Best Vacation Homes in Highland Hills
House
10.0(22 Reviews)
2 Bedrooms
2 Baths
6 Guests
1593 ft²
Parking
Balcony/Terrace
Kitchen
Air Conditioner
US $327/Night
7 Nights - US $2,289
House
10.0(2 Reviews)
1 Bedroom
2 Baths
8 Guests
1184.03 ft²
- Parking
View- Air Conditioner
Internet
US $533/Night
7 Nights - US $3,729
Cottage
8.0(2 Reviews)
1 Bedroom
1 Bath
- Parking
Ocean View- Balcony/Terrace
- View
US $351/Night
7 Nights - US $2,460
Apartment
10.0(13 Reviews)
2 Bedrooms
1 Bath
4 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $75/Night
7 Nights - US $527
Apartment
10.0(2 Reviews)
2 Bedrooms
1 Bath
4 Guests
1097.92 ft²
- Parking
- Air Conditioner
- Internet
Pet Friendly
US $180/Night
7 Nights - US $1,260
Apartment
10.0(3 Reviews)
2 Bedrooms
1 Bath
4 Guests
1200 ft²
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $104/Night
7 Nights - US $731
Apartment
10.0(3 Reviews)
2 Bedrooms
1 Bath
4 Guests
- Parking
- Kitchen
- Air Conditioner
- Internet
US $91/Night
7 Nights - US $638
Apartment
10.0(1 Review)
1 Bedroom
1 Bath
4 Guests
4844 ft²
- Kitchen
- Air Conditioner
- Internet
- Pet Friendly
US $111/Night
7 Nights - US $778
Highland Hills Luxury Rentals
House
10.0(2 Reviews)
4 Bedrooms
3 Baths
10 Guests
1615 ft²
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $1,145/Night
7 Nights - US $8,012
House
5 Bedrooms
6 Baths
16 Guests
- Parking
- Kitchen
- Air Conditioner
- Internet
US $971/Night
7 Nights - US $6,797
House
9.4(9 Reviews)
4 Bedrooms
2 Baths
8 Guests
3127 ft²
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $683/Night
7 Nights - US $4,778
House
1 Bedroom
4 Baths
10 Guests
1614.59 ft²
- Parking
- View
- Air Conditioner
- Internet
US $540/Night
7 Nights - US $3,780
House
9.8(12 Reviews)
3 Bedrooms
2 Baths
8 Guests
1189 ft²
- Parking
Spa- Balcony/Terrace
- Kitchen
US $461/Night
7 Nights - US $3,228
House
9.0(4 Reviews)
5 Bedrooms
2 Baths
10 Guests
- Parking
- Kitchen
- Air Conditioner
- Internet
US $436/Night
7 Nights - US $3,049
House
9.4(12 Reviews)
5 Bedrooms
3 Baths
12 Guests
3197 ft²
- Parking
- Kitchen
- Air Conditioner
- Internet
US $416/Night
7 Nights - US $2,911
House
9.3(3 Reviews)
4 Bedrooms
3 Baths
5 Guests
2002.09 ft²
Oceanfront- Parking
- Ocean View
- Balcony/Terrace
US $390/Night
7 Nights - US $2,732
Highland Hills Pet Friendly Vacation Rentals
Apartment
9.0(4 Reviews)
2 Bedrooms
1 Bath
6 Guests
7513 ft²
- Kitchen
- Air Conditioner
- Internet
- Pet Friendly
US $121/Night
7 Nights - US $849
Apartment
8.0(1 Review)
1 Bedroom
1 Bath
4 Guests
- Air Conditioner
- Internet
- Pet Friendly
Child Friendly
US $168/Night
7 Nights - US $1,176
Apartment
8.0(2 Reviews)
1 Bedroom
1 Bath
4 Guests
6458 ft²
- Kitchen
- Air Conditioner
- Internet
- Pet Friendly
US $114/Night
7 Nights - US $795
House
5.0(1 Review)
1 Bedroom
2 Baths
2 Guests
355.21 ft²
- View
- Air Conditioner
- Internet
- Pet Friendly
US $55/Night
7 Nights - US $387
Apartment
8.0(2 Reviews)
2 Bedrooms
1 Bath
4 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $83/Night
7 Nights - US $578
Apartment
6.0(2 Reviews)
2 Bedrooms
1 Bath
4 Guests
1100 ft²
- Parking
- Kitchen
- Air Conditioner
- Internet
US $117/Night
7 Nights - US $817
Apartment
6.0(1 Review)
1 Bedroom
1 Bath
4 Guests
- Kitchen
- Air Conditioner
- Internet
- Pet Friendly
US $111/Night
7 Nights - US $778
House
2 Bedrooms
1 Bath
4 Guests
538 ft²
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $182/Night
7 Nights - US $1,271
Highland Hills Large Vacation Homes
House
10.0(1 Review)
3 Bedrooms
1 Bath
11 Guests
1324 ft²
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $172/Night
7 Nights - US $1,204
House
4 Bedrooms
4 Baths
12 Guests
3078.48 ft²
- Parking
- Balcony/Terrace
- View
- Air Conditioner
US $351/Night
7 Nights - US $2,460
House
5 Bedrooms
1 Bath
10 Guests
- Parking
- Kitchen
- Air Conditioner
- Internet
US $208/Night
7 Nights - US $1,459
Villa
5 Bedrooms
2 Baths
10 Guests
2690.98 ft²
- Parking
- Balcony/Terrace
- Air Conditioner
- Internet
US $312/Night
7 Nights - US $2,181
House
9.6(4 Reviews)
4 Bedrooms
2 Baths
10 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $173/Night
7 Nights - US $1,213
House
7.6(5 Reviews)
4 Bedrooms
3 Baths
12 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $380/Night
7 Nights - US $2,660
House
4 Bedrooms
3 Baths
10 Guests
3500 ft²
- Parking
- Kitchen
- Air Conditioner
- Internet
US $220/Night
7 Nights - US $1,542
House
4.4(8 Reviews)
4 Bedrooms
4 Baths
12 Guests
- Kitchen
- Air Conditioner
- Internet
- Child Friendly
US $223/Night
7 Nights - US $1,561
Why Choose Rent By Owner for your Highland Hills Vacation Rental Homes?
What makes our Vacation Rentals special?
Verified Listings
Book with confidence knowing every property meets our quality and safety standards.
Unbeatable Value
Enjoy competitive pricing with no hidden fees, providing exceptional value for every stay.
Diverse Options
From cozy cabins to luxurious villas, find a rental that suits your style and needs.
Best Times to Visit Highland Hills
When should you plan your Vacation Rentals stay?
Choosing the ideal time to vacation in this destination can enhance your experience, as the region offers different attractions and weather conditions throughout the year for a memorable stay.
Peak Season Highlights
Summer (June to August)
During the summer months, this destination experiences warm weather, making it an ideal time for outdoor activities and exploring the area’s natural beauty.
Average Temperature Daytime: Upper 70s to mid-80s Fahrenheit - Nighttime: Mid to high 60s Fahrenheit
Fall (September to November)
Autumn brings mild temperatures and vibrant foliage, creating a picturesque setting that enhances your stay here during the peak season.
Average Temperature Daytime: High 60s to low 70s Fahrenheit - Nighttime: Low 50s to high 50s Fahrenheit
Off-Season Highlights
Winter (December to February)
The winter months feature cooler temperatures and occasional snow, offering a quieter experience for those seeking tranquility and cozy accommodations.
Average Temperature Daytime: High 30s to mid-40s Fahrenheit - Nighttime: Mid 20s to low 30s Fahrenheit
Spring (March to May)
In early spring, the area begins to warm up, but it remains relatively quiet before the busy summer season arrives. The parks and trails come alive with blooming flora.
Average Temperature Daytime: Mid 50s to mid-60s Fahrenheit - Nighttime: Low 40s to high 40s Fahrenheit
Weekly Weather Forecast for Highland Hills
How to Book Your Highland Hills 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 Highland Hills
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 a private outdoor patio or balcony for relaxing and dining amidst the fresh air.
- Take advantage of well-maintained gardens or landscaped yards that add charm to your stay.
- Benefit from access to outdoor swimming pools during warmer months, perfect for cooling off.
- Make use of spacious decks equipped with outdoor seating for entertaining friends or family.
- Explore nearby walking or biking trails that showcase the natural beauty of this area.
- Utilize outdoor grilling stations for preparing delicious meals in the open air.
- Relax in cozy fire pits or outdoor fireplaces, ideal for evening gatherings under the stars.
Top Attractions Around Highland Hills
What attractions are nearby?
In this vibrant region, you can enjoy a variety of activities such as exploring local parks, dining at nearby restaurants, and experiencing cultural attractions—all conveniently accessible from your Highland Hills, Ohio, USA vacation rental.
Family Activities
- Highland Hills Community Park: Enjoy a family picnic or outdoor games at this inviting park in the region, perfect for relaxing days with children.
- Cleveland Hopkins Zoo: Spend a fun-filled day discovering over 1,500 animals, making it an ideal outing for families staying near Highland Hills.
- Southpark Mall: Explore local shopping and entertainment options here, providing a convenient spot for family outings and dining experiences.
- Shaker Square Historic District: Take a stroll through this charming area known for its unique shops, eateries, and cultural heritage, great for exploring with loved ones.
Adult Activities
- Golfing at Highland Hills Golf Course: Enjoy a relaxing round of golf at this scenic course nestled in the area, perfect for outdoor enthusiasts looking to unwind amidst lush surroundings.
- Cultural exploration at the Cleveland Museum of Art: Spend your day immersing yourself in impressive art collections and exhibitions, conveniently located just a short drive from here in the nearby city.
- Shopping at local retail centers: Discover unique boutiques and retail stores in the region, ideal for those wanting to indulge in some retail therapy during their stay.
- Dining experiences in the area: Savor diverse culinary options at local restaurants that showcase the region’s rich flavors and welcoming atmosphere, making dining an enjoyable part of your visit.
Highland Hills Travel Tips
How Can You Make the Most of Your Stay?
- Explore Local Cuisine: Take time to enjoy the region’s culinary scene by visiting nearby restaurants and cafes to experience authentic flavors unique to here.
- Utilize Nearby Nature Spots: Maximize your stay by exploring local parks and green spaces that offer relaxing outdoor activities in the area.
- Plan Your Transportation: Consider renting a vehicle or checking public transit options to easily access all the attractions and amenities within this destination.
- Connect with Local Events: Stay informed about community events or festivals happening during your visit to immerse yourself in the area's vibrant culture.
Transportation Options
- Private Car Rentals: You can opt for car rentals in the area to enjoy flexible transportation around Highland Hills and explore nearby attractions at your own pace.
- Public Transit Services: The local bus services provide an affordable way to move throughout the region, connecting you conveniently to key destinations.
- Rideshare Options: Ridesharing apps operate here, offering quick and reliable transportation for trips within the city and surrounding neighborhoods.
- Bicycle Rentals: Biking is a popular eco-friendly mode of travel in the area, allowing you to enjoy scenic routes while reaching nearby points of interest.
Local Customs Options
- Local Festivals: Celebrating community spirit, the area hosts annual festivals that showcase regional music, crafts, and cuisine, giving you an authentic taste of the local culture.
- Traditional Cuisine: The region’s culinary customs emphasize hearty, comfort foods and locally sourced ingredients, offering a genuine dining experience during your stay.
- Community Events: Participating in neighborhood gatherings and markets provides insight into the area's friendly customs and social traditions that residents cherish.
- Historic Respect: Local residents uphold a deep respect for their history, often sharing stories and preserving sites that highlight the region’s cultural heritage.
Highland Hills Vacation Rental Frequently Asked Questions
1. What are the top vacation rentals in Highland Hills?
There are a lot of options in Highland Hills. If you plan on staying in the Highland Hills area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Vacation Rentals in Highland Hills:
- Modern Farmhouse Near Chagrin Falls Beachwoood Cuyahoga Valley National Park
- Historic District 2BR on 1st Floor near Cleveland Clinic ~ Family Friendly ~Safe
- Modern & Comfy ~ Close to Cleveland Clinic ~ Long-Stays Welcome ~ Safe Area
- Spacious 2 bed room apartment near Shaker, Cleveland clinic, CWRU, Van aken.
- Luxury|Pool Table|Movie Room|Poker|Nature Oasis
- Luxurious Retreat with Sauna and Modern Design
- Shaker Prestige - 4,000 sq ft - Calm and Quiet
- Near CLE Clinic - Long term stays accepted
- Family-Friendly 3BR with Sunroom & Outdoor Area
- Maple Heights - Libby Unit 1
2. How many vacation rentals have private pools in Highland Hills?
There are 3 vacation rentals with private pools near Highland Hills. Top-rated RBO homes that have access to a swimming pool include:
3. Which vacation homes in Highland Hills are best for families?
If you are looking for a family-friendly vacation home in Highland Hills, check out one of the following properties as all are highly-rated places to stay with excellent review for families or groups staying in Highland Hills:
4. How many Rentbyowner vacation rentals are available in Highland Hills?
Currently, the total number of properties listed by Rent By Owner in 2026 is over 176 in the Highland Hills 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 Highland Hills.
5. What is the cancellation policy for vacation rentals in this area?
Cancellation policies vary depending on the property you choose. It’s best to review the specific listing details or contact the property owner directly to understand their terms and any applicable fees.
6. How do I confirm my booking for a vacation rental in Highland Hills?
Once you select your preferred property, you'll typically complete the reservation through the platform's secure system. Confirmations are usually sent via email shortly after booking, but contacting the host can provide additional assurance.
7. Are there any minimum stay requirements for vacation rentals in this region?
Minimum stay requirements depend on the individual property. Please check the listing details or reach out to the owner to confirm if there are any restrictions during your intended dates.
8. What amenities should I expect in vacation rentals here?
Amenities vary by property, but common features include Wi-Fi, fully equipped kitchens, and parking. For specific amenities, always review the listing description or contact the host directly before booking.
9. Is there a secure process for paying for my vacation rental in Highland Hills?
Yes, most listings offer secure payment options through the booking platform. Always ensure you complete transactions on the official site or app to protect your financial information.
Highland Hills Top Rated Vacation Rentals
Hotel
9.4(1015 Reviews)
1 Bath
Hot Tub
Breakfast- Parking
Pool
US $170/Night
7 Nights - US $1,193
Hotel
9.0(1007 Reviews)
1 Bath
- Hot Tub
- Breakfast
- Parking
- Pool
US $161/Night
7 Nights - US $1,127
US $189/Night
7 Nights - US $1,321
Hotel
9.0(1000 Reviews)
1 Bath
- Hot Tub
- Breakfast
- Parking
- Pool
US $192/Night
7 Nights - US $1,343
Hotel
9.0(702 Reviews)
20 Baths
335.29 ft²
- Hot Tub
- Parking
- Pool
- Kitchen
US $196/Night
7 Nights - US $1,372
Hotel
9.0(269 Reviews)
2 Baths
379.81 ft²
Private Pool- Oceanfront
- Hot Tub
- Breakfast
US $150/Night
7 Nights - US $1,047
Hotel
8.8(106 Reviews)
17 Baths
331.78 ft²
- Private Pool
- Parking
- Pool
- Air Conditioner
US $199/Night
7 Nights - US $1,390
Hotel
8.7(212 Reviews)
1 Bath
10.76 ft²
- Private Pool
- Parking
- Pool
- Balcony/Terrace
US $141/Night
7 Nights - US $986
