Places to Stay

Oceanfront condos in Islamorada with stunning views, pool, tennis, and beach fun!

Topsider Resort is a unique beachfront retreat in Islamorada, featuring charming octagonal stilted bungalows perched over the bay.

Cheeca Lodge & Spa is a luxury oceanfront resort in Islamorada, offering upscale accommodations, a 9-hole golf course, spa services, and a private beach with water sports activities. Ideal for couples and families seeking a tranquil Keys getaway.

Little Basin Villas offers 3-bedroom, 3.5-bathroom waterfront townhomes with private balconies, a heated pool, and boat dockage in Islamorada’s Art District.

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.

Breezy Palms Resort offers a family-friendly, oceanfront experience with accommodations including poolside apartments, two-bedroom units, beach cottages, oceanfront apartments, and bungalows.

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

Mermaid’s Bay is a secluded boutique estate in Islamorada, offering three private waterfront homes with resort-style amenities, ideal for group getaways

Florida Keys Brewing Co. is the Upper Keys’ first microbrewery, serving award-winning craft beers in a vibrant beer garden and taproom located in Islamorada’s Morada Way Arts District—perfect for beer lovers and locals alike. Also offers a vacation rental.

Cozy, family-run motel in the heart of Islamorada, Florida Keys paradise.

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

Drop Anchor Resort & Marina offers oceanfront accommodations with full kitchens, a heated pool, complimentary kayaks, paddleboards, and bicycles, all set in a tropical garden atmosphere. Ideal for couples and families seeking a relaxing Florida Keys getaway.

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.

Islamorada Vacation Rentals offers a curated selection of vacation homes and cottages in the Florida Keys, providing travelers with diverse options for a memorable stay.