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.

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.

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 Home Close to Downtown, Fully Renovated

Book this centrally located home in an extremely safe and quiet part of town! It’s been fully renovated and contains amenities like: -Brand new appliances -Coffee bar -3 smart TV's -Exercise bike -Driveway parking -Back patio w/ seating -Black-out curtains -Pack ‘n Play The home is kept immaculately clean, and is professionally treated for pests. Less than 5 miles from I-4, Florida Southern, downtown Lakeland, great shopping, and tons of other convenient locations.

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!

Intimate and peaceful stay

Descansa en esta estancia íntima y serena, perfecta para dos huéspedes. Cuenta con un dormitorio con cama king, baño completo y cocina equipada. El diseño blanco transmite calma y frescura. Disfruta del patio privado con columpio y mesa al aire libre. Comienza el día con café bajo el cielo o relájate por la tarde en el columpio. Ideal para parejas o viajeros solitarios que buscan privacidad y tranquilidad.

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!

North breeze

Ideal location just 0.7 miles from Florida Southern University in Lakeland. Private space with a queen size bed, Smart TV and high-speed WiFi. Includes a fully equipped kitchen, with complimentary coffee and water. Private entrance with smart lock and free parking with 24-hour security cameras. Access to common areas with barbecue, trampoline and swing. Close to Publix, CVS, and malls.

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