Grassy Key Villa Rentals【 LUXURY 】Rent By Owner

Grassy Key Villa

Villa

Waterfront Island Escape with Private Plunge Pool

10.0

Exceptional

(25 Reviews)

2 Bedrooms 2 Baths 6 Guests 980 ft²

R6,858/Night 7 Nights - R48,010

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5035 "Villa del Sol"- Amazing Sunset Views! 2bed 3bath

Price Dropped

Villa

5035 "Villa del Sol"- Amazing Sunset Views! 2bed 3bath

10.0

Exceptional

(2 Reviews)

2 Bedrooms 3 Baths 6 Guests 904.17 ft²

R6,160/Night 7 Nights - R43,111

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Highly Rated

Villa

Waterfront Duck Key Villa

9.2

Exceptional

(61 Reviews)

3 Bedrooms 3 Baths 8 Guests

R17,334/Night 7 Nights - R121,335

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Crystal Waters - Kayaks, 2BR 2.5BA Coastal Villa

Price Dropped

Villa

Crystal Waters - Kayaks, 2BR 2.5BA Coastal Villa

10.0

Exceptional

(7 Reviews)

2 Bedrooms 2 Baths 6 Guests 900 ft²

R7,404/Night 7 Nights - R51,819

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Villa

Blue House Getaway - 2BR 3BA Coastal Villa

10.0

Exceptional

(1 Review)

2 Bedrooms 3 Baths 6 Guests 904.17 ft²

R5,841/Night 7 Nights - R40,885

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Villa

Villa with Resort Amenities | Full Kitchen

10.0

Exceptional

(1 Review)

2 Bedrooms 2 Baths 4 Guests

R11,994/Night 7 Nights - R83,963

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Oceanfront Duck Key Villa: 2 Marinas Steps Away!

House

Oceanfront Duck Key Villa: 2 Marinas Steps Away!

10.0

Exceptional

(1 Review)

2 Bedrooms 3 Baths 6 Guests 904.17 ft²

R8,862/Night 7 Nights - R62,028

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Villa

Villa 5008 on Duck Key Boat Slip Available - 2BD 1.5BA

10.0

Exceptional

(1 Review)

2 Bedrooms 1 Bath 6 Guests

R11,029/Night 7 Nights - R77,201

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House

Beach House Getaway - 2BR 2-5BA Coastal Villa

9.6

Exceptional

(22 Reviews)

2 Bedrooms 3 Baths 11 Guests 904.17 ft²

R11,036/Night 7 Nights - R77,251

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DUPLEX IN DUCK KEY, 2 Bedroom/2 Bath, W/Private 90' Dock, Trailer Storage INCL

Highly Rated

Villa

DUPLEX IN DUCK KEY, 2 Bedroom/2 Bath, W/Private 90' Dock, Trailer Storage INCL

9.8

Exceptional

(188 Reviews)

2 Bedrooms 2 Baths 6 Guests 1000 ft²

R8,147/Night 7 Nights - R57,031

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House

DK33 Harbor Hideaway Villa 7066

9.6

Exceptional

(5 Reviews)

4 Bedrooms 3 Baths 8 Guests

R8,444/Night 7 Nights - R59,109

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DUPLEX IN DUCK KEY, 2 Bedroom/2 Bath, W/Private 90' Dock, Trailer Storage

Highly Rated

Villa

DUPLEX IN DUCK KEY, 2 Bedroom/2 Bath, W/Private 90' Dock, Trailer Storage

9.8

Exceptional

(175 Reviews)

2 Bedrooms 2 Baths 4 Guests 1000 ft²

R8,147/Night 7 Nights - R57,031

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More Top-Rated Villa in Grassy Key Area

Why Choose Rent By Owner for your Grassy Key Villa?

What makes our Villa 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 Grassy Key

When should you plan your Villa stay?

Understanding the best time to visit the area can help you enjoy ideal weather and avoid peak crowds, making your vacation in this destination more relaxing and memorable when you choose to book your villas during shoulder seasons or off-peak months here.

Peak Season Highlights

Winter (December to February)

During the winter months, this destination experiences a peak season with warm weather that appeals to travelers seeking a sunny escape in Florida. Expect lively atmosphere and optimal conditions for outdoor activities.

Average Temperature Daytime: 75°F - Nighttime: 65°F

Spring Break (March to April)

Spring break brings an influx of visitors looking to enjoy pleasant temperatures and vibrant local events. The area becomes especially popular among families and groups seeking relaxation in a tropical setting.

Average Temperature Daytime: 78°F - Nighttime: 67°F

Off-Season Highlights

Summer (June to August)

Summer months tend to see fewer visitors, offering a quieter experience here. You can enjoy lower rates and less crowded beaches while still basking in warm, inviting weather.

Average Temperature Daytime: 88°F - Nighttime: 77°F

Fall (September to November)

Autumn signals a slowdown in travel activity, making it a great time to find value and tranquility in the region. The weather remains warm, ideal for peaceful escapes and scenic views.

Average Temperature Daytime: 85°F - Nighttime: 72°F

Weekly Weather Forecast for Grassy Key

How to Book Your Grassy Key Villa

What's our booking process?

Our platform allows you to browse a curated selection of villa. Once you find the ideal property, you’ll be redirected to a trusted booking partner to complete your reservation securely.

Booking Steps

Search Properties

Use our filters to find the right property that fits your needs.

Select a Rental

Click on your preferred listing to view details, amenities, and pricing.

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 Villa in Grassy Key Area

Common Villa Amenities

What amenities can you expect?

Our Villa 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 grilling facilities to prepare meals amid the tropical surroundings.
Take advantage of private pools or hot tubs for relaxation after a day exploring the area.
Benefit from scenic verandas or patios perfect for soaking in the Florida sunshine.
Make use of lush, well-maintained gardens or yard spaces for outdoor activities.
Experience peace and privacy with fenced outdoor areas suited for family gatherings.
Utilize boat docks or waterfront access if available, ideal for exploring local waters.
Relax on comfortable loungers or hammocks set up outdoors for a tranquil retreat.

Top Attractions Around Grassy Key

What attractions are nearby?

In this beautiful region, you can enjoy a variety of activities nearby, from exploring pristine beaches and engaging in water sports to discovering local wildlife and relaxing in scenic nature spots that make your stay truly memorable.

Family Activities

Snorkeling and Marine Exploration: Discover the vibrant underwater world just off the coast of this destination, where family-friendly snorkeling spots offer exciting aquatic adventures.
Everglades Excursions: Experience guided boat tours through nearby wetlands that showcase diverse wildlife and provide educational fun for all ages.
Bahia Honda State Park: Enjoy a day at this scenic park, perfect for picnicking, swimming, and exploring nature trails amidst breathtaking coastal views.
Local Eco Tours: Participate in eco-friendly tours that introduce your family to the region’s unique ecosystems and promote environmental awareness in an engaging way.

Adult Activities

Snorkeling and Diving Adventures: Explore the vibrant underwater world just off the coast, where you can discover colorful marine life and pristine coral reefs.
Wildlife Watching Tours: Enjoy guided excursions to observe native wildlife, including birdwatching and possibly spotting dolphins in their natural habitat.
Sunset Cruises: Experience breathtaking sunsets over the water on a relaxing boat cruise, perfect for unwinding after a day of exploration.
Fishing Excursions: Try your hand at deep-sea or backcountry fishing, an engaging activity that offers fresh catch and memorable experiences in this tranquil destination.

Grassy Key Travel Tips

How Can You Make the Most of Your Stay?

Plan Outdoor Activities Early: To fully enjoy the area’s natural beauty, schedule your outdoor adventures during the cooler parts of the day and take advantage of the region’s scenic waterfront views.
Explore Local Marine Life: Engage in water-based experiences by visiting nearby snorkeling or kayaking spots to discover the vibrant marine ecosystems that make this destination unique.
Choose Prime Accommodations: Select a villa located close to key attractions and the coast for easy access to the area's best beaches and activities, enhancing your overall experience.
Respect the Environment: Help preserve the region’s natural charm by following eco-friendly practices and adhering to local guidelines during your stay here.

Transportation Options

Shuttle Services: Reliable shuttle services operate in the region, offering convenient transportation to and from key points, making your stay more comfortable.
Rental Cars: Car rental companies available here provide flexible travel options, allowing you to explore nearby attractions at your own pace.
Public Transit: Local bus services connect this destination with other parts of the area, providing an affordable way to get around without a vehicle.
Taxi and Rideshare: Taxis and rideshare apps are readily accessible, offering quick and efficient transportation directly to your villa or local destinations.

Local Customs Options

Respect for the Marine Environment: Locals in this area highly value the preservation of their surrounding marine ecosystems, encouraging visitors to avoid disturbing wildlife and to participate in eco-friendly activities.
Local Seafood Traditions: Enjoying fresh seafood prepared according to regional recipes is a cherished custom that reflects the area's rich coastal heritage.
Community Festivals: Participating in or observing local festivals provides insight into the area's cultural identity and historical roots, fostering a deeper connection with local residents.
Respect for Quiet Hours: The community often observes quiet hours during the evening to maintain a peaceful environment, making it ideal for relaxing stays at your villa here.

Frequently Asked Questions About Grassy Key Rental Villas

1. What are the top Villas 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 Villas in Grassy Key:

2. How many Villas are available in Grassy Key?

Currently, the total number of properties listed by RBO in 2026 is over 78 in the Grassy Key area, and still counting. By aggregating listings from multiple websites, RBO offers an immense amount of choice of the best Villas in Grassy Key. 

3. What is the cancellation policy for villas in this destination?

Cancellation policies vary depending on the individual property listing. To understand specific terms, please review the cancellation details listed with each villa or contact the property owner directly before completing your booking.

4. Are there any additional fees I should be aware of when booking a villa in this area?

Additional fees such as cleaning charges, service fees, or security deposits are typically outlined in the villa listing. It’s recommended to read the detailed description and contact the owner if you have questions about extra costs.

5. Can I find villas with flexible check-in and check-out times here?

Flexible check-in and check-out options depend on the individual villa's policies. To ensure your preferred schedule, communicate directly with the property owner during the booking process.

6. What amenities can I expect from villas in this region?

Villas here generally offer a range of amenities including fully equipped kitchens, private pools, outdoor spaces, and modern furnishings. For specific amenities, please review the listing details or reach out to the owner.

7. How do I ensure my booking is secure when reserving a villa here?

To guarantee a safe booking experience, use the official booking platform’s secure payment system, read verified reviews, and contact the owner for any clarifications before confirming your reservation.