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 ₹72,744, price is now ₹42,503 per person
₹42,503
per person
16 May - 21 May
found 19 hours ago
Return flight included
New York (JFK) to Miami (MIA)
8.4/10 Very Good! (1,001 reviews)
Loved the location, room was nice, bathroom very small, very friendly staff, slow service at restaurant in the morning. Will go back
Reviewed on 24 Feb 2026
President Hotel
South Beach
Save 100% on your flight
Price was ₹83,572, price is now ₹49,067 per person
₹49,067
per person
16 May - 21 May
found 19 hours ago
Return flight included
New York (JFK) to Miami (MIA)
8.4/10 Very Good! (1,775 reviews)
Location is great, the rest is average or below average
Reviewed on 26 Feb 2026
The Penguin Hotel
South Beach
Save 100% on your flight
Price was ₹73,030, price is now ₹43,915 per person
₹43,915
per person
16 May - 21 May
found 19 hours ago
Return flight included
New York (JFK) to Miami (MIA)
8.2/10 Very Good! (1,491 reviews)
It was perfect. It was right across from the beach lots of shops lots of restaurants lovely area.
Reviewed on 24 Feb 2026
Solé Miami, A Noble House Resort
Ocean Four
Save 100% on your flight
Price was ₹91,888, price is now ₹57,500 per person
₹57,500
per person
16 May - 21 May
found 19 hours ago
Return flight included
New York (JFK) to Miami (MIA)
8.4/10 Very Good! (1,935 reviews)
Staff were nice. There's just not much in the area and have to uber everywhere
Reviewed on 22 Feb 2026
Pelican Hotel
South Beach
Save 100% on your flight
Price was ₹94,788, price is now ₹61,610 per person
₹61,610
per person
16 May - 21 May
found 19 hours ago
Return flight included
New York (JFK) to Miami (MIA)
9.2/10 Wonderful! (394 reviews)
Great cozy old hotel, location is very good, the restaurant and foods awesome, they made a mix up in our first included breakfast and took me a long time of argument with the hotel manager to convince him for their lack of information and to get my money back, that and 40 minutes waiting to get my car back from valet are the only reason to give them 4 stars otherwise the stay was pleasant
Reviewed on 24 Feb 2026
Where to stay in Islamorada
Find the best Islamorada areas and neighborhoods for the activities you enjoy most. Learn more about Islamorada
Matecumbe
6 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 Anne's Beach 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
Cheeca Lodge & Spa
81801 Overseas Highway, Mile Marker 82 Islamorada FL
Fully refundableReserve now, pay when you stay
The price is ₹39,925 per night from 28 Feb to 1 Mar
₹39,925
₹51,564 total
28 Feb - 1 Mar
includes taxes & fees
9.2/10 Wonderful! (1,297 reviews)
This Resort is unbelievable from the rooms to the beach, walking & biking trails, golf course 27 acres of lush property. Lots of shops & restaurants nearby including Bass Pro Shop, small artists shops & brewery within walking/biking distance.
Reviewed on 25 Feb 2026
Chesapeake Beach Resort
83409 Overseas Hwy Islamorada FL
Fully refundableReserve now, pay when you stay
The price is ₹24,522 per night from 1 Mar to 2 Mar
₹24,522
₹32,702 total
1 Mar - 2 Mar
includes taxes & fees
9.2/10 Wonderful! (1,657 reviews)
The room was clean. The beds were comfortable. The heated pool was great! The fishing and bikes were a great addition. We loved pur stay.
Reviewed on 27 Feb 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 ₹40,108 per night from 22 Mar to 23 Mar
₹40,108
₹51,157 total
22 Mar - 23 Mar
includes taxes & fees
9/10 Wonderful! (157 reviews)
All was fantastic. Very nice staff. Clean room. Highly recommended
Reviewed on 23 Feb 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
4.5/5(3 reviews)
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
3.5/5(2 reviews)
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.
