Vacation rentals in Highland City

4.85 out of 5 average rating, 185 reviews

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

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

ValueFamilyOutdoor spaces

4.96 out of 5 average rating, 305 reviews

Guesthouse in Lakeland

Cottage On Cambridge-Lake Hollingsworth/FSC Area

This cozy Studio Cottage is located steps away from Lake Hollingsworth and close to Florida Southern College. It's a separate home located behind the main one and is private. You can enjoy all outside living areas. If you've stayed in previous years it’s unrecognizable from before! I'm just re-listing after almost 2 years when Hurricane Milton decided to crash it with our big Oak tree. The Cottage has been completely rebuilt! Landscape is so different without our beloved Magnolia and Oak trees!

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The exterior of a spacious house is displayed, surrounded by lush green grass and mature trees. A pathway leads to the entrance, flanked by shrubbery. Bright daylight emphasizes the clean lines of the house and the inviting front porch.

4.98 out of 5 average rating, 47 reviews

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.

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5.0 out of 5 average rating, 51 reviews

Family Heated Pool Home Sleep 12 Near Tampa Disney

Wake up to sunshine, step outside to your PRIVATE HEATED POOL, and let the day unfold at your own pace. This is where FAMILY MEMORIES ARE MADE: kids laughing in the playground, slow mornings with coffee poolside, and evenings enjoying movie nights on the 75” TV. Tucked in one of Lakeland’s most peaceful neighborhoods, this spacious retreat is designed for connection and comfort. About 1 hour from Tampa or Disney, Publix minutes away, quick access to SEU, Florida Southern College, and Polk State.

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A serene lakeside view showcases the tranquil waters of Lake Hollingsworth, surrounded by lush greenery and walking paths. Patterns of vegetation are visible along the shoreline, while distant trees line the horizon, creating a peaceful natural landscape.

4.98 out of 5 average rating, 115 reviews

Lakeland LakeFront 4BD | 3BA FSC SEU Sun & Fun Tigers

Welcome to Laketitude—your spacious lakefront escape on Lake Hollingsworth! Just steps from Florida Southern College and Frank Lloyd Wright gems, minutes to downtown Lakeland, Sun ’n Fun, and Tiger Town, with Tampa and Orlando only 40 mins away. This 4BR/3BA retreat sleeps 10 and features a large backyard, 65” Smart TV, Xbox, coffee bar, and full kitchen—perfect for families, college visits, and getaways. Don’t miss out on our deep connection with FSC’s rich history- message us to learn more!

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A spacious outdoor patio area is softly illuminated by string lights against the night sky. A fire pit is set at the center, with comfortable seating areas including lounge chairs and a swing. Lush greenery adds a natural touch to the serene ambiance.

4.85 out of 5 average rating, 20 reviews

Epic Backyard, Cozy 3/2, (6 month minimum)

*6 months minimum* Priced way lower than any hotel. Quiet/safe cul-de-sac, 3BR/2BA in South Lakeland. 2 mins to Publix, 5 minutes from the Polk Parkway to connect to I-4. Short drive to Orlando & Tampa. Laminate flooring, vaulted ceiling, stainless steel fridge, tile kitchen, high water pressure showers. Epic outdoor space 900 sqft of custom-built paver patio with firepit and charcoal Weber grill plus, swing & privacy hedge. Blazing fast Wi-fi 400+Mbps & streaming (Netflix, Max, Peacock).

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4.99 out of 5 average rating, 139 reviews

Apartment in Lakeland

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 .

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5.0 out of 5 average rating, 43 reviews

Covered Lanai Bliss-4BR Lakeland Getaway

Modern 4BR home in a quiet South Lakeland neighborhood, close to Publix, Sam’s Club, and Walgreens. Walk to Banana Lake or explore Circle B Bar Reserve, just 10 minutes away. Enjoy our nearby lakes, trails and parks. Conveniently located between Orlando and Tampa/St. Pete, making it easy to visit Disney/Sea World/Busch Gardens/Legoland/Spring Training, Gulf Coast beaches, and Central Florida attractions. The perfect home base for work, vacation, graduations or visiting family and friends.

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Home in Lakeland Highlands

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.

LocationFamilyAir conditioning

5.0 out of 5 average rating, 18 reviews

4.97 out of 5 average rating, 38 reviews

“Pool Retreat, Sleeps 10. Near Downtown Lakeland”

Welcome to this beautiful house with a pool in Lakeland, ideal for families and groups of up to 10 guests. Large pool with covered terrace, loungers and barbecue. 3 bedrooms, 6 comfortable beds and 3 full bathrooms. Equipped kitchen, washer and dryer. Fenced-in garden, perfect for children. Close to downtown, Lake Hollingsworth and parks. Legoland is 25 minutes away, Tampa is 45 minutes away, and Orlando is 1 hour away. Self check-in, fast Wi-Fi and EV charger.

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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.

4.82 out of 5 average rating, 135 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!

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