Search Lakeland - Winter Haven Cottage Rentals from CA $110

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Browse Select Lakeland - Winter Haven Cottages

Lake Ida Beach Resort
Outdoor pool, pool umbrellas, sun loungers
Lake Ida Beach Resort
3.0 star property
7.6 out of 10, Good, (159)
"The room could use an upgrade but it had everything I needed and I was comfortable staying there. The pool was really clean "
The price is CA $114
CA $128 total
includes taxes & fees
Dec 18 - Dec 19
Lake Ida Beach Resort
Contemporary Home w/ Hot Tub: 4 Mi to Disney Magic
Terrace/patio
Contemporary Home w/ Hot Tub: 4 Mi to Disney Magic
9.4 out of 10, Exceptional, (26)
"Great place to stay. "
Contemporary Home w/ Hot Tub: 4 Mi to Disney Magic
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, (5)
"G"
Cozy Lakeside Cottage near Legoland, Winter Haven! Florida vacation ready!
Cottage w/ Private Pool - Walk to Lake Wales!
Dining
Cottage w/ Private Pool - Walk to Lake Wales!
10.0 out of 10, Exceptional, (52)
"The property is a quaint little cottage full of character. The contacts were friendly and constantly attentive to our needs. I would recommend the cottage to anyone wanting a quiet and safe place to stay."
Cottage w/ Private Pool - Walk to Lake Wales!
Lake Wales Vacation Rental w/ Screened-In Porch!
TV
Lake Wales Vacation Rental w/ Screened-In Porch!
10.0 out of 10, Exceptional, (6)
"The stay was wonderful but ended up being cut short due to a hurricane in the area. The host was very helpful and understanding."
Lake Wales Vacation Rental w/ Screened-In Porch!
River Ranch Private COTTAGE with FREE Golf Cart 401
Golf
River Ranch Private COTTAGE with FREE Golf Cart 401
9.6 out of 10, Exceptional, (4)
"Awesome ! "
River Ranch Private COTTAGE with FREE Golf Cart 401
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!
"Peachy Keen" 3BD Pool & Spa Cottage Near Disney
Bar (on property)
"Peachy Keen" 3BD Pool & Spa Cottage Near Disney
10.0 out of 10, Exceptional, (3)
"Near everything and convenient in and out to the property. Minor issue with the pool was rectified by the manager during our stay. Fast response to our questions and concerns."
"Peachy Keen" 3BD Pool & Spa Cottage Near Disney
Up to Scale With Margaritas
Property grounds
Up to Scale With Margaritas
3.0 star property
8.4 out of 10, Very good, (5)
"The only issue was the upstairs airconditioner was not working in terms the rooms were hot while hallway was cold. But nice for our family. "
Up to Scale With Margaritas
*Modern Tiny Lake Cottage*AceLoc*4miles*LEGOLAND*
Fridge, microwave, oven, stovetop
*Modern Tiny Lake Cottage*AceLoc*4miles*LEGOLAND*
9.2 out of 10, Wonderful, (31)
"The house was very clean and we enjoyed out stay. Would recommend!!!"
*Modern Tiny Lake Cottage*AceLoc*4miles*LEGOLAND*
Mulberry Garden Cottage
Property grounds
Mulberry Garden Cottage
9.0 out of 10, Wonderful, (18)
"I stayed in the cottage for 2 weeks until my wife was able to secure a rental home for our move to Florida from Pennsylvania. I felt welcomed and at home. I would recommend this VRBO to anyone wanting a home away from home!"
The price is CA $110
CA $222 total
includes taxes & fees
Nov 18 - Nov 19
Mulberry Garden Cottage
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!
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, (40)
"Lovely Home. Perfect spot."
Lakeland's Charming Luxury Cottage Retreat Near Downtown Walk Everywhere.
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!
Winter Haven Abode Near Lakes & Attractions
House (2 Bedrooms) | Private kitchen
Winter Haven Abode Near Lakes & Attractions
3.0 star property
Winter Haven Abode Near Lakes & Attractions
Our Camp at Lake Cannon
Property grounds
Our Camp at Lake Cannon
10.0 out of 10, Exceptional, (1)
"Everything was perfect"
Our Camp at Lake Cannon
Winter Haven Retreat w/ Private Pool!
Outdoor pool
Winter Haven Retreat w/ Private Pool!
3.0 star property
Winter Haven Retreat w/ Private Pool!
Bright Cypress Gardens Home Near Legoland!
House (3 Bedrooms) | Private kitchen
Bright Cypress Gardens Home Near Legoland!
3.0 star property
8.0 out of 10, Very good, (1)
"Pros: communication was great; key lime pie was very good; extremely convenient location to Legoland; pictures were accurate; place was obviously swept and linens were clean; appliances and bathroom fixtures were in good condition. Cons: Noticeable cigarette smell (we used a Glade plugin which helped); HVAC returns also showed signs of smoking; found a dead roach in kitchen on second night of stay; not much seating (we are a family of 5 and seating was meant for 4); more dinnerware would have...
Bright Cypress Gardens Home Near Legoland!
Vibrant Lakeland Home: 1 Mi to Lake Hollingsworth!
House (4 Bedrooms) | Private kitchen
Vibrant Lakeland Home: 1 Mi to Lake Hollingsworth!
3.0 star property
4.0 out of 10, (1)
"The place is nice and located in a great area. But the experience was a little troublesome due to a lot of inconveniences. We asked for early check in and had to be charged but Could not checkin when arrived due to poor communication and it still being cleaned. Once we entered we Had to remove towels and dispenser through house because they were still drying. No bathroom fans, master bathroom door broken, No bathrooms travel shampoos conditioner soap for 8 people, Not enough towels for 8...
Vibrant Lakeland Home: 1 Mi to Lake Hollingsworth!
Relaxing Stay in Duplex at Adams Estate
Miscellaneous
Relaxing Stay in Duplex at Adams Estate
10.0 out of 10, Exceptional, (6)
"Adams Estate is a beautiful, quiet place to stay with a row of cute cottages and landscaped grounds overlooking the scenic lake! The room was comfortable and kitchenette was convenient. It was too cold to use the pool but it looked nice! When an issue came up, the property manager immediately responded by text. This would be a great spot for a family reunion or wedding as well."
The price is CA $217
CA $408 total
includes taxes & fees
Nov 18 - Nov 19
Relaxing Stay in Duplex at Adams Estate
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, (1083)
"I loved the esthetic of the look of the homes. They were wonderful inside and out. Great for a family or couples looking for a getaway in Orlando. Every room had its own bathroom and the bed and pillows were super comfortable. "
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, (5020)
"Great stay! Property is very clean, so many different pool options water slides and different parcs. It’s the perfect destination for kids. The condo itself is huge (1300 SF) with 2 big bedrooms and balcony. It’s the 2nd time that I have stayed at this property and I would definitely stay here again. "
The price is CA $159
CA $223 total
includes taxes & fees
Dec 1 - Dec 2
Summer Bay Orlando by Exploria Resorts
The Berkley, Orlando
Lobby sitting area
The Berkley, Orlando
4.0 star property
9.4 out of 10, Exceptional, (1595)
"Great location and extra space in the rooms at this place. We’ve stayed there several times this year. "
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?
Rates for cottages in Lakeland - Winter Haven range between CA $110 and CA $217 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 62 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.