Highland Park vacation rentals

We found 90 vacation rentals — enter your dates for availability

Discover a selection of vacation rentals in Highland Park that are perfect for your trip. Whether you're staying in a vacation rental with friends, family, or even just your pets, you'll find the amenities you need and want, which might include air conditioning and a pool. You'll be able to choose a rental to meet everyone's needs, including options that are accessible or non-smoking.

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Find out more about Highland Park

Why visit Highland Park

  • Scenic Outdoor Activities: Enjoy a variety of outdoor adventures at beautiful lakes and urban parks, perfect for nature lovers.
  • Family-Friendly Attractions: Explore local parks and activities that cater to families, ensuring fun for all ages.
  • Charming Neighborhoods: Discover vibrant local neighborhoods with friendly faces and budget-friendly excursions.
  • Diverse Vacation Rentals: Choose from a range of accommodations, including cozy apartments, spacious homes, and villas.
  • Relaxing Beach Days: Spend sunny days at nearby beaches, soaking in the warm weather and stunning scenery.

Popular types of accommodation in Highland Park

If you’re looking for the perfect getaway in Highland Park, you’re in luck. Our most popular types of vacation rentals include houses, villas, and condos. Whether you’re seeking spacious house rentals or cozy Highland Park apartments, we have a variety of affordable rentals to suit your needs. Enjoy transparency and reassurance as you plan your stay in this charming destination.

  • Houses: The top choice for travelers in Highland Park, offering spacious accommodations ideal for families or groups seeking comfort and privacy.
  • Villas: A luxurious option, villas provide upscale amenities and beautiful settings, perfect for a relaxing getaway.
  • Condos: Popular among visitors, condos offer a blend of convenience and home-like comfort, often with shared facilities.
  • Apartments: A practical option for shorter stays, apartments provide essential living spaces in various neighborhoods.
  • Cottages: Quaint and charming, cottages offer a cozy atmosphere, ideal for a peaceful retreat in nature.**

Top attractions near Highland Park

Highland Park, Florida, is a fantastic destination for outdoor enthusiasts and families seeking scenic experiences. Visitors can explore beautiful lakes, urban parks, and historic towers, making it an ideal spot for those who love nature and leisurely activities. Whether you're enjoying a day at the beach or taking in the local scenery, Highland Park offers a variety of attractions that cater to all types of travelers looking for a memorable vacation.

  • Bok Tower Gardens: A stunning historic landmark featuring beautiful gardens, a serene atmosphere, and the impressive Singing Tower that offers cultural and musical experiences in a picturesque setting.
  • Crooked Lake: A scenic lake perfect for outdoor activities, relaxation, and romantic picnics, complete with a lovely beach area and tranquil views that invite you to unwind.
  • Grand Hotel: A charming monument that showcases local culture and history, offering a glimpse into the past with its elegant architecture and inviting ambiance.

Things to do recommended for couples

Planning a romantic getaway in Highland Park? Experience the thrill of skydiving at Jump Florida, just 7 miles away, or enjoy water sports at Chain Of Wakes, located 11 miles from town. Both promise adventure and unforgettable memories for couples seeking excitement.

Things to do recommended for families

In Highland Park, families can enjoy the sports atmosphere at Chain of Lakes Park, have fun at Indigo's Billiards, Bowling & Games, or unwind in the serene environment of Sertoma Park, each offering unique experiences just a short drive away.

Things to do recommended for groups

Explore the Eagle Ridge Mall for shopping and entertainment, enjoy a cultural night at Theatre Winter Haven, or hit the links at Baytree Golf Club for some outdoor fun. These activities offer a perfect mix of relaxation and excitement for your group getaway in Highland Park.

*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 Park

If you're traveling with a group, your family, or pets, or if you're considering extended stays, be sure to prioritize your filters accordingly. Here are some helpful tips for booking on Vrbo.

  • Traveling to Highland Park with a group: Think about how many bedrooms you require, along with features like a full kitchen or outdoor space for group gatherings. Thankfully, you can easily filter for these options and many others on Vrbo.
  • Traveling to Highland Park with young kids: Traveling with young kids can be tough. It's important to prioritize their comfort and safety, along with finding suitable amenities, like a private pool. Additionally, it's wise to think about how close you are to family-friendly attractions.
  • Taking your pets with you to Highland Park: For many families, a trip isn’t truly fulfilling without their furry companion by their side. If that resonates with you, explore Vrbo listings that welcome pets. Most pet-friendly properties come equipped with feeding bowls and cozy beds, ensuring that every member of your family feels comfortable and at home.
  • Planning for a long term stay visiting Highland Park: If you're in search of vacation rentals that offer 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 criteria as well.

Where to stay in Highland Park

Highland Park, Florida, offers a delightful blend of outdoor adventures and family-friendly activities. This charming village is perfect for those seeking sunny weather and a welcoming atmosphere. Explore nearby parks ideal for family outings, or discover the vibrant local neighborhoods that showcase friendly faces and budget-friendly excursions. Whether you're looking for a cozy vacation home or an exciting vacation spot, Highland Park promises an unforgettable experience for all ages.

  • Lake Wales: Lake Wales is a charming city located in the heart of Central Florida, where Highland Park is nestled. Known for its stunning outdoor scenery, this vibrant city offers a plethora of family-friendly activities. Outdoor enthusiasts can explore various recreational areas and enjoy the beauty of local lakes. Nearby attractions include the famous theme park and the picturesque Lake Wales Ridge State Forest, perfect for hiking and nature walks. With its rich history and beautiful landscapes, Lake Wales is a delightful destination for travelers seeking adventure and relaxation.
  • Crooked Lake Park: Just 3 miles away from Highland Park, Crooked Lake Park is a quaint village that offers a serene and romantic getaway. This picturesque locale is surrounded by lush greenery and tranquil lakes, making it ideal for outdoor activities like picnicking and bird-watching. Visitors can enjoy the local urban park or venture to nearby amusement parks for thrilling rides and entertainment. The scenic views and peaceful ambiance make Crooked Lake Park a fantastic spot for couples and families alike to unwind and connect with nature.
  • Babson Park: Located a mere 3 miles from Highland Park, Babson Park is a charming city known for its stunning outdoor scenery and romantic atmosphere. Travelers flock to this area for its beautiful lakes and recreational activities, including access to local resorts and amusement parks. The nearby theme parks provide exciting entertainment options, while the area's beaches offer relaxation by the water. Babson Park's inviting environment makes it a perfect destination for those looking to explore Florida's natural beauty and enjoy quality time with loved ones.

Best time to go to Highland Park

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

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
January61.2°F (16.2°C)Light RainMostly SunnySlightly LowSlightly Low
February64.9°F (18.3°C)No Rain (Dry)Mostly SunnySlightly LowSlightly Low
March68.0°F (20.0°C)Light RainMostly SunnySlightly HighAverage
April73.2°F (22.9°C)Light RainMostly SunnyAverageAverage
May77.4°F (25.2°C)Light RainMostly SunnyAverageAverage
June80.8°F (27.1°C)Moderate RainMostly SunnyAverageAverage
July81.9°F (27.7°C)Moderate RainMostly SunnyAverageSlightly High
August81.9°F (27.7°C)Moderate RainMostly SunnySlightly LowAverage
September79.7°F (26.5°C)Moderate RainMostly SunnyAverageSlightly Low
October74.8°F (23.8°C)Light RainMostly SunnyAverageAverage
November68.5°F (20.3°C)No Rain (Dry)Mostly SunnySlightly HighSlightly High
December64.6°F (18.1°C)No Rain (Dry)Mostly SunnySlightly HighSlightly High

Booking with Vrbo is a breeze

Are you hoping to cut costs on your upcoming journey? Being flexible with your travel dates can lead to better deals, as prices often fluctuate. Additionally, booking a longer stay can yield substantial savings. To discover a Vrbo property that aligns with your budget, utilize our filters to sort by price, location, and type of vacation rental. We're here to help you make the most of your travel experience.

Save more with One Key

When you reserve a qualifying Vrbo for your group getaway, you'll receive OneKeyCash on the full booking amount. Being the organizer truly has its benefits. Sign up for our One Key rewards program to enjoy exclusive savings available only to members and accumulate OneKeyCash on eligible stays. Register today and begin reaping the rewards.

Vrbo Trips: Planning as easy as it gets

Vrbo’s Trip Board provides a convenient way to plan new trips, manage your ongoing travel arrangements, or review and organize your reservations. Your saved or booked properties are now neatly categorized into Potential, Upcoming, or Current Trips. To check out your Trip Boards, simply visit: https://www.vrbo.com/trips.

**Based on Vrbo properties bookings.

Book a vacation rental for your Highland Park getaway

Experience the unique character of Highland Park with a stay in a vacation home rental. One of the city's many top draws is its restaurants. Many rental homes come with outdoor spaces, separate dining areas and full kitchens, perfect if you want to enjoy some home-cooked meals.

Activities and attractions in Highland Park

Are you searching for things to do in the area? Venture out of your vacation home and check out everything that makes Highland Park a fun spot to vacation. These are some of the top attractions to put on your list, all within 30 miles (48.2 km) of the city center:

  • LEGOLAND® Florida (11.9 mi / 19.1 km)
  • Mountain Lake (5.2 mi / 8.4 km)
  • Peppa Pig Theme Park Florida (11.5 mi / 18.5 km)
  • Lake Region Golf Club (13.2 mi / 21.3 km)
  • Camp Mack's River Resort Airboat Rides (13.7 mi / 22.1 km)
  • Chain Of Wakes (11 mi / 17.7 km)

Exploring the natural features in Highland Park

Whether you're looking for fun outdoor activities or just want to appreciate the scenery, Highland Park is a great place to get outside. Here are a few of the area's most enchanting sights, all within 30 miles (48.2 km) of the city center:

  • Crooked Lake (3.3 mi / 5.3 km)
  • Bok Tower Gardens (5.1 mi / 8.2 km)
  • Twin Lakes (7.1 mi / 11.4 km)
  • Snodgrass Island (10.2 mi / 16.4 km)
  • Lake Kissimmee State Park (12.9 mi / 20.8 km)
  • Lake Hatchineha (13.7 mi / 22.1 km)

Transportation options to and around Highland Park

Fly into Avon Park, FL (AVO-Avon Park Executive), the closest airport, located 18.8 mi (30.2 km) from the city center. If you're unable to find a flight that fits your schedule, you could book a flight to Lakeland Intl. Airport (LAL), which is 29 mi (46.7 km) away.

Frequently asked questions

What is the best area to stay in Highland Park, Florida, United States of America when booking a vacation rental?
When considering a vacation rental in Highland Park, Florida, a popular area to stay is near the charming downtown district. This area is vibrant and offers a variety of properties, from cozy cottages to modern condos, providing numerous options for visitors. Staying here puts you within walking distance of delightful local shops, cafes, and restaurants, making it easy to enjoy the local flavor.

Another appealing neighborhood is close to the scenic waterfront. This area features beautiful views and easy access to outdoor activities. The nearby parks and nature trails are great for those who enjoy spending time outdoors, and the proximity to the waterfront provides opportunities for fishing, kayaking, or simply relaxing by the water. The local farmers' market is also a must-visit, showcasing fresh produce and handmade goods, offering a taste of the community's vibrant culture.
How much does it cost to rent a vacation home in Highland Park?
Prices for vacation rentals in Highland Park 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 Park 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 Park vacation house rentals?
You can find great discounts on house rentals in Highland Park 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 Park?
A long-stay vacation rental in Highland Park 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 Park vacation rentals with parking?
Vrbo offers a wide selection of vacation rentals in Highland Park 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 Park for a vacation rental?
The best time to book a vacation rental in Highland Park is during the peak season from October to December, with December being particularly popular among travelers. This vibrant time of year attracts visitors seeking warm weather and festive cheer, making it an ideal choice for those looking to enjoy outdoor activities and local events.

During these months, you can expect pleasant temperatures ranging from the mid-50s to the low 80s Fahrenheit, providing a comfortable climate for exploring the area's parks, waterfronts, and nearby attractions. With the holiday season in full swing, this is also an excellent time to enjoy seasonal festivities, enhancing your overall experience.

If you're looking to save some money while still enjoying the area's charm, consider visiting in February. Although it's part of the low season, this month offers a quieter atmosphere, allowing you to explore Highland Park's natural beauty and local attractions more leisurely. The milder temperatures and less crowded spaces can make for a refreshing getaway, ideal for those who appreciate a slower pace.
How early should I book a Highland Park vacation rental?
Book your Highland Park 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 Park, Florida, United States of America?
In Highland Park, Florida, visitors can enjoy a variety of attractions that showcase the area's natural beauty and local culture. The scenic Lake Highland Park is a focal point, offering walking trails, picnic areas, and opportunities for water activities, making it ideal for outdoor enthusiasts. Nearby, the Highland Park Village provides a charming shopping experience with boutique stores and dining options in a picturesque setting.

For those interested in local history and art, the nearby city of Orlando features attractions such as the Orlando Museum of Art and the historic district of Winter Park, which is known for its beautiful lakes and parks. Families can also explore the Central Florida Zoo & Botanical Gardens, located a short drive away, which offers a fun day out with various animal exhibits and lush surroundings.
Can I change or cancel my Highland Park home rental booking on Vrbo?
To find Highland Park 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 Park 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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