Compare Adventure Sport Hotels in Islamorada

Name: Drop Anchor
Price range: $182

Secret Bargains - Save an extra 10% or more on select Adventure Sport Hotels

Get more for your budget and save up to 50% off select Secret Bargain hotels

Get even more value with CheapTickets Price Guarantee!

Change your flight without a fee on select flights

Featured Islamorada Adventure Sport Hotels

Cheeca Lodge & Spa

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

$364

includes taxes & fees

$323 per night

Jan 8 - Jan 9, 2025

With a stay at Cheeca Lodge & Spa in Islamorada (Matecumbe), you'll be a 4-minute walk from Matecumbe United Methodist Church and 5 minutes by foot from Florida Keys Brewing Co..

On private beach

Pool

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

84001 Overseas Hwy, Islamorada, FL

$503

includes taxes & fees

$447 per night

Jan 8 - Jan 9, 2025

Free Cancellation

Reserve now, pay when you stay

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

On private beach

Pool

Amara Cay Resort

80001 Overseas Hwy, Islamorada, FL

$345

includes taxes & fees

$306 per night

Jan 5 - Jan 6, 2025

Free Cancellation

Reserve now, pay when you stay

With a stay at Amara Cay Resort in Islamorada (Matecumbe), you'll be a 4-minute walk from Bud n' Mary's Dive Center and 13 minutes by foot from Indian Key Historic State Park.

La Siesta Resort & Villas

80241 Overseas Highway, Islamorada, FL

$319

includes taxes & fees

$283 per night

Jan 15 - Jan 16, 2025

Free Cancellation

Reserve now, pay when you stay

With a stay at La Siesta Resort & Villas in Islamorada (Matecumbe), you'll be within a 15-minute walk of Indian Key Historic State Park and Bud n' Mary's Dive Center.

Islander Resort

82100 Overseas Highway, Islamorada, FL

$368

includes taxes & fees

$327 per night

Jan 20 - Jan 21, 2025

Free Cancellation

Reserve now, pay when you stay

With a stay at Islander Resort in Islamorada (Matecumbe), you'll be steps from Keys History & Discovery Center and 9 minutes by foot from Islamorada Brewery & Distillery.

On private beach

Pool

Casa Morada

136 Madeira Road, Islamorada, FL

$521

includes taxes & fees

$471 per night

Jan 16 - Jan 17, 2025

With a stay at Casa Morada in Islamorada (Matecumbe), you'll be a 5-minute walk from Islamorada Brewery & Distillery and 9 minutes by foot from Keys History & Discovery Center.

Pool

Breakfast included

Conch On Inn Motel

103 Caloosa Street, Tavernier, FL

Located in Tavernier (Indian Waterways), Conch On Inn Motel is within a 5-minute drive of Old Road Gallery and Florida Keys Dive Center.

Pines & Palms Resort

80401 Old Hwy, Islamorada, FL

$297

includes taxes & fees

$264 per night

Jan 12 - Jan 13, 2025

With a stay at Pines & Palms Resort in Islamorada (Matecumbe), you'll be a 5-minute walk from Indian Key Historic State Park and 12 minutes by foot from Bud n' Mary's Dive Center.

On private beach

Pool

Chesapeake Beach Resort

83409 Overseas Hwy, Islamorada, FL

$319

includes taxes & fees

$289 per night

Jan 20 - Jan 21, 2025

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.

Hadley Resort and Marina

82749 Overseas Hwy, Islamorada, FL

$232

includes taxes & fees

$207 per night

Jan 26 - Jan 27, 2025

Free Cancellation

Reserve now, pay when you stay

With a stay at Hadley Resort and Marina in Islamorada (Matecumbe), you'll be within a 10-minute walk of Islamorada Brewery & Distillery and History of Diving Museum.

Drop Anchor

84959 Overseas Highway, 222, Islamorada, FL

$182

includes taxes & fees

$166 per night

Jan 9 - Jan 10, 2025

With a stay at Drop Anchor in Islamorada, you'll be on the waterfront, a 4-minute walk from Windley Key Fossil Reef Geological State Park and a 3-minute drive from Rain Barrel Village.

Creekside Inn Islamorada

90611 Old Highway, Tavernier, FL

$181

includes taxes & fees

$161 per night

Jan 20 - Jan 21, 2025

A stay at Creekside Inn Islamorada places you in the heart of Tavernier, just a 3-minute walk from Florida Keys Dive Center and within a 5-minute drive of Mariners Hospital.

Don't see what you're looking for?

See all available properties in Islamorada

View all properties

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.

Often, one of the most difficult things about booking a hotel is finding the best time to go. The cost of staying in hotels in could vary significantly, depending on the time of the year chosen. If you would like to figure out the most suitable time to take a trip then using CheapTickets could be the best option for you. We will be able to provide information on hotels in to ensure that you get the best deal possible. So if you are looking for a booking website that will streamline the process and offer good prices, then log in and get booking.

Islamorada hotels essential information

Accommodation	2,216 hotels
Lowest Price	$181
Highest Price	$521
Popular hotels	Cheeca Lodge & Spa, Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort, Amara Cay Resort, La Siesta Resort & Villas, Islander Resort, Casa Morada, Conch On Inn Motel, Pines & Palms Resort, Chesapeake Beach Resort, Hadley Resort and Marina, Drop Anchor, Creekside Inn Islamorada

Most Recent Islamorada Hotel Reviews

La Jolla Resort

5 out of 5

Posted 2 hours ago

CheapTickets Verified Review

"All"

A verified traveler stayed at La Jolla Resort