Islamorada Resorts on the Beach

Compare 7 top-rated Islamorada beach resorts with private beaches, pools, and free parking. Check rates and book your oceanfront escape now!

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Rooms and Guests2 Guests, 1 room
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Check-in
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Rooms and Guests2 Guests, 1 room
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Check-in
Fri, 07 Aug
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Check-out
Sat, 08 Aug
Rooms and Guests2 Guests, 1 room
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1-7 out of 7
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  • Price: high to low
  • Guest rating: high to low
  • Popularity: high to low
8.3
Great816 total reviews
our site & Booking.com
Map
1246 yd from City Center131 yd from Anne s Beach
Fishing PierAdult PoolGolf Course
  • Longest fishing pier in Keys
  • Adults-only pool with butler
  • Jack Nicklaus golf course
FromUS$ 185 /nightSelect
8.6
Great623 total reviews
our site & Booking.com
Private BeachSwim-up BarWater Taxi
  • Adults-only cove with private beach
  • Keys' only swim-up bar
  • Complimentary water taxi included
FromUS$ 180 /nightSelect
8.6
Great288 total reviews
our site & Booking.com
Map
1.2 mi from City Center838 yd from Anne s Beach
Private PoolsShuttle ServiceFishing Dock
  • Two-bedroom townhouse with full kitchen
  • Full access to sister resort's pools
  • On-site fishing dock for anglers
FromUS$ 191 /nightSelect
8.6
Great938 total reviews
our site & Booking.com
Map
1.2 mi from City Center231 yd from Islamorada
Private BeachHeated PoolComplimentary Kayaks
  • Guest-only private beach
  • Complimentary kayaks & paddleboards
  • Personalized breakfast delivery
FromUS$ 149 /nightSelect
9.0
Perfect1685 total reviews
our site & Booking.com
Map
571 yd from City Center487 yd from Upper Matecumbe Key
Private BeachDiscovery CenterBayside Villas
  • Islamorada's largest private beach
  • On-site Florida Keys History Center
  • Bayside Villas with private pool
FromUS$ 204 /nightSelect
8.1
Great423 total reviews
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Map
2.6 mi from City Center115 yd from Windley Key
Saltwater PoolPrivate BeachBoat Launch
  • Free kayaks and paddleboards
  • Retro Old Florida charm
  • Private beach with hammocks
FromUS$ 274 /nightSelect
9.3
Perfect797 total reviews
our site & Booking.com
Map
2.0 mi from City Center1.3 mi from Anne s Beach
Private BeachHeated PoolTiki Bar
  • Complimentary kayaks and paddleboards
  • Private beach with sunset views
  • Old Florida-style cottages
FromUS$ 134 /nightSelect

Islamorada's beach resorts offer direct access to the Florida Keys' turquoise waters, with amenities ranging from private beaches and multiple pools to on-site dining and watersports. Budgets vary from mid-range options like Pines & Palms to luxury escapes like Cheeca Lodge & Spa. Most resorts are along the oceanfront on Upper Matecumbe Key or Windley Key. Expect free parking, WiFi, and family-friendly facilities. For a quieter stay, consider adults-only sections like The Cove at Three Waters.

Cheeca Lodge & Spa stands out with its 9-hole golf course and 160-meter fishing pier. Islander Resort offers spacious lanais and two pools directly on the beach. Three Waters Resort features 12 dining venues and a water taxi. Pines & Palms provides full kitchens and kayak rentals. Chesapeake Beach Resort and Drop Anchor Resort are budget-friendly with ocean views and marina access. Bayside Villas by Islander Resort offers townhouses with kitchens steps from the beach.