5 signature stays  

$600/night

Hooked on Islamorada

OwnerRez
3 Bedrooms • 3 Baths • Sleeps 1-6
Internet Oceanfront Pool
Escape to Peaceful Palms in Islamorada, a luxury oceanfront 3BR/3BA townhouse with sunrise views, private dock access, an oceanfront pool, and walkable dining. Enjoy a fully stocked kitchen, balconies, fast Wi-Fi, Smart TVs, and resort-style amenities. Perfect for boating, fishing, family vacations, or relaxing Keys getaways. Pet-friendly with approval. 7-night minimum stay. Managed by Florida Keys Signature Stays. A 4% non-refundable credit card fee applies.

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$180/night

Incommunicado

OwnerRez
3 Bedrooms • 2 Baths • Sleeps 1-8
Internet Ocean Pool
Enjoy the best of Islamorada from this spacious 2 bedroom, 2 bath townhome with loft, comfortably sleeping up to 8 guests. Relax by the brand new resort-style pool, clubhouse, and sandy Florida Bay beach, where spectacular Keys sunsets await. Conveniently located just 1 hour from Miami and 2 hours from Key West.

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$300/night

Port Palermo

OwnerRez
4 Bedrooms • 2 Baths • Sleeps 1-8
Allows pets Internet Near Ocean
Port Palermo – Islamorada Waterfront Retreat
Classic ground-level Keys home with 120' of concrete dockage and immediate bay and ocean access. Sleeps 7 comfortably with 3 bedrooms plus a futon. Enjoy the updated kitchen with stainless appliances and a spacious open floor plan perfect for entertaining. Minutes from marinas, restaurants, shopping, fishing charters, and adventure tours. Conveniently located just 1 hour from Miami and 2 hours from Key West.

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$300/night

Surf Shack

OwnerRez
2 Bedrooms • 2 Baths • Sleeps 1-4
Internet Ocean View Downtown
Welcome to Surf Shack, a cozy beach bungalow in downtown Islamorada. Enjoy exclusive access to a white sandy residents-only beach just steps away. This 2BR/2BA retreat features relaxed Keys charm, an outdoor shower, and breezy outdoor dining.
Bring your boat—dockage, ramp, and trailer storage included. Kite surf, fish, snorkel, kayak, or hit the sandbar. Walk to top restaurants and shops. Concierge services available for a seamless stay.

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$400/night

Uncertain Tides

OwnerRez
4 Bedrooms • 3 Baths • Sleeps 1-12
Allows pets Internet Near Ocean Private Pool
Escape to this waterfront retreat in one of Islamorada’s most desired neighborhoods. This 4BR/3BA home sleeps 12, of which includes a private 1BR/1BA apartment downstairs. Enjoy a heated/chilled saltwater pool, two boat slips with lifts, dock, fish cleaning station, kayak, paddle boards, bikes, gazebo, fire table, grill, and Blackstone. Quick bay and ocean access via Tavernier Creek. Close to world-class fishing, diving, dining, and sunsets.

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