Cheap flights from Key West to Caribbean Islands from $147

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Key West to Caribbean Islands departing on 2/20. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
1 adult
0 bags

Discover deals from 900+ travel sites with momondo.

Save money when you book flights with momondo

Big names and deals

Big names and deals

Search 100s of travel sites to compare prices.

Filter for what you want

Filter for what you want

Free Wi-Fi? Stopover? Instantly customize your results.

Trusted and free

Trusted and free

We’re completely free to use - no hidden charges or fees.

Price Alerts

Price Alerts

Not ready to book? to track prices.

Find the cheapest flights from Key West to Caribbean Islands

Cheap round-trip flights

Enter your travel dates to find the best prices.
Multiple Airlines Logo
9:46 am - 11:09 pm
EYW
-
SJU
12h 23m
1 stop
Multiple Airlines Logo
5:30 am - 2:53 pm
SJU
-
EYW
9h 23m
1 stop
$293Multiple Airlines
Thu, Mar 5 - Mon, Mar 9
Multiple Airlines Logo
9:46 am - 11:09 pm
EYW
-
SJU
12h 23m
1 stop
Multiple Airlines Logo
9:12 pm - 11:11 am
SJU
-
EYW
37h 59m
2 stops
$320Multiple Airlines
Thu, Mar 5 - Mon, Mar 9
Multiple Airlines Logo
9:49 am - 2:25 pm
EYW
-
SJU
27h 36m
1 stop
Multiple Airlines Logo
5:30 am - 2:53 pm
SJU
-
EYW
9h 23m
1 stop
$341Multiple Airlines
Fri, Mar 6 - Mon, Mar 9
Multiple Airlines Logo
1:01 pm - 1:24 am
EYW
-
SJU
35h 23m
2 stops
Multiple Airlines Logo
11:52 am - 9:06 am
SJU
-
EYW
22h 14m
1 stop
$344Multiple Airlines
Tue, Feb 17 - Sat, Feb 21
Spirit Airlines Logo
2:25 pm - 11:09 pm
EYW
-
SJU
31h 44m
3 stops
Spirit Airlines Logo
1:59 am - 1:30 pm
SJU
-
EYW
11h 31m
2 stops
$405Spirit Airlines
Fri, Mar 6 - Sun, Mar 8
Spirit Airlines Logo
2:25 pm - 11:09 pm
EYW
-
SJU
31h 44m
3 stops
Spirit Airlines Logo
1:59 am - 1:30 pm
SJU
-
EYW
11h 31m
2 stops
$419Spirit Airlines
Thu, Mar 5 - Sun, Mar 8
American Airlines Logo
7:42 pm - 2:46 pm
EYW
-
NAS
19h 04m
1 stop
American Airlines Logo
5:26 pm - 10:58 pm
NAS
-
EYW
5h 32m
1 stop
$506American Airlines
Mon, Apr 6 - Wed, Apr 8
American Airlines Logo
7:42 pm - 9:42 am
EYW
-
FPO
14h 00m
1 stop
American Airlines Logo
10:22 am - 4:30 pm
FPO
-
EYW
6h 08m
1 stop
$577American Airlines
Mon, Apr 6 - Wed, Apr 8
United Airlines Logo
4:05 pm - 1:54 pm
EYW
-
KIN
46h 49m
2 stops
United Airlines Logo
2:59 pm - 3:15 pm
KIN
-
EYW
47h 16m
2 stops
$5,097United Airlines
Sun, May 31 - Wed, Jun 3
United Airlines Logo
4:05 pm - 1:54 pm
EYW
-
KIN
46h 49m
2 stops
United Airlines Logo
2:59 pm - 3:15 pm
KIN
-
EYW
23h 16m
2 stops
$6,786United Airlines
Sun, May 31 - Wed, Jun 3

American Airlines flights from Key West to Caribbean Islands

Our best American Airlines deals on Key West to Caribbean Islands flight tickets
American Airlines
Mar 7
EYW7:36 pmKey West
12h 24m
1 stop
SJU9:00 amSan Juan Luis Munoz Marin Intl
Mar 12
SJU6:00 amSan Juan Luis Munoz Marin Intl
13h 12m
1 stop
EYW7:12 pmKey West
$426
American Airlines
Feb 27
EYW1:55 pmKey West
8h 39m
1 stop
SJU11:34 pmSan Juan Luis Munoz Marin Intl
Mar 6
SJU10:50 amSan Juan Luis Munoz Marin Intl
9h 25m
1 stop
EYW7:15 pmKey West
$446
American Airlines
Mar 15
EYW7:42 pmKey West
15h 14m
1 stop
SJU10:56 amSan Juan Luis Munoz Marin Intl
Mar 22
SJU7:11 amSan Juan Luis Munoz Marin Intl
12h 01m
1 stop
EYW7:12 pmKey West
$486

United Airlines flights from Key West to Caribbean Islands

Our best United Airlines deals on Key West to Caribbean Islands flight tickets
United Airlines
May 13
EYW4:00 pmKey West
22h 57m
1 stop
NAS2:57 pmNassau Intl
May 16
NAS3:59 pmNassau Intl
23h 08m
1 stop
EYW3:07 pmKey West
$751
United Airlines
Feb 27
EYW7:00 amKey West
13h 00m
1 stop
SJU9:00 pmSan Juan Luis Munoz Marin Intl
Mar 5
SJU2:05 amSan Juan Luis Munoz Marin Intl
21h 14m
2 stops
EYW10:19 pmKey West
$917
United Airlines
Feb 22
EYW6:40 pmKey West
19h 00m
2 stops
SJU2:40 pmSan Juan Luis Munoz Marin Intl
Feb 26
SJU8:30 amSan Juan Luis Munoz Marin Intl
14h 39m
1 stop
EYW10:09 pmKey West
$942

momondo Fare Finder

 
Customize your flight search to find flights from Key West to Caribbean Islands that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, momondo users made 832,500 searches. Data last updated February 3, 2026.
Use the filters below to find and compare flights from Key West to Caribbean Islands that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Key WestSan Juan

EYW - SJU

EYWSJU

Key West

Thu 3/5

9:46 am-11:09 pm

1 stop12h 23m

San Juan Luis Munoz Marin Intl

Mon 3/9

5:30 am-2:53 pm

1 stop9h 23m

$293

Key WestSan Juan

EYW - SJU

EYWSJU

Key West

Thu 3/5

9:46 am-11:09 pm

1 stop12h 23m

San Juan Luis Munoz Marin Intl

Mon 3/9

9:12 pm-11:11 am

2 stops37h 59m

$320

Key WestSan Juan

EYW - SJU

EYWSJU

Key West

Fri 3/6

9:49 am-2:25 pm

1 stop27h 36m

San Juan Luis Munoz Marin Intl

Mon 3/9

5:30 am-2:53 pm

1 stop9h 23m

$341

Key WestSan Juan

EYW - SJU

EYWSJU

Key West

Tue 2/17

1:01 pm-1:24 am

2 stops35h 23m

San Juan Luis Munoz Marin Intl

Sat 2/21

11:52 am-9:06 am

1 stop22h 14m

$344

Key WestSan Juan

EYW - SJU

EYWSJU

Key West

Fri 3/6

2:25 pm-11:09 pm

3 stops31h 44m

San Juan Luis Munoz Marin Intl

Sun 3/8

1:59 am-1:30 pm

2 stops11h 31m

$405

Key WestSan Juan

EYW - SJU

EYWSJU

Key West

Thu 3/5

2:25 pm-11:09 pm

3 stops31h 44m

San Juan Luis Munoz Marin Intl

Sun 3/8

1:59 am-1:30 pm

2 stops11h 31m

$419

Key WestNassau

EYW - NAS

EYWNAS

Key West

Mon 4/6

7:42 pm-2:46 pm

1 stop19h 04m

Nassau Intl

Wed 4/8

5:26 pm-10:58 pm

1 stop5h 32m

$506

Key WestFreeport

EYW - FPO

EYWFPO

Key West

Mon 4/6

7:42 pm-9:42 am

1 stop14h 00m

Freeport Grand Bahama Intl

Wed 4/8

10:22 am-4:30 pm

1 stop6h 08m

$577

Key WestKingston

EYW - KIN

EYWKIN

Key West

Sun 5/31

4:05 pm-1:54 pm

2 stops46h 49m

Kingston Norman Manley

Wed 6/3

2:59 pm-3:15 pm

2 stops47h 16m

$5,097

Key WestKingston

EYW - KIN

EYWKIN

Key West

Sun 5/31

4:05 pm-1:54 pm

2 stops46h 49m

Kingston Norman Manley

Wed 6/3

2:59 pm-3:15 pm

2 stops23h 16m

$6,786

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
1
2

See travel insights to Caribbean Islands from

How to get the cheapest flight ticket from Key West to Caribbean Islands

Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip

Can stopping save me money on Key West to Caribbean Islands flights?

No. A direct flight is the cheapest option for a flight between Key West to Caribbean Islands.

Cheap Key West to Caribbean Islands flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Key West to Caribbean Islands

Fastest flight time

4h 34m

Direct flights

None
The fastest flight from Key West to Caribbean Islands takes 4h 34m
There are no direct flights from Key West to Caribbean Islands. There are no popular flight routes from Key West to Caribbean Islands.
  • When did momondo last update prices for flights from Key West Airport to Caribbean Islands?

    Prices for flights from Key West Airport to Caribbean Islands are refreshed on a daily basis.

  • How many operators does momondo search for flights from Key West Airport to Caribbean Islands?

  • How old do you have to be to fly from Key West Airport to Caribbean Islands?

    The minimum age a child must be to fly alone is five but airlines that offer an unaccompanied minor (UNMR) service will have their own age restrictions, including rules around flight length, timings, and stopovers. We always recommend checking with the individual airline you are booking with to travel from Key West Airport to Caribbean Islands.

  • What documentation or ID do you need to fly to Caribbean Islands?

    The necessary travel and health documents for your Caribbean Islands trip may vary depending on your travel plans and individual circumstances. Generally, you should have various documents, such as a national ID card or driver's license and a passport that is valid for six months beyond your scheduled arrival date. We recommend seeking advice from your airline or a trusted third party, such as IATA.

  • What is the most popular plane model from Key West to Caribbean Islands?

Best airlines flying from Key West to Caribbean Islands

Compare and see reviews for airlines that fly from Key West to Caribbean Islands with momondo
Airline
Rating
Free Cancellation
Price
American AirlinesPriceFrom $376Free CancellationRating
7.2
11,216 reviews
Search American Airlines flights

Why use momondo?

Why should I use momondo to find a flight deal from Key West to Caribbean Islands?

It is quick and easy to find Key West to Caribbean Islands flights on momondo. We search and return numerous flight options from various airlines and agents. You can then use our filters to narrow your search until you have found the most convenient flight to Caribbean Islands that suits you.

Can I find flights from Key West to Caribbean Islands with flexible booking policies on momondo?

All flight searches from Key West to Caribbean Islands on momondo can be filtered to show those which offer flexible booking policies.

How can momondo help me find flights from Key West to Caribbean Islands?

Once you have performed a search for Key West to Caribbean Islands flights, momondo helps you find the right one by offering useful filters to narrow down your flight selection. Flights can be filtered by multiple factors such as airline, airport and price; but also by other criteria like aircraft type and payment method.

I’m not ready to book a flight from Key West to Caribbean Islands right now. Can momondo alert me if prices change?

If you are simply researching potential flights to Caribbean Islands, momondo offers a useful price alert feature which will track prices for flights to Caribbean Islands from Key West and alert you when they change.

An easier way to manage your Caribbean Islands trip

We make it super easy to schedule, organize and travel with friends or family. Trips is free — and available to use no matter where you book.

Get notified when prices go down

Daily price changes in your inbox - only with Price Alerts.
1 adult
Thu 3/5
Thu 3/12

Find better results for your trip to Caribbean Islands

Popular cities in Caribbean Islands

Popular flights according to clicks in the last 7 days on momondo