Lakeland - Winter Haven Holiday Homes
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United States of America
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Holiday Homes in Lakeland - Winter Haven

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Our top choices for Lakeland - Winter Haven holiday homes

Holiday Home in Kissimmee

The Berkley, Orlando

4.0 star property

9.6 out of 10, Exceptional, (2003)

9.6/10

Exceptional

(2003)

"Recommended amazing stay."

Elf

The price is AU$232

AU$232

includes taxes & fees

16 Dec - 17 Dec

The Berkley, Orlando

1 bedroom, desk, iron/ironing board, free WiFi

Holiday Home in Lake Hollingsworth

Great quiet and comfortable, South Central Lakeland location.

9.8 out of 10, Exceptional, (169)

9.8/10

Exceptional

(169)

"The property is awesome, great location and very quiet. Will stay there again. "

Fred

The price is AU$161

AU$161

includes taxes & fees

16 Dec - 17 Dec

Great quiet and comfortable, South Central Lakeland location.

Holiday Home in Haines City

Modern Villa

2.5 star property

The price is AU$360

AU$360

includes taxes & fees

1 Jan - 2 Jan 2026

Modern Villa

Outdoor pool, open 7:00 AM to 11:00 PM, pool umbrellas, pool loungers

2 bedrooms, in-room safe, desk, iron/ironing board

Holiday Home in Orlando

Marriott's Sabal Palms

4.0 star property

9.6 out of 10, Exceptional, (204)

9.6/10

Exceptional

(204)

"Room was great, staff friendly and grounds are clean. "

DENNIS

The price is AU$430

AU$430

includes taxes & fees

6 Jan - 7 Jan 2026

Marriott's Sabal Palms

Holiday Home in Loughman

Harmony Haven Boutique Townhome At Azzure Resort Near Disney By Shine Villas 6 Bedroom Townhouse

3.0 star property

The price is AU$1,106

AU$1,106

includes taxes & fees

13 Dec - 14 Dec

Harmony Haven Boutique Townhome At Azzure Resort Near Disney By Shine Villas 6 Bedroom Townhouse

Holiday Home in Dixieland

NEW Lakeland Landing Cute Bungalow by Downtown

2.0 star property

NEW Lakeland Landing Cute Bungalow by Downtown

Luxury House, 3 Bedrooms, Garden View | Living area

Holiday Home in Winter Haven

BlockHaven near Legoland & Disney

3.5 star property

The price is AU$444

AU$444

includes taxes & fees

16 Dec - 17 Dec

BlockHaven near Legoland & Disney

Holiday Home in Tuscan Hills

Davenport Vacation Homes by Shine FM

4.0 star property

8.4 out of 10, Very good, (26)

8.4/10

Very good

(26)

"it was a great property to stay in!"

Nancy

The price is AU$361

AU$361

includes taxes & fees

8 Jan - 9 Jan 2026

Davenport Vacation Homes by Shine FM

Holiday Home in Lakeland

Lovely One Bedroom Home

9.6 out of 10, Exceptional, (14)

9.6/10

Exceptional

(14)

"Nice little cozy getaway. Just right for one or two people. Stayed there four nights while working in the area."

Darrell H.

The price is AU$298

AU$298

includes taxes & fees

14 Dec - 15 Dec

Lovely One Bedroom Home

2 bedrooms, desk, iron/ironing board, travel cot

Holiday Home in Lakeland

MODERN TWO BEDROOM HOME!

10.0 out of 10, Exceptional, (11)

10/10

Exceptional

(11)

"This place was perfect! We stayed for my son’s Weigjtlifting tournament and the area didn’t disappoint. The host was amazing and very accommodating! "

Kris

The price is AU$338

AU$338

includes taxes & fees

13 Dec - 14 Dec

MODERN TWO BEDROOM HOME!

2 bedrooms, iron/ironing board, WiFi, bed sheets

Holiday Home in Lake Wales

Charming 2-bedroom house in Downtown Lake Wales.

9.8 out of 10, Exceptional, (9)

9.8/10

Exceptional

(9)

"Our stay was enjoyable and close to everything. "

LaShunda M.

The price is AU$226

AU$226

includes taxes & fees

16 Dec - 17 Dec

Charming 2-bedroom house in Downtown Lake Wales.

Holiday Home in Cleveland Heights

Hidden Emerald-Apartment with Kitchen and Laundry

10.0 out of 10, Exceptional, (10)

10/10

Exceptional

(10)

"Very clean and comfortable. Would definitely stay there again!!"

Margaret S.

The price is AU$228

AU$228

includes taxes & fees

16 Dec - 17 Dec

Hidden Emerald-Apartment with Kitchen and Laundry

Holiday Home in Winter Haven

*3/2*GorgeousNEWLakeHome2AceLoc*4mi*LEGOLAND*1724

9.4 out of 10, Exceptional, (65)

9.4/10

Exceptional

(65)

"The accommodation at this property was exceptional. It felt safe, and was safe Parking was great, proximity to dinning and shopping was withing 5 minutes drive, and the location was peaceful and safe."

Dwight

The price is AU$431

AU$431

includes taxes & fees

15 Dec - 16 Dec

*3/2*GorgeousNEWLakeHome2AceLoc*4mi*LEGOLAND*1724

Holiday Home in Lakeland Highlands

Enjoy in this beautiful and serene south Lakeland area Perfect for 4 traveler

10.0 out of 10, Exceptional, (17)

10/10

Exceptional

(17)

"Nice quiet spot. Clean and comfortable. "

Michael C.

The price is AU$246

AU$246

includes taxes & fees

14 Dec - 15 Dec

Enjoy in this beautiful and serene south Lakeland area Perfect for 4 traveler

Holiday Home in Solterra Resort

5Br Davenport Home W/ Pool & Private Hot Tub

4.5 star property

5Br Davenport Home W/ Pool & Private Hot Tub

Holiday Home in Kissimmee

Super Cool- Sleeps 17 Newly Built Near Parks

2.0 star property

The price is AU$687

AU$687

includes taxes & fees

20 Dec - 21 Dec

Super Cool- Sleeps 17 Newly Built Near Parks

Holiday Home in Winter Haven

Heated Pool and Hot tub-near Legoland, Disney, Theme parks

9.8 out of 10, Exceptional, (39)

9.8/10

Exceptional

(39)

"We had a great stay!"

Harper B.

The price is AU$482

AU$482

includes taxes & fees

15 Dec - 16 Dec

Heated Pool and Hot tub-near Legoland, Disney, Theme parks

Design House, 6 Bedrooms, Private Pool | Private kitchen

Design House, 6 Bedrooms, Private Pool | Terrace/patio

Holiday Home in Kissimmee

FL- 1844 GOBI DR

3.0 star property

The price is AU$611

AU$611

includes taxes & fees

16 Dec - 17 Dec

FL- 1844 GOBI DR

1 bedroom, iron/ironing board, free WiFi, bed sheets

Holiday Home in South Lake Morton

RED DOOR HOUSE!

9.4 out of 10, Exceptional, (45)

9.4/10

Exceptional

(45)

"We found this place on VRBO and chose it for our stay. My wife graduated with her Doctorate at SEU. This place was perfect for location to SEU and downtown dining pleasures as well. We will definitely choose it again and again"

Larry D.

The price is AU$306

AU$306

includes taxes & fees

22 Dec - 23 Dec

RED DOOR HOUSE!

Holiday Home in Winter Haven

Getaway Clubhouse 5 mil Legoland & .5 mil Downtown

2.0 star property

9.8 out of 10, Exceptional, (7)

9.8/10

Exceptional

(7)

"Great location, clean and great communication with hosts "

Angie Y.

The price is AU$469

AU$469

includes taxes & fees

14 Dec - 15 Dec

Getaway Clubhouse 5 mil Legoland & .5 mil Downtown

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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