Upper Matecumbe Key, FL

Travel Guide

Upper Matecumbe Key
Upper Matecumbe Key
Upper Matecumbe Key
Upper Matecumbe Key
Upper Matecumbe Key
Chesapeake Beach Resort

Chesapeake Beach Resort

3.5 out of 5
83409 Overseas Hwy Islamorada FL
Fully refundable
$234 nightly
The price is $263 total per night from Jun 2 to Jun 3
$263 total
Jun 2 - Jun 3
Total with taxes and fees
Book a stay at this beach hotel in Islamorada. Enjoy free breakfast, free WiFi, and 2 outdoor pools. Our guests praise the breakfast and the pool in our reviews. ...
9.2/10 Wonderful! (1,738 reviews)
"I had a wonderful time on my getaway. The view from my room was beautiful. Everything was quite and pleasant perfect for a family. Everyone was polite, and the breakfast was delicious. The view of the breakfast was phenomenal."

Reviewed on May 26, 2026

Chesapeake Beach Resort
Cheeca Lodge & Spa

Cheeca Lodge & Spa

5 out of 5
81801 Overseas Highway, Mile Marker 82 Islamorada FL
$264 nightly
The price is $297 total per night from Jun 2 to Jun 3
$297 total
Jun 2 - Jun 3
Total with taxes and fees
Book a 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 ...
9.2/10 Wonderful! (1,319 reviews)
"My wife and I had an amazing experience. The staff were very friendly and helpful. We loved our room with the screened patio, we had our coffee there every morning overlooking the tennis courts. There’s so many things to do that are included, I don’t think we’ve ever stayed at a resort that had so ..."

Reviewed on May 28, 2026

Cheeca Lodge & Spa
Islander Resort

Islander Resort

4 out of 5
82100 Overseas Highway Islamorada FL
$285 nightly
The price is $321 total per night from Jun 18 to Jun 19
$321 total
Jun 18 - Jun 19
Total with taxes and fees
Book a stay at this beach hotel in Islamorada. Enjoy free WiFi, free parking, and 2 outdoor pools. Our guests praise the pool and the helpful staff in our reviews. ...
9.4/10 Exceptional! (1,023 reviews)
"We went for our anniversary and this property was paradise. Just beautiful and steps from the water. Plenty activities to do Bike riding/mini golf/fishing etc. The staff was very friendly and sunrise 🌅"

Reviewed on May 27, 2026

Islander Resort
See all 2,842 properties in Upper Matecumbe Key
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
Book a stay at this beach aparthotel in Islamorada. Enjoy free WiFi, a beach locale, and a marina. Our guests praise the helpful staff and the clean rooms in ...
8.8/10 Excellent! (683 reviews)
"Very clean, spacious, well located."

Reviewed on May 26, 2026

Breezy Palms Resort
The Islands of Islamorada

The Islands of Islamorada

4 out of 5
82779 Old Hwy Islamorada FL
Book a stay at this beach villa in Islamorada. Enjoy free WiFi, free parking, and 2 outdoor pools. Popular attractions History of Diving Museum and Islamorada ...
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

The Islands of Islamorada
Island Bay Resort

Island Bay Resort

2.5 out of 5
92530 OVERSEAS HIGHWAY Tavernier FL
Book a stay at this beach aparthotel in Tavernier. Enjoy free WiFi, free parking, and a private beach. Our guests praise the helpful staff in our reviews. Popular ...
10/10 Exceptional! (170 reviews)
"The hostess/ staff was amazing! Walking the property check in and making sure everyone had their needs met. She even decorated and brought a cupcake for my husband as we were celebrating his birthday. Very thoughtful! Very clean and enjoyable place. Love the quiet no kids, relaxing vibe! Kayaking ..."

Reviewed on May 27, 2026

Island Bay Resort
See all properties in Upper Matecumbe Key
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

Islamorada_BudnMarysDiveCenter_6069243-0004

Bud n' Mary's Dive Center

4.5/5(142 reviews)

Explore the waterfront of Bud n' Mary's Dive Center and enjoy other activities such as fishing in Islamorada. Discover the beautiful sunsets and seafood restaurants in this family-friendly area.

Bud n' Mary's Dive Center
Florida Keys Brewing Co.

Florida Keys Brewing Co.

You can take time to visit Florida Keys Brewing Co. during your travels to Islamorada.

Florida Keys Brewing Co.
Hurricane Monument

Hurricane Monument

4/5(66 reviews)

The memories of those lost to the 1935 Labor Day Hurricane live on at this moving tribute and burial site along the Overseas Highway.

Hurricane Monument
Islamorada_MatecumbeUnitedMethodistChurch_553248621532652347-0004

Matecumbe United Methodist Church

After visiting Matecumbe United Methodist Church, make a plan to see the other sights and activities in Islamorada. Discover the beautiful sunsets in this family-friendly area, or enjoy its fishing spots.

Matecumbe United Methodist Church
History of Diving Museum

History of Diving Museum

4.5/5(51 reviews)

Trace one of the world’s most astonishing watersports back through the centuries to see some of the first diving suits as you explore this interactive museum, featuring the world's largest international collection of diving artifacts.

History of Diving Museum

Islamorada Brewery & Distillery

You can take time to visit Islamorada Brewery & Distillery during your travels to Islamorada.

Islamorada Brewery & Distillery

Cities near Upper Matecumbe Key

Islamorada

Islamorada

Explore a world of travel with Expedia