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Compare 66 Cottages in Lakeland - Winter Haven with updated reviews, rates, and availability.

Lake Ida Beach Resort

3.0 star property
7.4 out of 10, Good, (174)
"Very nice stay...2 days. Very comfortable. Recommend. "
The price is ¥10,147
¥11,365 total
includes taxes & fees
Apr 19 - Apr 20
Lake Ida Beach Resort

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

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

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

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

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

2.0 star property
10.0 out of 10, Exceptional, (1)
"We absolutely loved our stay here! The house was well stocked with lots of games, movies, toys. All combined with the piano, foosball table, screened in porch and private backyard gave us plenty to do as a family with all ages. Everything was of very high quality and comfortable. We also really appreciated how responsive, friendly, and accommodating our hosts and their staff were. We will definitely stay here again!"
The price is ¥17,088
¥39,630 total
includes taxes & fees
Apr 20 - Apr 21
Sweet Cottage 5 mi to Legoland & 0.5 mi to dwntwn

Lakeland Cottage w/ Pool Access + Screened Porch!

9.6 out of 10, Exceptional, (4)
"This was the cutest little cottage! As soon as we walked in the door we felt at home. It was festively decorated and clean. We had everything we needed. We used the gym, basketball court and even did a little fishing! 10/10 recommended this place."
Lakeland Cottage w/ Pool Access + Screened Porch!

*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!

10.0 out of 10, Exceptional, (16)
"Good location in a quiet community. The house was clean and the host Michelle was great at answering any of our questions. She went above and beyond what we expected. "
Lake Wales Vacation Rental w/ Screened-In Porch!

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

9.8 out of 10, Exceptional, (49)
"This was our 3rd time staying in this cottage.We enjoy the home and how convenient it is for walking and driving to interesting and fun places!The home is decorated beautifully.It has 2 good size bedrooms with big closets!The kitchen is well supplied & spacious.The dining and front room areas are very nice.There is a great outside siting area with a grill!We enjoyed it all.We have family nearby and plan to return again.They enjoyed visiting us at this lovely cottage."
The price is ¥23,496
¥62,229 total
includes taxes & fees
Apr 19 - Apr 20
Lakeland's Charming Luxury Cottage Retreat Near Downtown Walk Everywhere.

Cottage w/ Private Pool - Walk to Lake Wales!

10.0 out of 10, Exceptional, (60)
"Perfect cottage for a weekend getaway! Fully stocked with everything you need. Great communication with host and easy check in process. Would definitely stay here again. "
Cottage w/ Private Pool - Walk to Lake Wales!

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

10.0 out of 10, Exceptional, (1)
"Nothing but wonderful things to say. Everything was beautiful and perfect. Even with an issue on the golf cart, the host got a replacement. "
Lake Home - 2 bd rm w/dock & pier on Lake Rosalie, Lake Wales

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

10.0 out of 10, Exceptional, (2)
"Overall we had a great time and everything was nice. "
RV Rental at River Ranch, 2Bed/2Ba! 251

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!

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!

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!

3.0 star property
Winter Haven Vacation Rental w/ Patio & Gas Grill!

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.
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Other property types in Lakeland - Winter Haven

Howard Johnson by Wyndham Lakeland

2.5 star property
6.2 out of 10, (1001)
"."
The price is ¥9,804
¥10,981 total
includes taxes & fees
Apr 20 - Apr 21
Howard Johnson by Wyndham Lakeland

Best Western Plus Winter Haven Inn & Suites 

3.5 star property
9.4 out of 10, Exceptional, (778)
"Staff was very friendly. "
The price is ¥19,392
¥21,719 total
includes taxes & fees
Apr 20 - Apr 21
Best Western Plus Winter Haven Inn & Suites 

Westgate River Ranch Resort & Rodeo

3.5 star property
8.0 out of 10, Very Good, (339)
"Austin my bartender was amazing and alway greeted me with a smile and was very attentive and responsive to all my needs. Good service was amazing and customer service from Austin was out of this world also"
The price is ¥13,889
¥19,539 total
includes taxes & fees
May 4 - May 5
Westgate River Ranch Resort & Rodeo
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.