Adventure Hotels in Islamorada from $148

Name: Drop Anchor
Price range: $357 total

Top Islamorada Adventure Hotels

Cheeca Lodge & Spa

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

Free Cancellation

Reserve now, pay when you stay

$202 nightly

$228 total

Sep 3 - Sep 4

Total with taxes and fees

This luxury resort features a private beach, a golf course, and a full-service spa. Enjoy beachfront dining and relax with sun loungers and beach umbrellas. ...

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

84001 Overseas Hwy, Islamorada, FL

Free Cancellation

Reserve now, pay when you stay

$237 nightly

$266 total

Sep 4 - Sep 5

Total with taxes and fees

This Art Deco resort features a private beach, a marina, and 4 restaurants. Enjoy a day at the beach snorkeling, or relax with sun loungers. Families will appreciate ...

Amara Cay Resort

80001 Overseas Hwy, Islamorada, FL

$246 nightly

$276 total

Sep 4 - Sep 5

Total with taxes and fees

A private beach, 2 restaurants, and an outdoor pool are all featured at this resort. If you want to take your pet along, this pet-friendly property offers everything ...

La Siesta Resort & Villas

80241 Overseas Highway, Islamorada, FL

Free Cancellation

Reserve now, pay when you stay

$222 nightly

$250 total

Sep 30 - Oct 1

Total with taxes and fees

The private beach and marina are among the highlights at this resort. Enjoy the outdoor pool and perks like a free area shuttle. There's a poolside bar on site, ...

Islander Resort

82100 Overseas Highway, Islamorada, FL

Free Cancellation

Reserve now, pay when you stay

$215 nightly

$242 total

Sep 8 - Sep 9

Total with taxes and fees

A private beach, 3 restaurants, and 2 outdoor pools are all featured at this hotel. Enjoy beachfront dining and relax with beach cabanas and sun loungers. Families ...

Casa Morada

136 Madeira Road, Islamorada, FL

$202 nightly

$228 total

Sep 8 - Sep 9

Total with taxes and fees

This hotel features a bar/lounge, a poolside bar, and an outdoor pool. Enjoy a day at the beach kayaking, or relax with beach umbrellas. There's no skimping ...

Conch On Inn Motel

103 Caloosa Street, Tavernier, FL

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This motel doesn't skimp on freebies - guests receive free WiFi and free self parking. A garden, concierge services, and barbecue grills are also on offer.

Pines & Palms Resort

80401 Old Hwy, Islamorada, FL

$198 nightly

$223 total

Sep 3 - Sep 4

Total with taxes and fees

The private beach and marina are among the highlights at this hotel. Enjoy a day at the beach snorkeling, or relax with sun loungers. Enjoy the outdoor pool ...

Chesapeake Beach Resort

83409 Overseas Hwy, Islamorada, FL

Free Cancellation

Reserve now, pay when you stay

$150 nightly

$169 total

Sep 22 - Sep 23

Total with taxes and fees

A private beach, a marina, and 2 outdoor pools are all featured at this smoke-free hotel. Enjoy a day at the beach kayaking, or relax with sun loungers. Unwind ...

Hadley Resort and Marina

82749 Overseas Hwy, Islamorada, FL

Free Cancellation

Reserve now, pay when you stay

$132 nightly

$148 total

Oct 1 - Oct 2

Total with taxes and fees

This traditional hotel's private beach and marina are among the highlights. Enjoy a day at the beach kayaking, or relax with sun loungers. Families will appreciate ...

Drop Anchor

84959 Overseas Highway, 222, Islamorada, FL

$321 nightly

$357 total

Sep 15 - Sep 16

Total with taxes and fees

An outdoor pool, free self parking, and barbecue grills are featured at this hotel. WiFi in public areas is free. A business center, a garden, and a picnic area ...

Creekside Inn Islamorada

90611 Old Highway, Tavernier, FL

Free Cancellation

Reserve now, pay when you stay

$139 nightly

$156 total

Sep 7 - Sep 8

Total with taxes and fees

This smoke-free motel's marina and 2 outdoor pools are some of the highlights. Guests will appreciate free perks like free self parking and WiFi in public areas. ...

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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.

Looking for a hotel that matches your active lifestyle? These are the adventure hotels in Islamorada that your mother warned you about!

Instead of playing it safe, book a stay at one of the Islamorada adventure hotels near the most exciting activities to take your trip up a notch. From down and dirty in the street to wet and wild in the water, you need a hotel that can help you remove all the grit and grime after a day full of adrenaline.

That’s why sport hotels in Islamorada are a great fit for your lifestyle. Not only are they in an area with plenty of adventure to choose from, but they’re also the perfect place to relax and unwind after a full day of excitement.

Enjoy clean and comfortable rooms with all the amenities you’d expect of a regular hotel, with the added convenience of being close to activities that get your heart pumping. From hot showers and high-thread-count sheets to tasty room service, you’ll be able to relax as you prepare to take on the day again tomorrow.

No matter what type of (slightly) dangerous activity you’re into, make sure you book your adventure hotels in Islamorada with Travelocity. You’ll get the best possible deal and have even more money to spend on your trip!

Islamorada hotels essential information

Accommodation	2,184 hotels
Lowest Price	$148
Highest Price	$357
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