Islamorada Guest Houses

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

Change your mind
Book hotels with free cancellation
Treat yourself
Sign in to save 10% or more on thousands of hotels
Sign in
Be picky
Search almost a million properties worldwide

Check prices for these dates

Next weekend

In two weeks

In one month

In two months

Our top choices for Islamorada guest houses

1. Ragged Edge Resort & Marina

Islamorada

Marianne

includes taxes & fees

8 Sept - 9 Sept

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

Matecumbe

includes taxes & fees

7 Oct - 8 Oct

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

Matecumbe

includes taxes & fees

13 Sept - 14 Sept

4. Jacuzzi Suite Overlooking the Sea @Islamorada - Iguana Suite

Matecumbe

5. Charming Suite @Islamorada With Pool Access - Twilight Suite

Matecumbe

includes taxes & fees

13 Sept - 14 Sept

View all properties

Save an average of 15% on thousands of hotels when you're signed in

Top Islamorada Hotel Reviews

Cheeca Lodge & Spa

10/10 Excellent

"We loved this place. The pool is beautiful and relaxing. Don’t expect swimming on the beach though, way too much sea weed. But you can take a kayak or paddle board out. Food in the restaurants was amazing. We loved the sushi restaurant for dinner. For lunch we just had a sandwich at the pool and it ended up being just delicious. Breakfast place had great food as well. The room was great. We did have some ants making trails through the bathroom sink, but that was not a big deal for us. Also, the ability to park under the building in the shade is very cool. Also, there is a shuttle that will take you around to explore islamorada, they will take you 2 miles out in one or another direction. We definitely will come back and enjoy this place again. Highly recommend!"

Pines & Palms Resort

10/10 Excellent

"Front desk, grounds crew, housekeeping and bartender are all friendly and helpful. Front desk team and bartender were attentive to our requests. Grounds crew was always busy keeping the property maintained and looking good. They even kept the beach cleaned up from seaweed and debris. The location is great with many good restaurants within a few miles and a couple within easy walking distance. This is our "go to" place in the Keys. Our many stays have always been great and we hate to leave."

Find out more about Islamorada