Islamorada Resorts: Your Guide to Waterfront Stays

Compare 6 top-rated Islamorada resorts, from family-friendly beachfront to adults-only coves. Check rates, free parking, and private beach access. Book now!

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Rooms and Guests2 Guests, 1 room
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1-6 out of 6
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9.4
Perfect781 total reviews
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3.2 km from City Centre2.0 km from Anne s Beach
Private BeachHeated PoolFishing Charters
  • Complimentary kayaks and paddleboards
  • Old Florida-style beach cottages
  • Heated pool with Tiki bar
FromC$ 187 /nightSelect
8.2
Great774 total reviews
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1.1 km from City Centre200 m from Anne s Beach
Fishing PierGolf CourseAdult Pool
  • 525-foot fishing pier in Florida Keys
  • Jack Nicklaus-designed golf course
  • Adult-only pool with butler service
FromC$ 259 /nightSelect
9.0
Perfect1642 total reviews
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600 m from City Centre500 m from Upper Matecumbe Key
Private BeachRooftop PoolPuttTek Course
  • Largest beachfront in Islamorada
  • Private screened porches in rooms
  • On-site flame-grilled dining
FromC$ 285 /nightSelect
8.5
Great143 total reviews
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Adults-Only CoveSwim-Up BarWater Taxi
  • Adults-only cove with private beach
  • Only swim-up bar in the Keys
  • Free water taxi to sister resorts
FromC$ 252 /nightSelect
8.6
Great283 total reviews
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1.9 km from City Centre800 m from Anne s Beach
Heated PoolFishing DockShuttle Service
  • Spacious townhomes with full kitchens
  • Private pools for select units
  • Direct fishing on-site at dock
FromC$ 267 /nightSelect
8.4
Great931 total reviews
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2.0 km from City Centre300 m from Islamorada
Private BeachKayak RentalsBreakfast Delivery
  • Private beach with loungers
  • Free kayak and paddleboard
  • Personalized breakfast delivery
FromC$ 208 /nightSelect

Islamorada, often called the Sportfishing Capital of the World, offers a collection of resorts that cater to different travel styles. At Three Waters Resort And Marina, the main area buzzes with family-friendly pools, a kids' arcade, and watersports like paddleboarding and kayaking, while The Cove provides an adults-only retreat for those seeking quiet. The Pines & Palms Resort, a short walk from the beach, features fully equipped kitchens, a private beach area, and a Tiki Bar, perfect for couples or families wanting a self-catering base. These resorts typically offer free WiFi, parking, and multiple pools, with nightly rates ranging from $200 to $500 depending on season and room type.

For a more tranquil stay, Chesapeake Beach Resort offers oceanfront rooms with balconies, an outdoor pool with sea views, and easy access to the History of Diving Museum. Meanwhile, Bayside Villas By Islander Resort provides townhouses with full kitchens and laundry facilities, ideal for extended stays, and is just minutes from snorkeling and diving spots. All these resorts lie along the Overseas Highway, giving you quick access to local attractions like Theater of the Sea. When booking, consider your priority: beachfront, family amenities, or adult-only seclusion-and remember that during peak season (December to April), it's wise to reserve well in advance.