
Vacation rentals in Pine Hills
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Top-rated vacation rentals in Pine Hills
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A SUITE RETREAT with a Garden View in the City
A lovely remodeled in-law suite in a 1920s Mission Styled home in College Park suited for 2 people with a separate entrance, private bath & a little kitchenette.The Suite looks out into a garden to offer a relaxing view. Even though you are in the Downtown area, the suite was designed to offer solitude. We are walking distance to many restaurants & only an easy 5 minute drive to downtown Orlando. I am looking forward to hosting any and all who would like to visit. All are welcome. #STR-1009437

Maitland-Orlando Area, FL. Pool House Bungalow
Large open space adjacent to a beautiful pool, waterfall, and fantastic lake view. 27 miles to Disney World, close to Park Avenue, local hospitals, Universities, and less than an hour to local beaches. Only 18 miles to MCO-Orlando International Airport. Great shopping within 3 miles. Location is secluded with large trees, lakeside, and adjacent to the commuter train track. The train runs by on regular basis. Please note in the pictures the pool creates the ambiance to make your stay complete.

Cozy Cottage in College Park.
Whether you're coming to Orlando for adventure at one of the theme parks, or a little R&R, the Cozy Cottage is the perfect place. It's charming, quiet and nestled in our back garden with a stock tank pool in College Park, in The city of Orlando. Winter Park, Rollins college, lou gardens, Orlando Science Center, Advent Heath, Orlando health, Dr. Phillips center, Ivanhoe, lake eola, camping world stadium and the Kia center, are all in the immediate area. UCF, Full Sail and Florida Central too.

1924 Spanish Carriage House Lower
Enjoy a shared but private compound resort in the heart of downtown Orlando! Centrally located and within walking distance to major events at the Kia Center, Dr. Phillips Performing Arts Center, restaurants, and downtown nightlife. Park on site, relax and enjoy all that this historic home has to share! Besides a fresh and clean private lodging, you'll enjoy use of the tropical pool, hot tub, gas grill, covered seating and dining area. A washer and dryer are just steps away for your use.

Contemporary Loft Near Downtown
Conveniently located between the foodie-friendly Milk District and Downtown Orlando, this impeccably thought-out space features a spacious loft style open floor plan perfect for a couple or small group. The floor to ceiling windows allow natural light to fill the space while providing complete privacy during your stay. Upscale Winter Park restaurants and the vibrant Thornton Park art scene are only a short drive away. Universal is only 20 minutes away, Disney is 35 minutes, MCO 20 minutes.

Oasis Garden Cottage -cozy, chic, near everything!
Our cozy cottage is located within minutes of some of the best areas, restaurants, bars, and attractions Orlando has to offer. Winter Park and College Park are 3-5 minute drives, Disney and Universal only 20 minutes, etc. The interior is chic and inviting, with a homey feel. Enjoy the fireplace, play some board games, soak in bath salts in the claw foot tub, curl up on the porch with a coffee and read one of our provided books— it’s so peaceful you’ll have a hard time leaving for the day!

New Mid Century-Modern Studio
Enjoy your stay in this beautifully decorated studio with all the conveniences of home. The bed is Queen. We are located in College Park of Orlando. On Edgewater Drive there are restaurants, bars, and boutique shops. Close to downtown , 30 min. from all the attractions, and 5 min. from one of the city’s largest hospitals, 23 miles from ORMC airport. Walking distance from the historic Dubsdread Golf Club and restaurant. Pet fee required. Please make sure to add the pet to the reservation.

Adorable, private studio in College Park
Currently opening up this space for long term rentals (20-60 days). Perfect for travel nurses- about 10 min drive to Orlando Advent Health Hospital. This spot is perfect for 1 or 2 people looking for a private, welcoming place to stay! It is completely separate but does share a wall with the owners unit, so you could potentially hear some noises through there. The fenced in back yard is shared as well, both back doors open up to the yard. Its about 10 mins from downtown Orlando

The Cottage A Pet Friendly Guesthouse
Welcome to The Cottage! A pet friendly, super cute, and quiet studio apartment built in 2016, located above the detached garage behind my house. Pets always stay for free, and no additional cleaning fees are charged. Private self access is provided so you come and go as you please. The unit has a full kitchen, king sized bed, 4 pillows, 100% cotton sheets and coverlet. Laundry detergent and dish soap are provided. Trash is located on the west sideof the building.

Downtown Winter Garden, Florida
Charming two bedroom, one bathroom home just three blocks from downtown Winter Garden Florida. Across the street from the West Orange Bike Trail and walking distance to restaurants, Splash pond, shopping and Farmers Market. The fenced in back yard is shaded by a 100 year old live oak tree. There is a “no pet policy” at the house. We do not accept guests under the age of 12. There are NO cameras on or around the property. I respect the privacy of my guests.

Luxury Container Home w/ {repaired} Hot Tub Oasis
Step into this unique experience: a shipping container transformed into a luxury 1 bedroom 1 bathroom suite. The space is perfect for couples, business travelers, tourists, and families. After a busy day in the parks or shopping, come back to a cozy outdoor paradise with lights strung up under a covered pergola. Lounge on the couch and enjoy a gas fireplace table, grill a meal on the Weber Spirit 2 gas grill, and soak your tired feet in the hot tub.

Priv. Modern Cozy CP 1B/1Ba Suite near DT Orl & WP
Private & Comfortable 1 bd/ba suite in a 2021 townhome with front view windows, queen size bed, walk-in shower& private entrance. Equipped w/ ceiling and portable fans, Roku smart TV, mini fridge/freezer, microwave, and Keurig. Located in a safe, quiet, walkable neighborhood. 5 minutes of College Park shops, 10 minutes from downtown Orlando, 25 minutes to Universal Studios, 30 minutes to Orlando International Airport, & 40 minutes to Disney.
Popular amenities for Pine Hills vacation rentals
Other great vacation rentals in Pine Hills

Orlando Oasis in the heart of Thornton Park

Hip RetroModern Lakefront Cabana w/ EV Charger

Jefferson St. Cottage

Paradise nook near Orlando's theme parks

NEW 1BRM Guesthouse | King Bed | Central Florida

Cozy container in College Park and near Downtown

King/Queen Bungalow w/ porch | central vibey area

College Park/Winter Pk 1 bed/bath private entrance
When is the best time to visit Pine Hills?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | R1,082 ZAR | R1,082 ZAR | R1,098 ZAR | R915 ZAR | R915 ZAR | R998 ZAR | R1,082 ZAR | R1,048 ZAR | R932 ZAR | R899 ZAR | R1,065 ZAR | R1,065 ZAR |
| Avg. temp | 16°C | 18°C | 20°C | 22°C | 25°C | 27°C | 28°C | 28°C | 27°C | 24°C | 20°C | 17°C |
Frequently Asked Questions
What are the best places to stay in Pine Hills?
Vacation rentals around Pine Hills neighborhoods give you easy access to parks and local eateries. Many homes are set up for families or groups looking for comfort and a lived-in feel.
What are the best things to do in Pine Hills with kids?
Try playtime in neighborhood parks, enjoy outdoor sports fields, or visit community centers that frequently suggest youth programs. Many families also explore nearby nature spots for a relaxed outing.
What are some of the best things to do in Pine Hills?
Explore locally rooted parks and community spaces, discover diverse food offerings from small neighborhood restaurants, or learn about the arts at nearby cultural centers. Pine Hills has easy access to green spaces and creative hubs.
How is the weather in Pine Hills?
Pine Hills has warm, humid summers around 90°F (32°C), with frequent afternoon rain, and mild winters near 70°F (21°C). Lightweight clothing and a raincoat come in handy throughout the year.
When is the best time to visit Pine Hills?
Milder temperatures and lower humidity in late fall or early spring are often recommended by travelers. Summer is popular for community gatherings but comes with frequent afternoon rain and warmth.
What are the best places to visit in Pine Hills?
Wander through neighborhood parks, stop by local art centers, or explore bustling multicultural markets around Pine Hills. These spots showcase the area's community spirit and variety.
What are some hiking trails in Pine Hills?
Explore paved walking paths in community parks or seek nature trails in nearby green spaces just outside Pine Hills. These areas are relaxed options for those interested in a gentle outdoor experience.
What are some family activities we can do in Pine Hills?
Families often enjoy spending time in local parks, picnic spots, and playgrounds around Pine Hills. Community centers sometimes host activities, and area recreation complexes have sports courts and open spaces for everyone.
What are some of the best day trip ideas from Pine Hills?
Spend a day exploring nearby lakes, visit larger art museums in Orlando, or enjoy family-friendly attractions around central Florida. Nature reserves and regional gardens are also frequently suggested.
Are there any pet friendly accommodations available in Pine Hills?
Many vacation rentals in Pine Hills neighborhoods welcome pets, and several homes have fenced yards or easy park access. Trails and local green spaces make spending time with your companion animal convenient.
What are some local tips for visiting Pine Hills?
Support locally owned eateries for a taste of Pine Hills’ culinary traditions, and relax in shaded parks during warmer afternoons. Engaging with community events can give insight into the area's vibrant cultures.
What is Pine Hills known for?
Pine Hills is known for its multicultural community, locally owned restaurants with Caribbean and Latin American influences, and accessible parks. The area also has a history of strong neighborhood involvement.
What are the best hidden gems to explore in Pine Hills?
Discover small multicultural bakeries, tucked-away art studios, and local gardens around Pine Hills. These less-traveled spots highlight everyday creativity and community roots.
What are the best foods to try in Pine Hills?
Pine Hills has diverse Caribbean, Latin American, and Southern-inspired dishes, like jerk chicken, pastelitos, or fried fish. Local bakeries often feature sweet breads and pastries reflecting the area's cultural mix.
What should I bring for a trip to Pine Hills?
Pack breathable clothing for warm, often humid weather, a rain jacket for summer months, and comfortable walking shoes for exploring parks or trails. Sunscreen and a reusable water bottle are frequently suggested.
What is the nightlife in Pine Hills like?
Nightlife in Pine Hills centers around neighborhood bars, relaxed lounges, and local restaurants featuring live music or karaoke. For bigger venues and a wider variety of music, visitors usually explore nearby Orlando.
What are the most popular events or festivals in Pine Hills?
Pine Hills hosts multicultural community celebrations, seasonal festivals in area parks, and neighborhood cultural fairs. These gatherings often feature local music, regional foods, and art activities.
Are there family friendly vacation rentals in Pine Hills?
Family friendly stays are available in Pine Hills, with many homes featuring kitchens, multiple bedrooms, and yard space. Neighborhoods are close to parks and community centers, making outings easy for families.
Quick stats about vacation rentals in Pine Hills

Total vacation rentals
Explore 250 vacation rentals in Pine Hills

Nightly prices starting at
Pine Hills vacation rentals start at R166 ZAR per night before taxes and fees

Verified guest reviews
Over 5,500 verified reviews to help you choose

Family-friendly vacation rentals
70 properties offer extra space & kid-friendly amenities

Pet-friendly vacation rentals
Find 30 rentals that welcome pets

Vacation rentals with a pool
50 properties feature pools

Rentals with dedicated workspaces
100 properties have a dedicated workspace

Wi-Fi availability
240 of Pine Hills vacation rentals include wi-fi access

Popular amenities for guests
Guests love Kitchen, Wifi, and Pool across Pine Hills rentals

4.5 Average rating
Pine Hills stays receive an average rating of 4.5 out of 5 from guests
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