Islamorada Guest Houses

A beach with white lounge chairs, a covered pavilion, and palm trees.

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Our top choices for Islamorada guest houses

Ragged Edge Resort & Marina

Islamorada

Lauren

HK$1,822 total

includes taxes & fees

4 Aug - 5 Aug

Coconut Bay Resort Key Largo

Rock Harbor

carlos

HK$1,544 total

includes taxes & fees

17 Aug - 18 Aug

Charming Suite @Islamorada With Pool Access - Twilight Suite

Matecumbe

HK$19,867 total

includes taxes & fees

27 Jul - 28 Jul

Jacuzzi Suite Overlooking the Sea @Islamorada - Iguana Suite

Matecumbe

HK$19,849 total

includes taxes & fees

27 Jul - 28 Jul

Private Hideaway w/ Balcony + Lush Views @Islamorada - Hideaway suite

Matecumbe

HK$18,866 total

includes taxes & fees

27 Jul - 28 Jul

Romantic Suite With Jacuzzi & Garden Oasis @Islamorada - Jungles Suite Room

Matecumbe

HK$9,933 total

includes taxes & fees

27 Jul - 28 Jul

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Top Islamorada Hotel Reviews

Chesapeake Beach Resort

10/10 Excellent

"Good stay"

Cheeca Lodge & Spa

10/10 Excellent

"We had a wonderful stay! Although our room wasn’t ready at the scheduled check-in time, the staff handled the situation exceptionally well by upgrading us to a beautiful suite. Every member of the team was friendly, welcoming, and genuinely helpful throughout our stay. The excellent service more than made up for the delay, and we truly appreciated how well we were taken care of. We would happily stay here again."

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

10/10 Excellent

"Conveniently located. So much to do in the area. Walked out to beach or a short walk to the pool overlooking the ocean. Tiki bar was a pleasant visit most nights there. Room was updated and clean ."

Bayside Villas by Islander Resort

10/10 Excellent

"This place is an absolute gem. Check-in was absolutely amazing and they treated my mother-in-law and father-in-law like royalty as we were there to celebrate their 50th wedding anniversary.. at reception we were greeted by Sarah who went above and beyond in so many aspects I have done so much traveling and I will say this is one of my favorite stops. We will always try and stay at this location or their Sister location. Each fillet is equipped in furnished so beautifully with a breathtaking view of the sunset we were delighted by the manatees every morning in the Marina and walking around property felt comfortable, relaxing and safe. One guest accidentally left their vehicle door doors open all night and didn’t have a single problem. The staff were happy to help in anyway, and we saw them accommodating everyone just as well as we were. I do not do a lot of reviews as I feel like they’re isolated incidents and not really a clear picture as to how people are treated over overall. I felt deeply compelled to leave a review about how wonderful this place was, including its immaculate beauty and cleanliness this place deserves. It’s five star review."

Find out more about Islamorada