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Discover Your Perfect Grassy Key Rentals by Owner

Grassy Key Rentals by Owner

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10.0 (1 Review)
House
Sea and Sky
  • Air Conditioner
  • Pet Friendly
  • Balcony/Terrace
View Availability
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9.6 (5 Reviews)
House
Harbor Hideaway Villa 7066
  • Air Conditioner
  • Pet Friendly
  • Wheelchair Accessible
View Availability
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9.5 (4 Reviews)
Apartment
Harbor Villa
  • Air Conditioner
  • Wheelchair Accessible
  • Balcony/Terrace
View Availability
More Top-Rated Rentals by Owner in Grassy Key Area

Why Choose Rent By Owner for your Grassy Key vacation rental?

What makes our Rentals by Owner 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 Grassy Key

When should you plan your Rentals by Owner stay?

Timing your visit to the area can greatly enhance your vacation experience, so consider planning during the region's optimal seasons when weather and local events align to create the perfect getaway.

Peak Season Highlights

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Winter (December to February)

During the winter months, this destination experiences its peak visitor period as travelers seek warm escapes from colder climates. You can enjoy pleasant daytime temperatures and lively local activities in the area.

Average Temperature Daytime: 75°F to 80°F - Nighttime: 65°F to 70°F
spring
Spring (March to May)

As spring arrives, visitors flock here for its mild weather and scenic beauty, making it one of the most popular times to rent a vacation home. The region offers comfortable temperatures ideal for outdoor activities and exploration.

Average Temperature Daytime: 78°F to 85°F - Nighttime: 68°F to 73°F

Off-Season Highlights

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Summer (June to August)

In the summer, you might find fewer crowds in this area as some travelers prefer cooler or more temperate times. The region remains warm, perfect for relaxing by the water and enjoying quieter surroundings.

Average Temperature Daytime: 88°F to 92°F - Nighttime: 75°F to 78°F
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Fall (September to November)

During fall, the region sees a slowdown in visitors, offering a peaceful retreat with fewer tourists. Temperatures are still warm enough for outdoor pursuits while providing a more relaxed atmosphere overall.

Average Temperature Daytime: 82°F to 86°F - Nighttime: 70°F to 74°F

Weekly Weather Forecast for Grassy Key

How to Book Your Grassy Key vacation rental

What's our booking process?

Our platform allows you to browse a curated selection of rentals by owner. 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 Grassy Key

More Top-Rated Rentals by Owner in Grassy Key Area

Common Rentals by Owner Amenities

What amenities can you expect?

Our Rentals by Owner 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 dining areas perfect for savoring meals with a view of the surrounding scenery.
  • Take advantage of private or communal pools to relax and cool off after exploring the area.
  • Relax in lush landscaped gardens or patios that provide tranquil outdoor spaces.
  • Make use of well-maintained BBQ grills for outdoor cooking and entertaining guests.
  • Benefit from direct access to private or shared dock facilities for boating or fishing excursions.
  • Use outdoor lounge furniture to unwind while soaking in the scenic views of the region’s natural beauty.
  • Take advantage of shaded porches or verandas, ideal for enjoying the fresh air in this coastal destination.

Top Attractions Around Grassy Key

What attractions are nearby?

In this charming destination, you can explore a variety of outdoor activities and water-based adventures just moments from your rental, making it perfect for those looking to enjoy the natural beauty and tranquility of the area.

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Family Activities

  • Florida Keys Aquarium Encounters: Discover an engaging marine life experience perfect for families, where you can interact with local sea creatures and learn about the region's vibrant aquatic ecosystem.
  • Curry Hammock State Park: Enjoy a day of outdoor adventures with activities like kayaking, paddleboarding, and family picnics amid the scenic beauty of this natural Florida Keys park.
  • Snorkeling Excursions in the Area: Explore the colorful coral reefs and abundant marine life just off the coast, making it a memorable adventure for children and adults alike.
  • Wild Bird Rehabilitation Center: Visit this educational sanctuary dedicated to restoring local bird populations, offering children a hands-on learning experience about regional wildlife conservation.
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Adult Activities

  • Snorkeling and Diving Adventures: Explore the vibrant marine life just off the coast, experiencing the crystal-clear waters that make this destination ideal for underwater exploration.
  • Kayaking and Paddleboarding: Enjoy paddling through calm waters around the area, offering a peaceful way to take in the scenic views and local wildlife.
  • Visit Local Marine Sanctuaries: Discover protected areas where you can observe diverse sea creatures and learn about the region’s unique ecosystem.
  • Relaxing on Pristine Beaches: Unwind on the soft sands while soaking up the sun, making it perfect for a tranquil day in this tropical setting.

Grassy Key Travel Tips

How Can You Make the Most of Your Stay?

  • Embrace the Outdoors: Take advantage of the region’s scenic waterways and nearby parks to enjoy kayaking, paddleboarding, or relaxing by the water during your stay.
  • Opt for a Rental with Local Insights: Choose a private rental that offers personalized tips from owners familiar with hidden gems and the best local experiences here.
  • Plan Your Travel During Off-Peak Times: Visiting outside peak seasons can provide a more tranquil atmosphere and better rates in this coastal area.
  • Utilize Convenient Amenities: Prioritize rentals that include essentials like outdoor spaces or cozy kitchens to enhance your comfort while exploring the region.

Transportation Options

  • Rental Car Services: You can easily access rental car companies near this destination, offering flexibility to explore the scenic area and its surroundings at your own pace.
  • Taxi and Ride-Sharing Services: Reliable taxi and ride-sharing options are available here, providing convenient transportation directly to your vacation rental or local attractions.
  • Public Transportation: Public transit buses serve the region, making it a cost-effective way to travel without worrying about parking or driving logistics.
  • Bicycle Rentals: Biking is a popular option in this area, with bike rentals readily available for exploring the tranquil coastlines and natural scenery comfortably.

Local Customs Options

  • Respect for Marine Life: When visiting the area, you are encouraged to observe local marine creatures responsibly and avoid disturbing their natural habitats.
  • Local Fishing Traditions: Engaging in or respecting traditional fishing practices is common here, reflecting the area's rich maritime culture.
  • Community Celebrations: Participating in regional festivals and events offers insight into the area's customs and fosters a sense of connection with locals.
  • Environmental Stewardship: Visitors are welcomed to practice eco-friendly habits, supporting conservation efforts vital to maintaining this region’s natural beauty.

Frequently Asked Questions About Grassy Key Rentals by Owner

1. What are the top vacation rentals in Grassy Key?

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

2. How many Rentbyowner vacation rentals are available in Grassy Key?

Currently, the total number of properties listed by Rent By Owner in 2025 is over 436 in the Grassy Key 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 Grassy Key. 

3. What is the cancellation policy for rental properties in this area?

Cancellation policies vary by individual owner; you should review the specific listing details or contact the owner directly to understand their policies regarding cancellations and refunds.

4. How do I secure my booking with a rental owner in the region?

Booking typically involves submitting a reservation request through the platform and completing the payment process as outlined. Ensure you read the listing thoroughly and communicate with the owner if needed.

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

Additional fees such as cleaning, service charges, or taxes may apply depending on the property. These details are usually listed on the property page or disclosed by the owner during your inquiry.

6. What amenities are generally available in rental properties by owner in this destination?

Amenities can range from basic essentials to luxury features. For specific offerings like Wi-Fi, kitchens, or pools, check the individual property listing or contact the owner for precise information.

7. Is it possible to modify or extend my stay after booking a rental in this area?

Modifications depend on the owner's policies and availability. You should reach out directly to the owner before making changes to your reservation to confirm if extensions or adjustments can be accommodated.

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More Top-Rated Rentals by Owner in Grassy Key Area