Vacation rentals in Highland City

Heated Pool Kids Playground Sleeps 12 Tampa Disney

WELCOME to YOUR PERFECT FLORIDA ESCAPE! Step into a PRIVATE, SPACIOUS RETREAT where sun-filled days and relaxing evenings flow effortlessly, in a space designed for comfort and unforgettable moments. Enjoy an exceptional stay featuring a saltwater HEATED pool and a fun-filled playground for the kids. Ideally located just a short drive from TAMPA and DISNEY. Ask about our Friday Arrival Experience, available for select stays to make your getaway special. Perfect for LARGE FAMILIES or GROUPS (12).

Sunshine Studio + Courtyard, mins historic downtwn

Your cozy retreat awaits you in Sunshine Studio! It is centrally located in Lakeland, a short drive from downtown, Florida Southern College(1.4 miles) SEU(1 mile) 17 mins from SUN N FUN!The studio comes fully equipped with everything you need to enjoy a relaxing or adventurous stay! Cook a dinner for two in the well appointed modern kitchen! Enjoy a glass of wine in the warm lit courtyard to cap the night! Private parking is just a few steps down the pathway through the courtyard from your door!

Tranquility! Cozy and quiet home

Spacious house on a quiet street where you can relax and recharge during your central Florida vacation. Sleeps up to 7 people. Guests have access to a full kitchen, a dining room, a large living room and a patio. Guests can also park up to two cars in the enclosed garage and do laundry in the laundry room. Master bedroom has a king size bed, an en-suite bathroom and a walk-in closet for anything you need to store. bedroom two has a king size bed. bedroom three has one queen and one double bed.

Gorgeous Gem in the Heart of Lakeland

LOCATION, LOCATION! This gorgeous, spacious, newly renovated home is located on one of the most desired and safest streets in all of Lakeland, and steps away from the beautiful Lake Hollingsworth and Trail. Close to the lake, and a short drive to downtown Lakeland, this gem is in the perfect location! This home features zero gravity beds, a gourmet kitchen, private laundry, smart TVs and WiFi, comfortable sofas with ample seating for entertainment, dining and more. You'll love this place!

Quiet Guesthouse in S. Lakeland, Fast Wi-Fi.

✨ LIVE authentically, LAUGH daily, and feel the LOVE of being HOME. ✨ Our home is a clean, welcoming shared space with a minimalist design for comfort and peace. Enjoy: • Fast WiFi (400mbps) • Smart TV • Kitchen essentials (sponges, soap, paper towels) • Refreshed common areas • Extended stay discounts This is a shared space, so you may meet other travelers, but we ensure a respectful, comfortable atmosphere. Experience warmth, simplicity, and convenience that feels like home.

Roe Family Lake House (Lake Mcleod)

We can't wait for you to enjoy our fully renovated, family friendly lake house. It's a happy home that provides a wonderful backdrop to any vacation. Centrally located to many Florida destinations- Legoland is only 7 miles away, Disney World is 35 miles away, and you are less than 50 miles from Tampa. The house is located on over an acre of lakefront property. The lake has a public boat launch if your family enjoys water sports or fishing or use the kayaks we provide on site!

Luxury Modern Home In S Lakeland

Two story luxurious modern home in South Lakeland. This home offers a peaceful urban oasis for any traveler. Large living space with a beautifully designed kitchen w/ refrigerator & freezer. Lounge and unwind on the comfortable outdoor furniture in the private patio. Or retreat to the plush beds in the bedrooms. All rooms equipped with 50"+ smart TVs. Ideally located, close to grocery stores, shops, cultural attractions, the interstate, and the city's best restaurants.

Charming Lakeside Cottage

Escape to our cozy lakeside cottage, featuring a dock that’s perfect for watching sunrises, fishing, and launching your kayak. The property is on Lake Howard, which is part of the Winter Haven Chain of Lakes. Inside, you’ll find a fully equipped kitchen and comfortable living space for unwinding. Located just a short drive from the excitement of Legoland and Disney World, you can easily explore the area’s attractions while having a peaceful haven to return to.

Relax in Heated Saltwater Pool w/ Screened Lanai

Experience luxury and comfort in this spacious rental featuring a master suite with king bed and en suite bath, fully equipped kitchen, dedicated office, and cozy living areas. Enjoy a heated saltwater pool, outdoor TV, grill, and large fenced yard. All bedrooms have large beds, TVs, and ample storage. Includes free WiFi, private driveway, and welcome snacks. Perfect for families, couples, or business travelers!

Dottie's Place, Comfy Home w/ a BIG Yard!

Peaceful comfy home on ¾ of an acre, tucked into a great neighborhood. Watch birds. Enjoy relaxing on the front or back porch, or an evening by the firepit. Take a short walk in the neighborhood and you’ll find a pasture with animals. Downtown Bartow has many charming shops, antiques, a brewery, & restaurants and there are many more attractions nearby! Ask about camper hook-up for an extra lodging option.

Heart of South Lakeland in adorable neighborhood!

In the heart of South Lakeland, in one of the most sought out locations. Easy access to a variety of restaurants, shopping and minutes away from the Polk Parkway and South Florida Ave. Whether your destination is here in Lakeland, to the beach, or off to see Mickey, our goal is to make you feel at home! The home features a newly remodeled kitchen, a smart tv, memory foam mattresses, and all the coffee!

Charming Lakefront Cottage with Stunning Views

Welcome to our lake house retreat in Lakeland, Florida. You can enjoy a peaceful getaway with beautiful sunset views and tranquil waters during the evenings, and still visit major cities such as Orlando and Tampa during the day which are less than an hour away. Minutes from Southeastern University, Florida Southern, Lake Hollingsworth, and other attractions in the Lakeland area.