Islamorada Travel Guide

Tourist Guide

Islamorada
Islamorada
Islamorada
Islamorada
Islamorada

Where to stay in Islamorada

Matecumbe

Matecumbe

If you're spending some time in Matecumbe, Bud n' Mary's Dive Center and Robbie’s of Islamorada 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 Founders 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 Founders Park and Islamorada County Park.

Seabreeze Trailer Park
Cheeca Lodge & Spa

Cheeca Lodge & Spa

5 out of 5
81801 Overseas Highway, Mile Marker 82 Islamorada FL
The price is 7.136.086 ₫ per night from 14 Jun to 15 Jun
7.136.086 ₫
9.952.366 ₫ total
14 Jun - 15 Jun
includes taxes & fees
Stay at this luxury resort in Islamorada. Enjoy free parking, 3 outdoor pools and a full-service spa. Our guests praise the pool and the helpful staff in their ...
9.2/10 Wonderful! (1,311 reviews)
"Much batter than bigger hotels we were used to staying at. Staff was great and everything felt more purposeful and curated."

Reviewed on 30 May 2026

Cheeca Lodge & Spa
Chesapeake Beach Resort

Chesapeake Beach Resort

3.5 out of 5
83409 Overseas Hwy Islamorada FL
The price is 4.724.499 ₫ per night from 2 Jun to 3 Jun
4.724.499 ₫
6.795.167 ₫ total
2 Jun - 3 Jun
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! (1,733 reviews)
"Property was clean and very smooth check in process. I would definitely return."

Reviewed on 31 May 2026

Chesapeake Beach Resort
Islander Resort

Islander Resort

4 out of 5
82100 Overseas Highway Islamorada FL
The price is 5.702.553 ₫ per night from 23 Jun to 24 Jun
5.702.553 ₫
8.191.501 ₫ total
23 Jun - 24 Jun
includes taxes & fees
Stay at this beach hotel in Islamorada. Enjoy free Wi-Fi, free parking and 2 outdoor pools. Our guests praise the pool and the helpful staff in their reviews. ...
9.4/10 Exceptional! (1,021 reviews)
"Pool was very dirty, rooms super clean and look great"

Reviewed on 31 May 2026

Islander 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.
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! (686 reviews)
"We got room 308 which is a must!! Beautiful! Great lobby check in person!!!"

Reviewed on 30 May 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! (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 18 May 2026

The Islands of Islamorada
Caloosa Cove Resort by CoolVacay

Caloosa Cove Resort by CoolVacay

3 out of 5
73801 Overseas Hwy Islamorada FL
Stay at this condo in Islamorada. Enjoy free Wi-Fi, free parking and a marina. Popular attractions Anne's Beach and Sunset Drive Beach are located nearby.
9.4/10 Exceptional! (3 reviews)
"Easy check in if you come After business hours. Kayaks and sport equipment available. Has a small beach which is unique to the Keys. Pool pretty much vacant at all times. Great views. Highly recommend."

Reviewed on 31 May 2026

Caloosa Cove Resort by CoolVacay
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.

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