Luxury Hotels in Islamorada

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Luxury Hotels in Islamorada

Popular Islamorada luxury hotels with all you need

Cheeca Lodge & Spa
Private beach, sun loungers, beach umbrellas, beach towels

Cheeca Lodge & Spa

5.0 star property
9.0 out of 10, Wonderful, (1156)
$205 nightly
The price is $231
Aug 26 - Aug 27
Total with taxes and fees
Cheeca Lodge & Spa
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Top neighborhoods in Islamorada

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Matecumbe

Matecumbe gives you the full Florida Keys experience without trying too hard. Snorkel crystal waters at Anne's Beach, grab a cold one at Florida Keys Brewing Co, or watch fishermen haul in their catch at Bud n' Mary's. The Hurricane Monument and Indian Key Historic State Park tell stories of this laid-back paradise, while the MoradaWay Arts District adds cultural flair. Waterfront tiki bars serve fresh mahi-mahi as the sun sets over Florida Bay. Most visitors stay in charming resorts with private beaches and pools, though vacation rentals offer more space. You'll need a car to explore properly, but many resort areas are perfectly walkable.

Anne’s beach is on Lower Matecumbe Key

Lower Matecumbe Beach

Lower Matecumbe Beach offers pristine Atlantic shorelines where powder-soft sand meets crystal-clear turquoise waters. Sunset Drive Beach and nearby Anne's Beach provide perfect spots for swimming and sunbathing in the shallow, calm waters. You'll discover scenic overlooks at mile markers, historic fishing piers extending into Florida Bay, and the popular Founder's Park with its recreational facilities. Waterfront seafood restaurants serve fresh mahi-mahi and key lime pie with stunning ocean views. Accommodations range from luxury beachfront resorts to intimate bed-and-breakfasts. Getting around requires a rental car, though the beachfront areas are highly walkable with bike-friendly roads.

Venetian Shores

Venetian Shores offers the Keys dream—canal-front homes with private docks where dolphins practically introduce themselves at breakfast. Spend your days boating from your backyard to snorkeling spots or fishing the flats between the Atlantic and Florida Bay. This upscale residential enclave lets you live like a local without the tourist crowds. You'll need wheels to explore nearby attractions like Founders Park and the History of Diving Museum. The neighborhood itself has no restaurants or shops—just peaceful streets lined with luxury vacation rentals featuring pools and tropical gardens. For dining out, a quick 5-10 minute drive takes you to Islamorada's waterfront eateries.

Coastline of Islamorada, panoramic view at dusk

Seabreeze Trailer Park

Seabreeze Trailer Park offers a laid-back slice of Florida Keys paradise without the resort price tag. You'll get direct beach access for swimming and snorkeling in crystal-clear waters. Nearby Founders Park and Windley Key Fossil Reef Geological State Park provide perfect day trips. Rain Barrel Village offers local shopping when you need a break from all that sunshine. Seafood restaurants and waterfront dining options are just a short drive away in Islamorada. While public transit is limited, having a rental car or golf cart makes exploring the surrounding Keys a breeze. The peaceful, no-frills atmosphere makes this spot ideal for travelers seeking an authentic Keys experience on a budget.

Top landmarks in Islamorada

Theater of the Sea
Theater of the Sea

Theater of the Sea

Get lost in halls of wondrous fish and exotic marine mammals at Theater of the Sea, located 2.3 mi (3.7 km) from central Islamorada. Hotels.com travelers also say the area is family-friendly and has lots of nice beaches. If you'd also like to explore some of the parks in Islamorada, Islamorada County Park and Founders Park are both nearby.

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Anne's Beach
Anne\'s Beach featuring a bridge

Anne's Beach

If you can't wait to get to the beach, you might enjoy a trip to Anne's Beach located 8.8 mi (14.1 km) from central Islamorada. If you want to continue walking by the waves, head to Sunset Drive Beach located nearby.

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Frequently asked questions

What are the best luxury hotels in Islamorada?
Guests can't get enough of Islander Resort. You can take advantage of treatment rooms and concierge services at this Islamorada luxury hotel.
What are the cheapest luxury hotels in Islamorada?
Live the luxe life for less when you stay in an affordable luxury hotel in Islamorada from $145 on your next adventure. If you're on a budget, use our "Price: low to high" filter to look for upscale properties within your price range. Be on the lookout for discounts to help make your getaway even more affordable. You can also become a member of our rewards program to access Member Prices and earn discounts on future stays.
What is the best time to stay in a luxury hotel in Islamorada?
If you're after the warmest weather, organize your trip for August. The temperatures are around 84ºF (29ºC) to 86ºF (30ºC) at this time. January has the coolest temperatures between 68ºF (20ºC) and 72ºF (22ºC). For a more relaxed setting and potentially more affordable luxury hotels in Islamorada, visit in October when it's less busy.
Are there any luxury hotels in Islamorada with parking?
Search for luxury hotels in Islamorada on Hotels.com. Then use the "Parking" filter under "Amenities" to find options with room for your ride. If you're planning to explore by car, these stays give you the convenience you need to hit the road whenever you like.
Are all taxes and fees included in the Islamorada hotel prices shown on Hotels.com?
Hotels.com provide upfront pricing so you can relax knowing you won't be met with surprise additional fees or taxes when you're ready to confirm your booking. From the time you start your search on Hotels.com, the price you see is what you pay. This makes it much easier to compare properties and secure our best deal for your next getaway.