Book a Lakeland - Winter Haven Cottage

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Check prices for these dates

Next weekend
28 Mar - 30 Mar
In two weeks
4 Apr - 6 Apr
In one month
18 Apr - 20 Apr
In two months
16 May - 18 May

Featured Cottages in Lakeland - Winter Haven

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 NZ$140
includes taxes & fees
30 Mar - 31 Mar
Lake Ida Beach Resort
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
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!
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!
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
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!
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 NZ$476
includes taxes & fees
15 Apr - 16 Apr
Sweet Cottage 5 mi to Legoland & 0.5 mi to dwntwn
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
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!
Lake Wales Vacation Rental w/ Screened-In Porch!
TV

Lake Wales Vacation Rental w/ Screened-In Porch!

10.0 out of 10, Exceptional, (12)
"Perfect place for a family wedding we were attending. Close to downtown Lake Wales which was really cute and not too far from Disney world which we went to for 1 day."
Lake Wales Vacation Rental w/ Screened-In Porch!
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. "
The price is NZ$914
includes taxes & fees
21 Mar - 22 Mar
Lakeland's Charming Luxury Cottage Retreat Near Downtown Walk Everywhere.
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!
Lakefront Frostproof Vacation Rental w/ Beach!
Beach

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!
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!
*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*
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!
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!
Lake Home - 2 bd rm w/dock & pier on Lake Rosalie, Lake Wales
Miscellaneous

Lake Home - 2 bd rm w/dock & pier on Lake Rosalie, Lake Wales

Lake Home - 2 bd rm w/dock & pier on Lake Rosalie, Lake Wales
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, (5244)
"I liked the size of the units for the price. They do need some updating. There was no vanity counter top in our unit. We were force to drag an extra chair to help hold toiletries. Poor vanity lighting for shaving etc… Given the price and short stay… We dealt with it. "
The price is NZ$271
includes taxes & fees
1 Apr - 2 Apr
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, (1270)
"The property is amazing ,safe comfortable,clean,and spacious.its very good condition "
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, (1710)
"This was our second stay at this property and it did not disappoint! Everything from check in to check out was easy and the staff was great! Close enough to the parks and super quiet with tons of space for my Disney crew!! Will definitely be returning!!"
The price is NZ$461
includes taxes & fees
1 Apr - 2 Apr
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 NZ$140 and NZ$914 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 68 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.
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.