Vacation rentals in Highland City

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Top-rated vacation rentals in Highland City

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

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Guest favourite
Guest suite in Lakeland
4.86 out of 5 average rating, 180 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
5 out of 5 average rating, 42 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.

Top guest favourite
A view from inside the dining area showcases a sliding glass door leading to a wooden deck. Two white chairs and a round table are visible on the patio, surrounded by a lush green yard and distant trees under a clear blue sky.
Home in Lakeland
4.98 out of 5 average rating, 41 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.

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
4.87 out of 5 average rating, 153 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
An inviting outdoor living space features a cozy seating area with wicker chairs and vibrant cushions. A rustic table and barstools complement the area, surrounded by lush greenery and potted plants. Overhead fans provide comfort, while colorful wall art adds character to the ambiance.
Apartment in Lakeland
4.99 out of 5 average rating, 114 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
Guesthouse in Bartow
4.79 out of 5 average rating, 140 reviews

Simple Apartment in quiet suburb

This property is about 1 hour from Tampa & Orlando, away from traffic and noise. This 1 bedroom apartment offers a comfortable bed with simple amenities. We are not far from many attractions such as Disney, Universal Studios, LegoLand, Busch Gardens, Seaworld, and more. The property has its own private entrance to come and go as you wish. Pickelball are courts nearby as well as grocery stores, local coffee shops, and local restaurants - all within 5 min. driving distance of the property.

Superhost
Home in Lakeland
4.83 out of 5 average rating, 12 reviews

Sun N Fun Retreat 2

Quiet, contemporary and well-maintained 3/2 home with a distant view of the lake, public access to a boat ramp and a nearby walking trail. A quick drive to restaurants and shopping. We welcome our Sun N Fun community! We are a few exits from the Lakeland Linder airport! This space has recently been remodeled - new kitchen cabinetry, master bath, furnishings and linen. Pictures are being updated as we speak. Whether you are in town for business or pleasure, this space won't disappoint.

Guest favourite
Home in Lakeland
4.87 out of 5 average rating, 15 reviews

Cozy 3BR Home |Pet-Friendly |Near Legoland & Tampa

Welcome to your perfect Lakeland getaway — where comfort meets convenience in the heart of Central Florida. This beautifully updated 3-bedroom home is ideally located just minutes from Downtown Lakeland, Lake Mirror, Florida Southern College, SUN ’n FUN, and Legoland Florida — making it the perfect home base for families, couples, and business travelers alike. Enjoy a peaceful neighborhood setting while staying close to everything. Quick access to Tampa & Orlando attractions

Superhost
Apartment in Lakeland
5 out of 5 average rating, 3 reviews

The Crestview

Enjoy your home away from home in South Lakeland. This stylish apartment offers two cozy bedrooms with one king bed and one queen bed, perfect for a comfortable stay. Relax in the inviting living room with a comfortable sectional sofa, and enjoy a modern bathroom with shower and hair dryer. Central heating and air conditioning ensure year-round comfort. Ideal for families, couples, and business travelers, and conveniently located to restaurants, and local attractions.

Top guest favourite
A wooden dock extends over the calm waters of Lake Howard, bordered by lush grass on either side. A sign indicating 'Private Property' stands at the dock's entrance, while the clear blue sky is dotted with fluffy white clouds in the background.
Guesthouse in Winter Haven
5 out of 5 average rating, 114 reviews

Charming Lakeside Cottage

Escape to our cozy lakeside cottage, featuring a dock that’s perfect for watching sunrises, fishing, and launching your kayak. The property is on Lake Howard, which is part of the Winter Haven Chain of Lakes. Inside, you’ll find a fully equipped kitchen and comfortable living space for unwinding. Located just a short drive from the excitement of Legoland and Disney World, you can easily explore the area’s attractions while having a peaceful haven to return to.

Guest favourite
The saltwater heated pool is enclosed within a screen patio, surrounded by a well-maintained white fence. Comfortable cushioned seating is visible nearby, along with potted plants adding a touch of greenery. Clear blue skies enhance the peaceful atmosphere of the outdoor space.
Home in Lakeland
4.94 out of 5 average rating, 34 reviews

Relax in Heated Saltwater Pool w/ Screened Lanai

Experience luxury and comfort in this spacious rental featuring a master suite with king bed and en suite bath, fully equipped kitchen, dedicated office, and cozy living areas. Enjoy a heated saltwater pool, outdoor TV, grill, and large fenced yard. All bedrooms have large beds, TVs, and ample storage. Includes free WiFi, private driveway, and welcome snacks. Perfect for families, couples, or business travelers!

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
4.83 out of 5 average rating, 119 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 Highland City vacation rentals

  1. Airbnb
  2. United States
  3. Florida
  4. Polk County
  5. Highland City