming Lakeside Cottage

5. Lakefront Tiny Cottage 4 Miles to LEGOLAND.

6. Sweet Cottage 5 mi to Legoland & 0.5 mi to dwntwn

7. Family Resort Home w Pool, BBQ & Game Room

8. Peaceful 2-bedroom Tiny House with private parking lot in charming Lakeland

9. Cozy Forest Retreat Mid-Century Charm Fireplace 20 Min to Disney

10. Serenity - Family & Pet Friendly, Amazing Location

11. Lakeside Escape, 2BR 1 BA, Cozy Lux Cottage near Disney, Universal and Legoland

12. Legoland & Lakes Pool Home w/ Private Suite

13. Tiny house close to Disney KISSIMMEE

14. "Casa Kiwi" Margaritaville Cottage 5 minutes to Disney

15. Perfect Place for a Perfect Vacation

16. Beautiful Cottage! Your Home Away From Home. 4 miles from Disney, Kissimmee

17. Upstay Luxury Home With Pool, Hot Tub, Games Room

18. Mickey's Hideaway Cottage 4 miles from Disney in Kissimmee with WiFi and AC

19. Mvy7664 - 3BR House Near Disney With Hot Tub

20. Family-Friendly Cottage Near Orlando’s Top Attractions

Find vacation rentals that suit your style

Top Lakeland - Winter Haven Hotel Reviews

The Grove Resort & Water Park Orlando

Embassy Suites By Hilton Orlando Sunset Walk

Hilton Vacation Club Aqua Sol Orlando West

Margaritaville Cottages Orlando by Rentyl with H2O Waterpark

The Berkley, Orlando

Westgate Vacation Villas Resort

Meliá Orlando Celebration

Westgate Town Center Resort

Holiday Inn Winter Haven by IHG

Frequently asked questions

Explore a world of travel with Expedia

Search Cottages in Lakeland - Winter Haven

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Lakeland - Winter Haven cottages

1. Lake Ida Beach Resort

2. Hook, Line & Leisure: Lakefront Gem w/ Porch!

3. This old Florida feeling getaway is 420 friendly and a great place to just relax

4. Charming Lakeside Cottage

5. Lakefront Tiny Cottage 4 Miles to LEGOLAND.

6. Sweet Cottage 5 mi to Legoland & 0.5 mi to dwntwn

7. Family Resort Home w Pool, BBQ & Game Room

8. Peaceful 2-bedroom Tiny House with private parking lot in charming Lakeland

9. Cozy Forest Retreat Mid-Century Charm Fireplace 20 Min to Disney

10. Serenity - Family & Pet Friendly, Amazing Location

11. Lakeside Escape, 2BR 1 BA, Cozy Lux Cottage near Disney, Universal and Legoland

12. Legoland & Lakes Pool Home w/ Private Suite

13. Tiny house close to Disney KISSIMMEE

14. "Casa Kiwi" Margaritaville Cottage 5 minutes to Disney

15. Perfect Place for a Perfect Vacation

16. Beautiful Cottage! Your Home Away From Home. 4 miles from Disney, Kissimmee

17. Upstay Luxury Home With Pool, Hot Tub, Games Room

18. Mickey's Hideaway Cottage 4 miles from Disney in Kissimmee with WiFi and AC

19. Mvy7664 - 3BR House Near Disney With Hot Tub

20. Family-Friendly Cottage Near Orlando’s Top Attractions

Find vacation rentals that suit your style

Top Lakeland - Winter Haven Hotel Reviews

The Grove Resort & Water Park Orlando

Frequently asked questions

Explore a world of travel with Expedia