Islamorada Boutique Hotels

Every hotel in Islamorada, United States is carefully verified and handpicked for your stay.
Check-in
20Mar2026Select date
Check-out
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Rooms and Guests2 Guests, 1 Room
Islamorada is home to the beautiful Anne's Beach, the historic Windley Key Fossil Reef Geological State Park, and the popular Theater of the Sea, where you can enjoy marine life shows. This tropical paradise boasts a range of hotels with beach access that cater to different tastes. From charming boutique hotels to larger resorts with ocean views, each option offers unique amenities and experiences, hand-picked for their excellent reviews. For your stay, consider booking early, especially during winter months, to secure the best hotels for a fun-filled trip.
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Map2.4 mi from City Centre1.7 mi from Anne s Beach
FromUS$ 266 /nightSelect
FromUS$ 180 /nightSelect
Map1.2 mi from City Centre900 yd from Anne s Beach
FromUS$ 191 /nightSelect
FromUS$ 617 /nightSelect
Map600 yd from City Centre500 yd from Upper Matecumbe Key
FromUS$ 204 /nightSelect
Map2.3 mi from City Centre1.6 mi from Anne s Beach
FromUS$ 142 /nightSelect

Prices table for hotels in Islamorada

We are happy to offer accommodations for every travel style and budget.

⬆️ The highest price
US$ 617
⬇️ The lowest price
US$ 142
💸 Average price for
5-star hotels
US$ 560
4-star hotels
US$ 205
3-star hotels
US$ 129

Finest boutique hotels across Islamorada

Insights and ratings from travelers who stayed

Charming tropical escape with lush gardens:
Casa Morada
Family friendly resort with fun activities:
Islander Resort
Stunning waterfront views from every room:
Amara Cay Resort
Intimate boutique experience by the beach:
Breezy Palms Resort
Luxurious villas with private docks:
Bayside Villas By Islander Resort
Unique nautical themed accommodations:
Three Waters Resort And Marina, Islamorada, A Tribute Portfolio Resort

Questions about Islamorada boutique hotels

Helping you plan your trip

What is the cheapest month to book a hotel in Islamorada?
The cheapest month to book a hotel in Islamorada is typically September, with an approximate average price of $107. The most expensive month is December, averaging around $405. A good hotel recommendation for budget travelers is Breezy Palms Resort.
What is the cheapest day to stay in a hotel in Islamorada?
The cheapest day to stay in a hotel in Islamorada is generally Wednesday, with an approximate average nightly price of $110. Conversely, Saturday is often the most expensive day, averaging about $160. A great option for staying is the Islander Resort.
How much is a hotel in Islamorada tonight?
Tonight, hotel prices in Islamorada start as low as $107, with an average price rising to about $130 based on the last 72 hours. For a comfortable stay, consider the Amara Cay Resort.
How far ahead should you book?
To save money, it's recommended to book a hotel in Islamorada approximately 3 months in advance, with the lowest price found being $107. For a pleasant stay, the Casa Morada is a fantastic choice.

Stay Hacks for Islamorada

Discover simple strategies to enhance your stay in the beautiful Islamorada, known for its stunning waters and laid-back vibe.

Fast Fact: Did you know? Approximately 75% of hotels in Islamorada provide complimentary water sports equipment, like Amara Cay Resort with its complimentary kayak rentals.

Local Hack: Instead of dining out, consider picking up fresh fish from local markets and asking your hotel if they can grill it for you.

Hidden Gem: Check out the Florida Keys History and Discovery Center (12 mins from the main hotel area) for insightful exhibits on local culture that tourists often overlook.

Smart Tip: Weekend bookings average 20% higher than weekdays, so if your schedule allows, plan your stay from Sunday to Thursday for better rates.

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Check-in
20Mar2026Select date
Check-out
21Mar2026Select date
Rooms and Guests2 Guests, 1 Room