Highland City vacation rentals

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Scroll through and select from vacation rentals in Highland City to find one that's perfect for your trip. Whether you’re traveling with friends, family, or even pets, vacation rentals have the amenities you expect for your stay, which might include air conditioning and a pool. You'll be able to choose a rental that has what everyone needs, including places that are non-smoking or accessible.

Vacation rentals with weekly discounts - Highland City

Showing deals for:Aug 14 - Aug 21

Image gallery for Home sweet home under the oaks, Large Patio, Central Location

Exterior
10 out of 10, Exceptional, (29 reviews)
Exceptional
(29 reviews)

Home sweet home under the oaks, Large Patio, Central Location

Lakeland

9% off
Price is $313
$2,188 for 7 nights
All fees included
Home sweet home under the oaks, Large Patio, Central Location

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Find out more about Highland City

Why visit Highland City

  • Family-friendly attractions: Highland City is ideal for families, offering a mix of urban parks and outdoor activities.
  • Beautiful lakes: Explore the serene beauty of nearby lakes, perfect for relaxation and recreation.
  • Aviation museum: Discover aviation history at the local museum, a unique highlight for enthusiasts.
  • Charming neighborhoods: Visit nearby Winter Haven and Haines City for local history and hospitality.
  • Variety of accommodations: Choose from private vacation homes, villas, and condos for a comfortable stay.

Popular types of accommodation in Highland City

Planning a getaway to Highland City? You're in for a treat. Discover a variety of popular accommodations, including houses, villas, and condos. Whether you're seeking affordable rentals, spacious house rentals, or cozy apartments in Lakeland, we've got you covered. Dive into our selection and find the perfect place to unwind and make lasting memories.

  • Houses: The top choice for visitors to Highland City, offering spacious accommodations ideal for families, friends, or couples seeking privacy.
  • Villas: A luxurious option that combines comfort and style, perfect for those wanting a bit more elegance during their stay.
  • Condos: A popular choice that provides the convenience of home with access to shared amenities in a community setting.
  • Apartments: Affordable and practical, these rentals are great for travelers looking for a cozy place to unwind.
  • Cottages: Quaint and charming, these delightful retreats offer a unique ambiance for a memorable experience.**

Top attractions near Highland City

Highland City, Florida, is perfect for families seeking outdoor and entertainment-themed vacations. Visitors can enjoy a variety of attractions, including urban parks, beautiful lakes, and an aviation museum. Whether you're looking for outdoor adventures or a city experience, Highland City offers a range of points of interest that cater to every traveler's needs, making it an ideal destination for your getaway.

  • The Circle B Bar Reserve: Located 2 miles from Highland City, this nature reserve offers adventure vibes with its scenic trails, diverse wildlife, and opportunities for birdwatching and hiking.
  • RP Funding Center: Situated 7 miles away, this entertainment facility is perfect for family fun, hosting various events from concerts to sports games, ensuring a lively atmosphere.
  • Lake Mirror: Just 7 miles from Highland City, this picturesque lake features stunning scenery and outdoor activities, making it an ideal spot for a romantic stroll or a relaxing day by the water.

Things to do recommended for couples

For a romantic getaway in Highland City, visit Keel & Curley Winery, just 20 miles away. Enjoy a delightful wine tasting experience amidst a charming atmosphere that sets the perfect mood for couples. Don't miss the entertainment vibes that enhance your romantic escape.

Things to do recommended for families

In Highland City, families can unwind at Mary Holland Park, enjoy arcade fun at the Family Fun Center, or catch a game at Bryant Stadium, all within a short drive. These activities promise a perfect mix of relaxation, adventure, and sports for everyone.

Things to do recommended for groups

In Highland City, groups can enjoy a round of golf at The Club at Eaglebrooke, shop and dine at Southgate Shopping Center, or take in a show at the historic Polk Theatre. Each venue offers unique experiences perfect for creating lasting memories together.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

What do I need to keep in mind when booking a vacation in Highland City

When you're planning a trip—whether it's with a group, your family, or even your pets, or if you're considering an extended stay—it's important to prioritize your preferences. Here are some helpful Vrbo booking tips to guide you.

  • Traveling to Highland City with a group: Think about how many bedrooms you'll require, as well as additional features like a full kitchen or outdoor areas for group activities. Thankfully, you can easily refine your search for all of these options and more on Vrbo.
  • Traveling to Highland City with young kids: Traveling with young kids can be quite demanding. It's important to prioritize their comfort and safety, along with suitable amenities like a private swimming pool. Additionally, think about how close you'll be to family-friendly attractions.
  • Taking your pets with you to Highland City: For many families, a vacation isn’t truly fulfilling unless their furry companion is along for the adventure. If this resonates with you, explore Vrbo listings that welcome pets. Many of these pet-friendly accommodations offer feeding bowls and cozy beds, ensuring that everyone feels comfortable and at home.
  • Planning for a long term stay visiting Highland City: If you're in search of vacation rentals offering discounts for stays of a month or more, you've come to the right spot. By using the appropriate filters, you can effortlessly discover and save on monthly rentals. Don’t forget to include amenities like a parking space, a well-equipped kitchen, or a private pool in your search.

Where to stay in Highland City

Highland City, Florida, offers a delightful vacation experience for families and outdoor enthusiasts alike. Explore nearby Winter Haven with its charming neighborhoods and family-friendly attractions. Visit Haines City for a taste of local history and hospitality, or enjoy the serene beauty of Lake Hamilton. With a welcoming atmosphere and plenty of excursions, you'll create lasting memories in this lovely region of Central Florida.

  • Lakeland: Lakeland, where Highland City is situated, is a vibrant city known for its family-friendly atmosphere and outdoor adventures. With a variety of entertainment options, visitors can enjoy local resorts, amusement parks, and an arena that hosts various events. The nearby theme parks and sports stadiums offer exciting experiences for all ages, making Lakeland a hub for fun and leisure. Explore the beautiful lakes that give the city its name, or attend a conference at one of the many event venues in the area.
  • Winter Haven: Located 10 miles from Highland City, Winter Haven is a charming city perfect for families seeking adventure and outdoor activities. Known for its stunning natural beauty, Winter Haven features local resorts and amusement parks that cater to thrill-seekers and relaxation enthusiasts alike. The city is also home to shopping areas for those looking to indulge in retail therapy. Don't miss the nearby theme parks and film studios, as well as access to beautiful beaches that make for perfect day trips.
  • Eaton Park: Just 3 miles away from Highland City, Eaton Park is a quaint village that offers a delightful outdoor and family-oriented experience. With its local resorts, amusement parks, and golf courses, there's something for everyone in this charming community. Visitors can enjoy the inviting atmosphere of nearby urban parks and explore the local neighborhoods. Eaton Park serves as a great base for those who want to experience both relaxation and entertainment while being close to the excitement of theme parks.

Best time to go to Highland City

If you're planning a trip to Highland City, it's a good idea to check both the weather and property rates. The warmest months are July and August. Peak season runs in January to February and July, while off-peak times, like April, August and November tend to have fewer bookings and better deals.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
January60.6°F (15.9°C)Light RainMostly SunnySlightly HighSlightly Low
February64.6°F (18.1°C)No Rain (Dry)Mostly SunnySlightly HighSlightly Low
March67.6°F (19.8°C)No Rain (Dry)Mostly SunnyAverageAverage
April73.0°F (22.8°C)Light RainMostly SunnySlightly LowSlightly High
May77.4°F (25.2°C)Light RainMostly SunnyAverageAverage
June80.8°F (27.1°C)Light RainMostly SunnyAverageAverage
July81.9°F (27.7°C)Moderate RainMostly SunnySlightly HighSlightly High
August81.9°F (27.7°C)Moderate RainMostly SunnySlightly LowAverage
September79.7°F (26.5°C)Light RainMostly SunnyAverageSlightly Low
October74.8°F (23.8°C)Light RainMostly SunnyAverageAverage
November68.2°F (20.1°C)No Rain (Dry)Mostly SunnySlightly LowAverage
December64.4°F (18.0°C)No Rain (Dry)Mostly SunnyAverageSlightly High

Booking with Vrbo is a breeze

Looking to save on your next vacation? Consider being flexible with your travel dates, as prices can change significantly. Plus, booking an extended stay often results in substantial savings. To discover the ideal Vrbo property that fits your budget, utilize our filters to search by price, location, and type of vacation rental.

Vrbo Trips: Planning as easy as it gets

Vrbo’s Trip Board is a helpful tool designed for you to create new travel plans, manage ongoing arrangements, or review your bookings. It conveniently organizes the properties you've saved or reserved into categories: Potential, Upcoming, or Current Trips. To discover your Trip Boards, simply visit: https://www.vrbo.com/trips.

**Based on Vrbo properties bookings.

Find the perfect vacation rental for your Highland City getaway

Learn about the unique charm of Highland City with a stay in a private vacation home. You'll find plenty to explore during your stay in the area. With a vacation rental, you get a home away from home. Many rentals offer full kitchens and outdoor grills for some home cooking.

Sightseeing in and around Highland City

Do you want to discover attractions to see in the area? Although it can be tempting to stay in your comfortable vacation rental, you'll want to experience everything that Highland City has to offer. These are some of the top attractions to explore, all within 30 miles (48.2 km) of the city center:

  • LEGOLAND® Florida (11.5 mi / 18.5 km)
  • The Club at Eaglebrooke (4.4 mi / 7 km)
  • City of Bartow Golf Course (5.9 mi / 9.6 km)
  • Lake Myrtle Sports Complex (9.5 mi / 15.2 km)
  • Peppa Pig Theme Park Florida (11.6 mi / 18.7 km)
  • Cypresswood Golf and Country Club (14.4 mi / 23.2 km)

Exploring the natural features in Highland City

Whether you're an adventurous traveler or just want to appreciate the scenery, Highland City is a great place to get out in nature. Here are a few of the area's most stunning features, all within 30 miles (48.2 km) of the city center:

  • The Circle B Bar Reserve (1.7 mi / 2.8 km)
  • Sanlan Bird and Wildlife Sanctuary (2.3 mi / 3.8 km)
  • Common Ground Park (5.2 mi / 8.4 km)
  • Lake Mirror (7.1 mi / 11.4 km)
  • Lake Parker (7.8 mi / 12.5 km)
  • Bryant Stadium (8 mi / 12.9 km)

Transportation to and around Highland City

Fly into Lakeland Intl. Airport (LAL), the closest airport, located 8.6 mi (13.8 km) from the city center.

Frequently asked questions

What is the best area to stay in Highland City, Florida, United States of America when booking a vacation rental?
When looking for the best area to stay in Highland City, Florida, you might want to consider the Highland City neighborhood itself, known for its charming atmosphere and convenient access to nearby attractions. This area is surrounded by lush landscapes and offers a variety of vacation rental options, from cozy homes to spacious rooms.

One of the top attractions nearby is the beautiful Lake Eva Park, which features a playground, picnic areas, and walking trails, great for enjoying the Florida sunshine. Additionally, the Polk County History Center, located not too far away, offers a glimpse into the local heritage and is a great spot for those interested in cultural experiences.

Highland City boasts a welcoming community vibe, making it an ideal place for families and travelers looking to explore the region while enjoying a comfortable stay.
How much does it cost to rent a vacation home in Highland City?
Prices for vacation rentals in Highland City vary based on factors like travel dates, length of stay, accommodation type, and location. Simply enter your trip details to explore a wide range of options—whether you're traveling solo, as a couple, with family, or in a group. Vrbo offers something for every taste and budget, from affordable rentals in Highland City to more spacious homes. To get the best value, book early and take advantage of Vrbo's free rewards program.
Are there any discounts for Highland City vacation house rentals?
You can find great discounts on house rentals in Highland City on Vrbo, including special rates on new listings and savings for weekly or monthly stays with top amenities such as a pool or parking. There are several discounts for Last minute bookings, and Early bird bookings too. The best part is, there's no need for a discount code—just enter your travel dates and apply the discount filters to view the top rates.
Can I find long-stay vacation rentals in Highland City?
A long-stay vacation rental in Highland City is the best way to experience local living. Plus, you can make the most of long-stay discounts. For month-long stays, save an average of 19%, and for week-long bookings you can save an average of 10%.* Long-stay discounts are applied automatically when you enter your vacation dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
Are there any Highland City vacation rentals with parking?
Vrbo offers a wide selection of vacation rentals in Highland City with parking available—perfect for families or travelers who value the convenience of having a car during their stay. To easily find these properties, simply enter your travel details on Vrbo and use the "Parking available" filter under the amenities section. This makes it quick and easy to browse listings that suit your needs, whether you're planning a short city break or a longer stay.
When is the best time to visit Highland City for a vacation rental?
The best time to visit Highland City for a vacation rental is from December to February, with January being particularly popular. This peak season attracts visitors looking to escape the colder climates elsewhere, offering a comfortable and inviting atmosphere for outdoor activities. During these months, you can enjoy pleasant temperatures, typically ranging from the low 50s to mid-70s Fahrenheit, making it ideal for exploring local parks and enjoying various recreational opportunities.

Highland City's peak season coincides with winter, drawing families and adventure seekers eager to indulge in the area's natural beauty. Visitors can take advantage of nearby hiking trails, wildlife viewing, and tranquil picnics in the sunshine, all while soaking in the warm Florida weather. The vibrant community often hosts events and activities during this time, creating a lively environment for travelers.

For those seeking a more budget-friendly option, consider visiting in August. Although this month sees a dip in tourism, it can still offer great experiences and a chance to enjoy the local culture with fewer crowds.

Ultimately, the best time to book your vacation rental in Highland City hinges on your personal preferences—whether you desire vibrant socializings during the peak season or the more relaxed charm of the off-peak months.
How early should I book a Highland City vacation rental?
Book your Highland City vacation rental at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your vacation rental, the better the price.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
What are the top attractions in Highland City, Florida, United States of America?
In Highland City, Florida, visitors can explore a range of attractions that highlight the area's natural beauty and local culture. The nearby Lake Mirror is a scenic spot great for leisurely walks, picnics, and enjoying the serene waterfront views. Just a short drive away, the historic downtown area of Lakeland features charming shops, restaurants, and the iconic Frank Lloyd Wright-designed Florida Southern College campus, which is worth a visit for architecture enthusiasts.

For those who enjoy outdoor activities, the nearby Circle B Bar Reserve offers trails for hiking and birdwatching, allowing visitors to immerse themselves in the local wildlife. Additionally, the Polk Museum of Art in Lakeland provides cultural enrichment with its diverse art collections and rotating exhibitions, making it a great option for art lovers.
Can I change or cancel my Highland City home rental booking on Vrbo?
To find Highland City vacation rentals with free cancellation, just use Vrbo's handy "Free cancellation" search filter. We get that plans can change, so it's easy to filter properties that give you flexibility. If you need to make changes to an existing booking, drop your host a message. Go to "My Trips" in your account, click "Change or Cancel" and then "Message Host". Vrbo rentals give you the privacy of having the entire place to yourself, and for extra flexibility, some travelers can choose to pay over time with Affirm. Whether you're adjusting your plans or looking for flexible payment options, Vrbo makes it easy to book with confidence.
Why should I join Vrbo as a host?
Joining Vrbo as a host opens the door to a global community of travelers seeking unique stays, giving you the opportunity to earn income from your property on your terms. With user-friendly tools, dedicated support, and exposure on major travel sites, Vrbo makes it easy to list, manage, and succeed. Whether it's a cozy cabin or a beach condo, you can turn your space into a standout destination, become a host and let Vrbo handle the heavy lifting to help you thrive.

Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.
Are all fees included in the Highland City vacation rental prices shown on Vrbo?
Vrbo provides upfront pricing from the moment you start your search. There are no hidden fees added during the check-out process. This allows you to compare properties with ease and plan your trip with confidence.
What is VrboCare™ and how does it work?
Vrbo's mission is to help guests relax, reconnect, and enjoy precious time together. With VrboCare™, you can have peace of mind knowing you're protected and that if something goes wrong, we will do our best to make it right as applicable.

If a significant issue arises that your host can't resolve, we'll help you address it, find a similar property, or get your reservation refunded if applicable. That's our promise. If a home is significantly different than listed, we'll get you into a new space that meets your needs and makes it right, or if a host cancels before your stay, you have a dedicated support team to get you into a similar home as applicable.
What can I expect from Vrbo customer service and VrboCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, VrboCare™ is here to support you every step of the way. For urgent situations like last-minute cancellations, booking issues, or potential fraud, Vrbo customer service is available 24/7 to help resolve problems quickly and effectively.

Vrbo also offers support via live chat through our Help Center, where you can find helpful resources on bookings, payments, property management, and safety, making it easy to get instant answers to many common questions.
Can I plan a group trip on Vrbo?
Vrbo's Trip Planner makes organizing group trips easy and stress-free. Whether you're planning with friends or coordinating a large group, you can collaborate in one place, save and share properties, vote on favorites, and build the perfect itinerary together.

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