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

Heron Haven Comfy 2BR condo w/pool Great Location

Heron Haven provides a comfortable, peaceful retreat for singles, couples or a small family wanting a quiet place to work, play, relax. Working travelers will find a dedicated work space with fast wifi. Nature-lovers will enjoy watching birds & other wildlife from the patio. Conveniently located in the Imperial Lakes Area of S. Lakeland, close to many stores/restaurants, walking distance to Publix grocery, and not far from Lakeland-Lindbergh Airport. Convenient to both theme parks and beaches.

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.

Cute, Historic District Home - GREAT LOCATION

Enjoy a stylish experience at this centrally-located place 5 mins from downtown Lakeland, 8 mins from I-4, 40 mins from Tampa and Orlando (Disney World/Universal), 1 hour from several beaches including Clearwater. 🐕 Pet friendly but you MUST include your pets in the reservation Nearby places of interest: - Downtown Lakeland - Southeastern University and Florida Southern College - RP Funding Center - Lakeland Linder International Airport - Polk Theatre - Circle B Nature Reserve - and more!

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.

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

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!

Cozy Suite in the Heart of Lakeland

This cozy, private suite is located on one of the most desired streets in all of Lakeland, and right near the beautiful Lake Hollingsworth. It is less than a block away from both the lake and Commonground Park. It is located along the I-4 between Tampa (40 min drive) and Orlando/Disney and its attractions (1 hr drive). It has close access to route 98 and the 570 Polk Pkwy and many other attractions, shopping, restaurants, and entertainment. You will love this place!

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!

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!