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Discover Your Perfect Pinecrest Winter Rental

Pinecrest Winter Rental

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8.5 (685 Reviews)
Hotel
Hilton Miami Dadeland
  • Air Conditioner
  • Parking
  • Pet Friendly
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More Top-Rated Winter Rental in Pinecrest Area

Why Choose Rent By Owner for your Pinecrest Winter Rental?

What makes our Winter Rental 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 Pinecrest Winter Rental

Where are the best neighborhoods to stay in Pinecrest?

In Pinecrest, Florida, you can enjoy staying in neighborhoods known for their peaceful residential charm and convenient access to local amenities. This area offers a variety of options that cater to those seeking a comfortable and relaxing stay during the winter season. Whether you're looking for quiet tree-lined streets or family-friendly communities, Pinecrest provides an ideal setting for your seasonal retreat.

Gables By The Sea

This neighborhood offers a peaceful residential setting with beautiful waterfront views, making it an ideal choice for those seeking relaxing winter rentals in the region. You'll find that here, tranquility and scenic surroundings define the experience.

View 30+ Rentals in Gables By The Sea

Hammocks

Known for its lush greenery and spacious lots, the Hammocks provides a comfortable environment for winter rentals that want to blend privacy with natural beauty. Staying here grants easy access to outdoor activities while enjoying the serenity of this desirable area.

View 234+ Rentals in Hammocks

Best Times to Visit Pinecrest

When should you plan your Winter Rental stay?

To make the most of your winter stay in this destination, consider visiting during the cooler months when the region offers a tranquil escape and ideal conditions for a relaxing getaway in comfortable winter rentals.

Peak Season Highlights

winter
Winter (December to February)

During winter, you can enjoy the mild and pleasant weather, making it ideal for exploring the area’s natural beauty while avoiding the peak tourist crowds.

Average Temperature Daytime: 70°F - Nighttime: 50°F
spring
Spring (March to May)

Springtime brings vibrant landscapes and comfortable temperatures, perfect for outdoor activities and experiencing the region’s lush scenery at its best.

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

Off-Season Highlights

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Summer (June to August)

In summer, the area experiences warmer temperatures and higher humidity, offering a quieter and more relaxed environment for your winter stay.

Average Temperature Daytime: 85°F - Nighttime: 65°F
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Fall (September to November)

Autumn features cooler temperatures and less crowded surroundings, providing a peaceful setting for your winter escape.

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

Weekly Weather Forecast for Pinecrest

How to Book Your Pinecrest Winter Rental

What's our booking process?

Our platform allows you to browse a curated selection of winter rental. 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 Pinecrest

More Top-Rated Winter Rental in Pinecrest Area

Common Winter Rental Amenities

What amenities can you expect?

Our Winter Rental 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 deck to relax and unwind amidst scenic views.
  • Take advantage of spacious yards perfect for outdoor activities and gatherings.
  • Make the most of on-site BBQ grills for outdoor cooking during your stay.
  • Benefit from access to swimming pools or hot tubs, ideal for year-round relaxation.
  • Utilize outdoor dining areas to savor meals in the fresh air with family and friends.
  • Explore well-maintained walking trails or nature paths nearby for outdoor excursions.
  • Relish in outdoor fire pits or fireplaces to enjoy cozy evenings under the stars.

Top Attractions Around Pinecrest

What attractions are nearby?

Nearby, you can enjoy a variety of outdoor activities such as exploring scenic parks, engaging in nature walks, and experiencing local wildlife within the lush surroundings of Pinecrest, Florida, making it an ideal destination for those seeking relaxing winter rentals in the region.

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Family Activities

  • Everglades National Park Airboat Tours: Experience a thrilling airboat ride through the unique ecosystem of nearby Everglades National Park, perfect for nature-loving families seeking an adventurous day out in the region.
  • Coral Castle Museum: Discover the fascinating artistry of Coral Castle, where you and your family can explore impressive sculptures and learn about its intriguing history within this distinctive Florida attraction.
  • Crandon Park Beach: Relax and unwind on this scenic beach, offering gentle waves and soft sand, making it an ideal spot for family beach days in the area’s coastal surroundings.
  • Miami Seaquarium: Enjoy a fun-filled visit to this popular marine park, showcasing captivating aquatic shows and interactive exhibits that entertain and educate children about marine life in the region.
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Adult Activities

  • Everglades National Park Tours Experience a guided tour through the vast wetlands of this renowned park, where you can observe unique wildlife and enjoy the tranquility of this natural wonder.
  • Fishing Excursions Engage in a fishing trip tailored for adults, offering opportunities to catch local species while appreciating the scenic views surrounding the area.
  • Birdwatching Expeditions Join expert-led birdwatching outings in the region’s diverse habitats, perfect for nature enthusiasts seeking to spot rare or interesting bird species.
  • Golfing at Local Courses Play a round on well-maintained golf courses nearby, combining leisure and sport amidst the picturesque surroundings of this destination.

Other Places to Stay in Pinecrest, FL

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Pinecrest Travel Tips

How Can You Make the Most of Your Stay?

  • Plan Ahead: Book your winter rental early to secure the best properties and enjoy a stress-free stay here in the region during peak season.
  • Explore Local Nature: Take advantage of nearby outdoor areas to experience the area's natural beauty and make the most of your visit.
  • Discover Hidden Gems: Ask your host or local guides about lesser-known spots that offer authentic experiences beyond the usual attractions.
  • Prepare for Weather: Pack appropriate clothing and essentials to comfortably enjoy all the seasonal activities this destination has to offer.

Transportation Options

  • Local Bus Services Public buses are available for convenient transportation around this region, making it easy to explore without a car during your stay.
  • Taxi and Rideshare Options Taxis and services like Uber and Lyft operate here, offering flexible and reliable transportation within the area and to nearby destinations.
  • Car Rentals Renting a vehicle is a popular choice for visitors wanting the convenience of exploring the broader region at their own pace.
  • Bicycle Rentals For shorter trips and eco-friendly travel, bicycle rentals provide an enjoyable way to navigate through the scenic surroundings.

Local Customs Options

  • Respect for Nature: Locals here take pride in preserving the area's lush landscapes, so you'll often see residents practicing eco-friendly habits during your visit.
  • Quiet Hours: Maintaining a peaceful environment is important, with residents adhering to specific quiet hours, especially in residential areas and during evening times.
  • Celebration of Local Artistry: The community values its artistic heritage, encouraging the display and appreciation of local artwork and cultural expressions within public spaces.
  • Community Gatherings: Participating in neighborhood events or casual gatherings is common, fostering a welcoming atmosphere for visitors and locals alike.

Frequently Asked Questions About Pinecrest Winter Rentals

1. What are the top Winter Rentals in Pinecrest?

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

2. How many Winter Rentals are available in Pinecrest?

Currently, the total number of properties listed by RBO in 2026 is over 28 in the Pinecrest area, and still counting. By aggregating listings from multiple websites, RBO offers an immense amount of choice of the best Winter Rentals in Pinecrest. 

3. What is the cancellation policy for winter rentals in this area?

The cancellation policy varies depending on the property listing. To ensure you understand the specific terms, please review the cancellation details provided in the listing or contact the property owner directly.

4. Are there any special requirements or restrictions for booking a winter rental here?

Certain properties may have specific requirements or restrictions, such as minimum stay durations or age limits. Details are outlined in each listing, so it’s best to read through these carefully or reach out to the owner for clarification.

5. How do I confirm my reservation and what payment methods are accepted?

Reservations are confirmed through the booking platform, with payment options typically including credit cards and other secure payment methods. For exact procedures and accepted forms of payment, consult the booking details or contact the property owner directly.

6. Is there a minimum stay requirement during the winter season?

Many properties in this region enforce minimum stay requirements, especially during peak winter months. The specific duration can be found in the listing details, and you can also inquire with the owner for personalized assistance.

7. What amenities are included with my winter rental in this destination?

The available amenities vary by property but often include essentials like heating, Wi-Fi, and kitchen facilities. For a complete list of what’s offered, review the property description or contact the owner for more information.

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