6 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 3% non-refundable credit card fee applies.

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$950/night

Islamorada Palm Cove

OwnerRez
2 Bedrooms • 3 Baths (2 full, 1 half) • Sleeps 1-4
Internet Ocean View Private Pool
Islamorada Palm Cove is a private, gated two-bedroom sanctuary in Islamorada, set on a protected lagoon with private dockage, boat ramp, and direct access to Florida Bay and the Atlantic. Unwind in the sparkling pool surrounded by lush palms. Peaceful and refined, yet moments from Islamorada’s finest dining, shopping, and world-class boating.

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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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$800/night

Sunset Shores

OwnerRez
4 Bedrooms • 3 Baths • Sleeps 1-10
Internet Oceanfront Private Pool
This private waterfront home on the open Florida Bay features four bedrooms, three baths, a screened-in pool, a gourmet kitchen, and an expansive dock perfect for boating and sunsets. Gated and fully fenced, it offers spacious indoor and outdoor areas for relaxing or entertaining. Sleeping up to ten guests, it provides the ideal setting for a comfortable and memorable Key Largo getaway.

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$325/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
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, boat slip with lift, 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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