Holiday rentals in Lakeland Highlands

Charming Tiny House on 5 acres with POOL/ HOT TUB

Escape to the heart of Lakeland where our charming Tiny House awaits. Nestled on 5 acres of tranquility, you'll experience the best of both worlds: a peaceful retreat and easy access to local shopping centers just a stone's throw away. The Tiny House is furnished with a queen size bed and a king sized bed in the upstairs loft, kitchen, full bath as well as a designated work area. Take a refreshing dip in the shared pool, unwind in the hot tub, or simply soak up some sun on the lounge chairs.

Romantic Lakefront – Feed Swans – Walkable Dining

Discover SWAN LAKE VACATIONS. Swan elegance meets city charm steps away. Highlights: • Lake Views • Downtown Stroll • King-sized bed • Modern Comfort • Full Kitchen • Semiprivate Patio • Between Tampa & Orlando Why Swan Lake Vacations? • Central Hub • Safety Assurance • Easy drive to beaches and Walt Disney World • Experienced Hosts Escape to Swan Lake Vacations—a place where swans grace the surroundings next to quaint downtown life. Book for a perfect blend of nature and urban comfort!

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!

Studio apt in Historic area of Lakeland

This second story studio is on our homes property. It has a Queen bed, bathroom and kitchen. It is nestled in the historic area of Lakeland, one block in from The "Frank Lloyd Wright" designed Florida Southern college, tours are available! Our Cobblestone streets take you to our neighborhood restaurants, the art museum, library, Hollis garden, we are between two lakes-Hollingsworth it has a great walking/running path, and Lake Morton a bird paradise. All within walking distance.

The White House+Pet Friendly+Fenced yard

Pet friendly with fully fenced home! Discover our 3-bedroom, 2-bathroom home in Lakeland, designed for your ultimate relaxation. Unwind in the sunroom or the spacious living area, where comfort is a priority. The fully equipped kitchen and cozy bedrooms ensure a pleasant stay. Enjoy our coffee bar and outdoor BBQ grill, perfect for leisurely mornings and evening gatherings. With nearby amenities for outdoor fun, this retreat perfectly balances convenience and relaxation.

Private and Cozy Suite

Discover your home away from home in this stylish 1-bedroom, 1-bathroom apartment, with a fully equipped kitchen! Located just minutes from Walmart (2 min), Southgate Shopping Center (6 min) and Merchants Walk (4 min). Enjoy dining options like IHOP, Texas Roadhouse, and Chipotle, all less than 5 minutes away. With nearby universities and attractions like Downtown Lakeland and Sun n' Fun, this is the perfect base for your adventures. Book now for an unforgettable stay!

Cozy 2B/1 Downtown Hideaway

This cozy mother in law suite is a duplex that shares a wall with the main house but not an entrance. You will be blocks away from a neighborhood playground as well as beautiful Lake Hollingsworth. Being in the heart of Lakeland, you are never far from entertainment or nature. It's almost equally distant from Orlando and Tampa at about a 45-minute drive and the beach being about an hour and 20 minutes away. All that downtown has to offer is just 2 miles away.

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, front porch & beach. The queen bed and large couch sleeps 3 adults. Only 1 mile from Southeastern University and 3 miles to Florida Southern College. Kayaks, 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!

Hidden Ruby Apartment

Your family will be close to everything when you stay at this centrally-located place. Within walking distance to restaurants, major grocery stores, parks, and much more. Midway between major cities of Orlando and Tampa for the urban seekers. Reserved guest parking, front porch sitting area, washer and dryer, work station, and a children-safe environment. This apartment was designed to accommodate all of your needs.

Azure Escape

🔷 Bienvenido a Azure Escape, un alojamiento privado, moderno y bien ubicado en Lakeland. Ideal para parejas o viajeros, cuenta con dormitorio con cama para dos, baño completo, cocina equipada, área de trabajo, WiFi rápido, Smart TV y patio privado. A menos de 10 min del aeropuerto y del Sun ’n Fun Aerospace Expo , y cerca de Bonnet Springs Park, restaurantes y tiendas.

Charming Guesthouse

Unwind and rejuvenate in this serene and stylish haven. Nestled in a prime location and neighborhood. Relax in the comforts of home and enjoy lightning-fast WiFi. We’re a top-notch location in Lakeland, and we’re the perfect starting point for exploring lots of amusement parks, lakes, and exciting activities!

Spacious 1 bed 1 bath with office and free parking

Airy and spacious duplex, centrally located in Lakeland downtown. Nice park across the street for exercising or spending time with kids. Walgreens one block away, local bars, restaurants, antique stores and lots of beautiful historic bungalows