Compare Hotels with Tennis Courts in Islamorada

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Featured Islamorada Hotels with Tennis Courts

Cheeca Lodge & Spa

81801 Overseas Highway, Mile Marker 82, Marker 82, Islamorada, FL

$290

per night

May 23 - May 24

Free Cancellation

Reserve now, pay when you stay

With a stay at Cheeca Lodge & Spa in Islamorada (Matecumbe), you'll be a 4-minute walk from Matecumbe United Methodist Church and 6 minutes by foot from Florida Keys Brewing Co..

Pool

On private beach

Chesapeake Beach Resort

83409 Overseas Hwy, Islamorada, FL

$179

per night

Apr 30 - May 1

Free Cancellation

Reserve now, pay when you stay

Located in Islamorada (Matecumbe), Chesapeake Beach Resort is within a 5-minute drive of History of Diving Museum and Windley Key Fossil Reef Geological State Park.

Guarantee Best Sunsets in the Keys!

A stay at this vacation home places you in the heart of Islamorada, within a 5-minute drive of History of Diving Museum and Matecumbe United Methodist Church.

RESERVE QUICKLY! YOU’LL LOVE IT! EVERYONE DOES!

With a stay at this condo in Tavernier, you'll be on the beach, within a 15-minute drive of Jimmy Johnson's Big Chill and Florida Keys Dive Center.

Topsider Resort by Capital Vacations

75500 Overseas Hwy, Islamorada, FL

With a stay at this condo in Islamorada (Matecumbe), you'll be steps from Sunset Drive Beach and a 2-minute drive from San Pedro Underwater Archaeological Preserve State Park.

Pelican Cove Resort & Marina

84457 Overseas Highway, Islamorada, FL

Located in Islamorada, Pelican Cove Resort & Marina is by the ocean, within a 5-minute drive of Windley Key Fossil Reef Geological State Park and History of Diving Museum.

Pool

On private beach

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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.

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Islamorada hotels essential information

Accommodation	2,093 hotels
Lowest Price	$179
Highest Price	$290
Popular hotels	Cheeca Lodge & Spa, Chesapeake Beach Resort, Guarantee Best Sunsets in the Keys!, RESERVE QUICKLY! YOU’LL LOVE IT! EVERYONE DOES!, Topsider Resort by Capital Vacations, Pelican Cove Resort & Marina

Most Recent Islamorada Hotel Reviews

Chesapeake Beach Resort

5 out of 5

Posted 2 days ago

CheapTickets Verified Review

"This is my first time on the property since the remodel. It was a great stay and very clean. Love what they did with the place. The staff was great, super attentive, and super nice. The price for the hotel was great for what you get. And better than other hotels in the area which do not look as good as this. The only item I would like to see improved is the boat dock area. They should put some funds into this area so people can park their boats temporarily. I have booked my Memorial trip already and will be back. :) "

A verified traveler stayed at Chesapeake Beach Resort