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Holiday houses in Lakeland Highlands

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Top-rated holiday rentals in Lakeland Highlands

Guests agree: these stays are highly rated for location, cleanliness and more.

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A small outdoor seating area is presented with a black round table and two folding chairs, situated on a green lawn area. A door adorned with a floral wreath provides access to the suite. Surrounding plants add greenery to the tranquil space.
Guest suite in Lakeland
4.85 out of 5 average rating, 184 reviews

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

Top Guest favourite
Home in Lakeland Highlands
5 out of 5 average rating, 36 reviews

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!

Guest favourite
A rectangular pool is framed by a stone patio, featuring steps leading into the clear water. Sunlight creates gentle ripples on the surface, while the surrounding screened enclosure offers a view of the lush greenery beyond.
Home in Lakeland
4.83 out of 5 average rating, 81 reviews

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.

Top Guest favourite
The bedroom features a large tufted bed with soft linens, complemented by a decorative bench at the foot. Industrial-style accents are visible in the exposed brick wall and ceiling beams, while natural light fills the space through floor-to-ceiling windows, framed by navy curtains.
Apartment in Lakeland
4.95 out of 5 average rating, 100 reviews

Downtown Lkld-Urban Luxury Loft

Discover urban comfort in our Downtown Lakeland Studio Loft! This trendy third floor apartment accommodates 4 guests, boasting open industrial ceilings and historic brick walls that add a chic touch to the space. The floor to ceiling windows bring in gorgeous natural sunlight. Step outside and immerse yourself in the heart of the city, with cafes, shops, and attractions just a stroll away. Whether you're here for business or leisure, our loft offers the perfect blend of style and convenience!

Guest favourite
A quaint green cabin is nestled among tall trees, featuring a sloping roof and large windows that invite natural light. String lights are visible, adding a touch of charm, while the front porch offers a welcoming space for relaxation.
Home in Lakeland
4.88 out of 5 average rating, 160 reviews

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.

Top Guest favourite
Apartment in Lakeland
4.98 out of 5 average rating, 132 reviews

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 .

Top Guest favourite
A bright workspace is showcased with large windows offering views of the lake. Two yellow armchairs sit beside a glass-top table. A desk with a lamp is positioned against the wall, with a potted plant adding a touch of greenery.
Apartment in Lakeland
5 out of 5 average rating, 148 reviews

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!

Top Guest favourite
Home in Lakeland Highlands
5 out of 5 average rating, 17 reviews

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.

Top Guest favourite
A bedroom showcases a leafy green accent wall, complemented by a light wood bed frame. Natural wood flooring adds warmth to the space. The bathroom features a modern vanity with dual sinks and a potted plant, while the outdoor area reveals a pool surrounded by a screened enclosure, illuminated by soft blue lighting.
Guest suite in Lakeland
5 out of 5 average rating, 118 reviews

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.

Top Guest favourite
Guesthouse in Lakeland Highlands
5 out of 5 average rating, 39 reviews

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.

Top Guest favourite
A spacious bedroom features a large bed dressed in soft pink bedding, complemented by decorative pillows. A bedside table holds a modern lamp, and a full-length mirror reflects the soft ambiance. A wall-mounted television is visible, enhancing the room's functionality.
Guesthouse in Lakeland
4.99 out of 5 average rating, 99 reviews

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.

Guest favourite
A spacious living area features a sectional sofa with an ottoman and two accent chairs, set on a soft, light rug. A ceiling fan provides cooling, while natural light filters through a large window dressed with sheer curtains. A small side table with a lamp complements the decor.
Home in Lakeland
4.82 out of 5 average rating, 128 reviews

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!

Popular amenities for Lakeland Highlands holiday rentals