Vacation rentals 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!

Family · Value · Bathroom

South Lakeland Pool Home, Near Streamsong Golf

Spacious 3BR/2.5BA pool home in quiet South Lakeland (Christina neighborhood), sleeps 7. Relax by your private pool after golf, travel, or tournaments. Just 25 min to Streamsong Resort. Loyce Harper Park (baseball/softball, biking) is 2 min away; Christina Park across the street hosts softball tournaments. Eaglebrook Golf & Country Club is nearly walking distance. Minutes from great dining, Bonnet Springs Park, and LEGOLAND. Visit in April for Sun 'N Fun, one of the country's largest air shows!

Location · Family · Getting around

5/3 Luxury Oasis Resort- Pool - Full Gym - Balcony

. Discover a spacious 5-bedroom gem in a prime Lakeland location. This beautiful home sits on a private 1 acre lot, features a sparkling screened pool , a specious backyard, a complete gym to keep you active and a BBQ grill area. Perfect for large families vacationing, visiting family or to host your unforgettable event/family gathering (only under approval) with plenty of parking! With easy access to restaurants, grocery, I4, Disney. This home was Designed to create memorable stays

Family · Value · Quiet

Gorgeous Gem in the Heart of Lakeland

LOCATION, LOCATION! This gorgeous, spacious, newly renovated home is located on one of the most desired and safest streets in all of Lakeland, and steps away from the beautiful Lake Hollingsworth and Trail. Close to the lake, and a short drive to downtown Lakeland, this gem is in the perfect location! This home features zero gravity beds, a gourmet kitchen, private laundry, smart TVs and WiFi, comfortable sofas with ample seating for entertainment, dining and more. You'll love this place!

Location · Family · Hospitality

Private Pool + Arcade | Near Hospitals & Downtown

Spacious 4BR Lakeland home with private pool, arcade game room, free parking, king & queen beds, fast Wi-Fi, workspace, full kitchen, and roomy living areas. Near Christina Park, Elite Fall Classic Volleyball Center, Advent Health Field House, ISPS August Heat – Softball, Lake Myrtle Sports Park, Lakeland Square Mall, Downtown Lakeland, Lakeland Linder Airport, Orlando Health Lakeland Highlands Hospital, Watson Clinic, Bonnet Springs Park, First Friday events, and LEGOLAND Florida.

Location · Family · 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 · Air conditioning

Sage & Serenity- Lakeland Boho style retreat

Escape to Sage & Serenity, a stylish 4 bedroom retreat in peaceful Mulberry! 🌿 Perfect for families, friends, golfers, or anyone looking to relax while staying close to Central Florida’s best attractions. Enjoy a spacious, open-concept, beautifully decorated home, fully equipped kitchen, comfy bedrooms, and plenty of room to unwind. Conveniently located between Tampa & Orlando, with Lakeland, LEGOLAND, Disney, golf & more within easy reach. Come relax, recharge & feel at home!

Location · Value · Cleanliness

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.

Family · Location · Comfort

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 · Value · Decor

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!

Location · Value · Decor

Karen’s Happy House

Enjoy a stylish experience at this centrally-located place. A cozy, charming 1925 cedar shake modern English style home. Experience a unique, warm & welcoming stay. There is a separate small cottage in the back that can be rented under a separate listing if you are looking for a family gathering spot!

Family · Value · Parks

Florida Creek studio

More than just a place to stay, this is a space for creating memories. Here, you will find tranquility, comfort, and an atmosphere that invites you to relax. Whether you come for rest or adventure, this home will serve as the perfect setting for your experience.

Location · Cleanliness · Decor