Holiday rentals in Highland City

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.

Luxury 3BR Near Downtown | Pet Friendly + Peaceful

Welcome to your Lakeland retreat! This charming 3-bedroom home is thoughtfully styled, exceptionally clean, and fully equipped with all the conveniences of home. Located in the peaceful Lake Hunter neighborhood—just minutes from downtown, colleges, and spring training—it’s perfect for families, couples, or business travelers. Relax inside or enjoy the private backyard patio. Pets stay free! 8 mins to FSC 10 mins to Detroit Tigers 13 mins to Sun ’n Fun 30–45 min to Legoland, Disney & Tampa

The Woodsy Weekender

Take it easy at this unique and tranquil getaway in the woods. Wake up in one of our cozy queen or full sized beds, and enjoy coffee and hot chocolate on the 2nd story deck. 10 minutes from downtown Lakeland, spend your day walking our beautiful lakes and eating at our foodie hotspots. End your day back the at Woodsy Weekender making dinner in our full kitchen and sipping wine on the screened in back porch swings watching the sunset. The perfect little "Safe Haven" cabin for all occasions.

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!

House on the Heights

Welcome to your Lakeland retreat! The House on the Heights is a beautifully updated 3-bedroom, 2-bath home offers the perfect blend of comfort and convenience—just minutes from Cleveland Heights Golf Course, Lake Hollingsworth, and Downtown Lakeland. We can comfortably host up to 8 guests with the queen sleeper sofa. Come be our guest and enjoy our coffee bar, comfy cozy sofa, and relax in our enclosed sunroom!

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!