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Check prices for these dates

Next weekend
28 Saf. - 2 Rab. I
In two weeks
7 Rab. I - 9 Rab. I
In one month
21 Rab. I - 23 Rab. I
In two months
18 Rab. II - 20 Rab. II

Compare 57 Cottages in Lakeland - Winter Haven with updated reviews, rates, and availability.

Lake Ida Beach Resort
Room

Lake Ida Beach Resort

3.0 star property
7.4 out of 10, Good, (169)
"Very nice stay...2 days. Very comfortable. Recommend. "
The price is SAR 248
SAR 277 total
includes taxes & fees
26 Mar - 27 Mar
Lake Ida Beach Resort
Large Villa W/private Pool & Game Room! Waterpark
Pool

Large Villa W/private Pool & Game Room! Waterpark

3.5 star property
9.6 out of 10, Exceptional, (10)
"We are in Kissimmee 6 times a year! We usually stay at Margaritaville Cottages. They were booked solid, so I took a chance on this property! They had one review and that was all it took for me! So glad I did! Exactly like the pics! Exactly like them! Being our home is about 1000sqft larger than this, we(myself and 2 kids) were extremely comfortable our whole trip! If I had to nick pick anything, I’d say the pool was freezing. But it’s February, it was expected! So no pool heater is the only...
The price is SAR 1,706
SAR 3,310 total
includes taxes & fees
26 Feb - 27 Feb
Large Villa W/private Pool & Game Room! Waterpark
Cottage w/ Private Pool - Walk to Lake Wales!
Lake Wales Vacation Rental | 2BR | 2BA | 1,000 Sq Ft | Steps Required

Cottage w/ Private Pool - Walk to Lake Wales!

10.0 out of 10, Exceptional, (58)
"We enjoyed this retreat while attending a wedding nearby. Our hosts were friendly & helpful. Enjoy!"
Cottage w/ Private Pool - Walk to Lake Wales!
Home w/ Hot Tub: 4 Mi to Disney!
Kissimmee Vacation Rental | 4BR | 3BA | 2 Stories | 1,500 Sq Ft

Home w/ Hot Tub: 4 Mi to Disney!

9.4 out of 10, Exceptional, (30)
"Family friendly home. We stayed here for a multi family trip to Disney. We especially love that there were two primary rooms with king beds and on suites. The house has all the necessities in the kitchen, with coffee /keurig combo , cups and plates, and other cookie necessities. Very comfortable and specious stay and would highly recommend. "
Home w/ Hot Tub: 4 Mi to Disney!
Lakeland Cottage w/ Pool Access + Screened Porch!
Lakeland Vacation Rental | 2BR | 1BA | 960 Sq Ft | 6 Steps Required

Lakeland Cottage w/ Pool Access + Screened Porch!

10.0 out of 10, Exceptional, (1)
"Clean and great locating! "
Lakeland Cottage w/ Pool Access + Screened Porch!
Lake Wales Vacation Rental w/ Screened-In Porch!
Lake Wales Vacation Rental | 3BR | 2BA | 1,380 Sq Ft | 3 Steps Required to Enter

Lake Wales Vacation Rental w/ Screened-In Porch!

10.0 out of 10, Exceptional, (8)
"Very nice place to stay. Very quiet and peaceful. Michelle provided all the amenities needed to make our stay enjoyable."
Lake Wales Vacation Rental w/ Screened-In Porch!
Sleek Home Near Downtown Lakeland w/ Yard!
Living area

Sleek Home Near Downtown Lakeland w/ Yard!

3.0 star property
10.0 out of 10, Exceptional, (1)
"This was a REALLY NICE place. The host provided everything you could possibly need. The residence was spotless. The beds were firm but comfortable. The neighborhood was quiet. We will stay here again next time we’re in the area (if it’s available!). "
Sleek Home Near Downtown Lakeland w/ Yard!
Family-friendly Winter Haven Home w/ Pool!
Living area

Family-friendly Winter Haven Home w/ Pool!

3.0 star property
8.0 out of 10, Very Good, (1)
"Property was clean and very functional. Had the opportunity to speak with the host after a miscommunication with his property manager and he was first class. Great property and would stay again for sure. Host was exceptional!!"
Family-friendly Winter Haven Home w/ Pool!
Cozy Lakeside Cottage near Legoland, Winter Haven! Florida vacation ready!
Exterior

Cozy Lakeside Cottage near Legoland, Winter Haven! Florida vacation ready!

10.0 out of 10, Exceptional, (6)
"This place is great. Can hold 4 boats with 4 people. Great place!!!"
Cozy Lakeside Cottage near Legoland, Winter Haven! Florida vacation ready!
Lakeland House < Half Mi to Tigers Spring Training
Exterior

Lakeland House < Half Mi to Tigers Spring Training

3.0 star property
Lakeland House < Half Mi to Tigers Spring Training
Charming Tiny Home w/ Private Hot Tub!
Outdoor dining

Charming Tiny Home w/ Private Hot Tub!

3.0 star property
8.0 out of 10, Very Good, (3)
"It was a great little place but is a bit run down. There’s broken furniture and the hot tub seemed a bit cloudy"
Charming Tiny Home w/ Private Hot Tub!
Family-friendly Lakeland Home w/ Private Hot Tub!
Outdoor spa tub

Family-friendly Lakeland Home w/ Private Hot Tub!

3.0 star property
9.0 out of 10, Wonderful, (2)
"This home is laid out nicely and met our needs for a quick weekend stay in Lakeland. The host, Letty, was a pleasure and provided very clear and easy to follow instructions. The home needs some updating, but was clean, comfortable and in a great location. "
Family-friendly Lakeland Home w/ Private Hot Tub!
Mid-century Modern Escape in Central Lakeland!
Dining

Mid-century Modern Escape in Central Lakeland!

3.0 star property
10.0 out of 10, Exceptional, (1)
"Communication with the host was simple and she was accessible. The basic amenities were readily available and we did not have to rush to go to the supermarket when we arrived. The place is spacious, clean and neighbourhood very quiet."
Mid-century Modern Escape in Central Lakeland!
Lakefront Frostproof Vacation Rental w/ Beach!
Dining

Lakefront Frostproof Vacation Rental w/ Beach!

3.0 star property
10.0 out of 10, Exceptional, (1)
"We thoroughly enjoyed our stay! The home was very clean. The floors were so clean when wiping up some water drips, there was not one spec of dirt on the paper towel! That is my measure for being clean! Home owners were excellent to work with. Texting answers to my many questions. We stayed while we were in town for the 12 Hours of Sebring race. Easy 30 minute drive to the track. Beautiful view of the lake with lounge chairs on a private beach behind the house. I can't say enough about...
Lakefront Frostproof Vacation Rental w/ Beach!
Private Pool/spa, Free Waterpark, Lazy River!
Living area

Private Pool/spa, Free Waterpark, Lazy River!

4.0 star property
10.0 out of 10, Exceptional, (5)
"Nice house good upkeep and good communication."
Private Pool/spa, Free Waterpark, Lazy River!
Lakeland's Charming Luxury Cottage Retreat Near Downtown Walk Everywhere.

Lakeland's Charming Luxury Cottage Retreat Near Downtown Walk Everywhere.

10.0 out of 10, Exceptional, (44)
"Beautiful property. Well maintained with every amenity needed. We will come again. Owners super nice and very helpful."
Lakeland's Charming Luxury Cottage Retreat Near Downtown Walk Everywhere.
Winter Haven Vacation Rental w/ Patio & Gas Grill!
Exterior

Winter Haven Vacation Rental w/ Patio & Gas Grill!

3.0 star property
Winter Haven Vacation Rental w/ Patio & Gas Grill!
*Modern Tiny Lake Cottage*AceLoc*4miles*LEGOLAND*
Terrace/patio

*Modern Tiny Lake Cottage*AceLoc*4miles*LEGOLAND*

9.2 out of 10, Wonderful, (32)
"It was a cute place with lakefront sunrises! It worked well for our stay. Note bring a flashlight its dark walking down the path at night. We did come across a racoon one evening. "
*Modern Tiny Lake Cottage*AceLoc*4miles*LEGOLAND*
Lake Hunter Historic Cottage
Room

Lake Hunter Historic Cottage

9.8 out of 10, Exceptional, (14)
"We had a wonderful stay. There were absolutely zero issues. The cottage was clean and comfortable. The neighborhood was very quiet and provided easy access to all of the local activities."
Lake Hunter Historic Cottage
Lake of the Hills Cottage - Sleeps 4

Lake of the Hills Cottage - Sleeps 4

Lake of the Hills Cottage - Sleeps 4
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

Margaritaville Resort Orlando Cottages by Rentyl
Front of property

Margaritaville Resort Orlando Cottages by Rentyl

4.0 star property
8.8 out of 10, Excellent, (1209)
"We had a fantastic stay at Margaritaville Resort Orlando Cottages! The cottages were incredibly spacious and perfect for our family of seven—everyone was comfortable, and we never felt cramped. The location was ideal for our Disney World trip, with easy access to the parks while also providing a peaceful and relaxing retreat after long days of adventure. The atmosphere was wonderful, and it truly felt like a home away from home. We would absolutely stay here again and highly recommend it to...
Margaritaville Resort Orlando Cottages by Rentyl
Summer Bay Orlando by Exploria Resorts
Property amenity

Summer Bay Orlando by Exploria Resorts

3.5 star property
8.4 out of 10, Very Good, (5161)
"Me and my bf stay for 5 days in the junior suite, it was very accommodating and lots of pools and activities for families, we felt very safe and welcomed. Rooms were very clean, the only thing that we didn’t care for was the living room, it’s very big with small tv and furniture but that’s nothing we just spent most of our time in the nice comfy king bed, will definitely stay again but may just upgrade our room next time! "
The price is SAR 473
SAR 649 total
includes taxes & fees
23 Mar - 24 Mar
Summer Bay Orlando by Exploria Resorts
Holiday Inn Club Vacations Orlando Breeze Resort
Property amenity

Holiday Inn Club Vacations Orlando Breeze Resort

3.5 star property
9.4 out of 10, Exceptional, (414)
"Loved the big space in the apartment-sized living room/kitchen/eating area and bedroom and bathroom. Having a full sized kitchen and stove was wonderful. We really enjoyed the large pool and hot tub one evening. Close to lots of restaurants and shopping. Not too far from the highway. "
The price is SAR 484
SAR 599 total
includes taxes & fees
24 Feb - 25 Feb
Holiday Inn Club Vacations Orlando Breeze Resort
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 cottages in Lakeland - Winter Haven cost?
Rates for cottages in Lakeland - Winter Haven range between SAR 281 and SAR 281 per night. No matter your budget, you’re sure to find the ideal place to get reacquainted with nature. 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?
You can choose from 57 cottages in Lakeland - Winter Haven. Whether you’re traveling with the kids, as a table-for-two or with a group of close friends, Expedia makes it simple to find your ideal digs.
Why book your cottage in Lakeland - Winter Haven with Expedia?
Expedia has some wonderful cottages in Lakeland - Winter Haven, so start packing your bags for an unforgettable vacation on nature’s doorstep. If you have a budget, choose how much you want to spend and the star rating of your property. Or, try out our filters to search for cottages with a kitchen or a pool. We’ll help you find a suitable place whatever your plans or style of travel.
How can I find cheap cottages in Lakeland - Winter Haven?
A wonderful way to spot cheap cottages in Lakeland - Winter Haven is with Expedia’s useful filter tool. Refine your search by budget, star rating and amenities to snag excellent rates with only a few clicks.