Discover Your Perfect Grassy Key Vacation Homes

Why Choose Rent By Owner for your Grassy Key Vacation Rental Homes?

What makes our Vacation Rentals special?

image
Verified Listings
Book with confidence knowing every property meets our quality and safety standards.
image
Unbeatable Value
Enjoy competitive pricing with no hidden fees, providing exceptional value for every stay.
image
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 Vacation Rentals stay?

Choosing the optimal time to visit here ensures you experience the region’s perfect blend of pleasant weather and ideal conditions for relaxing in your vacation rental.

Peak Season Highlights

winter
Winter (December to February)

During the winter months, this destination experiences its peak season, attracting visitors seeking warm weather and beach relaxation. You can enjoy the area's vibrant atmosphere and ideal temperatures for outdoor activities.

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

Springtime brings a lively ambiance as travelers flock here to enjoy pleasant weather and scenic beauty. It’s a popular period for booking vacation rentals, offering comfortable daytime temperatures for exploring or relaxing by the water.

Average Temperature Daytime: around 78°F to 82°F - Nighttime: around 70°F to 75°F

Off-Season Highlights

image
Summer (June to August)

In the summer, fewer visitors come here, making it a quieter time to experience the region’s natural serenity. This is an ideal season if you prefer less crowded surroundings and warm weather for water activities.

Average Temperature Daytime: around 85°F to 90°F - Nighttime: around 75°F to 80°F
image
Fall (September to November)

Autumn offers a tranquil escape with milder temperatures and less tourism. It’s perfect for those looking to enjoy the region's peaceful environment while still experiencing pleasant weather for outdoor pursuits.

Average Temperature Daytime: around 78°F to 84°F - Nighttime: around 68°F to 73°F

Weekly Weather Forecast for Grassy Key

How to Book Your Grassy Key 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 Grassy Key

More Top-Rated Vacation Rentals in Grassy Key Area

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 access to private or community swimming pools, perfect for relaxing under the sun.
  • Take advantage of outdoor grilling areas to dine al fresco with family and friends.
  • Benefit from spacious patios or decks ideal for lounging and soaking up the Florida sunshine.
  • Make use of well-maintained outdoor dining spaces for meals with scenic views of the region's natural beauty.
  • Engage in water activities with waterfront access or boat docks available at many properties.
  • Experience the benefits of lush landscaped gardens and tropical greenery surrounding your rental.
  • Utilize outdoor showers or shower stations for rinsing off after a day exploring here and along the coast.

Top Attractions Around Grassy Key

What attractions are nearby?

In this destination, you can enjoy a variety of outdoor activities such as snorkeling, kayaking, and boat tours that highlight the natural beauty of the nearby waters and marine life.

image
image

Family Activities

  • Blue Heron Bridge Exploration: Discover the vibrant marine life and colorful coral reefs just offshore, perfect for family snorkeling adventures within the region’s calm, clear waters.
  • Local Dolphin Tours: Embark on a guided dolphin watching cruise where your family can enjoy close encounters with playful dolphins native to the area’s warm, coastal environment.
  • Kayaking in the Mangroves: Glide through scenic mangrove channels, offering an exciting way for kids and adults alike to explore this unique ecosystem native to the area.
  • Wildlife Viewing at Nearby Sanctuaries: Visit local wildlife refuges or sanctuaries where your family can observe native birds and animals thriving in their natural habitat, highlighting the region's rich biodiversity.
image

Adult Activities

  • Snorkeling and Diving: Explore the vibrant coral reefs and marine life just off the coast, offering an unforgettable underwater experience in this tropical destination.
  • Kayaking and Paddleboarding: Enjoy tranquil waters by paddling along scenic waterways, perfect for both relaxation and a bit of adventure here in the region.
  • Fishing Excursions: Embark on deep-sea or flats fishing trips that provide excellent opportunities to catch local species, appealing to avid anglers visiting this area.
  • Wildlife Watching: Observe diverse bird species and marine mammals in their natural habitat, making it a rewarding activity for nature enthusiasts in this destination.

Grassy Key Travel Tips

How Can You Make the Most of Your Stay?

  • Plan Your Outdoor Adventures: Make the most of the region's natural beauty by exploring nearby water activities like kayaking or paddleboarding to enjoy the scenic coastal environment.
  • Discover Local Flavors: Sample fresh seafood and regional cuisine at local eateries to immerse yourself in the authentic tastes of the area.
  • Explore Hidden Spots: Take time to visit lesser-known beaches or nature trails that offer peaceful retreats away from typical tourist areas.
  • Schedule Relaxing Moments: Prioritize downtime within your vacation rental to unwind and soak in the tranquil ambiance unique to this destination.

Transportation Options

  • Car Rentals: Renting a car provides you with the flexibility to explore the area and visit nearby attractions at your own pace.
  • Public Transit: The regional bus services offer an affordable way to get around here, connecting you to key points in the region.
  • Taxi and Rideshare Services: Taxis and rideshare options like Uber or Lyft are convenient for short trips within this destination.
  • Bicycle Rentals: Biking is an eco-friendly and enjoyable way to experience the natural beauty of the surrounding region.

Local Customs Options

  • Local Seafood Cuisine: You’ll find that enjoying fresh seafood is a cherished tradition, with many local restaurants highlighting regional flavors that reflect the area’s coastal heritage.
  • Community Festivals: Participating in seasonal festivals offers an authentic glimpse into the region’s vibrant culture and community spirit, often showcasing local arts and crafts.
  • Respect for Marine Life: It’s customary to observe guidelines that protect the marine environment, ensuring the health of the area’s diverse aquatic ecosystems for future visitors.
  • Casual Beach Attire: Embracing the relaxed, laid-back style is typical here, making it easy to blend in while exploring the scenic beaches and waterfront areas.

Frequently Asked Questions About Grassy Key?

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 vacation rentals have private pools in Grassy Key?

There are 114 vacation rentals with private pools near Grassy Key. Top-rated RBO homes that have access to a swimming pool include:

3. Which vacation homes in Grassy Key are best for families?

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

4. 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 489 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. 

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

The cancellation policy varies by property, so it's important to review the specific listing details or contact the host directly to understand the terms and any potential fees involved.

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

Additional fees such as cleaning fees, service charges, or security deposits are common and will be detailed in the listing. Be sure to read the full description before confirming your reservation.

7. How do I find the best vacation rentals available in this destination?

To find the most suitable options, filter search results based on your preferences and read reviews from previous guests. Reaching out to hosts with questions can also help ensure you select the right property for your stay.

8. What amenities are typically included in vacation rentals in the region?

Most properties offer essential amenities such as Wi-Fi, kitchens, and outdoor spaces. However, specific features vary, so check each listing for detailed information about what is included during your stay.

9. Is there a minimum stay requirement for booking accommodations here?

Minimum stay requirements depend on the individual property and the time of year. Review the booking policies listed on each property’s page or contact the host directly for clarification before making a reservation.

Grassy Key Top Rated Vacation Rentals

See More Grassy Key Vacation Rentals