Explore top 2026 4 Star Hotels in Islamorada

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Top Islamorada 4 Star hotels

Baker's Cay Resort Key Largo, Curio Collection by Hilton

97000 Overseas Hwy Key Largo FL

$327 nightly

$368 total

Jun 16 - Jun 17

Total with taxes and fees

A private beach, 2 restaurants, and 2 outdoor pools are all featured at this resort. Enjoy beachfront dining and relax with sun loungers and beach umbrellas. ...

8.6/10 Excellent! (1,071 reviews)

"Always have a great time when I stay in Baker’s Cay! I love the private beach on the property and the food is delicious! You don’t need to leave the property to have a good time."

Reviewed on May 18, 2026

Amara Cay Resort

80001 Overseas Hwy Islamorada FL

Fully refundableReserve now, pay when you stay

$254 nightly

$286 total

May 28 - May 29

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)

"Absolutely loved this resort! Amazing service and Happy Hour at the Pool! Excellent Transportation options and within walking distance to some really nice restaurants. Great stay after 3 nights in Key West for our Anniversary. Hotel staff communicated with us to plan our arrival and was able to accommodate ..."

Reviewed on May 20, 2026

Islander Resort

82100 Overseas Highway Islamorada FL

Fully refundableReserve now, pay when you stay

$290 nightly

$326 total

Jun 16 - Jun 17

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 ...

9.2/10 Wonderful! (1,017 reviews)

"Was not worth the 1200 per night we spent!"

Reviewed on May 19, 2026

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

84001 Overseas Hwy Islamorada FL

Fully refundableReserve now, pay when you stay

$319 nightly

$359 total

Jun 1 - Jun 2

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 ...

9/10 Wonderful! (198 reviews)

"My only suggestion is to clean the garbage littered in the beach-lounging area. There’s also litter in the ocean (under Little Limon deck) that we picked up and a strong smell of sewage that hits the nostrils as soon as we exit our room or walk towards the Tiki bar. The ice cream place also needs ..."

Reviewed on May 16, 2026

Playa Largo Resort & Spa, Autograph Collection

97450 Overseas Highway Key Largo FL

Fully refundableReserve now, pay when you stay

$392 nightly

$441 total

Jun 2 - Jun 3

Total with taxes and fees

This luxury resort features a full-service spa, a marina, and 3 restaurants. Enjoy beachfront dining and relax with beach cabanas and sun loungers. Enjoy the ...

8.8/10 Excellent! (1,001 reviews)

"The staff here is outstanding. They are professional and will go out of their way to accommodate the guest. The resort is amazing and provides a lot of events throughout the days. We will definitely be returning."

Reviewed on May 13, 2026

La Siesta Resort & Villas

80241 Overseas Highway Islamorada FL

Fully refundableReserve now, pay when you stay

$230 nightly

$259 total

May 27 - May 28

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, ...

8.6/10 Excellent! (1,000 reviews)

"La Siesta has so much potential. Beautiful grounds, spacious rooms, pool and views. The front counter staff and bike staff were very nice. Unfortunately they don’t clean up the trash around the compound. To either side of our entrance was trash that had been there before us and Is probably still ..."

Reviewed on May 17, 2026

The Islands of Islamorada

82779 Old Hwy Islamorada FL

$649 nightly

$730 total

May 21 - May 22

Total with taxes and fees

A marina, 2 outdoor pools, and a 24-hour gym are all featured at this smoke-free villa. Spend a day at the beach kayaking, or relax with sun loungers and beach ...

9.6/10 Exceptional! (76 reviews)

"I am not usually about leaving reviews however this property definitely needs it. Heard a lot about being pampered when I was checked in and that they will bring you anything and to let them know what our needs were. Property does not have any coffee shop or restaurant. We were told we could come ..."

Reviewed on May 18, 2026

Condo in the Keys

500 Burton Dr Tavernier FL

The private beach and full-service spa are among the highlights at this apartment. There's fun for all ages with a playground and an arcade/game room, and families ...

8/10 Very Good! (14 reviews)

"Nice kitchen. Great view."

Reviewed on Mar 27, 2026

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The Sanctuary Islet by Florida Keys Luxury Rentals

1565 Ocean Bay Drive Key Largo FL

This vacation home features a private beach and free WiFi in public areas. Take advantage of the free self parking.

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Pineapple Beach by Florida Keys Luxury Rentals

130 Aregood Lane Islamorada FL

This vacation home features a private beach and free WiFi in public areas. Take advantage of the free self parking.

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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.

4 Star Hotels Islamorada

Looking to live it up on your vacation with a bit of luxury? Or maybe you’ve decided that your boss can afford to put you up at a place of your choice on your next business trip?

Come on, you deserve it!

The best part about staying in Islamorada 4 star hotels is that you’ll often be close to all the local sights and attractions. Whether you’re visiting the area for the first time or you’re back in town for more fun, a 4 star hotel is going to put you right in the heart of all the action.

Plus, you can rest easy knowing that you’re being well taken care of during your visit. Instead of worrying about where to eat or what to see, your friendly hotel staff will be happy to help you get whatever you need.

The best four star hotels in Islamorada will also frequently include access to high-quality fitness centers and pools, so you’ll feel like you’re staying in an exclusive resort rather than a hotel. You won’t have any excuse for not keeping up with your workout routine!

If you’re looking for 4 star hotels in Islamorada, you’ll find the most bang for your buck by booking your stay with Travelocity. Go explore a new city, and know you’re getting the best deal on a great hotel with the Travelocity Price Guarantee.