Luxury Hotels in Islamorada

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Sep 8 - Sep 9
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Sep 9 - Sep 10
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Sep 11 - Sep 13
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Sep 18 - Sep 20

Luxury Hotels in Islamorada

The Islands of Islamorada

The Islands of Islamorada
Matecumbe
  • On the beach
  • Hot tub
  • Poolside bar
  • Concierge services
$450
$570 total
includes taxes & fees
Sep 9 - Sep 10
The Islands of Islamorada

Playa Largo Resort & Spa, Autograph Collection

Playa Largo Resort & Spa, Autograph Collection
Rock Harbor
  • On the beach
  • Beachfront dining
  • Full-service spa
  • Poolside bar
  • Concierge services
$255
$342 total
includes taxes & fees
Sep 21 - Sep 22
Playa Largo Resort & Spa, Autograph Collection

Baker's Cay Resort Key Largo, Curio Collection by Hilton

Baker's Cay Resort Key Largo, Curio Collection by Hilton
Key Largo
  • On private beach
  • Beachfront dining
  • Hot tub
  • Poolside bar
  • Concierge services
$237
$322 total
includes taxes & fees
Sep 28 - Sep 29
Baker's Cay Resort Key Largo, Curio Collection by Hilton

Islander Resort

Islander Resort
Matecumbe
  • On private beach
  • Beachfront dining
  • 24-hour gym
  • Poolside bar
  • Concierge services
$196
$288 total
includes taxes & fees
Sep 14 - Sep 15
Islander Resort

Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort

Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort
Islamorada
  • On private beach
  • 4 restaurants
  • 24-hour gym
  • Poolside bar
$183
$279 total
includes taxes & fees
Sep 14 - Sep 15
Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort

La Siesta Resort & Villas

La Siesta Resort & Villas
Matecumbe
  • On private beach
  • Poolside bar
La Siesta Resort & Villas

Cheeca Lodge & Spa

Cheeca Lodge & Spa
Matecumbe
  • On private beach
  • Beachfront dining
  • Full-service spa
  • 2 poolside bars
  • Concierge services
$149
$241 total
includes taxes & fees
Sep 9 - Sep 10
Cheeca Lodge & Spa

Amara Cay Resort

Amara Cay Resort
Matecumbe
  • On private beach
  • Ocean-view dining
  • Poolside bar
$155
$247 total
includes taxes & fees
Sep 21 - Sep 22
Amara Cay Resort

Villas At Hawks Cay Resort

Villas At Hawks Cay Resort
Marathon
  • On private beach
  • Ocean-view dining
  • Full-service spa
  • 2 poolside bars
  • Concierge services
$379
$488 total
includes taxes & fees
Sep 13 - Sep 14
Villas At Hawks Cay Resort

Reefhouse Resort & Marina

Reefhouse Resort & Marina
Key Largo
  • On private beach
  • Beachfront dining
  • Full-service spa
  • Poolside bar
  • Concierge services
$219
$286 total
includes taxes & fees
Sep 9 - Sep 10
Reefhouse Resort & Marina

Grassy Flats Resort & Beach Club

Grassy Flats Resort & Beach Club
Marathon
  • Ocean-view dining
  • Hot tub
  • Poolside bar
  • Concierge services
$217
$293 total
includes taxes & fees
Sep 20 - Sep 21
Grassy Flats Resort & Beach Club

Hawks Cay Resort

Hawks Cay Resort
Marathon
  • On private beach
  • Ocean-view dining
  • Full-service spa
  • 2 poolside bars
  • Concierge services
$185
$286 total
includes taxes & fees
Sep 14 - Sep 15
Hawks Cay Resort
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Top neighborhoods in Islamorada

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.

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.

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

A sandy beach with green vegetation and a calm sea.

Anne's Beach

7.8/10 (597 reviews)
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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A marina with boats docked, a motel, and a cafe.

Bud n' Mary's Dive Center

8.8/10 (504 reviews)
You can stroll along Bud n' Mary's Dive Center for relaxing water views when you're in Matecumbe. Hotels.com travelers also say the area is relaxing and has lots of nice beaches.
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A modern architectural structure with a white canopy, surrounded by a well-maintained grassy area and concrete pathways.

Founders Park

8.8/10 (450 reviews)
Founders Park is 4.6 mi (7.4 km) from central Islamorada, why not stop by during your stay. Why not take a stroll along the beaches and watch the sunset while you're here? Want to stretch your legs some more? Head to Islamorada County Park, just a short walk away.
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A colorful building with a sign reading "Florida Keys Brewing Co." and a Santa Claus decoration.

Florida Keys Brewing Co.

9.2/10 (520 reviews)
Matecumbe is home to Florida Keys Brewing Co., so why not stop by during your stay in Islamorada.
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A small green leaf growing on a rough, textured surface.

Windley Key Fossil Reef Geological State Park

8.8/10 (184 reviews)
Windley Key Fossil Reef Geological State Park is 2.4 mi (3.8 km) from central Islamorada, why not stop by during your stay. Hotels.com travelers also say the area is family-friendly and has lots of nice beaches.
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Robbie’s of Islamorada

8.4/10 (15 reviews)
You can stroll along Robbie’s of Islamorada for relaxing water views when you're in Matecumbe.
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Islamorada County Park

8.8/10 (198 reviews)
Islamorada County Park is 4.5 mi (7.2 km) from central Islamorada, why not stop by during your stay. Why not take a stroll along the beaches and watch the sunset while you're here? Want to stretch your legs some more? Head to Founders Park, just a short walk away.
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Islamorada Brewery & Distillery

9.4/10 (8 reviews)
Matecumbe is home to Islamorada Brewery & Distillery, so why not stop by during your stay in Islamorada.
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