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.

Matty’s Citrus Connection

You are going to love this Citrus themed hideaway with its Old Florida feel that takes you back to simpler times. Rest and relax in this backyard paradise while enjoying all that Lakeland has to offer. Whether you choose a relaxing day enjoying the many local activities , take a day trip to a beautiful Florida-beach , or decide to visit one of Florida’s theme parks , this is the place to stay . We are centrally located and have quick access to Polk Pkwy , so your adventures are unlimited .

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.

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

Modern lakeside retreat by SEU and FSC

This 1920’s 1 bedroom 1 bath lakefront historic cottage is separate from the main house with its own entrance, parking, screened front porch, fire pit dock & beach. The queen bed and large couch sleeps 3 adults. Only 1 mile from Southeastern University and 3 miles to Florida Southern College. Kayaks, stand up paddle board, 4 seater pedal boat, and fishing poles and tackle are provided for your enjoyment. Come unwind and enjoy the lake views from the hammock and private beach!

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!

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.

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