Business Hotels in Islamorada

October 2026
November 2026

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Next weekend
Sep 25 - Sep 27
In two weeks
Oct 2 - Oct 4

Business Hotels in Islamorada

1. Cheeca Lodge & Spa

Cheeca Lodge & Spa
Matecumbe
$149
$241 total
includes taxes & fees
Sep 21 - Sep 22
Cheeca Lodge & Spa

2. Islander Resort

Islander Resort
Matecumbe
$196
$288 total
includes taxes & fees
Sep 27 - Sep 28
Islander Resort

3. Lime Tree Bay Resort

Lime Tree Bay Resort
Long Key
$124
$184 total
includes taxes & fees
Oct 4 - Oct 5
Lime Tree Bay Resort

4. Dove Creek Resort & Marina, Trademark Collection by Wyndham

Dove Creek Resort & Marina, Trademark Collection by Wyndham
Key Largo
$94
$137 total
includes taxes & fees
Sep 27 - Sep 28
Dove Creek Resort & Marina, Trademark Collection by Wyndham

5. Bayside Inn Key Largo

Bayside Inn Key Largo
Key Largo
$118
$158 total
includes taxes & fees
Sep 21 - Sep 22
Bayside Inn Key Largo

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

Baker's Cay Resort Key Largo, Curio Collection by Hilton
Key Largo
$237
$322 total
includes taxes & fees
Sep 29 - Sep 30
Baker's Cay Resort Key Largo, Curio Collection by Hilton

7. Playa Largo Resort & Spa, Autograph Collection

Playa Largo Resort & Spa, Autograph Collection
Rock Harbor
$263
$351 total
includes taxes & fees
Oct 4 - Oct 5
Playa Largo Resort & Spa, Autograph Collection

8. Hampton Inn Key Largo Manatee Bay

Hampton Inn Key Largo Manatee Bay
Key Largo
$130
$147 total
includes taxes & fees
Sep 28 - Sep 29
Hampton Inn Key Largo Manatee Bay

9. Courtyard by Marriott Key Largo

Courtyard by Marriott Key Largo
Key Largo
$143
$161 total
includes taxes & fees
Sep 27 - Sep 28
Courtyard by Marriott Key Largo

10. Hampton Inn Marathon - Florida Keys

Hampton Inn Marathon - Florida Keys
Marathon
$130
$147 total
includes taxes & fees
Sep 27 - Sep 28
Hampton Inn Marathon - Florida Keys

11. Siesta Motel

Siesta Motel
Marathon
$74
$83 total
includes taxes & fees
Sep 21 - Sep 22
Siesta Motel

12. Gilbert's Resort

Gilbert's Resort
Key Largo
$237
$267 total
includes taxes & fees
Sep 21 - Sep 22
Gilbert's Resort

13. Fairfield Inn & Suites by Marriott Marathon Florida Keys

Fairfield Inn & Suites by Marriott Marathon Florida Keys
Marathon
$134
$151 total
includes taxes & fees
Sep 27 - Sep 28
Fairfield Inn & Suites by Marriott Marathon Florida Keys

14. Skipjack Resort & Marina

Skipjack Resort & Marina
Marathon
$159
$219 total
includes taxes & fees
Sep 21 - Sep 22
Skipjack Resort & Marina
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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 beach with a wooden structure, clear blue sky, and dense green foliage.

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 white tower with a dome, surrounded by palm trees and greenery.

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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About the destination

Visitors really like Islamorada, especially its seaside, entertainment, and seafood. Enjoy fun activities like fishing and diving. You can easily spend a relaxing day visiting Founders Park and Everglades National Park. You might find that sights like Bud n' Mary's Dive Center and Robbie’s of Islamorada are worth a visit.