Islamorada, Florida, is known as the Village of Islands, where calm turquoise waters, sandy coastlines, and a peaceful atmosphere set the tone for an unforgettable getaway. Wander’s luxury vacation rentals in Islamorada give you a place to make the most of it, combining privacy, comfort, and modern amenities in one beautiful setting.
Luxury Vacation Rentals in Islamorada, Florida
Book a Wander with inspiring views, hotel-grade amenities, modern workstations, top-tier cleaning and 24/7 concierge service. It’s a vacation home, but better.
Premium Islamorada, FL, Vacation Homes for a Relaxed Island Escape
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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.
What Makes a Wander Stay Special in Islamorada, Florida
Wander homes in Islamorada are designed for travelers who want flexibility, style, and the space to recharge. The island’s gentle waves and clear water create an incredible backdrop, and your Wander home helps you enjoy it at your own pace.
Guests can expect:
- Bright, comfortable interiors filled with natural light
- Outdoor areas perfect for ocean breezes, grilling, or sunset views
- Functional workspaces and fast Wi-Fi that support remote work
- Friendly guest support to help personalize your itinerary
Whether you plan to spend your days on the water or simply soaking up the warm island sun, Wander’s luxury vacation properties in Islamorada offer a welcoming place to return to.
Best Times to Visit Islamorada
Islamorada’s warm, coastal climate makes it inviting year-round. Here’s what each season has to offer:
- Spring is ideal for snorkeling, sandbar visits, and reef adventures
- Summer brings long days that pair perfectly with paddleboarding and boating
- Fall offers relaxed island energy and great conditions for fishing
- Winter stays bright and warm, creating a peaceful setting for extended getaways
Whenever you arrive, you can count on plenty of sunshine, ocean breezes, and a Wander home designed for comfort.
Plan Your Luxury Islamorada Getaway with Wander
If you’re dreaming of island views and effortless comfort, Wander’s Islamorada homes are ready to welcome you. Enjoy the privacy of a vacation home with the consistency and care of a trusted travel brand.
Discover homes with direct water access, private outdoor spaces, airy interiors, and layouts that work for couples, families, or groups. Every property features reliable Wi-Fi, high-quality cleaning, and the comfort standards Wander is known for, so your stay feels seamless from the moment you walk through the door.
FAQs About Islamorada Luxury Vacation Rental Properties
Do Wander Homes in Islamorada Have Private Outdoor Space?
Many properties feature patios, decks, or waterfront areas designed for relaxing outdoors, enjoying the breeze, or dining under the palm trees.
Is a Rental Car Recommended in Islamorada?
Yes. While the islands are easygoing and walkable in parts, having a car makes it easier to explore restaurants, beaches, boating charters, and nearby Florida Keys attractions.
Where Else Can I Book a Wander Stay?
Beyond Islamorada, Wander offers exclusive vacation homes across the U.S., Canada, Mexico, and beyond, including:
- Sedona, Arizona
- East Hampton, New York
- Lake Tahoe, California
- Telluride, Colorado
- Ponte Vedra Beach, Florida
- Yucatán, Mexico
- Tulum, Mexico
- Punta Cana, Dominican Republic
- Bolívar, Colombia
Wander's properties include beachfront escapes, desert retreats, lakefront homes, forest getaways, and contemporary villas.