Explore 16 Luxury Hotels in Islamorada

Name: Drop Anchor
Price range: $124 total
Rating: 8.6

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Best Luxury Hotels in Islamorada

Casa Morada

136 Madeira Road, Islamorada, FL

$441 nightly

$496 total

Nov 10 - Nov 11

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 ...

9.4/10 Exceptional! (409 reviews)

Beautiful

Reviewed on Aug 18, 2025

Chesapeake Beach Resort

83409 Overseas Hwy, Islamorada, FL

Fully refundableReserve now, pay when you stay

$180 nightly

$203 total

Nov 10 - Nov 11

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 ...

9.2/10 Wonderful! (1,552 reviews)

Friendly staff

Reviewed on Nov 2, 2025

Cheeca Lodge & Spa

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

Fully refundableReserve now, pay when you stay

$249 nightly

$281 total

Nov 20 - Nov 21

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. ...

9/10 Wonderful! (1,266 reviews)

Always a great stay at Cheeca. Lovely property, great restaurants, clean rooms and wonderful service by the staff.

Reviewed on Oct 30, 2025

Amara Cay Resort

80001 Overseas Hwy, Islamorada, FL

Fully refundableReserve now, pay when you stay

$207 nightly

$233 total

Nov 30 - Dec 1

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 ...

8.8/10 Excellent! (1,278 reviews)

Water Taxi is the best perk ever ..

Reviewed on Nov 6, 2025

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

84001 Overseas Hwy, Islamorada, FL

Fully refundableReserve now, pay when you stay

$271 nightly

$304 total

Nov 19 - Nov 20

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 ...

8.8/10 Excellent! (103 reviews)

Our view of the beach was beautiful

Reviewed on Nov 2, 2025

Drop Anchor

84959 Overseas Highway, 222, Islamorada, FL

$114 nightly

$124 total

Nov 10 - Nov 11

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 ...

8.6/10 Excellent! (1,004 reviews)

Quiet peaceful nice beds view kitchen 😍

Reviewed on Oct 31, 2025

Creekside Inn

90611 Old Highway, Tavernier, FL

Fully refundableReserve now, pay when you stay

$189 nightly

$213 total

Nov 24 - Nov 25

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. ...

7.8/10 Good! (1,000 reviews)

Yes

Reviewed on Oct 28, 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

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More 4 star hotels in Islamorada

The Sanctuary Islet by Florida Keys Luxury Rentals

1565 Ocean Bay Drive, Key Largo, FL

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5 star hotels in Islamorada

Cheeca Lodge & Spa

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

$249 nightly

$281 total

Nov 20 - Nov 21

Total with taxes and fees

9/10 Wonderful! (1,266 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	2,217 hotels
Lowest Price	$124
Highest Price	$496
Popular hotels	Cheeca Lodge & Spa, Amara Cay Resort, Drop Anchor, Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort, Creekside Inn, Chesapeake Beach Resort, Conch On Inn Motel, Casa Morada