Luxury Vacation Rentals in Grassy Key

Luxury Vacation Rentals in Grassy Key

Never book a bad vacation home again. Every Wander comes with hotel-grade amenities, inspiring views, pristine cleaning and 24/7 concierge service.
We found 1 vacation rentals – enter your dates for availability.

Top-rated vacation rentals in Grassy Key

Casa Feliz property photo 1

Casa Feliz

4 bedrooms•4 baths
11,261 US dollars for 7 nights•
New

~$890 less than other sites

Welcome to Grassy Key

Welcome to Grassy Key

Elevate your escape with Wander’s luxury vacation rentals in Grassy Key. Waterfront homes bring sweeping Atlantic or Florida Bay views, generous outdoor lounges, and private pools. Spaces flow effortlessly from sleek kitchens to terraces made for sunrise and starlight.
Expect hotel-grade polish, pristine cleaning, and 24/7 concierge support. Chef-ready kitchens, premium linens, and ultra fast WiFi come standard. Select homes add private docks and hot tubs, so you can settle into a Keys rhythm without giving up modern comforts.

Destinations near Grassy Key

Tavernier
Miami
Key Biscayne
Miami Beach
Marco Island
Marco Island
North Miami
Hallandale Beach
Davie
Hollywood
Fort Lauderdale
Oakland Park
Coral Springs
Delray Beach
Fort Myers Beach
Wellington
Palm Springs

Featured vacation rentals in Grassy Key

Casa Feliz property photo 1

Casa Feliz

4 bedrooms•4 baths
11,261 US dollars for 7 nights•
New

~$890 less than other sites

All homes in Grassy Key

Casa Feliz property photo 1

Casa Feliz

4 bedrooms•4 baths
11,261 US dollars for 7 nights•
New

~$890 less than other sites

View all homes

Highlights in Grassy Key

Discover a laid-back Middle Keys escape filled with marine life encounters, pristine state parks, and thrilling water sports.
Dolphin Research Center
Curry Hammock State Park
Keys Cable Park
The Turtle Hospital
Sombrero Beach
Crane Point Hammock Museum & Nature Center

IT'S A VACATION HOME, BUT BETTER

The Wander difference

Wander is different because we combine the quality of a luxury hotel with the comfort of a private vacation home. Your best trip ever is just a few clicks away.

Only the best homes

We’ll never not look like the pictures. Every Wander is beautiful and expertly operated, so you can leave any stress at the door.

Hotel-grade amenities

We’ll never leave you with nothing to do. From ultra fast WiFi to gyms and pools, our homes make it easy to blend work and play.

24/7 concierge service

We’ll never leave you hanging. Our chat-based Concierge is always available to help – from trip questions to special requests.

Inspiring and stunning views

We’ll never leave you uninspired. Every Wander has stunning views to refresh and inspire your soul. Adventure awaits.

Meticulous cleaning

We’ll never have you check in to a dirty house. Our cleaning teams are meticulous, and there are no chores at checkout.

Safety and security

We’ll never pass you off to a stranger. Every Wander location meets our industry-leading safety standards to give you peace of mind.

Most popular amenities for vacation rentals in Grassy Key

Private chef (1)
Jacuzzi (1)
Hot tub (1)
Ocean view (1)
Beachfront (1)
Gym (1)
Heated pool (1)
Waterfront (1)
Outdoor pool (1)
Sound system (1)
Beach access (1)
Patio (1)
Game console (1)
Garden (1)
Bbq area (1)
Balcony (1)

Other popular amenities & vacation types in Grassy Key

Family vacation rentals in Grassy Key
Hot tub vacation rentals in Grassy Key
Private pool vacation rentals in Grassy Key
Discover more of Grassy Key

Discover more of Grassy Key

Set between Marathon and Islamorada, Grassy Key is a serene stretch of the Middle Keys with glassy flats and mangrove shorelines. Sunrises glow over the Atlantic and sunsets melt into Florida Bay, carried by soft trade winds.
Life moves at an easy tempo. Drift to nearby sandbars or follow the Overseas Highway for sweeping sea views. The Dolphin Research Center is on the island, and Bahia Honda State Park is an effortless day trip. This calm, scenic setting is why Wander’s luxury vacation rentals in Grassy Key are the perfect choice, whether you are traveling for work or leisure.

FAQs: Vacation Rentals in Grassy Key

Why should I book a Wander in Grassy Key over other vacation rentals?

Wander offers a level of consistency and quality you won’t find with most vacation rentals.
Every home in Grassy Key delivers the quality of a luxury hotel, paired with the comfort and space of a private vacation home. You get hotel-grade amenities, meticulous cleaning, stunning views, and 24/7 concierge support in every stay. Why would you want to stay anywhere else?

Which are Wander’s most popular vacation rentals in Grassy Key?

Some of our most popular vacation rentals in Grassy Key include Casa Feliz and Casa Feliz. Guests love the quality of a luxury hotel, the comfort of a private vacation home, and the consistently exceptional experience Wander is known for. Explore the full collection to find the perfect home for your next stay.

How many different vacation rentals does Wander have available in Grassy Key?

Wander offers 1 vacation rentals in Grassy Key, each carefully designed and expertly operated. Browse the full collection to see what’s available for your trip.

What time is check-in and check-out at Wander’s vacation rentals in Grassy Key?

You can check-in to Wander vacation rentals in Grassy Key after 4.00pm and check-out before 10.00am.

Do Wander’s vacation rentals in Grassy Key have WiFi access?

Yes. Every Wander home in Grassy Key has ultra fast, reliable WiFi so you can stay connected throughout your stay.

What is Wander’s cancellation policy?

You can cancel your reservation within 24 hours of booking for a full refund.
For stays of less than 15 nights, you can cancel or reschedule up to 14 days before check-in for a full refund. For stays of 15 nights or longer, the cancellation window is 60 days.
For some homes, a 30-day deadline applies; this will be clearly shown before you book.