Islamorada Holidays
- Plan, book, travel with confidence
- Better togetherSave up to €185 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 Flight + Hotel Deals in Islamorada
Price found within the past 48 hours. Click for updated prices.
Hotel Riu Plaza Miami Beach
Mid Beach
Price was €2,354, price is now €1,624 per person
€1,624
per person
14 Jan - 19 Jan
found 1 day ago
Return direct flight included
Johannesburg (JNB) to Miami (MIA)
16/10 Exceptional! (1,120 reviews)
Big room, nice pool and beach, good breakfast. Slow hot water and not sure what facility fee invoice was for.
Reviewed on 19 Nov 2025
72 Park - Miami Beach by Nomada
North Beach
Price was €2,142, price is now €1,608 per person
€1,608
per person
14 Jan - 19 Jan
found 1 day ago
Return direct flight included
Johannesburg (JNB) to Miami (MIA)
18/10 Exceptional! (83 reviews)
Room was so well prepared VIEW WAS AMAZING, STAFF was COURTEOUS and ATTENTIVE
Reviewed on 16 Nov 2025
Trump International Beach Resort
Price was €2,023, price is now €1,528 per person
€1,528
per person
14 Jan - 19 Jan
found 1 day ago
Return direct flight included
Johannesburg (JNB) to Miami (MIA)
16.8/10 Exceptional! (4,514 reviews)
We’ve been going to this hotel for the last 13 years at least once a year. We’re noticing a change in the last year, no tea or coffee provided as before, rooms are not stocked with water or coffee, room service is not as prompt or efficient as previous years,
Reviewed on 18 Nov 2025
Hotel Croydon
Mid Beach
Price was €1,784, price is now €1,405 per person
€1,405
per person
14 Jan - 19 Jan
found 1 day ago
Return direct flight included
Johannesburg (JNB) to Miami (MIA)
18/10 Exceptional! (1,000 reviews)
Love this little gem! All staff are
Very friendly. Bar and restaurant are great quality and service. Price for location is unbeatable.
Reviewed on 5 Nov 2025
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 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 €184 per night from 3 Dec to 4 Dec
€184
3 Dec - 4 Dec
includes taxes & fees
9.2/10 Wonderful! (1,574 reviews)
Good spot.
Reviewed on 15 Nov 2025
Cheeca Lodge & Spa
81801 Overseas Highway, Mile Marker 82 Islamorada FL
Fully refundableReserve now, pay when you stay
The price is €345 per night from 14 Dec to 15 Dec
€345
14 Dec - 15 Dec
includes taxes & fees
9/10 Wonderful! (1,261 reviews)
Amazing!
Reviewed on 14 Nov 2025
Amara Cay Resort
80001 Overseas Hwy Islamorada FL
Fully refundableReserve now, pay when you stay
The price is €207 per night from 1 Dec to 2 Dec
€207
1 Dec - 2 Dec
includes taxes & fees
8.8/10 Excellent! (1,251 reviews)
Very nice resort! Nice pool and the tiki bar was amazing. Great service and so close to Bud and Mary’s since we were fishing a few days. Definitely will return.
Reviewed on 12 Nov 2025
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
Bud n' Mary's Dive Center
4.5/5(3 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 relaxing area.
Sunset Drive Beach
Why not spend a lazy afternoon at Sunset Drive Beach during your trip to Islamorada?
What to do in Islamorada
Mangroves and Manatees - Guided Kayak Eco Tour
€58
per adult
96% of travellers recommend
Explore Mangrove Creeks with an All Day SUP/single kayak Rental
€41
per adult
Explore the Mangrove Creeks with an ALL Day Tandem Kayak Rental
€56
per adult
More trip options
Expedia's Latest Trends
Flights
Activities
Holiday Rentals
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
