Explore 16 Luxury Hotels in Islamorada

Name: Drop Anchor
Price range: $163 total
Rating: 8.6

Seize Your Someday with our amazing deals for the whole family!

Save an extra 10% or more on select hotels with Member Discounts

Access exclusive hotel deals, only with the Travelocity app

Best Luxury Hotels in Islamorada

Casa Morada

136 Madeira Road, Islamorada, FL

$274 nightly

$309 total

Jul 22 - Jul 23

Total includes 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 ...

9.2/10 Wonderful! (403 reviews)

"I have been coming here for years! With my daughter and or my husband We love the surroundings the tranquility of it. The staff is wonderful as well Sam, Eric friendly and lovely Great buffet in the am always inviting We Will continue our tradition at the Casa Morada"

Reviewed on Jul 17, 2025

Cheeca Lodge & Spa

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

Fully refundableReserve now, pay when you stay

$317 nightly

$357 total

Aug 21 - Aug 22

Total includes 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. ...

9/10 Wonderful! (1,137 reviews)

"Stayed here for one night. Unfortunately the weather wasn’t great so we didn’t get to experience the pool areas and such. We walked around the grounds at night in the rain and it was still breath taking. Would love to stay longer the next time I am back in the area."

Reviewed on Jul 20, 2025

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

84001 Overseas Hwy, Islamorada, FL

Fully refundableReserve now, pay when you stay

$237 nightly

$266 total

Aug 19 - Aug 20

Total includes 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 ...

9/10 Wonderful! (47 reviews)

Great, but eat off property

"Property and service were great. Food was not great. Very difficult to find options for a picky eater. Had to DoorDash Wendy’s several times."

Reviewed on Jul 2, 2025

Chesapeake Beach Resort

83409 Overseas Hwy, Islamorada, FL

Fully refundableReserve now, pay when you stay

$188 nightly

$212 total

Aug 14 - Aug 15

Total includes 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 ...

9/10 Wonderful! (1,480 reviews)

"Great view! Sweet ppl that work there!"

Reviewed on Jul 19, 2025

Amara Cay Resort

80001 Overseas Hwy, Islamorada, FL

Fully refundableReserve now, pay when you stay

$217 nightly

$245 total

Aug 20 - Aug 21

Total includes taxes and fees

A private beach, 2 restaurants, and an outdoor pool are all featured at this resort. Unwind with a drink at one of the 3 bars/lounges and enjoy perks like a ...

8.8/10 Excellent! (1,237 reviews)

"Cool atmosphere. Lobby/lounge area was cute and the bar looked nice. We're here in the off season so the hours for the tiki bar werent super ideal, but it was still nice."

Reviewed on Jul 16, 2025

Drop Anchor

84959 Overseas Highway, 222, Islamorada, FL

$148 nightly

$163 total

Jul 22 - Jul 23

Total includes 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 ...

8.6/10 Excellent! (1,001 reviews)

"This was our second stay in a month. Great location, beautiful property on the water. We love it here and cant wait to go back."

Reviewed on Jul 18, 2025

Creekside Inn Islamorada

90611 Old Highway, Tavernier, FL

Fully refundableReserve now, pay when you stay

$149 nightly

$168 total

Jul 27 - Jul 28

Total includes 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. ...

7.8/10 Good! (1,004 reviews)

"OMG! I DONT WANT TO SHARE!. I WANT TO KEEP THIS ONE ALL TO MY SELF! This place is so quiet and comfy, i cant believe i haven't found this place sooner."

Reviewed on Jul 17, 2025

Conch On Inn Motel

103 Caloosa Street, Tavernier, FL

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.

"The room was about 90° when we got there and never did cool off for two days we were there. Water pressure in the bathroom was bad. And one of the owners gave us a real bad attitude when we inquired about checking out a little bit late on our last day. We will never go back there again I would not ..."

Reviewed on Aug 6, 2018

Get rates

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.

More 4 star hotels in Islamorada

Lime Key by Florida Keys Luxury Rentals

25 N. Bounty Lane, Key Largo, FL

Get rates

5 star hotels in Islamorada

Cheeca Lodge & Spa

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

$317 nightly

$357 total

Aug 21 - Aug 22

Total includes taxes and fees

9/10 Wonderful! (1,137 reviews)

Islamorada Luxury Hotels

Do you want to stay at an elegant 5 star hotel for your next getaway? Do you want to be pampered like royalty? When you're ready, the Islamorada luxury hotels are the plush oasis you’ve been looking for.

Choose from the best luxury hotels in Islamorada to make your stay as comfortable and memorable as possible. Deluxe amenities await you upon check-in—perks like a heated pool, luxurious spa, and 24-hour reception service will cater to your every need, no matter the hour. If you’re tired from the day’s activities and don’t feel like wandering around to look for a meal, sit down to dinner at one of the high-end restaurants on property or contact room service for a sophisticated dining experience in the comfort of your own suite. Getting to and from the airport will be an easy task as well because most of these fancy hotels offer a free shuttle service for easy transportation.

We want you to enjoy your next vacation in style and the top luxury resorts in Islamorada will help you do just that. Browse Travelocity right now to find amazing deals on the best luxury hotels and 4 star hotels in Islamorada, and plan your next opulent escape.

Islamorada hotels essential information

Accommodation	2,187 hotels
Lowest Price	$163
Highest Price	$357
Popular hotels	Cheeca Lodge & Spa, Amara Cay Resort, Drop Anchor, Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort, Creekside Inn Islamorada, Chesapeake Beach Resort, Conch On Inn Motel, Casa Morada