Islamorada Trip
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to ₹43,962 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
Top Islamorada Flight + Hotel Deals
Price found within the past 48 hours. Click for updated prices.
Cavalier Hotel South Beach
South Beach
Save 100% on your flight
Price was ₹120,629, price is now ₹76,583 per person
₹76,583
per person
19 Mar - 22 Mar
found 7 hours ago
Return flight included
Detroit (DTW) to Miami (MIA)
8.4/10 Very Good! (1,001 reviews)
Main road in front of hotel was closed. When we arrived, the concierge had no idea where to tell us to park.
If they were transparent about it, ok. I would be ok. Then they said they are out of the 'free' wine, but could charge me $8 for a Heineken. Then couldn't get the elevator to work (we were on the 2nd floor thank God)
The room was in good shape. The parking is what set off the chain for me. It's not hard to update a website. Or at least tell your staff what to say. Ended up parking in the City parking garage. I'd give it like a 75/100.
Reviewed on 6 Jan 2026
The Penguin Hotel
South Beach
Price was ₹112,729, price is now ₹74,603 per person
₹74,603
per person
19 Mar - 22 Mar
found 7 hours ago
Return flight included
Detroit (DTW) to Miami (MIA)
8.2/10 Very Good! (1,491 reviews)
Very nice staff, helpful. The only thing is you have to walk through the back alley to go to breakfast. Lol.
But rather than that we enjoyed it very much!
Will recommend to friends and family!
Reviewed on 9 Jan 2026
President Hotel Villa
South Beach
Price was ₹111,873, price is now ₹74,208 per person
₹74,208
per person
19 Mar - 22 Mar
found 7 hours ago
Return flight included
Detroit (DTW) to Miami (MIA)
8.2/10 Very Good! (997 reviews)
Breakfast was better than La Quinta, but not especially good. Balcony was worthless, no view and over a noisy alleyway.
Reviewed on 7 Jan 2026
Where to stay in Islamorada
Find the best Islamorada areas and neighborhoods for the activities you enjoy most. Learn more about Islamorada
Matecumbe
5 out of top 10 points of interest in this area
If you're spending some time in Matecumbe, Bud n' Mary's Dive Center and Florida Keys Brewing Co. are top sights worth seeing.
Islamorada Beach Holiday
Relax along the shoreline and feel the wind through your hair during your Islamorada holiday. If it's your first time, why not collect some unique seashells as a souvenir of your trip to Islamorada? Spend your nights near Anne's Beach, a popular stretch of coast just 14 kilometres from the town centre. We also offer fantastic Islamorada packages closer to Sunset Drive Beach, another great nearby option.
Things You Should Know About Islamorada
- Escape the daily grind at one of our Islamorada beach hotels. The sound of the waves and seagulls cawing high in the sky are just a few clicks away.
- If you're searching for lots of room to spread out and relax, Islamorada private holiday homes are a great choice. After a much-needed family getaway or a few nights escape with your best friends? Treasure Harbour and Bud N' Mary's Fishing Marina will fit the bill.
- Roughly 7,100 people reside in Islamorada. If you're after a few helpful tips on what to see and do during your stay, have a chat to some of the friendly locals or have a look at our Islamorada things to do page.
Top hotels in Islamorada
Chesapeake Beach Resort
83409 Overseas Hwy Islamorada FL
Fully refundableReserve now, pay when you stay
The price is ₹16,339 per night from 28 Jan to 29 Jan
₹16,339
₹23,446 total
28 Jan - 29 Jan
includes taxes & fees
9.2/10 Wonderful! (1,621 reviews)
One of the most beautiful hotel I have ever stayed. It's on the pricey side, but worth staying it. We loved everything about it.
Reviewed on 4 Jan 2026
Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort
84001 Overseas Hwy Islamorada FL
Fully refundableReserve now, pay when you stay
The price is ₹26,707 per night from 21 Jan to 22 Jan
₹26,707
₹36,021 total
21 Jan - 22 Jan
includes taxes & fees
8.8/10 Excellent! (124 reviews)
Amazing place - so much variety
Reviewed on 6 Jan 2026
Cheeca Lodge & Spa
81801 Overseas Highway, Mile Marker 82 Islamorada FL
Fully refundableReserve now, pay when you stay
The price is ₹23,439 per night from 29 Jan to 30 Jan
₹23,439
₹32,953 total
29 Jan - 30 Jan
includes taxes & fees
9.2/10 Wonderful! (1,287 reviews)
Generally nice place. Leftover food and drinks in our hotel refrigerator upon arrival. Understaffed at dining facilities meaning long waits and order mistakes.
Reviewed on 8 Jan 2026
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
Anne's Beach
If a restful holiday is part of your travel plans, Anne's Beach might be the perfect place to visit during your trip to Islamorada.
Florida Keys Brewing Co.
You can take time to visit Florida Keys Brewing Co. during your travels to Islamorada.
Founders Park
Play soccer, baseball and volleyball just meters from the Atlantic Ocean before you dive into the water at this family-friendly beach park.
Explore a world of travel with Expedia
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
