Search Lakeland - Winter Haven Cottage Rentals from CA $92

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Check prices for these dates

Next weekend
Feb 28 - Mar 2
In two weeks
Mar 7 - Mar 9
In one month
Mar 21 - Mar 23
In two months
Apr 18 - Apr 20

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, (169)
"Very nice stay...2 days. Very comfortable. Recommend. "
The price is CA $92
CA $104 total
includes taxes & fees
Mar 25 - Mar 26
Lake Ida Beach Resort
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, (10)
"Great property! Was perfect for our family and made down time from the parks really nice."
Large Villa W/private Pool & Game Room! Waterpark
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!
Home w/ Hot Tub: 4 Mi to Disney!
Terrace/patio

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!
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, (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!
Interior

Sleek Home Near Downtown Lakeland w/ Yard!

3.0 star property
10.0 out of 10, Exceptional, (1)
Sleek Home Near Downtown Lakeland w/ Yard!
Family-friendly Winter Haven Home w/ Pool!
Books

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!
Pool

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
House (2 Bedrooms) | Private kitchen

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!
House (1 Bedroom) | Private kitchen

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!
House (3 Bedrooms) | Private kitchen

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!
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!
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!
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.

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!
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, (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
3 bedrooms, iron/ironing board, free WiFi, bed sheets

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
Fridge, microwave, oven, stovetop

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
Interior

Margaritaville Resort Orlando Cottages by Rentyl

4.0 star property
8.8 out of 10, Excellent, (1209)
"I was initially hesitant about booking this cottage due to a few negative reviews, but I’m so glad we decided to stay! The cottage was spacious, clean, and well-maintained. The pool and hot tub were both spotless and perfect for relaxing. Almost everything that you would need for a home away from home is included. Check-in was smooth and hassle-free, making for a great start to our stay. The only small suggestion I’d make is to provide a dishwasher rinse aid, as we noticed that the dishwasher...
Margaritaville Resort Orlando Cottages by Rentyl
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, (5159)
"This resort was beautiful. We really enjoyed our stay and look forward to coming back! "
The price is CA $155
CA $220 total
includes taxes & fees
Mar 6 - Mar 7
Summer Bay Orlando by Exploria Resorts
Holiday Inn Club Vacations Orlando Breeze Resort
2 outdoor pools, open 8 AM to 10 PM, sun loungers

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 CA $183
CA $227 total
includes taxes & fees
Feb 23 - Feb 24
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 CA $92 and CA $92 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.
What is there to do in Lakeland - Winter Haven near my cottage?
Whatever you’re into, there are so many things to do in Lakeland - Winter Haven. If you’re visiting Lakeland, don’t miss Polk Museum of Art, Polk Theatre and Explorations V Children s Museum. Planning a getaway in Lake Wales? KICCO Wildlife Management Area, Bok Tower Gardens and Mountain Lake are among the top sights in this city.