Places to Stay

The Caribbean Resort in Islamorada offers 22 private, Caribbean-style homes with ocean views, a beach-entry pool, fishing pier, and complimentary use of bicycles, kayaks, and paddleboards.

Florida Keys Vacation Rentals makes finding your perfect Keys getaway easy, featuring a wide selection of beachfront homes and condos from Key Largo to Key West—book securely with a trusted local provider.

Escape to Islander Resort: vibrant Florida Keys stays, beachside dining, and endless adventures!

Keys Holiday Rentals offers vacation homes and condos in Islamorada, Florida Keys, perfect for waterfront stays, fishing trips, and family getaways.

Osprey Bay Villa is a luxurious 5-bedroom, 3-bathroom bayfront home in Islamorada, offering a private pool, hot tub, deep-water dock, and breathtaking sunset views, accommodating up to 10 guests.

Discover Island Villa: Luxury Florida Keys getaways await.

Luxurious 4BR/4BA Keys rental with pool, dock, and canal views.

Pines & Palms Resort — a boutique, ocean-front retreat in Islamorada offering a peaceful Keys-style village with cottages and suites.

Coconut Cove Beach Resort & Marina is a family-friendly, waterfront resort in Islamorada, offering a zero-entry pool, private beach, and event spaces for weddings and private functions. Located on a 7-acre tropical estate, it's ideal for both relaxation and special events.

Fisher Inn Resort & Marina is an oceanfront boutique resort in Islamorada offering stylish rooms with kitchenettes, a heated pool with ocean views, and unique amenities like its own boat ramp and marina. Ideal for anglers, boaters, and families seeking waterfront comfort.

Discover unforgettable Florida Keys vacations with cozy condos to oceanfront estates!

White Gate Court is a charming, pet-friendly boutique resort nestled on three lush acres in Islamorada, offering seven unique cottages with old Keys-style charm.

Cheeca Lodge & Spa is a luxury oceanfront resort in Islamorada, offering elegant rooms, a 9-hole golf course, multiple dining options, and a full-service spa. Ideal for couples and families seeking a tranquil Keys getaway.

Coral Bay Resort is a waterfront resort in Islamorada offering spacious accommodations, private balconies, a heated pool, and direct access to the bay. Ideal for relaxation and water activities.