Search Lakeland - Winter Haven Cottage Rentals from CA $105

  • Plan, book, stay with confidence

    • bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    Sign in
    today icon
    Change your mind
    Book hotels with free cancellation

Check prices for these dates

Next weekend
Apr 4 - Apr 6
In two weeks
Apr 11 - Apr 13
In one month
Apr 25 - Apr 27
In two months
May 23 - May 25

Browse Select Lakeland - Winter Haven Cottages

Lake Ida Beach Resort
Outdoor pool, pool umbrellas, sun 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 CA $105
CA $118 total
includes taxes & fees
Apr 6 - Apr 7
Lake Ida Beach Resort
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!
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
Margarita Porch Paradise
House, Multiple Beds, Patio (Margarita Porch Paradise) | View from room

Margarita Porch Paradise

5.0 star property
10.0 out of 10, Exceptional, (2)
"The house was beautiful and comfortable for our family, we would have stayed longer! The resort is fun, plenty of stores and good restaurants. We will definitely come back. "
Margarita Porch Paradise
8081 Knee Deep Rd
Miscellaneous

8081 Knee Deep Rd

3.0 star property
10.0 out of 10, Exceptional, (2)
"greqt host"
8081 Knee Deep Rd
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
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 CA $171
CA $404 total
includes taxes & fees
Apr 7 - Apr 8
Sweet Cottage 5 mi to Legoland & 0.5 mi to dwntwn
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, (2)
"Very clean. Really nice park. Pool and clubhouse area outstanding "
Lakeland Cottage w/ Pool Access + Screened Porch!
*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/ 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. "
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!
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
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!
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!
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.
Don't see what you're looking for?
See all available properties in Lakeland - Winter Haven
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

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, (5282)
"The only place I will stay when visiting Orlando. I love it! Very clean and friendly. The workout facility is the best!"
The price is CA $150
CA $214 total
includes taxes & fees
Apr 20 - Apr 21
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, (1293)
"The property is beautiful. If you are looking for a way to stay off Disney property and still be close by, this is a good choice. We stayed at the Villas so we had a full kitchen and laundry which was a nice way to save money on breakfast lunch and dinner. Theres a Super Target and Publix nearby. The biggest issue is they seem short staffed. Every staff member we interacted with was wonderful. There just arent enough of them. 10 minute hold times when we called the front for something simple...
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, (1717)
"Good place. Quiet clean and the staff very good ,and nice everything close "
The price is CA $258
CA $306 total
includes taxes & fees
Apr 20 - Apr 21
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 CA $105 and CA $171 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 65 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.
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 Center and Publix Field at Joker Marchant Stadium are among the leading sights if you’re off to Lakeland. Winter Haven also lures travelers with its wonderful attractions, such as Indigo’s Family Fun Center. Eager to add to your to-do list? Drop by Chain of Lakes Park and Theatre Winter Haven too.