Discover Your Perfect Pinecrest Vacation Homes

Best Vacation Homes in Pinecrest

House
Map-icon
3 Bedrooms 2 Baths 6 Guests
  • Private Pool
    Private Pool
  • Hot Tub
    Hot Tub
More amenities
R10,149/Night 7 Nights - R71,044
House
like-icon10.0
Exceptional
(2 Reviews)
1 Bedroom 1 Bath 2 Guests 215.28 ft²
  • Pool
    Pool
  • Balcony/Terrace
    Balcony/Terrace
More amenities
R1,236/Night 7 Nights - R8,652
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Condo
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like-icon9.2
Exceptional
(411 Reviews)
1 Bedroom 1 Bath 4 Guests
  • Fireplace/Heating
    Fireplace/Heating
  • Pool
    Pool
More amenities
R3,597/Night 7 Nights - R25,181
Apartment
Map-icon
like-icon10.0
Exceptional
(2 Reviews)
1 Bedroom 1 Bath 4 Guests
  • Oceanfront
    Oceanfront
  • Fireplace/Heating
    Fireplace/Heating
More amenities
R3,182/Night 7 Nights - R22,264
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House
Map-icon
like-icon10.0
Exceptional
(1 Review)
4 Bedrooms 2 Baths 10 Guests 2443.41 ft²
  • Pool
    Pool
  • View
    View
More amenities
R7,699/Night 7 Nights - R53,889
R5,361/Night 7 Nights - R37,524
Apartment
Map-icon
like-icon10.0
Exceptional
(1 Review)
1 Bedroom 1 Bath 1 Guest
  • Hot Tub
    Hot Tub
  • Pool
    Pool
More amenities
R3,577/Night 7 Nights - R25,033

Pinecrest Luxury Rentals

Boat Rental
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5 Bedrooms 6 Baths 12 Guests
  • Balcony/Terrace
    Balcony/Terrace
  • Air Conditioner
    Air Conditioner
More amenities
R111,733/Night 7 Nights - R782,130
House
Map-icon
5 Bedrooms 4 Baths 16 Guests 4628.48 ft²
  • Fireplace/Heating
    Fireplace/Heating
  • View
    View
More amenities
R81,926/Night 7 Nights - R573,479
Villa
Map-icon
like-icon10.0
Exceptional
(2 Reviews)
6 Bedrooms 7 Baths 10 Guests
  • Fireplace/Heating
    Fireplace/Heating
  • Balcony/Terrace
    Balcony/Terrace
More amenities
R62,350/Night 7 Nights - R436,450
House
Map-icon
8 Bedrooms 7 Baths 12 Guests
  • Fireplace/Heating
    Fireplace/Heating
  • Pool
    Pool
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R54,383/Night 7 Nights - R380,683
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Villa
Map-icon
5 Bedrooms 4 Baths 10 Guests 10763.91 ft²
  • Parking
    Parking
  • Child Friendly
    Child Friendly
More amenities
R45,336/Night 7 Nights - R317,351
Villa
Map-icon
4 Bedrooms 3 Baths 10 Guests
  • Private Pool
    Private Pool
  • Pool
    Pool
More amenities
R24,472/Night 7 Nights - R171,307
New
Villa
Map-icon
4 Bedrooms 4 Baths 8 Guests
  • Fireplace/Heating
    Fireplace/Heating
  • Air Conditioner
    Air Conditioner
More amenities
R22,967/Night 7 Nights - R160,777
House
Map-icon
5 Bedrooms 4 Baths 16 Guests 4629 ft²
  • Fireplace/Heating
    Fireplace/Heating
  • Balcony/Terrace
    Balcony/Terrace
More amenities
R22,607/Night 7 Nights - R158,255

Pinecrest Pet Friendly Vacation Rentals

Cottage
Map-icon
like-icon10.0
Exceptional
(1 Review)
1 Bedroom 1 Bath 2 Guests 684 ft²
  • Fireplace/Heating
    Fireplace/Heating
  • Balcony/Terrace
    Balcony/Terrace
More amenities
R2,894/Night 7 Nights - R20,254
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House
Map-icon
like-icon9.0
Exceptional
(3 Reviews)
1 Bedroom 1 Bath 2 Guests 688.89 ft²
  • Fireplace/Heating
    Fireplace/Heating
  • View
    View
More amenities
R1,879/Night 7 Nights - R13,151
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Apartment
Map-icon
like-icon8.4
Excellent
(208 Reviews)
1 Bedroom 1 Bath 4 Guests
  • Fireplace/Heating
    Fireplace/Heating
  • Pool
    Pool
More amenities
R3,793/Night 7 Nights - R26,549
House
Map-icon
like-icon9.4
Exceptional
(13 Reviews)
2 Bedrooms 1 Bath 6 Guests
  • Oceanfront
    Oceanfront
  • Fireplace/Heating
    Fireplace/Heating
More amenities
R4,836/Night 7 Nights - R33,849
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Apartment
like-icon8.4
Excellent
(999 Reviews)
80 Bedrooms 10 Baths 36 Guests 1018.98 ft²
  • Fireplace/Heating
    Fireplace/Heating
  • Pool
    Pool
More amenities
R3,329/Night 7 Nights - R23,302
House
Map-icon
like-icon9.4
Exceptional
(3 Reviews)
4 Bedrooms 2 Baths 9 Guests 3281 ft²
  • Fireplace/Heating
    Fireplace/Heating
  • Pool
    Pool
More amenities
R8,492/Night 7 Nights - R59,443

Pinecrest Large Vacation Homes

House
Map-icon
like-icon10.0
Exceptional
(8 Reviews)
4 Bedrooms 2 Baths 10 Guests 2446 ft²
  • Private Pool
    Private Pool
  • Pool
    Pool
More amenities
R9,256/Night 7 Nights - R64,782
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Villa
Map-icon
like-icon8.1
Excellent
(15 Reviews)
4 Bedrooms 3 Baths 14 Guests 1743.75 ft²
  • Oceanfront
    Oceanfront
  • Pool
    Pool
More amenities
R12,474/Night 7 Nights - R87,326
House
Map-icon
like-icon10.0
Exceptional
(2 Reviews)
4 Bedrooms 3 Baths 10 Guests
  • Fireplace/Heating
    Fireplace/Heating
  • Air Conditioner
    Air Conditioner
More amenities
R13,184/Night 7 Nights - R92,287
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House
Map-icon
like-icon7.0
Very Good
(2 Reviews)
4 Bedrooms 3 Baths 12 Guests 2400.35 ft²
  • Hot Tub
    Hot Tub
  • Pool
    Pool
More amenities
R12,525/Night 7 Nights - R87,672
House
Map-icon
4 Bedrooms 2 Baths 10 Guests
  • Private Pool
    Private Pool
  • Fireplace/Heating
    Fireplace/Heating
More amenities
R5,370/Night 7 Nights - R37,590
New
House
Map-icon
4 Bedrooms 3 Baths 10 Guests 11 ft²
  • Pool
    Pool
  • Kitchen
    Kitchen
More amenities
R13,403/Night 7 Nights - R93,819
House
Map-icon
4 Bedrooms 6 Baths 10 Guests 3604 ft²
  • Private Pool
    Private Pool
  • Pool
    Pool
More amenities
R32,136/Night 7 Nights - R224,949
Villa
Map-icon
like-icon10.0
Exceptional
(7 Reviews)
4 Bedrooms 3 Baths 8 Guests
  • Private Pool
    Private Pool
  • Pool
    Pool
More amenities
R10,630/Night 7 Nights - R74,406

Why Choose Rent By Owner for your Pinecrest 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 Pinecrest

When should you plan your Vacation Rentals stay?

Choosing the ideal time to visit this destination can enhance your experience, as the weather and local events here vary throughout the year, making it important to plan your trip accordingly for the best stay in the region.

Peak Season Highlights

spring
Spring (March to May)

During spring, the area experiences mild and pleasant weather, making it an ideal time for outdoor activities and exploring. This season attracts visitors seeking comfortable temperatures and vibrant natural scenery.

Average Temperature Daytime: 75°F - Nighttime: 55°F
autumn
Fall (September to November)

In fall, the region offers cooler temperatures and fewer crowds, providing a peaceful retreat for your stay. It's perfect for enjoying the scenic beauty and serene atmosphere of this destination.

Average Temperature Daytime: 70°F - Nighttime: 50°F

Off-Season Highlights

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Summer (June to August)

Summertime brings hotter weather, which can be less comfortable for some travelers. However, this is still a quieter period for those who prefer avoiding peak tourist times while enjoying the warm climate.

Average Temperature Daytime: 85°F - Nighttime: 65°F
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Winter (December to February)

Winter months tend to be cooler and less crowded, making it a good choice for low-season travelers looking for budget-friendly options. The weather remains relatively mild here compared to more northern destinations.

Average Temperature Daytime: 65°F - Nighttime: 45°F

Weekly Weather Forecast for Pinecrest

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 outdoor dining areas perfect for relaxing meals in the sunshine.
  • Take advantage of landscaped gardens or private yards to unwind after a day of exploring.
  • Experience outdoor fire pits or seating areas ideal for evening gatherings.
  • Make the most of shaded patios or verandas for enjoying the fresh air in comfort.
  • Discover private pools or hot tubs to cool off or relax under the stars.
  • Benefit from ample parking spaces suitable for outdoor activities or excursions.
  • Utilize well-maintained pathways or trails for walking, jogging, or biking around the property.
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Family Activities

  • Coral Castle Museum: Discover the fascinating history of this unique attraction, where you can explore impressive stone sculptures and learn about local artistry in the region.
  • Everglades National Park Tours: Experience an exciting airboat adventure that takes you through the iconic Everglades, offering unforgettable wildlife sightings and nature exploration nearby.
  • Bird Watching at Blackwater River State Forest: Enjoy peaceful mornings observing diverse bird species in this scenic natural setting close to your Pinecrest area stay.
  • Picnic and Recreational Activities at Matheson Hammock Park: Relax with family-friendly picnics and outdoor games while taking in beautiful waterfront views in this popular park here.
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Adult Activities

  • Exploring the Pinecrest Gardens: Discover lush botanical gardens that offer tranquil walking trails and native Florida flora, perfect for a relaxing day out.
  • Fishing at the local lakes: Enjoy a peaceful afternoon casting lines in nearby lakes, where you can unwind amid scenic surroundings unique to this area.
  • Hiking in the regional parks: Venture into nearby parks featuring well-maintained trails that showcase the natural beauty of the region's landscape.
  • Attending community events: Participate in local festivals and markets held throughout here, providing authentic regional experiences and entertainment for adults.

Other Places to Stay in Pinecrest, FL

Pinecrest Travel Tips

How Can You Make the Most of Your Stay?

  • Plan your outdoor adventures early: Take advantage of the region’s natural beauty by scheduling activities such as hiking or kayaking during the daylight hours to fully enjoy the area's scenic landscapes.
  • Explore local dining options: Discover authentic flavors and cozy eateries nearby, making your stay more memorable without having to venture far from your rental.
  • Utilize nearby amenities carefully: Check out what facilities are available locally, like grocery stores and recreational spots, to ensure a convenient and comfortable visit.
  • Respect the environment and community: Preserve the natural surroundings by following eco-friendly practices and engaging thoughtfully with the local area during your trip.

Transportation Options

  • Miami International Airport: This major airport offers numerous domestic and international flights, making it a convenient gateway for travelers visiting the region.
  • Local Bus Services: The area is served by several local bus routes that provide affordable and reliable transit options within Pinecrest and to nearby destinations.
  • Car Rentals: Renting a vehicle here allows you to explore the region at your own pace, with many rental agencies available close to key transportation hubs.
  • Taxi and Rideshare Services: Taxis and rideshare options like Uber and Lyft are readily accessible, providing convenient door-to-door transportation throughout this destination.

Local Customs Options

  • Respect for Local Nature: Visitors often observe a strong appreciation for the area's natural surroundings, emphasizing conservation and eco-friendly practices during their stay.
  • Community Hospitality: Welcoming attitudes are typical here, with residents taking pride in sharing their local customs and traditions with visitors exploring the region.
  • Farmers' Market Traditions: Engaging in local farmers' markets is a common custom, providing an authentic taste of regional produce and fostering community connections.
  • Sunset Gatherings: Participating in informal sunset viewing events along scenic spots reflects the area's laid-back lifestyle and appreciation for natural beauty.

Frequently Asked Questions About Pinecrest?

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

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

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

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

Currently, the total number of properties listed by Rent By Owner in 2026 is over 153 in the Pinecrest 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 Pinecrest. 

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

Cancellation policies vary depending on the specific listing. You should review the rental's cancellation terms on the property’s page or contact the owner directly to understand their specific policy.

6. Are there any additional fees I should be aware of when booking in this destination?

Additional fees such as cleaning, service charges, or local taxes are often outlined in the listing details. Be sure to read through all the provided information carefully or reach out to the property owner for clarification.

7. How do I ensure my reservation in this region is secure?

Reservations are protected by a secure booking system that encrypts your personal information. For added confidence, verify the listing’s reviews and communicate directly with the host through the platform’s messaging system.

8. What amenities are typically included in vacation rentals here?

Most properties offer amenities like Wi-Fi, kitchen facilities, and parking. To confirm specific features, review the listing description or contact the owner before booking.

9. Is it possible to modify or cancel my booking if my plans change?

Modifications and cancellations depend on the individual rental’s policies. Check the property's terms on the listing page or contact the owner directly to discuss any changes you need to make.

Pinecrest Top Rated Vacation Rentals

star-icons-4
House
like-icon10.0
Exceptional
(1 Review)
3 Bedrooms 3 Baths 8 Guests 2400.35 ft²
  • Spa
    Spa
  • Fireplace/Heating
    Fireplace/Heating
More amenities
R5,125/Night 7 Nights - R35,876
House
Map-icon
like-icon9.4
Exceptional
(43 Reviews)
3 Bedrooms 3 Baths 8 Guests 2400 ft²
  • Private Pool
    Private Pool
  • Fireplace/Heating
    Fireplace/Heating
More amenities
R7,201/Night 7 Nights - R50,412
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Hotel
Map-icon
like-icon9.2
Exceptional
(1258 Reviews)
1 Bath
  • Fireplace/Heating
    Fireplace/Heating
  • Pool
    Pool
More amenities
R2,380/Night 7 Nights - R16,661
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Hotel
Map-icon
like-icon9.2
Exceptional
(987 Reviews)
1 Bath
  • Pool
    Pool
  • Balcony/Terrace
    Balcony/Terrace
More amenities
R2,961/Night 7 Nights - R20,732
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Apartment
like-icon9.0
Exceptional
(619 Reviews)
24 Bedrooms 3 Baths 9 Guests 952.61 ft²
  • Oceanfront
    Oceanfront
  • Fireplace/Heating
    Fireplace/Heating
More amenities
R3,329/Night 7 Nights - R23,302
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Hotel
Map-icon
like-icon8.9
Fabulous
(386 Reviews)
8 Baths 305.42 ft²
  • Oceanfront
    Oceanfront
  • Fireplace/Heating
    Fireplace/Heating
More amenities
R2,186/Night 7 Nights - R15,310
Hotel
Map-icon
like-icon8.8
Fabulous
(1158 Reviews)
1 Bath
  • Hot Tub
    Hot Tub
  • Fireplace/Heating
    Fireplace/Heating
More amenities
R2,444/Night 7 Nights - R17,106
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Cottage
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like-icon8.8
Fabulous
(29 Reviews)
1 Bedroom 1 Bath 2 Guests
  • Fireplace/Heating
    Fireplace/Heating
  • Pool
    Pool
More amenities
R3,723/Night 7 Nights - R26,071