Holiday houses in Lakeland Highlands

Christina Casa - a South Lakeland Getaway

Welcome to Christina Casa, your ultimate vacation retreat! Nestled in a quiet South Lakeland Neighborhood, this charming 3-bedroom has 2 full baths. The fully stocked kitchen invites culinary adventures, while the cozy living room offers a plethora of games and books for endless entertainment. Step outside to the inviting patio area, complete with a grill for delightful outdoor dining experiences. Embrace relaxation and adventure at Christina Casa, where making memories await! Come be our guest!

Value · Location · Comfort

Updated home with heated & screened in pool

Recently renovated from top to bottom. The bedrooms have a king, queen, and bunk beds. Have a movie night with the 4k projector on the 125 inch screen and a Dolby Atmos soundbar. Cool off and away from bugs in the screened in heated/cooled pool that goes from 3 to 6 feet deep, then relax on the patio furniture. Newly landscaped spacious back yard. Quiet neighborhood so absolutely no parties. Centrally located between Tampa & Orlando. Theme parks, beaches and so much more within an hour or two.

Location · Family · Accuracy

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

Value · Family · Check-in

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.

Family · Location · Sleep quality

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 .

Location · Value · Decor

The Highland House • Cozy 3BR • Fireplace • Patio

Stylish and spacious, this South Lakeland retreat is the perfect home base for your stay. Enjoy a beautifully updated interior with an open-concept layout, modern kitchen, and cozy living space for relaxing or gathering. With comfortable bedrooms, a large dining area, and plenty of room to unwind, it’s ideal for families, groups, or work trips. Features a screened patio, fenced yard, and keyless entry, all in a quiet neighborhood close to shopping, dining, and local attractions.

Family · Location · Layout

Casa Planta Cozy Tropical Oasis Pool View Suite

Casa Planta is a garden-inspired oasis where nature & relaxation meet. Our tropical landscape is currently in a seasonal restoration phase due to extreme winter freezes, w/ an evolving garden setting. Enjoy a peaceful walk to your private entrance & unwind poolside in your 2BR/1BA suite. The pool and interior remain exactly as pictured—private, comfy, & serene. The guest suite is attached to the main house but completely blocked off from it.

Location · Value · Sleep quality

Family Friendly 3BR Home | Quiet | Near Hospitals

Welcome to your home away from home in Lakeland, FL! This fully furnished 3-bedroom, 2-bath home is ideal for travel nurses and healthcare professionals, as well as families or extended stays. Located in a quiet neighborhood near local hospitals, the home features a comfortable living space, fully equipped kitchen, high-speed Wi-Fi, and in-unit washer and dryer. Convenient access to shopping, dining, and major roads between Tampa and Orlando.

Value · Family · Quiet

Charming Guesthouse

Escape to a beautifully styled South Lakeland retreat, loved by guests for its comfort, peaceful setting, and convenient location. Settle into a cozy, thoughtfully designed space with fast WiFi, relaxing touches, and a quiet neighborhood feel. Spend your days exploring nearby lakes, dining, shopping, and Central Florida attractions, then return home to unwind, recharge, and enjoy a stay that feels effortless.

Location · Family · Indoor spaces

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.

Value · Location · Outdoor spaces

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!

Family · Location · Quiet

Karen's Cottage

Enjoy a stylish experience at this centrally-located place. Private entrance and fenced back yard. Between Tampa and Orlando so there’s a lot of things to do. Lakeland has a wonderful and thriving community.

Value · Location · Accuracy