Islamorada Boutique Hotels

6 boutique hotels in Islamorada with beachfront access, outdoor pools, and free WiFi. Compare rates, guest scores, and perks. Book now for exclusive deals.

Check-in
Fri, 25 Sept
Check-out
Sat, 26 Sept
Rooms and Guests2 Guests, 1 room
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Check-in
Fri, 25 Sept
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Check-out
Sat, 26 Sept
Rooms and Guests2 Guests, 1 room
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Check-in
Fri, 25 Sept
-
Check-out
Sat, 26 Sept
Rooms and Guests2 Guests, 1 room
2Filter & Sort
View map
View map
1-6 out of 6
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8.5
Great143 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
7.8
Very good779 total reviews
our site & Booking.com
Map
2.4 mi from City Center1.7 mi from Anne s Beach
Private BeachZero-Entry PoolTiki Bar
  • Access to three sister resorts
  • Zero-entry pool with in-pool loungers
  • Complimentary water taxi service
FromUS$ 266 /nightSelect
8.6
Great283 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
7.7
Very good280 total reviews
our site & Booking.com
Private IslandBoat House BarYoga Classes
  • Private island with freshwater pool
  • Complimentary daily yoga sessions
  • Pet-friendly for all dog sizes
FromUS$ 301 /nightSelect
9.0
Perfect1642 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
Great1741 total reviews
our site & Booking.com
Map
2.3 mi from City Center1.6 mi from Anne s Beach
Private BeachHeated PoolBoat Docking
  • 320-ft private oceanfront beach
  • Full kitchens in all units
  • Deep-water boat docking on-site
FromUS$ 142 /nightSelect

Islamorada's boutique hotels combine the laid-back Florida Keys vibe with personalized service and distinctive design. Expect beachfront properties like Amara Cay Resort and Breezy Palms Resort, where you can wake up to sea views, step onto private sand, and spend afternoons by outdoor pools. Most hotels offer free WiFi, some include breakfast, and many place you within minutes of attractions like the History of Diving Museum or Theater of the Sea. Whether you're a couple seeking a romantic hideaway or a family looking for activity-packed stays, these hotels cater to specific moods-from adults-only enclaves to resort-style complexes with watersports and multiple dining options.

Budget-wise, rates vary: boutique options such as Casa Morada offer a more intimate, adults-oriented experience, while Three Waters Resort And Marina provides a larger resort footprint with family-friendly amenities and an adults-only cove. For a balanced stay, Bayside Villas By Islander Resort delivers townhouse-style accommodations with kitchens and direct beach access. To get the most from your visit, consider staying in the Upper Matecumbe Key area, where many properties are clustered, and ask about included perks like bike rentals, kayaks, or shuttle services. With guest scores ranging from 78 to 90, you can book confidently knowing these hotels are consistently rated well for cleanliness, location, and service.