Discover Your Perfect Pine Hills Vacation Homes

Best Vacation Homes in Pine Hills

Apartment
Map-icon
like-icon8.6
Fabulous
(10 Reviews)
1 Bedroom 1 Bath 4 Guests
  • Pool
    Pool
  • Ocean View
    Ocean View
More amenities
US $89/Night 7 Nights - US $626
Apartment
Map-icon
like-icon9.7
Exceptional
(3 Reviews)
1 Bedroom 1 Bath 2 Guests
  • Balcony/Terrace
    Balcony/Terrace
  • Parking
    Parking
More amenities
US $73/Night 7 Nights - US $510
US $56/Night 7 Nights - US $392
Apartment
Map-icon
2 Bedrooms 1 Bath 4 Guests
  • Air Conditioner
    Air Conditioner
  • Internet
    Internet
More amenities
US $223/Night 7 Nights - US $1,559
House
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like-icon8.8
Fabulous
(22 Reviews)
5 Bedrooms 5 Baths 10 Guests 55.97 ft²
  • Parking
    Parking
  • Air Conditioner
    Air Conditioner
More amenities
US $62/Night 7 Nights - US $434
Apartment
Map-icon
1 Bedroom 1 Bath 4 Guests 750 ft²
  • Kitchen
    Kitchen
  • Air Conditioner
    Air Conditioner
More amenities
US $119/Night 7 Nights - US $835
House
Map-icon
1 Bedroom 1 Bath 4 Guests 868 ft²
  • Fireplace/Heating
    Fireplace/Heating
  • Balcony/Terrace
    Balcony/Terrace
More amenities
US $92/Night 7 Nights - US $642
House
Map-icon
like-icon10.0
Exceptional
(2 Reviews)
4 Bedrooms 2 Baths 8 Guests
  • Fireplace/Heating
    Fireplace/Heating
  • Kitchen
    Kitchen
More amenities
US $235/Night 7 Nights - US $1,642

Pine Hills Luxury Rentals

House
Map-icon
like-icon9.0
Exceptional
(2 Reviews)
4 Bedrooms 2 Baths 11 Guests
  • Oceanfront
    Oceanfront
  • Fireplace/Heating
    Fireplace/Heating
More amenities
US $411/Night 7 Nights - US $2,880
House
Map-icon
like-icon10.0
Exceptional
(1 Review)
3 Bedrooms 2 Baths 6 Guests
  • Fireplace/Heating
    Fireplace/Heating
  • Balcony/Terrace
    Balcony/Terrace
More amenities
US $405/Night 7 Nights - US $2,835
House
Map-icon
like-icon5.5
Average
(2 Reviews)
4 Bedrooms 2 Baths 16 Guests 1905.21 ft²
  • Pool
    Pool
  • Balcony/Terrace
    Balcony/Terrace
More amenities
US $338/Night 7 Nights - US $2,366
House
Map-icon
like-icon9.2
Exceptional
(15 Reviews)
6 Bedrooms 3 Baths 14 Guests 2425 ft²
  • Fireplace/Heating
    Fireplace/Heating
  • Balcony/Terrace
    Balcony/Terrace
More amenities
US $332/Night 7 Nights - US $2,327
House
Map-icon
like-icon8.6
Fabulous
(4 Reviews)
4 Bedrooms 2 Baths 7 Guests
  • Fireplace/Heating
    Fireplace/Heating
  • Balcony/Terrace
    Balcony/Terrace
More amenities
US $323/Night 7 Nights - US $2,264
House
Map-icon
like-icon2.0
Average
(1 Review)
3 Bedrooms 1 Bath 8 Guests
  • Child Friendly
    Child Friendly
US $318/Night 7 Nights - US $2,228
House
Map-icon
like-icon10.0
Exceptional
(1 Review)
3 Bedrooms 2 Baths 6 Guests
  • Fireplace/Heating
    Fireplace/Heating
  • Balcony/Terrace
    Balcony/Terrace
More amenities
US $288/Night 7 Nights - US $2,016
House
Map-icon
like-icon2.0
Average
(1 Review)
4 Bedrooms 2 Baths 8 Guests
  • Fireplace/Heating
    Fireplace/Heating
  • Kitchen
    Kitchen
More amenities
US $285/Night 7 Nights - US $1,997

Pine Hills Pet Friendly Vacation Rentals

House
Map-icon
like-icon9.6
Exceptional
(7 Reviews)
3 Bedrooms 2 Baths 7 Guests
  • Fireplace/Heating
    Fireplace/Heating
  • Pool
    Pool
More amenities
US $236/Night 7 Nights - US $1,652
star-icons-5
House
Map-icon
like-icon6.7
Good
(12 Reviews)
3 Bedrooms 1 Bath 8 Guests 904.17 ft²
  • View
    View
  • Pet Friendly
    Pet Friendly
More amenities
US $216/Night 7 Nights - US $1,514
House
Map-icon
like-icon8.6
Fabulous
(4 Reviews)
3 Bedrooms 2 Baths 9 Guests
  • Fireplace/Heating
    Fireplace/Heating
  • Pet Friendly
    Pet Friendly
More amenities
US $215/Night 7 Nights - US $1,504
star-icons-3
House
Map-icon
3 Bedrooms 2 Baths 8 Guests 1496.18 ft²
  • Pet Friendly
    Pet Friendly
  • Air Conditioner
    Air Conditioner
More amenities
US $269/Night 7 Nights - US $1,881
House
Map-icon
4 Bedrooms 2 Baths 8 Guests 1069 ft²
  • Fireplace/Heating
    Fireplace/Heating
  • Balcony/Terrace
    Balcony/Terrace
More amenities
US $163/Night 7 Nights - US $1,141
House
Map-icon
3 Bedrooms 2 Baths 8 Guests
  • Fireplace/Heating
    Fireplace/Heating
  • Pool
    Pool
More amenities
US $312/Night 7 Nights - US $2,181
House
Map-icon
4 Bedrooms 2 Baths 8 Guests
  • Pet Friendly
    Pet Friendly
  • Air Conditioner
    Air Conditioner
More amenities
US $220/Night 7 Nights - US $1,540

Pine Hills Large Vacation Homes

House
Map-icon
like-icon10.0
Exceptional
(2 Reviews)
3 Bedrooms 2 Baths 11 Guests
  • Balcony/Terrace
    Balcony/Terrace
  • Kitchen
    Kitchen
More amenities
US $189/Night 7 Nights - US $1,323
House
Map-icon
like-icon5.3
Average
(3 Reviews)
1 Bedroom 2 Baths 10 Guests 107.64 ft²
  • Fireplace/Heating
    Fireplace/Heating
  • Balcony/Terrace
    Balcony/Terrace
More amenities
US $235/Night 7 Nights - US $1,644
House
Map-icon
like-icon1.0
Average
(1 Review)
5 Bedrooms 2 Baths 10 Guests 2018 ft²
  • Private Pool
    Private Pool
  • Pool
    Pool
More amenities
US $159/Night 7 Nights - US $1,113
House
Map-icon
like-icon10.0
Exceptional
(1 Review)
4 Bedrooms 2 Baths 12 Guests
  • Private Pool
    Private Pool
  • Hot Tub
    Hot Tub
More amenities
US $290/Night 7 Nights - US $2,030
House
Map-icon
3 Bedrooms 2 Baths 10 Guests
  • Fireplace/Heating
    Fireplace/Heating
  • Air Conditioner
    Air Conditioner
More amenities
US $358/Night 7 Nights - US $2,506
Villa
Map-icon
like-icon3.0
Average
(2 Reviews)
5 Bedrooms 3 Baths 17 Guests 2430 ft²
  • Private Pool
    Private Pool
  • Oceanfront
    Oceanfront
More amenities
US $275/Night 7 Nights - US $1,925
House
Map-icon
4 Bedrooms 2 Baths 10 Guests
  • Air Conditioner
    Air Conditioner
  • Child Friendly
    Child Friendly
More amenities
US $200/Night 7 Nights - US $1,400

Why Choose Rent By Owner for your Pine Hills 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.

Best Times to Visit Pine Hills

When should you plan your Vacation Rentals stay?

To make the most of your stay, consider visiting during the shoulder seasons when the area offers pleasant weather and fewer crowds, ensuring an enjoyable vacation experience in this vibrant destination.

Peak Season Highlights

winter
Winter (December to February)

During the winter months, this destination experiences its peak season as visitors seek warm escapes and holiday festivities in Orlando. The pleasant daytime temperatures make it ideal for exploring your vacation rentals and enjoying outdoor activities.

Average Temperature Daytime: 70-75°F - Nighttime: 50-55°F
spring
Spring Break (March to April)

Spring break attracts travelers to the area looking for a lively atmosphere and comfortable weather. It's a popular time to book vacation rentals, especially for those wanting to enjoy the region's natural beauty and local events.

Average Temperature Daytime: 75-80°F - Nighttime: 55-60°F

Off-Season Highlights

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Summer (June to August)

Summer tends to see fewer visitors in the region, offering a quieter experience for those staying in vacation rentals. The hot weather is perfect if you prefer a more relaxed pace and less crowded attractions.

Average Temperature Daytime: 85-90°F - Nighttime: 70-75°F
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Fall (September to November)

Autumn offers cooler temperatures and fewer tourists, making it an excellent time to enjoy this destination’s rental properties at a more leisurely pace. It’s also when the region’s scenery begins to change, adding to its appeal.

Average Temperature Daytime: 75-80°F - Nighttime: 55-60°F

Weekly Weather Forecast for Pine Hills

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.

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 swimming pool to relax after exploring local attractions.
  • Take advantage of spacious patios or decks for outdoor dining and gatherings.
  • Make use of lush landscaped gardens perfect for outdoor entertainment or quiet reflection.
  • Benefit from access to outdoor grills for preparing delicious meals in the fresh air.
  • Relax on comfortable outdoor seating areas designed for enjoying the sunshine.
  • Participate in outdoor activities like volleyball or badminton with family and friends.
  • Utilize fenced yards ideal for outdoor play or accommodating pets during your stay.
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Family Activities

  • Exploring Local Parks: You can enjoy family picnics and outdoor adventures at nearby parks that offer playgrounds and scenic walking trails within the area.
  • Visiting Community Centers: Engage in activities like arts and crafts or sports at local community centers designed for family fun in this region.
  • Discovering Nearby Attractions: Take a short trip to explore popular attractions and entertainment venues that cater to families staying here.
  • Enjoying Recreational Activities: Participate in sports, swimming, or other leisure pursuits available at facilities conveniently located for visitors in the neighborhood.
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Adult Activities

  • Golfing at the Pine Hills Golf Course: Enjoy a relaxing day on the lush fairways of this local golf course, perfect for unwinding and practicing your swing amidst scenic surroundings.
  • Exploring the West Orange Trail: Cycle or walk along this popular trail that connects the area to nearby parks and attractions, offering scenic views and outdoor recreation opportunities.
  • Visiting local dining spots: Savor diverse cuisines at charming restaurants in the region, providing a taste of Florida's vibrant culinary scene close to your vacation rental.
  • Shopping at nearby retail centers: Browse through quaint shops and larger shopping areas that cater to various tastes, making it easy to find souvenirs and essentials during your stay.

Other Places to Stay in Pine Hills, FL

Lake Ellenor Village Shopping Center
Sliver Pines Village Shopping Center
Rosemont Village Shoppes Shopping Center

Pine Hills Travel Tips

How Can You Make the Most of Your Stay?

  • Explore Local Dining Options: Take advantage of the area’s diverse eateries to enjoy authentic Florida flavors during your stay.
  • Plan Outdoor Activities: Make the most of nearby parks and recreational spots to experience the natural beauty of this destination.
  • Check for Exclusive Deals: Keep an eye out for special offers on vacation rentals here to maximize your budget while enjoying comfort and convenience.
  • Arrive Prepared: Familiarize yourself with the neighborhood layout and amenities in your chosen property for a smooth and enjoyable visit.

Transportation Options

  • Orlando International Airport (MCO): This major airport offers convenient flights for travelers arriving in the region, making it an accessible gateway to your stay near Pine Hills.
  • Public Bus Services: Local bus routes provide economical transportation options around the area and connect you to Orlando’s attractions and neighboring communities.
  • Shuttle Services: Reliable shuttle services operate between key locations like the airport and your selected vacation rental, ensuring a hassle-free transfer throughout your trip.
  • Car Rentals: Renting a vehicle is a flexible way to explore here at your own pace and easily reach nearby attractions within the region.

Local Customs Options

  • Respect for Local Cuisine: Dining etiquette here emphasizes enjoying traditional Floridian flavors and local specialties with appreciation and courtesy.
  • Community Festivals: Participating in vibrant neighborhood festivals is a cherished custom that celebrates the area's diverse cultural heritage.
  • Greeting Traditions: It is common to greet neighbors with friendly gestures, reflecting the warm and welcoming spirit of this destination.
  • Environmental Awareness: Many locals observe sustainable practices, such as recycling and conserving water, which you might notice during your stay in this region.

Frequently Asked Questions About Pine Hills?

1. What are the top vacation rentals in Pine Hills?

2. Which vacation homes in Pine Hills are best for families?

If you are looking for a family-friendly vacation home in Pine 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 Pine Hills:

3. How many Rentbyowner vacation rentals are available in Pine Hills?

Currently, the total number of properties listed by Rent By Owner in 2026 is over 57 in the Pine 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 Pine Hills. 

4. What is the cancellation policy for booking vacation rentals here?

Cancellation policies vary depending on the property owner and listing details. To understand the specific terms, including refund eligibility and notice periods, please review the property's cancellation policy listed on the booking page or contact the host directly.

5. Are there any additional fees I should be aware of when booking a vacation rental in this area?

Additional fees such as cleaning fees, service charges, or security deposits are often detailed within each listing. Be sure to read the full description and fee breakdown on the property page to avoid surprises during your booking process.

6. How do I know if the vacation rental has enough amenities for my stay?

Property amenities are listed clearly on each rental's profile, including details about kitchens, Wi-Fi, parking, and other features. For specific needs, you can reach out to the host before booking to ensure all your requirements are met.

7. What steps should I take to secure my reservation at a popular vacation rental here?

To guarantee your booking, you'll typically need to complete the reservation process promptly after selecting your preferred dates. Some listings may require verification or deposits, so reviewing the booking instructions on the listing will help streamline your reservation.

8. Is it possible to modify or cancel my reservation once booked?

Modification or cancellation options depend on the property's policies set by the owner. Details on how to change or cancel your reservation can be found in the terms provided at booking or by contacting the host directly for assistance.

Pine Hills Top Rated Vacation Rentals

House
Map-icon
like-icon8.6
Fabulous
(4 Reviews)
3 Bedrooms 2 Baths 7 Guests
  • Fireplace/Heating
    Fireplace/Heating
  • Pool
    Pool
More amenities
US $198/Night 7 Nights - US $1,388
House
Map-icon
3 Bedrooms 2 Baths 6 Guests
  • Fireplace/Heating
    Fireplace/Heating
  • Pool
    Pool
More amenities
US $325/Night 7 Nights - US $2,278