Holiday rentals in Highland City

Private Studio Suite

🧳 Perfect for a solo traveler or couple looking to visit the peaceful city of Lakeland. 📍Located about 40 minutes from Tampa and an hour from Orlando, in the family friendly area of Lakeland Highlands. - There’s nearby trails, grocery stores, convenience stores and eateries. - Polk Parkway is less then 10 minutes away, it’s the quickest route to get to i4. 🏠 The suite includes a private entrance with full bathroom and backyard area. 🚗 Free Parking Space(s) 👐🏽 Flexible & Contactless Entry

Family Heated Pool Home Sleep 12 Near Tampa Disney

Wake up to sunshine, step outside to your PRIVATE HEATED POOL, and let the day unfold at your own pace. This is where FAMILY MEMORIES ARE MADE: kids laughing in the playground, slow mornings with coffee poolside, and evenings enjoying movie nights on the 75” TV. Tucked in one of Lakeland’s most peaceful neighborhoods, this spacious retreat is designed for connection and comfort. About 1 hour from Tampa or Disney, Publix minutes away, quick access to SEU, Florida Southern College, and Polk State.

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.

Relaxing Lakeland Getaway Near Downtown & Lakes

Unwind in this remodeled 2BR/1BA detached apartment within a historic 1925 structure. This retreat provides modern comfort, and a serene escape in a park-like setting under a stunning Spanish oak tree. Enjoy a full kitchen, fast Wi-Fi, and living space perfect for relaxing or working remotely. Half a mile from Lakeland Regional Health, ideal for traveling nurses, and minutes from downtown shops, dining, and lakes. Within an hours drive to Tampa or Orlando. Your relaxing Lakeland getaway awaits.

Cozy Guesthouse in Winter Haven 2

Relax at this cozy and quiet guesthouse in Winter Haven where you are close to plenty of attractions in Central Florida. Our guesthouse offers a queen size bed with a sofa-style bed allowing up to 3 guests with private access, parking and laundry. We are located 5.8 miles from Legoland and 8 miles from Lake Myrtle Sports Park. Winter Haven is perfectly located between Tampa and Orlando making it a simple commute to attractions such as Universal, Sea World, Disney World and Busch Gardens.

Sun N Fun Retreat 2

Quiet, contemporary and well-maintained 3/2 home with a distant view of the lake, public access to a boat ramp and a nearby walking trail. A quick drive to restaurants and shopping. We welcome our Sun N Fun community! We are a few exits from the Lakeland Linder airport! This space has recently been remodeled - new kitchen cabinetry, master bath, furnishings and linen. Pictures are being updated as we speak. Whether you are in town for business or pleasure, this space won't disappoint.

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.

Cozy 3BR Home |Pet-Friendly |Near Legoland & Tampa

Welcome to your perfect Lakeland getaway — where comfort meets convenience in the heart of Central Florida. This beautifully updated 3-bedroom home is ideally located just minutes from Downtown Lakeland, Lake Mirror, Florida Southern College, SUN ’n FUN, and Legoland Florida — making it the perfect home base for families, couples, and business travelers alike. Enjoy a peaceful neighborhood setting while staying close to everything. Quick access to Tampa & Orlando attractions

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!

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!

3/2 Beautiful Pool Home + Garage + Pet Friendly

Experience resort-style living in this elegant 3-bedroom, 2-bath pool retreat. Unwind by the sparkling pool and enjoy the fenced yard, perfect for kids and pets . Relax in sophisticated comfort and enjoy secure garage parking. Thoughtfully designed with upscale finishes and timeless style—your luxurious Lakeland escape awaits. PET FEE apply