Vacation rentals in Highland City

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Top-rated vacation rentals in Highland City

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Top guest favorite
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
4.86 out of 5 average rating, 161 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

Guest favorite
Guesthouse in Lakeland
4.96 out of 5 average rating, 189 reviews

Swan City Studio + Cozy Courtyard, near downtown

Your cozy retreat awaits you in Swan City Studio! It is centrally located in Lakeland, a short drive from downtown, Florida Southern College (1.4 miles) Southeastern University (1 mile) The studio comes fully equipped with everything you need to enjoy a relaxing or adventurous stay! Cook a dinner for two in the well appointed modern kitchen! Enjoy a glass of wine in the warm lit courtyard to cap the night! Private parking is just a few steps down the pathway through the courtyard from your door!

Top guest favorite
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.
Home in Lakeland
5 out of 5 average rating, 27 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.

Top guest favorite
The Tiny House is situated in a serene outdoor setting, featuring a light-blue exterior with a metal roof. A wooden porch with rocking chairs extends at the front, while the surrounding landscape includes lush green grass and landscaping along a gravel path.
Tiny home in Lakeland
4.99 out of 5 average rating, 111 reviews

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.

Top guest favorite
The open living area features a comfortable sofa set, a stylish area rug, and large windows allowing natural light to fill the space. An island kitchen with contemporary bar seating and modern appliances is visible, creating a seamless flow between dining and living spaces.
Home in Lake Hollingsworth
4.98 out of 5 average rating, 139 reviews

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, smart TVs and WiFi throughout, comfortable sofas with ample seating for entertainment, dining and more. You'll love this place!

Guest favorite
A two-story green studio building is prominently displayed, featuring white accents and large windows. A set of stairs leads to the entrance. The surrounding area is landscaped with small plants and a paved path, offering a welcoming and tidy exterior.
Guesthouse in South Lake Morton Historic District
4.9 out of 5 average rating, 120 reviews

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.

Top guest favorite
A wooden dock extends over calm waters, reflecting hues of orange and pink from the sunset. Surrounding vegetation adds a natural frame to the serene lake view, while the distant shoreline is faintly visible against the evening sky.
Guesthouse in Lakeland
4.98 out of 5 average rating, 252 reviews

Modern lakeside retreat by SEU and FSC

This 1/1 lakefront historic cottage, built in 1920, 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 and fishing poles are provided for your enjoyment during your stay. Come unwind and enjoy the lake views from the hammock and private beach!

Superhost
An inviting outdoor pool area features a rock waterfall and is surrounded by a screened enclosure. Soft lighting enhances the tranquil blue water, while tropical plants can be seen in the background. A few chairs are positioned nearby for relaxation.
Guesthouse in Lakeland
4.87 out of 5 average rating, 113 reviews

Luxury Cottage on Prestigious Million$ Property

Close to everything. Away from it all. Situated on 5 grassy acres and home to the Lewman family, this pristine south Lakeland home is fully fenced with a gated entry. The Guest House sits detached next to the main house with plenty of shared parking. Enjoy the outside without the worry of traffic. Free Wifi. We pride ourselves in providing a clean and safe home for you to make your own while you are here.

Guest favorite
A spacious outdoor area includes a pool surrounded by a white deck. Seating options are available, featuring lounge chairs and tables. The two-story building provides multiple balconies, framed by lush greenery and palm trees, contributing to a serene environment.
Loft in Auburndale
4.93 out of 5 average rating, 222 reviews

2 Bedroom Apartment near Legoland and Disney

This Private Studio features 2 bedrooms, kitchenette with dining area, private bath, walk-in closet, own entrance and from the Main Studio bedroom a large Balcony with Spectacular lake views. The Kitchenette with dining table and the bathroom is located in between of the 2 Bedrooms. The second Bedroom is only 10'x10' with a Queen bed and Wardrobe. Early Check in or late check outs are not available

Guest favorite
The image captures a serene lake view from a grassy area, with a wooden deck overlooking calm waters. Lush trees frame the scene, providing shade and a natural ambiance. Water lilies are visible on the surface, enhancing the tranquil lakeside setting.
Home in Lakeland
4.95 out of 5 average rating, 146 reviews

Charming Lakefront Cottage with Stunning Views

Welcome to our lake house retreat in Lakeland, Florida. You can enjoy a peaceful getaway with beautiful sunset views and tranquil waters during the evenings, and still visit major cities such as Orlando and Tampa during the day which are less than an hour away. Minutes from Southeastern University, Florida Southern, Lake Hollingsworth, and other attractions in the Lakeland area.

Top guest favorite
A wooden deck offers a view of a spacious yard featuring a horse and a playset for children. The area is surrounded by trees and fencing, creating a serene outdoor space that showcases the natural surroundings.
Farm stay in Winter Haven
4.99 out of 5 average rating, 172 reviews

Quiet, Country and close to Legoland!

Unwind between theme parks! Relax at our 2-bedroom, 1-bath guest house on a 2.5 acre hobby farm. Meet our horse, collect fresh eggs, and enjoy ceramics to paint! Just minutes from the stunning Circle B Bar Reserve — a favorite for wildlife lovers, photographers, and sunset chasers. Limit 5 guests only please.

Superhost
A living area features a blue sofa adorned with decorative pillows, a wooden coffee table, and a cozy armchair. A wall-mounted television is positioned above a white fireplace. Natural light filters through a window with sheer curtains, while a wooden table stands against the wall.
Apartment in Dixieland
4.89 out of 5 average rating, 203 reviews

Adorable 1 bed/1bath with office and free parking

This beautiful duplex is located in a Historic Bungalow built in the late 1920s, centrally located in Lakeland downtown. Nice park across the street for exercising or spending time with kids. Walgreens is one block away, and local bars, restaurants, antique stores, and lots of beautiful historic bungalows

Popular amenities for Highland City vacation rentals

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