Luxury Vacation Rentals in Islamorada

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 8 vacation rentals – enter your dates for availability.

Top-rated vacation rentals in Islamorada

The Coquina House at Coral Cove

3 bedrooms•3.5 baths

•

New

Save ~$675 booking direct

Luxury

Islamorada Island

6 bedrooms•6 baths

•

Save ~$2,355 booking direct

The Oasis

3 bedrooms•3.5 baths

•

Save ~$640 booking direct

The Meridian at Oceanside Residences

4 bedrooms•4.5 baths

•

New

Save ~$810 booking direct

Sunset + Boat Basin, Islamorada

4 bedrooms•4 baths

•

New

Save ~$195 booking direct

Elevated Retreat, Sunset Access + Boat Basin

2 bedrooms•2 baths

•

New

Save ~$85 booking direct

Sunset Access + Boat Basin, Walkable Islamorada

2 bedrooms•2 baths

•

New

Save ~$85 booking direct

Luxury

Front Beach, Paradise Villa, Islamorada FL Keys

7 bedrooms•8 baths

•

New

Save ~$2,130 booking direct

Welcome to Islamorada

Escape to the Keys with Wander. Our collection of luxury vacation rentals in Islamorada blends the polish of a luxury hotel with the comfort of a private coastal home.

Choose from waterfront villas with sweeping Atlantic or Florida Bay views, contemporary coastal homes with private pools and outdoor lounges, and airy retreats designed for both focus and downtime. Every stay delivers hotel-grade amenities including ultra fast WiFi, premium linens, pristine housekeeping, and 24/7 concierge.

Each home is expertly operated and looks exactly like the photos, so all you have to do is arrive and unwind.

Destinations near Islamorada

Available soon in Islamorada

Luxury

Front Beach, Paradise Villa, Islamorada FL Keys

7 bedrooms•8 baths

•

New

Save ~$2,130 booking direct

Featured vacation rentals in Islamorada

The Coquina House at Coral Cove

3 bedrooms•3.5 baths

•

New

Save ~$675 booking direct

Luxury

Islamorada Island

6 bedrooms•6 baths

•

Save ~$2,355 booking direct

The Oasis

3 bedrooms•3.5 baths

•

Save ~$640 booking direct

The Meridian at Oceanside Residences

4 bedrooms•4.5 baths

•

New

Save ~$810 booking direct

Luxury

Front Beach, Paradise Villa, Islamorada FL Keys

7 bedrooms•8 baths

•

New

Save ~$2,130 booking direct

Highlights in Islamorada

Discover the sportfishing capital of the world, where turquoise waters, vibrant marine life, and laid-back island charm await your arrival.

Theater of the Sea

Robbie's of Islamorada

History of Diving Museum

Anne's Beach

Lignumvitae Key Botanical State Park

Windley Key Fossil Reef Geological State Park

Indian Key Historic State Park

Florida Keys Brewing Co.

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.

All homes in Islamorada

The Coquina House at Coral Cove

3 bedrooms•3.5 baths

•

New

Save ~$675 booking direct

Luxury

Islamorada Island

6 bedrooms•6 baths

•

Save ~$2,355 booking direct

The Oasis

3 bedrooms•3.5 baths

•

Save ~$640 booking direct

The Meridian at Oceanside Residences

4 bedrooms•4.5 baths

•

New

Save ~$810 booking direct

Sunset + Boat Basin, Islamorada

4 bedrooms•4 baths

•

New

Save ~$195 booking direct

Elevated Retreat, Sunset Access + Boat Basin

2 bedrooms•2 baths

•

New

Save ~$85 booking direct

Sunset Access + Boat Basin, Walkable Islamorada

2 bedrooms•2 baths

•

New

Save ~$85 booking direct

Luxury

Front Beach, Paradise Villa, Islamorada FL Keys

7 bedrooms•8 baths

•

New

Save ~$2,130 booking direct

View all homes

Most popular amenities for vacation rentals in Islamorada

Other popular amenities & vacation types in Islamorada

Family vacation rentals in Islamorada

Large group vacation rentals in Islamorada

Pet-friendly vacation rentals in Islamorada

Beachfront vacation rentals in Islamorada

Hot tub vacation rentals in Islamorada

Private pool vacation rentals in Islamorada

Discover more of Islamorada

Strung across a chain of islands between Key Largo and Marathon, Islamorada sits where the Atlantic meets Florida Bay. Water clarity is exceptional, the flats glow turquoise, and sunsets paint the horizon in saturated color.

Days revolve around blue water adventure. Cast for trophy fish, snorkel luminous reefs at Alligator Reef Light, paddle quiet mangrove creeks, or drift to the famous Islamorada Sandbar. When you slow the pace, browse local galleries and soak up easygoing island culture.

From sunrise boat runs to golden hour by the bay, this island chain invites a slower rhythm without losing sophistication. This is why Wander’s luxury vacation rentals in Islamorada are the perfect choice, whether you are traveling for work or leisure.

FAQs: Vacation Rentals in Islamorada

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

Wander offers a level of consistency and quality you won’t find with most vacation rentals.

Every home in Islamorada 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 Islamorada?

Some of our most popular vacation rentals in Islamorada include The Coquina House at Coral Cove, Wander Islamorada Island, and The Oasis. 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 Islamorada?

Wander offers 8 vacation rentals in Islamorada, 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 Islamorada?

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

Do Wander’s vacation rentals in Islamorada have WiFi access?

Yes. Every Wander home in Islamorada 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.