Islamorada Travel Guide

Tourist Guide

Islamorada showing a beach and tropical scenes
Islamorada showing a beach and tropical scenes
Islamorada featuring a beach
Islamorada showing a bay or harbor
Islamorada showing outdoor eating as well as a small group of people

Where to stay in Islamorada

Cheeca Pier 🎣 🛶

Matecumbe

If you're spending some time in Matecumbe, Bud n' Mary's Dive Center and Florida Keys Brewing Co. are top sights worth seeing.

Matecumbe
Colorful Island Palm Tree Sunset

Venetian Shores

Though Venetian Shores may not have many top sights, you can venture to the surrounding area to see attractions like Islamorada County Park and Windley Key Fossil Reef Geological State Park.

Venetian Shores
Anne’s beach is on Lower Matecumbe Key

Lower Matecumbe Beach

While Lower Matecumbe Beach may not have many sights to explore, venturing just a little farther will lead you to top things to see and do like Anne's Beach and Sunset Drive Beach.

Lower Matecumbe Beach
Coastline of Islamorada, panoramic view at dusk

Seabreeze Trailer Park

While there might not be top attractions in Seabreeze Trailer Park, you can explore the larger area and discover places like Islamorada County Park and Founders Park.

Seabreeze Trailer Park
Chesapeake Beach Resort

Chesapeake Beach Resort

3.5 out of 5
83409 Overseas Hwy Islamorada FL
The price is 6.416.246 ₫ per night from 2 Feb to 3 Feb
6.416.246 ₫
8.684.945 ₫ total
2 Feb - 3 Feb
includes taxes & fees
Stay at this beach hotel in Islamorada. Enjoy free breakfast, free Wi-Fi and 2 outdoor pools. Our guests praise the breakfast and the pool in their reviews. ...
9.2/10 Wonderful! (1,655 reviews)
Staff was very nice. Nice to use the complimentary clear bottom kayaks. Breakfast was good, Didi made a great omelette!

Reviewed on 24 Jan 2026

Chesapeake Beach Resort
Cheeca Lodge & Spa

Cheeca Lodge & Spa

5 out of 5
81801 Overseas Highway, Mile Marker 82 Islamorada FL
The price is 7.797.023 ₫ per night from 3 Feb to 4 Feb
7.797.023 ₫
10.678.662 ₫ total
3 Feb - 4 Feb
includes taxes & fees
Stay at this 5-star luxury resort in Islamorada. Enjoy free parking, 3 outdoor pools and a full-service spa. Our guests praise the pool and the helpful staff ...
9.2/10 Wonderful! (1,301 reviews)
This palce is awesome. Clean rooms. 2 large pools with a view. Covered garage spot.

Reviewed on 22 Jan 2026

Cheeca Lodge & Spa
Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort

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

3.5 out of 5
84001 Overseas Hwy Islamorada FL
The price is 8.865.381 ₫ per night from 4 Feb to 5 Feb
8.865.381 ₫
11.708.727 ₫ total
4 Feb - 5 Feb
includes taxes & fees
Stay at this beach resort in Islamorada. Enjoy free Wi-Fi, 3 outdoor pools and 4 restaurants. Our guests praise the helpful staff and the clean rooms in their ...
9/10 Wonderful! (136 reviews)
Very clean nice location friendly staff wish the bar stayed open last 11:00 pm but was great

Reviewed on 25 Jan 2026

Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort
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.
Treasure Harbor

Treasure Harbor

3 out of 5
200 Treasure Harbor Dr Islamorada FL
Stay at this hotel in Islamorada. Enjoy free Wi-Fi, free parking and premium bedding. Our guests praise the helpful staff in their reviews. Popular attractions ...
8.8/10 Excellent! (127 reviews)
There were a few problems with the room when we arrived but the staff took care of it promptly. The stay was very relaxing. Manatees off the bow of the boat every day. It was our second trip here and hope to come back again.

Reviewed on 24 Jan 2026

Treasure Harbor
Breezy Palms Resort

Breezy Palms Resort

2.5 out of 5
80015 Overseas Highway Islamorada FL
Stay at this beach aparthotel in Islamorada. Enjoy free Wi-Fi, a beach locale and a marina. Our guests praise the helpful staff and the clean rooms in their ...
8.8/10 Excellent! (615 reviews)
Room was good staff was excellent

Reviewed on 20 Jan 2026

Breezy Palms Resort
The Islands of Islamorada

The Islands of Islamorada

4 out of 5
82779 Old Hwy Islamorada FL
Stay at this beach villa in Islamorada. Enjoy free Wi-Fi, free parking and 2 outdoor pools. Popular attractions History of Diving Museum and Islamorada Brewery ...
9.6/10 Exceptional! (70 reviews)
Beautiful accommodations and location, very clean, many activities available at resort

Reviewed on 25 Nov 2025

The Islands of Islamorada
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.

Popular places to visit

Reviews of Islamorada

4.7
Top destination
5 - Excellent
11
5 - Excellent 69%
4 - Good
5
4 - Good 31%
3 - Okay
0
3 - Okay 0%
2 - Disappointing
0
2 - Disappointing 0%
1 - Terrible
0
1 - Terrible 0%

5/5 - Excellent

Verified traveller

Beautiful location

5/5 - Excellent

Verified traveller

Perfect spot if you are into fishing or boating and great for sunbathing and drinking rum runners. Plenty of places to eat and small interesting souvenir shops and a fantastic new supermarket!

Cities near Islamorada