Search Cottages in Lakeland - Winter Haven

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Check prices for these dates

Next weekend
21 Mar - 23 Mar
In two weeks
28 Mar - 30 Mar
In one month
11 Apr - 13 Apr
In two months
9 May - 11 May

Featured Cottages in Lakeland - Winter Haven and around

Lake Ida Beach Resort
Outdoor pool, pool umbrellas, pool loungers

Lake Ida Beach Resort

3.0 star property
7.4 out of 10, Good, (171)
"Very nice stay...2 days. Very comfortable. Recommend. "
The price is €77
includes taxes & fees
16 Mar - 17 Mar
Lake Ida Beach Resort
Spacious River Ranch Private COTTAGE with private porch! 401
Golf

Spacious River Ranch Private COTTAGE with private porch! 401

9.6 out of 10, Exceptional, (5)
"Very quiet, great environment for nature"
Spacious River Ranch Private COTTAGE with private porch! 401
8000 Lost Shaker Lane
Miscellaneous

8000 Lost Shaker Lane

3.0 star property
9.8 out of 10, Exceptional, (6)
"Beautiful and clean! Easy to find, great location, easy check in and out and very roomy space! Everything you need is provided! Comfortable beds! Only thing I’d change is find an easier way to contact host with questions, such as direct texting. Otherwise, it’s call them, leave a message and wait for a call back. Or send a message through their chat and days to get a response. That said everything I needed - check in/check out proceedings was sent on time through email . Overall, a great...
8000 Lost Shaker Lane
Large Villa W/private Pool & Game Room! Waterpark
Miscellaneous

Large Villa W/private Pool & Game Room! Waterpark

3.5 star property
9.6 out of 10, Exceptional, (11)
"Large family , wonderful beds !! Nice big house tons of bathrooms, would stay again 4 sure "
Large Villa W/private Pool & Game Room! Waterpark
Private Pool/spa, Free Waterpark, Lazy River!
Miscellaneous

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.
Fridge, microwave, oven, stovetop

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

9.8 out of 10, Exceptional, (47)
"This is my second stay at this property, 4 1/2 years apart. The property is just as cute, clean, and comfortable now as it was in 2020. We enjoyed staying here while in town to visit family. The location is convenient to the college, downtown, and everything you might need. Highly recommend. "
Lakeland's Charming Luxury Cottage Retreat Near Downtown Walk Everywhere.
Cottage w/ Private Pool - Walk to Lake Wales!
Dining

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!
Sweet Cottage 5 mi to Legoland & 0.5 mi to dwntwn
TV

Sweet Cottage 5 mi to Legoland & 0.5 mi to dwntwn

2.0 star property
The price is €278
includes taxes & fees
13 Mar - 14 Mar
Sweet Cottage 5 mi to Legoland & 0.5 mi to dwntwn
Townhome W/private Pool & Themed Rooms, Near Wdw!
Miscellaneous

Townhome W/private Pool & Themed Rooms, Near Wdw!

4.0 star property
9.6 out of 10, Exceptional, (5)
"Great home and great resort! Loved having a private pool at the house and then all amenities included with the resort. Family had a great time. "
Townhome W/private Pool & Themed Rooms, Near Wdw!
8 Mi to Legoland: Winter Haven Home w/ Lanai!
Interior

8 Mi to Legoland: Winter Haven Home w/ Lanai!

3.0 star property
8 Mi to Legoland: Winter Haven Home w/ Lanai!
Lakeland Cottage w/ Pool Access + Screened Porch!
Fridge, microwave, stovetop, coffee/tea maker

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!
Family-friendly Winter Haven Home w/ Pool!
Interior

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!
RV Rental at River Ranch, 2Bed/2Ba! 251
Outdoor dining

RV Rental at River Ranch, 2Bed/2Ba! 251

10.0 out of 10, Exceptional, (1)
"Bunk beds are made for children-too small for adults"
RV Rental at River Ranch, 2Bed/2Ba! 251
Cozy Lakeside Cottage near Legoland, Winter Haven! Florida vacation ready!
Pool

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

10.0 out of 10, Exceptional, (7)
"This “Old Florida” lakefront cottage was perfect for us! It was spotless with plenty of linens and a well-equipped kitchen. We had a Celebration of Life and asked folks to bring chairs to enjoy the huge grass yard by Eagle Lake. The lot runs from the road to the Lake so there was plenty of parking. Highly recommend this property and its responsive and thoughtful host."
Cozy Lakeside Cottage near Legoland, Winter Haven! Florida vacation ready!
Mid-century Modern Escape in Central Lakeland!
House (3 Bedrooms) | Interior

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!
8416 Blue Lagoon Dr
Miscellaneous

8416 Blue Lagoon Dr

3.0 star property
8416 Blue Lagoon Dr
Lake Wales Vacation Rental w/ Screened-In Porch!
TV

Lake Wales Vacation Rental w/ Screened-In Porch!

10.0 out of 10, Exceptional, (9)
"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!
Winter Haven Vacation Rental w/ Patio & Gas Grill!
Microwave, oven, stovetop, blender

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*
Fridge, microwave, oven, stovetop

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

9.2 out of 10, Wonderful, (33)
"Perfect size, price with all amenities along with location. We were very pleased with our experience. Will definitely stay again if available next visit!"
*Modern Tiny Lake Cottage*AceLoc*4miles*LEGOLAND*
Lake Wales Vacation Rental w/ Direct Canal Access!
Terrace/patio

Lake Wales Vacation Rental w/ Direct Canal Access!

3.0 star property
Lake Wales Vacation Rental w/ Direct Canal Access!
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

Summer Bay Orlando by Exploria Resorts
5 outdoor pools

Summer Bay Orlando by Exploria Resorts

3.5 star property
8.4 out of 10, Very good, (5214)
"There was no cool water, only about 150 degrees, but once we told someone, the maintenance guy was there within the hour and fixed it. The place definitely has seen better days and looks rough in some spots but it was comfortable and convenient. "
The price is €145
includes taxes & fees
30 Mar - 31 Mar
Summer Bay Orlando by Exploria Resorts
Margaritaville Cottages Orlando with H2O Waterpark by Rentyl
Interior

Margaritaville Cottages Orlando with H2O Waterpark by Rentyl

4.0 star property
8.8 out of 10, Excellent, (1247)
"We loved our stay!"
Margaritaville Cottages Orlando with H2O Waterpark by Rentyl
The Berkley, Orlando
Lobby sitting area

The Berkley, Orlando

4.0 star property
9.4 out of 10, Exceptional, (1701)
"This is the 5th time we have stayed. Bedroom layouts work great for us. "
The price is €215
includes taxes & fees
13 Mar - 14 Mar
The Berkley, Orlando
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?
Cottages in Lakeland - Winter Haven range between €77 and €278 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 58 cottages in Lakeland - Winter Haven. Whether you’re travelling 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 traveller 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.
What is there to do in Lakeland - Winter Haven near my cottage?
One of the best travel accessories for your Lakeland - Winter Haven adventure is an awesome itinerary! Polk Museum of Art, RP Funding Centre and Publix Field at Joker Marchant Stadium are among the leading sights if you’re off to Lakeland. Winter Haven also lures travellers with its wonderful attractions, such as Indigo’s Family Fun Centre. Eager to add to your to-do list? Drop by Chain of Lakes Park and Theatre Winter Haven too.