Best Vacation Homes in Pinewood
House
10.0(1 Review)
6 Bedrooms
3 Baths
12 Guests
3000 ft²
Private Pool
Fireplace/Heating
Pool
Balcony/Terrace
US $1,145/Night
7 Nights - US $8,012
House
10.0(9 Reviews)
1 Bedroom
1 Bath
2 Guests
602.78 ft²
- Balcony/Terrace
Pet Friendly
Parking
Air Conditioner
US $76/Night
7 Nights - US $532
Condo
7.0(12 Reviews)
1 Bedroom
1 Bath
2 Guests
Kitchen- Air Conditioner
Internet
Child Friendly
US $189/Night
7 Nights - US $1,321
New
House
1 Bedroom
6 Baths
12 Guests
- Fireplace/Heating
- Kitchen
- Parking
- Air Conditioner
US $2,629/Night
7 Nights - US $18,404
House
10.0(5 Reviews)
1 Bedroom
1 Bath
2 Guests
204.51 ft²
- Balcony/Terrace
Breakfast- Pet Friendly
- Parking
US $258/Night
7 Nights - US $1,808
New
House
4 Bedrooms
4 Baths
14 Guests
3200 ft²
- Private Pool
- Pool
- Pet Friendly
- Kitchen
US $1,229/Night
7 Nights - US $8,606
New
House
3 Bedrooms
3 Baths
6 Guests
- Fireplace/Heating
- Pet Friendly
- Air Conditioner
- Internet
US $574/Night
7 Nights - US $4,015
Condo
3 Bedrooms
2 Baths
4 Guests
Oceanfront- Fireplace/Heating
Ocean View
View
US $349/Night
7 Nights - US $2,444
Pinewood Luxury Rentals
Villa
9.8(7 Reviews)
3 Bedrooms
2 Baths
10 Guests
- Oceanfront
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
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Villa
9 Bedrooms
10 Baths
18 Guests
- Fireplace/Heating
- Pet Friendly
- Air Conditioner
- Internet
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Villa
6 Bedrooms
4 Baths
12 Guests
3498.27 ft²
- Oceanfront
- Fireplace/Heating
- Pool
- Ocean View
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Villa
10.0(6 Reviews)
4 Bedrooms
2 Baths
12 Guests
- Oceanfront
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
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House
9.2(21 Reviews)
10 Bedrooms
7 Baths
20 Guests
- Private Pool
- Fireplace/Heating
- Pool
- Balcony/Terrace
US $4,904/Night
7 Nights - US $34,330
House
8 Bedrooms
5 Baths
24 Guests
- Private Pool
Hot Tub- Fireplace/Heating
- Pool
US $4,051/Night
7 Nights - US $28,357
Villa
9.0(1 Review)
5 Bedrooms
3 Baths
8 Guests
5381.95 ft²
- Oceanfront
- Hot Tub
- Fireplace/Heating
- Pool
US $3,951/Night
7 Nights - US $27,659
House
7.0(2 Reviews)
6 Bedrooms
4 Baths
16 Guests
- Private Pool
- Pool
- Air Conditioner
- Internet
US $3,890/Night
7 Nights - US $27,230
Pinewood Pet Friendly Vacation Rentals
House
2 Bedrooms
1 Bath
4 Guests
- Pet Friendly
- Air Conditioner
- Internet
- Child Friendly
US $183/Night
7 Nights - US $1,281
New
House
10.0(3 Reviews)
6 Bedrooms
3 Baths
12 Guests
4197.92 ft²
- Fireplace/Heating
- Pool
- Balcony/Terrace
- View
US $1,381/Night
7 Nights - US $9,665
House
1 Bedroom
1 Bath
5 Guests
500 ft²
- Balcony/Terrace
- Pet Friendly
- Kitchen
- Parking
US $229/Night
7 Nights - US $1,600
Apartment
10.0(7 Reviews)
2 Bedrooms
1 Bath
6 Guests
- Oceanfront
- Fireplace/Heating
- Ocean View
- View
US $192/Night
7 Nights - US $1,342
Villa
10.0(2 Reviews)
5 Bedrooms
3 Baths
16 Guests
10763.91 ft²
- Oceanfront
- Fireplace/Heating
- Pool
- Ocean View
US $2,668/Night
7 Nights - US $18,679
House
10.0(3 Reviews)
2 Bedrooms
1 Bath
6 Guests
657 ft²
- Private Pool
- Oceanfront
- Fireplace/Heating
- Pool
US $437/Night
7 Nights - US $3,061
House
10.0(2 Reviews)
2 Bedrooms
1 Bath
6 Guests
- Balcony/Terrace
- Pet Friendly
- Kitchen
- Air Conditioner
US $485/Night
7 Nights - US $3,398
Apartment
10.0(2 Reviews)
1 Bedroom
1 Bath
3 Guests
- Balcony/Terrace
- Pet Friendly
- Kitchen
- Parking
US $177/Night
7 Nights - US $1,237
Pinewood Large Vacation Homes
House
9.8(11 Reviews)
2 Bedrooms
4 Baths
10 Guests
2400 ft²
- Private Pool
- Fireplace/Heating
- Pool
- Ocean View
US $545/Night
7 Nights - US $3,813
Apartment
10.0(2 Reviews)
3 Bedrooms
2 Baths
12 Guests
- Balcony/Terrace
- View
- Parking
- Air Conditioner
US $343/Night
7 Nights - US $2,401
US $5,705/Night
7 Nights - US $39,935
Villa
8.0(1 Review)
2 Bedrooms
1 Bath
4 Guests
1200 ft²
- Oceanfront
- Fireplace/Heating
- Pool
- Ocean View
US $307/Night
7 Nights - US $2,152
Villa
10.0(1 Review)
1 Bedroom
2 Baths
4 Guests
1097.92 ft²
- Oceanfront
- Fireplace/Heating
- Pool
- Ocean View
US $305/Night
7 Nights - US $2,134
House
1 Bedroom
4 Baths
16 Guests
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
US $2,023/Night
7 Nights - US $14,163
Apartment
1 Bedroom
1 Bath
45 Guests
- Fireplace/Heating
- Kitchen
- Parking
- Air Conditioner
US $165/Night
7 Nights - US $1,153
Villa
10.0(42 Reviews)
3 Bedrooms
3 Baths
8 Guests
1700 ft²
- Private Pool
- Oceanfront
- Fireplace/Heating
- Pool
US $484/Night
7 Nights - US $3,391
Why Choose Rent By Owner for your Pinewood 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 Pinewood
When should you plan your Vacation Rentals stay?
Choosing the ideal time to vacation here can enhance your experience, as understanding the seasonal trends in this vibrant destination helps you make the most of your stay in the area.
Peak Season Highlights
Winter (December to February)
During the winter months, you'll enjoy warm, sunny weather ideal for exploring this vibrant region without the summer crowds.
Average Temperature Daytime: 75°F - Nighttime: 60°F
Spring (March to May)
Spring offers pleasant temperatures and blooming landscapes, making it a popular time for visitors seeking comfortable outdoor activities in this destination.
Average Temperature Daytime: 80°F - Nighttime: 65°F
Off-Season Highlights
Summer (June to August)
The summer months see fewer travelers as the region experiences higher humidity and afternoon rain showers, providing a quieter experience here.
Average Temperature Daytime: 88°F - Nighttime: 75°F
Fall (September to November)
Autumn brings cooler temperatures and less crowded streets, offering a relaxed atmosphere for enjoying the area's natural beauty and local culture.
Average Temperature Daytime: 82°F - Nighttime: 70°F
Weekly Weather Forecast for Pinewood
How to Book Your Pinewood 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 Pinewood
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 outdoor lounging areas with comfortable seating to relax and unwind.
- Take advantage of private or shared outdoor pools for a refreshing swim in the warm Florida sun.
- Benefit from well-maintained barbecue grills perfect for outdoor cooking and social gatherings.
- Relish landscaped gardens or lush green spaces that add natural beauty to your stay.
- Make the most of spacious patios or decks ideal for outdoor dining and entertaining.
- Explore nearby walking or biking paths that showcase the area's scenic beauty.
- Use outdoor shower facilities, convenient for rinsing off after beach visits or outdoor activities.
Top Attractions Around Pinewood
What attractions are nearby?
In this vibrant area, you can enjoy a variety of outdoor activities and explore local attractions that showcase the best of Miami’s lively culture and scenic beauty.
Family Activities
- Bill Baggs Cape Florida State Park: Explore this beautiful park with your family, where you can enjoy beach activities, picnic areas, and scenic lighthouse tours that showcase the natural beauty of the area.
- Miami Seaquarium: Discover engaging marine life exhibits and shows perfect for children, offering an educational and entertaining day out near the region's coastal attractions.
- Crandon Park: Relax and play at this family-friendly park featuring a tranquil beach, nature trails, and playgrounds nestled within the lush surroundings of South Florida.
- Matheson Hammock Park: Experience a peaceful escape with its calm man-made lagoon, scenic picnicking spots, and walking paths ideal for exploring here in the region.
Adult Activities
- Golfing at Miami Golf Course: Enjoy a relaxing day on the greens at one of the region's top golf courses, just a short drive from your Pinewood vacation rentals.
- Sailing and Water Sports: Take advantage of the area's access to Biscayne Bay by exploring sailing, kayaking, or paddleboarding adventures suitable for adults.
- Exploring Art Deco Historic District: Discover the vibrant art scene and architectural beauty with guided tours through nearby Miami’s iconic Art Deco district.
- Culinary Experiences in Local Restaurants: Indulge in diverse culinary delights at renowned restaurants, offering everything from fresh seafood to international cuisine, all close to your destination here.
Other Places to Stay in Pinewood, FL
North Shore Medical Center
Pinewood Travel Tips
How Can You Make the Most of Your Stay?
- Plan Ahead for Local Events: Check the regional calendar to align your stay with popular happenings and avoid peak travel times, ensuring a more relaxed experience here.
- Choose a Strategic Location: Opt for vacation rentals close to key transportation hubs or attractions within the area to maximize your exploration opportunities.
- Dive into Local Cuisine: Take advantage of nearby restaurants and eateries to enjoy authentic flavors that highlight the region’s culinary scene during your visit.
- Prepare for Weather Variability: Pack versatile attire suitable for the area's climate, allowing you to comfortably enjoy outdoor activities whether it’s sunny or rainy.
Transportation Options
- Car Rentals: Renting a car gives you the flexibility to explore all that this vibrant area has to offer at your own pace.
- Public Transit: The regional transit system offers convenient bus routes, making it easy to navigate around the neighborhood and nearby attractions.
- Taxi Services: Taxis are readily available for quick trips within the region, providing a reliable transportation option during your stay.
- Ride-Sharing Apps: Popular ride-sharing services operate here, offering an easy and affordable way to get around without the need for personal vehicle ownership.
Local Customs Options
- Respect for Local Art and Culture: You’ll notice that appreciating Miami's vibrant art scene is a common custom, reflecting the community’s pride in its creative expressions.
- Greeting Etiquette: When engaging with locals, it’s customary to offer a friendly greeting or handshake to foster positive connections throughout your stay.
- Fashion and Dress Code: Visitors often dress casually yet stylishly, embracing the region’s warm climate while respecting the area's relaxed but fashionable standards.
- Celebration of Festivals: Participating in local festivals and events shows your respect for the area’s traditions and enhances your cultural experience here.
Frequently Asked Questions About Pinewood?
1. What are the top vacation rentals in Pinewood?
There are a lot of options in Pinewood. If you plan on staying in the Pinewood area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Vacation Rentals in Pinewood:
- Miami Tropical Retreat - Villa Tropical
- Boho Chic House-POOL & FIREPIT - 15 mins to South Beach
- Luxury 4BR Retreat w/Heated Pool + Free Car Rental – Near Miami & Beaches
- Pool Home in North Miami Beach. Everyone gets their own bed !
- Hot tub Paradaise: outdoor kitchen and personalized attention. Pet-friendly
- Miami Heart Retreat – Stylish & Central With Games
- FIFA 2026 HQ | 8mi to Stadium | Sleeps 10 | Private Heated Pool & Games
- Spacious 4-bedroom house with WiFi and AC in central Miami
- 5 BDR, 9 beds, Sleeps 12, Luxury Oasis Pool, 6 miles to beach
- SunBright Studio Miami - Free Parking & Patio
2. How many vacation rentals have private pools in Pinewood?
There are 160 vacation rentals with private pools near Pinewood. Top-rated RBO homes that have access to a swimming pool include:
3. Which vacation homes in Pinewood are best for families?
If you are looking for a family-friendly vacation home in Pinewood, check out one of the following properties as all are highly-rated places to stay with excellent review for families or groups staying in Pinewood:
4. How many Rentbyowner vacation rentals are available in Pinewood?
Currently, the total number of properties listed by Rent By Owner in 2026 is over 1589 in the Pinewood 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 Pinewood.
5. What is the cancellation policy for booking a vacation rental here?
The cancellation policy varies depending on the property listing. It is important to review the specific terms outlined in each listing before confirming your reservation, or contact the owner directly for detailed information.
6. How do I find available dates and book a vacation rental in this area?
You can check the availability calendar on the listing page and proceed with the booking process online. For personalized assistance or special requests, reaching out to the property owner is recommended.
7. Are there any fees or additional costs when booking a vacation rental in this destination?
Additional charges such as cleaning fees, service fees, or taxes are typically specified within each listing. Always review the total cost breakdown before completing your reservation.
8. Is it possible to modify or cancel my reservation if my plans change?
Modifications or cancellations depend on the policies set by the property owner. You should refer to the specific listing's terms or contact the owner directly to discuss any changes to your booking.
9. What amenities and features can I expect from vacation rentals in this region?
Amenities vary between properties, but most offer essentials along with extras like Wi-Fi, parking, and kitchen facilities. Detailed information about amenities is available on each listing, so review those details or ask the owner for clarification.
Pinewood Top Rated Vacation Rentals
House
10.0(27 Reviews)
4 Bedrooms
2 Baths
8 Guests
1900 ft²
- Private Pool
- Oceanfront
- Fireplace/Heating
- Pool
US $509/Night
7 Nights - US $3,564
House
10.0(18 Reviews)
4 Bedrooms
3 Baths
8 Guests
2925 ft²
- Private Pool
- Oceanfront
- Fireplace/Heating
- Pool
US $791/Night
7 Nights - US $5,537
House
10.0(15 Reviews)
5 Bedrooms
3 Baths
15 Guests
- Private Pool
- Oceanfront
- Fireplace/Heating
- Pool
US $605/Night
7 Nights - US $4,238
House
10.0(13 Reviews)
3 Bedrooms
2 Baths
7 Guests
1400 ft²
- Oceanfront
- Hot Tub
- Fireplace/Heating
- Pool
US $411/Night
7 Nights - US $2,877
House
10.0(12 Reviews)
4 Bedrooms
3 Baths
10 Guests
2379 ft²
- Private Pool
- Oceanfront
- Fireplace/Heating
- Pool
US $678/Night
7 Nights - US $4,749
House
10.0(10 Reviews)
5 Bedrooms
3 Baths
12 Guests
- Private Pool
- Hot Tub
- Fireplace/Heating
- Pool
US $798/Night
7 Nights - US $5,585
House
10.0(6 Reviews)
7 Bedrooms
3 Baths
16 Guests
3500 ft²
- Private Pool
- Oceanfront
- Fireplace/Heating
- Pool
US $1,115/Night
7 Nights - US $7,805
House
10.0(6 Reviews)
4 Bedrooms
2 Baths
10 Guests
2300 ft²
- Private Pool
- Hot Tub
- Fireplace/Heating
- Pool
US $587/Night
7 Nights - US $4,109
