Discover Your Perfect Highpoint Vacation Homes

Best Vacation Homes in Highpoint

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10.0 (1 Review)
House
Clearwater Cheer
  • Air Conditioner
  • Wheelchair Accessible
  • Balcony/Terrace
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Highpoint Luxury Rentals

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Highpoint Pet Friendly Vacation Rentals

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Highpoint Large Vacation Homes

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Why Choose Rent By Owner for your Highpoint Vacation Rental Homes?

What makes our Vacation Rentals special?

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Verified Listings
Book with confidence knowing every property meets our quality and safety standards.
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Unbeatable Value
Enjoy competitive pricing with no hidden fees, providing exceptional value for every stay.
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Diverse Options
From cozy cabins to luxurious villas, find a rental that suits your style and needs.

Popular Areas for Highpoint Vacation Rentals

Where are the best neighborhoods to stay in Highpoint?

When selecting the perfect neighborhood to stay in Highpoint, Clearwater, Florida, you will find a variety of options that suit different preferences and lifestyles. Whether you prefer a quiet residential area or a lively community close to local amenities, the neighborhoods here provide convenient access to the best of what Clearwater has to offer. Exploring these neighborhoods allows you to experience the relaxed Florida lifestyle while enjoying easy access to nearby attractions and beaches. With a wide selection of vacation rentals in Highpoint, Clearwater, you can find accommodations that fit your needs and ensure a comfortable, memorable stay.

Shady Lane Village

This neighborhood offers a quiet setting within the region, making it ideal for those seeking a relaxed stay close to local amenities. Here, you can enjoy comfortable and convenient vacation rentals that provide easy access to the area's attractions.

View 363+ Rentals in Shady Lane Village

Shady Lane Master Mhp

Set in a welcoming community, this area is perfect for travelers looking for spacious accommodations with a friendly atmosphere. Choose from a variety of vacation rentals that make exploring the region simple and enjoyable.

View 368+ Rentals in Shady Lane Master Mhp

Best Times to Visit Highpoint

When should you plan your Vacation Rentals stay?

Timing your visit to this sunny destination can significantly enhance your experience, so consider planning your stay during the area's peak seasons or shoulder periods to enjoy ideal weather and availability in your vacation rentals here.

Peak Season Highlights

spring
Spring (March to May)

During the spring months, you'll experience warm weather and plenty of sunshine, making it an ideal time to enjoy outdoor activities and relax by the coast in this destination.

Average Temperature Daytime: 75°F to 85°F - Nighttime: 60°F to 70°F
summer
Summer (June to August)

The summer season brings hot temperatures and lively beach scenes, perfect for those seeking vibrant energy and long days along the coast in the area.

Average Temperature Daytime: 85°F to 90°F - Nighttime: 70°F to 75°F

Off-Season Highlights

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Fall (September to November)

As the region transitions into fall, you'll notice cooler temperatures and fewer crowds, providing a peaceful setting for your stay in these vacation rentals.

Average Temperature Daytime: 70°F to 80°F - Nighttime: 55°F to 65°F
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Winter (December to February)

During winter, the weather remains mild and comfortable, offering a quiet atmosphere that is perfect for relaxing escapes away from peak tourist times in this part of Florida.

Average Temperature Daytime: 65°F to 75°F - Nighttime: 50°F to 60°F

Weekly Weather Forecast for Highpoint

How to Book Your Highpoint Vacation Rental Home

What's our booking process?

Our platform allows you to browse a curated selection of vacation rentals. Once you find the ideal property, you’ll be redirected to a trusted booking partner to complete your reservation securely.

Booking Steps

01

Search Properties

Use our filters to find the right property that fits your needs.
02

Select a Rental

Click on your preferred listing to view details, amenities, and pricing.
03

Book Online

Follow the link to finalize your reservation directly on the partner’s website.

Explore and book the perfect rental in Highpoint

More Top-Rated Vacation Rentals in Highpoint Area

Common Vacation Rentals Amenities

What amenities can you expect?

Our Vacation Rentals are designed to offer all the comforts of home, often with added perks to make your stay unforgettable. Here’s some common amenities to look forward to:

Indoor Features

  • Fully-equipped kitchens with modern appliances
  • Comfortable living areas with flat-screen TVs
  • Free Wi-Fi for staying connected
  • Air conditioning and heating for year-round comfort
  • In-unit washers and dryers for convenience
  • Luxurious bedrooms with premium bedding
  • Spa-like bathrooms with soaking tubs or walk-in showers

Outdoor Amenities

  • Enjoy lounging by the private outdoor swimming pool, perfect for relaxing under the sun.
  • Take advantage of outdoor grilling areas or barbecues available on the property.
  • Relax on spacious patios or decks with comfortable outdoor furniture to unwind after a day of exploring.
  • Benefit from well-maintained landscaped gardens and lush green spaces surrounding your rental.
  • Make use of designated outdoor dining spaces for enjoying meals al fresco with family or friends.
  • Engage in outdoor recreational activities such as walking or jogging along scenic pathways nearby.
  • Utilize secure outdoor storage spaces for equipment, bicycles, or beach gear during your stay.

Top Attractions Around Highpoint

What attractions are nearby?

In the area, you can enjoy a variety of water-based activities such as swimming and boating, or explore nearby parks and recreational spots perfect for outdoor relaxation and family fun during your stay.

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Family Activities

  • Clearwater Marine Aquarium: Discover marine life exhibits and interactive experiences that are perfect for engaging the whole family in this family-friendly attraction.
  • The Gulf to Bay Bicycle Trail: Rent bikes and explore scenic views along this popular trail, offering a fun outdoor activity suitable for all ages here in the region.
  • Captain Bligh's Pirate Cruise: Embark on an entertaining pirate-themed boat tour designed to delight children and adults alike in the local waterfront area.
  • Beach Day at Clearwater Beach: Spend leisure hours lounging, swimming, or building sandcastles on one of the most renowned beaches nearby, ideal for family fun and relaxation.
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Adult Activities

  • Beachcombing and Sunbathing: Take advantage of the pristine beaches nearby to relax, soak up the sun, and enjoy the stunning coastal scenery.
  • Fishing Charters: Embark on a guided fishing trip in the region’s waters, offering a memorable experience for anglers seeking local marine life.
  • Golfing at Premier Courses: Play a round at some of the area's top golf courses, perfect for enjoying the warm weather and scenic views.
  • Dining Experiences: Indulge in contemporary or local cuisine at restaurants within walking distance, showcasing the region's fresh seafood and culinary flair.

Other Places to Stay in Highpoint, FL

Shady Lane Village
Shady Lane Village Vacation Rentals
More Places to Stay Near Highpoint

Highpoint Travel Tips

How Can You Make the Most of Your Stay?

  • Plan Ahead: Research the local area to identify must-visit beaches and dining options near your vacation rentals in Clearwater for a well-rounded experience.
  • Explore Local Tips: Seek advice from hosts or previous guests about hidden gems and the best times to enjoy popular attractions here.
  • Utilize Public Transportation: Make the most of local transit options to easily access the region’s scenic spots and avoid parking hassles during your stay.
  • Pack Smart: Bring essentials suited for the area's climate, including sun protection and lightweight clothing, to ensure comfort during your time here.

Transportation Options

  • Car Rentals: Renting a vehicle provides you with the flexibility to explore the region at your own pace, making it easy to reach nearby beaches and attractions from your vacation rental.
  • Public Transit: The area's bus services offer an affordable and reliable way to navigate locally, connecting you conveniently to key destinations around here.
  • Shuttle Services: Shuttle options are available for direct transportation between the airport, popular attractions, and your vacation rentals, ensuring a stress-free arrival and departure experience.
  • Taxis and Rideshare Apps: Taxis and ride-sharing services like Uber and Lyft operate throughout the region, offering quick and convenient transportation right from your doorstep.

Local Customs Options

  • Southern Hospitality: Locals here take pride in their warm and friendly demeanor, welcoming visitors with genuine kindness and a relaxed attitude.
  • Beach Traditions: Enjoy the region's laid-back approach to beach etiquette, where respecting private property and keeping beaches clean are highly valued customs.
  • Local Festivals: Participating in community events, especially those celebrating coastal culture, offers insight into the area's vibrant heritage and friendly spirit.
  • Seafood Appreciation: Embracing local dining customs, you'll find that fresh seafood is a staple and is often enjoyed with a laid-back, communal attitude along this scenic coast.

Frequently Asked Questions About Highpoint?

1. What are the top vacation rentals in Highpoint?

There are a lot of options in Highpoint. If you plan on staying in the Highpoint area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Vacation Rentals in Highpoint:

2. How many vacation rentals have private pools in Highpoint?

There are 83 vacation rentals with private pools near Highpoint. Top-rated RBO homes that have access to a swimming pool include:

3. Which vacation homes in Highpoint are best for families?

If you are looking for a family-friendly vacation home in Highpoint, check out one of the following properties as all are highly-rated places to stay with excellent review for families or groups staying in Highpoint:

4. How many Rentbyowner vacation rentals are available in Highpoint?

Currently, the total number of properties listed by Rent By Owner in 2025 is over 410 in the Highpoint area, and still counting. By aggregating listings from multiple websites, Rent By Owner offers an immense amount of choice of the best RBO properties in Highpoint. 

5. What is the cancellation policy for vacation rentals in this area?

Cancellation policies vary depending on the individual listing. To ensure you understand the specifics, review the cancellation terms outlined in the property’s listing or contact the property owner directly before booking.

6. Are there any additional fees associated with booking a vacation rental here?

Additional fees such as cleaning fees, service charges, or security deposits are listed in the property details. Be sure to check the listing for a complete breakdown of all costs prior to confirming your reservation.

7. How do I know if the vacation rental has the amenities I need?

Each property listing includes a detailed list of available amenities. If you have specific requirements, it's best to review these details carefully or reach out to the host for confirmation before booking.

8. Is there a minimum stay requirement for vacation rentals in this region?

Minimum stay requirements can differ between properties. These details are specified in each listing, so consult the property description or contact the owner for clarification.

9. What should I do if I encounter issues during my stay?

In case of any problems during your stay, contact the property owner or support team listed on the booking page. They are available to assist and ensure your experience is seamless.

Highpoint Top Rated Vacation Rentals

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