Search Islamorada Flights

Change your flight without a fee on select flights

Money Saving Bundle when you purchase Hotel + Flight! 

Get mobile alerts about flight delays, gate changes and more with the FREE Wotif app

How Much Does it Cost To Fly To Islamorada?

Prices were available within the past 7 days for one-way flights and round trip tickets for the period specified. Prices and availability are subject to change. Additional terms apply.

American Airlines
Mon, 22 Dec - Thu, 25 Dec
BOS
Boston
EYW
Key West
NZ$498 Return, found 20 hours ago
NZ$498
Return
found 20 hours ago
Select American Airlines flight, departing Mon, 22 Dec from Boston to Key West, returning Thu, 25 Dec, priced at NZ$498 found 20 hours ago
American Airlines
Mon, 22 Dec - Thu, 25 Dec
BOS
Boston
EYW
Key West
NZ$549 Return, found 20 hours ago
NZ$549
Return
found 20 hours ago
Select American Airlines flight, departing Mon, 22 Dec from Boston to Key West, returning Thu, 25 Dec, priced at NZ$549 found 20 hours ago
American Airlines
Tue, 23 Dec - Thu, 25 Dec
BOS
Boston
EYW
Key West
NZ$595 Return, found 1 day ago
NZ$595
Return
found 1 day ago
Select American Airlines flight, departing Tue, 23 Dec from Boston to Key West, returning Thu, 25 Dec, priced at NZ$595 found 1 day ago
United
Tue, 23 Dec - Thu, 25 Dec
BOS
Boston
EYW
Key West
NZ$612 Return, found 1 day ago
NZ$612
Return
found 1 day ago
Select United flight, departing Tue, 23 Dec from Boston to Key West, returning Thu, 25 Dec, priced at NZ$612 found 1 day ago
American Airlines
Mon, 22 Dec - Thu, 25 Dec
BOS
Boston
EYW
Key West
NZ$631 Return, found 20 hours ago
NZ$631
Return
found 20 hours ago
Select American Airlines flight, departing Mon, 22 Dec from Boston to Key West, returning Thu, 25 Dec, priced at NZ$631 found 20 hours ago
United
Mon, 22 Dec - Mon, 29 Dec
BOS
Boston
EYW
Key West
NZ$632 Return, found 1 day ago
NZ$632
Return
found 1 day ago
Select United flight, departing Mon, 22 Dec from Boston to Key West, returning Mon, 29 Dec, priced at NZ$632 found 1 day ago
American Airlines
Mon, 22 Dec - Sun, 28 Dec
BOS
Boston
EYW
Key West
NZ$634 Return, found 1 day ago
NZ$634
Return
found 1 day ago
Select American Airlines flight, departing Mon, 22 Dec from Boston to Key West, returning Sun, 28 Dec, priced at NZ$634 found 1 day ago
Delta
Mon, 22 Dec - Thu, 25 Dec
BOS
Boston
EYW
Key West
NZ$639 Return, found 20 hours ago
NZ$639
Return
found 20 hours ago
Select Delta flight, departing Mon, 22 Dec from Boston to Key West, returning Thu, 25 Dec, priced at NZ$639 found 20 hours ago
American Airlines
Mon, 22 Dec - Thu, 25 Dec
BOS
Boston
EYW
Key West
NZ$641 Return, found 20 hours ago
NZ$641
Return
found 20 hours ago
Select American Airlines flight, departing Mon, 22 Dec from Boston to Key West, returning Thu, 25 Dec, priced at NZ$641 found 20 hours ago
United
Mon, 22 Dec - Sun, 28 Dec
BOS
Boston
EYW
Key West
NZ$649 Return, found 1 day ago
NZ$649
Return
found 1 day ago
Select United flight, departing Mon, 22 Dec from Boston to Key West, returning Sun, 28 Dec, priced at NZ$649 found 1 day ago
Flight Info
Destination airport
Key West Intl.
Destination city name
Key West
Return price
NZ$497

Need a Car For After Your Flight?

Economy

Chevrolet Spark or similar
  • 4 people
Chevrolet Spark
Economy Chevrolet Spark

Compact

Ford Focus or similar
  • 4 people
Ford Focus
Compact Ford Focus

Midsize

Toyota Corolla or similar
  • 5 people
Toyota Corolla
Midsize Toyota Corolla

SUV

Jeep Compass or similar
  • 5 people
Jeep Compass
SUV Jeep Compass

Hotels in Islamorada

Cheeca Lodge & Spa

Cheeca Lodge & Spa

5 out of 5
81801 Overseas Highway, Mile Marker 82, Marker 82, Islamorada, FL
The price is NZ$490 per night from 20 Nov to 21 Nov
NZ$490
per night
20 Nov - 21 Nov
Stay at this 5-star luxury resort in Islamorada. Enjoy free parking, 3 outdoor pools, and a full-service spa. Our guests praise the pool and the helpful staff ...
9/10 Wonderful! (1,248 reviews)
Jess was great when checked in, made us feel right at home. The entire resort is beautiful, clean, well maintained. Although the rooms are spacious they’re starting to show their wear and tare, carpets needs a good cleaning or just install tile. Butch and Cole are great at the pool bar and as always ...

Reviewed on 3 Nov 2025

Cheeca Lodge & Spa
Chesapeake Beach Resort

Chesapeake Beach Resort

3.5 out of 5
83409 Overseas Hwy, Islamorada, FL
The price is NZ$383 per night from 10 Nov to 11 Nov
NZ$383
per night
10 Nov - 11 Nov
Stay at this 3.5-star 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! (1,560 reviews)
Beautiful location. The room was very comfortable and clean. The ocean view room with a balcony was perfect. The continental breakfast was great. I would highly recommend staying here.

Reviewed on 9 Nov 2025

Chesapeake Beach Resort
Islander Resort

Islander Resort

4 out of 5
82100 Overseas Highway, Islamorada, FL
The price is NZ$632 per night from 16 Nov to 17 Nov
NZ$632
per night
16 Nov - 17 Nov
Stay at this 4-star 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. ...
9.2/10 Wonderful! (1,002 reviews)
Not much on menu for healthy options, need more! A microwave in the room would be nice!

Reviewed on 9 Nov 2025

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.

Airport

^Savings based on all package bookings made with Flight + Hotel on Wotif.co.nz from , as compared to the price of the same components booked separately. Savings will vary based on origin/destination, length of trip, stay dates and selected travel supplier(s). Savings not available on all packages.